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Изучение основно-катализируемых реакций циклизации гидрокси-и орто-(ацил) гидроксикумаринов

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Mosti L., Lo Presti E., Menozzi G., Marzano C., Baccichetti F., Falcone G., Filippelli W., Piucci B. Synthesis of angelicin heteroanalogues: preliminary photobiological and pharmacological studies. // Farmaco. 1998. — Vol. 53, N 8−9.-P. 602−610. Dall’Acqua F., Caffieri S. and Rodighiero G. Photoreactions of furocoumarins (psoralens and angclicins). / Primary photoprocesses in biology and… Читать ещё >

Содержание

  • I. Введение 4 И. Основные методы получения ангелицина, псоралена и их производных (обзор литературы)
    • II. 1. Синтезы на основе аллилоксикумаринов
    • 11. 2. Реакция Виттига в синтезе фурокумаринов
    • 11. 3. Синтезы на основе ацилметиловых эфиров кумаринов
    • 11. 4. Синтез фурокумарин-5'-карбоновых кислот и их производных
    • 11. 5. Синтез 5'(4')-ацилфурокумаринов
    • 11. 6. Синтез фурокумаринов с электроноакцепторными заместителями в пироновом кольце
    • 11. 7. Синтез гидрокси-и алкоксифурокумаринов
    • 11. 8. Синтез аминофурокумаринов 37 III. Обсуждение результатов 46 III. 1. Новый метод синтеза эфиров фурокумарин-5 '-карбоновых кислот
  • III. 1.2. Синтез 5 '-карбэтоксифурокумаринов
  • III. 1.2. Синтез холестериловых эфиров
    • 111. 2. Синтез новых фурокумаринов 55 III.2.1. Синтез 5'-ацилфурокумаринов 55 III.2.2 Синтез арил- и алкил- псораленов
    • 111. 3. Новые реакции трансформации лактонного кольца производных кумарина в присутствии слабых оснований
    • 111. 4. Синтез гидрокси- и метоксифурокумаринов
    • 111. 5. Синтез и восстановление оксимов ацилфурокумаринов
    • III. 6. Прикладные свойства новых фурокумаринов

    IV. Экспериментальная часть 80 IV. 1. Синтез исходных гидроксикумаринов 80 IV.2. Синтез сложных эфиров гидроксикумаринов 82 IV.3. Синтез орто-ацил-7-гидроксикумаринов 83 IV.4. Синтез тозилата холестерина 84 IV.5. Синтез хлорацетата холестерина 84 IV.6. Синтез сложных эфиров 5'-фурокумаринкарбоновых кислот 84 IV.7. Синтез холестериловых эфиров 86 IV.8. Синтез этилового эфира 2-(4-метил-2-оксо-2Н-[1] бензопиранил-7-окси)бутановой кислоты

    IV.9. Синтез карбоновых кислот

    IV. 10. Синтез холестерил 2-(4-метил-2-оксо-2Н-[1 ] бензопиранил-7окси)бутаноата

    IV.11. Синтез 8-ацил-2Н-фуро[2,3−11][1]бензоприран-2-онов и

    2-ацил-7Н-фуро [3,2-g] [ 1 ] бензопиран-7-онов

    IV. 12. Синтез ацилметиловых эфиров кумаринов

    IV.13. Синтез производных 7Н-фуро[3,2-g][1]бензопиран-7-она

    IV. 14. Синтез оксимов 5'-ацилфурокумаринов

    IV. 15. Восстановление оксима

    IV. 16. Восстановление 5'-ацилфурокумаринов

    IV. 16.1. Синтез спиртов

    IV. 16.2. Синтез простых метиловых эфиров

    IV. 17. Реакции трансформации приронового цикла

    V. Выводы

Изучение основно-катализируемых реакций циклизации гидрокси-и орто-(ацил) гидроксикумаринов (реферат, курсовая, диплом, контрольная)

V. Выводы.

1. Разработан новый способ синтеза эфиров фурокумарин-5'-карбоновых кислот, основанный на конденсации орто-ацил (гидрокси)кумаринов с эфирами моногалогенуксусных кислот.

2. Указанным способом впервые получены холестериловые эфиры фурокумаринкарбоновых кислот.

3. Разработаны удобные способы получения гидрокси-, метокси-, ацил-, аминометили бензилфурокумаринов.

4. Обнаружены новые реакции трансформации пиронового цикла 3-карбоэтоксикумарина в присутствии слабых оснований, протекающие с сокращением и циклопропанированием лактонного кольца. Изучено влияние заместителей в бензольном кольце кумарина на направление трансформации.

5. Синтезированы и охарактеризованы методами спектроскопии ПМР и масс-спектрометрии 74 новых производных кумарина, в том числе 52 новых фурокумарина.

6. Установлено, что холестериловые эфиры карбоновых кислот фурокумаринов и кумаринов образуют устойчивые мономолекулярные слои Ленгмюра-Блоджетт, и перспективны для создания на их основе материалов молекулярной электроники (по данным НИИ физических проблем, г. Зеленоград).

7. Ряд фурокумаринов передан для изучения их взаимодействия с ДНК в Центральный научно-исследовательский рентгено-радиологической институт РАМН (г. Санкт-Петербург). Найдено высокое значение темновой константы связывания для 2-ацетил-3,5,9-триметилпсоралена.

1. Chakraborty DP., Roy S. and Chakraborty A.K. Vitiligo, psoralen, and melanogenesis: some observations and understanding. // Pigment Cell Res. -1996. -Vol. 9, N3, — P. 107−116.

2. Murray R.D.H. The natural coumarins: occurrence, chemistry and biochemistry. Wiley Interscience. New York. 1982. — P. 290−311.

3. Edelson R.L. Photopheresis: present and future aspects. // J. Photochem. Photobiol., B: Biology. 1991. — Vol. 10, N 1. — P. 165−174.

4. Gasparro F.P. Psoralen photobiology: recent advances. // Photochem. Photobiol. 1996. — Vol. 63, N 5. — P. 553−557.

5. Анцыпович С. И., Орецкая Т. С. Двуспиральные нуклеиновые кислоты с ковалентно связанными цепями синтез и применение в молекулярной биологии. // Успехи химии. — 1998. — Т. 67, Вып. 3. — С. 274−293.

6. Dall’Acqua F., Caffieri S. and Rodighiero G. Photoreactions of furocoumarins (psoralens and angclicins). / Primary photoprocesses in biology and medicine. Eds. Bensasson R.V., Jori G., Land E.J. and Truscott T.G. Plenum. New York. -1985. P. 259−272.

7. Potapenko A.Ya. New Trends in Photobiology (Invited Review). Mechanisms of photodynamic effect of furocoumarins. // J. Photochem. Photobiol., B: Biology. -1991.-Vol. 9, N 1. P. 1−33.

8. Miolo G., Dall’Acqua F., Moustacchi E. and Sage E. Monofunctional angular furocoumariris: sequence specificity in DNA photobinding of 6,4,4'-trimethylangelicin and other angelicin. // Photochem. Photobiol. 1989. — Vol. 50, N 1.-P. 75−84.

9. Jakobs A., Christians L. and Renson M. Synthesis of monosulfur and monoselenium analogues of psoralen // Tetrahedron. 1994. — Vol. 50, N 45. -P. 9315−9324.

10. Vedaldi D., Caffieri S., Frank S., Dall’Acqua F., Jakobs A. and Piette J. Sulfur and selenium analogues of psoralen as novel potential photochemotherapeutic agents. // Farmaco. 1995. — Vol. 50, N 6. — P. 527−536.

11. Jakobs A. and Christians L. A convenient synthesis of thiopyrano2,3-e. benzofuran a new sulfur analogue of angelicin. // J. Org. Chem. — 1996. — Vol. 61, N 14. — P. 4842−4844.

12. Collet M., Sage E. and Piette J. Photoreactions of new psoralen analogs with DNA: sequence and mutation specificity in the Escherichia coli IacZ gene. // Photochem. Photobiol. 1997. — Vol. 66, N 2. — P. 214−223.

13. Guiotto A., Chilin A., Manzini P., Dall’Acqua F., Bordin F., Rodighiero P. Synthesis and antiproliferative activity of furocoumarin isosters. // Farmaco. -1995. Vol. 50, N 6. — P. 479−489.

14. Bordin F., Marzano C., Carlassare F., Rodighiero P., Guiotto A., CafFieri S., Baccichetti F. Photobiological properties of a new tetramethylfuroquinolinone // J. Photochem., Photobiol. B: Biology. 1996. — Vol. 34, N 2−3. — P. 159−168.

15. Mosti L., Lo Presti E., Menozzi G., Marzano C., Baccichetti F., Falcone G., Filippelli W., Piucci B. Synthesis of angelicin heteroanalogues: preliminary photobiological and pharmacological studies. // Farmaco. 1998. — Vol. 53, N 8−9.-P. 602−610.

16. Marzano C., Caffieri S., Iester M., Bordin F., Averbeck D. Photobiological activity of 3- carbethoxyangelicin in Saccharomyces cerevisial. // Med., Biol., Environ. 1994. — Vol. 22, N 1. — P. 15−19.

17. Mosti L., Iester M., Carlassare F., Bordin F., Simonato M., Baccichetti F. Photobiological properties of 3- carbethoxyangelicin. // Med., Biol., Environ. -1993.-Vol. 21, N2.-P. 595−598.

18. Iester M., Fossa P., Menozzi G., Mosti L., Baccichetti F., Marzano C., Simonato M. Synthesis and photobiological properties of 3-acylangelicins, 3-alkoxycarbonylangelicins and related derivatives. // Farmaco. 1995. — Vol. 50, N 10.-P. 669−678.

19. Marzano C., Caffieri S., Fossa P., Bordin F. Activity of 3-carbethoxyangelicin photolisis products. // J. Photochem. Photobiol., B: Biology. 1997. — Vol. 38, N 2−3. — P. 189−195.

20. Carlassare F., Baccichetti F., Guiotto A., Rodighiero P., Gia O., Capozzi A., Pastorini G. and Bordin F. Synthesis and photobiological properties of acetylpsoralen derivatives. // J. Photochem. Photobiol., B: Biology. 1990. -Vol. 5, N 1. — P. 25−39.

21. Aneja R., Mukerjee S.K. and Seshadri T.R. A study of the origin and modification of the Cs unit in plant products: new synthesis of angelicin and psoralen. // Tetrahedron. 1958. — Vol. 4, N 3. — P. 256−270.

22. Raizada K.S., Sarin P. S. and Seshadri T.R. New synthesis of benzofuran derivatives: synthesis of karanjin, angelicin, some furanoisoflavones and dihydrodimethoxyelliptone. // J. Sci. Indian Research. 1960. — Vol. 19B. — P. 76−77.

23. Seshadri T.R. and Sood M.S. Synthesis of sphondin. // J. Indian Chem. Soc. -1962. Vol. 39, N 8. — P. 539−544.

24. Ahluwalia V.K. and Mehta S. Synthesis of 4-methoxy and 4,5-dimethoxy-3-phenyl coumarins. // Indian J. Chem., Sect. B. 1977. — Vol. 15, N 12. — P. 1097−1099.

25. Ahluwalia V.K., Prakash C. and Rani N. Synthesis of furocoumarins, heratomol and heratomin. // Indian J. Chem., Sect. B. 1977. — Vol. 15, N 12. — P. 11 371 138.

26. Ahluwalia V.K., Gupta M.C. Synthesis of 3-phenylangelicin-bergapten, allobergapten and isobergapten. // Indian J. Chem., Sect. B. 1977. — Vol. 15, N 12.-P. 1094−1096.

27. Ahluwalia V.K., Khanduri C.H. and Sharma N.D. Synthesis of 3,4-dimethylpsoralen, angelicin and their derivatives. // Indian J. Chem., Sect. B. -1988. Vol. 27, N 8. — P. 748−751.

28. Ahluwalia V.K. and Tripathi R.P. A facile synthesis of 4-propylpsoralene and angelicin derivatives. // J. Indian Chem. Soc. 1984. — Vol. 61, N 12. — P. 10 231 027.

29. Souza N.J., Nayak P.V. and Secco E. Synthetic furocoumarins. Xanthotoxin and methylxanthotoxin. // J. Heterocycl. Chem. 1966. — Vol. 3, N 1. — P. 42−45.

30. Kaufman K.D., Erb D.J., Blok T.M., Carlson R.W., Knoechel D. Reactions of furocoumarins II (1). Synthetic aminomethyl psoralens via chloromethylation or benzylic bromination. // J. Heterocycl. Chem. 1982. — Vol. 19, N 5. — P. 10 511 056.

31. Pardanani N.H. and Trivedi K.N. Studies in the synthesis of furocoumarins. // Aust. J. Chem. 1972. — Vol. 25, N 7. — P. 1537−1542.

32. Ahluwalia V.K., Prakash C. and Singh R.P. A convenient synthesis of psoralen derivatives oxygenated in the pyrone ring: 4-methoxypsoralen and 3,4-dimethoxypsoralen (halkendin). // Aust. J. Chem. 1979. — Vol. 32, N 6. — P. 1361−1367.

33. Desai S.M. and Trivedi K.N. Studies in the synthesis of fiirocoumarins. Part XXVII. Synthesis of 5'-methyl-3,4-diphenylpsoralen and angelicin. // Indian J. Chem., Sect. B. 1985. — Vol. 24, N 1. — P. 47−50.

34. Seshadri T.R. and Soods. A convenient synthesis of isobergapten. // Indian J. Chem. 1965. — Vol. 3, N 8. — P. 354.

35. Black ML, Cadogan J.I.G., McNab H., MacPherson A.D., Roddam V.P., Smith C. and Swenson H.R. Synthesis of fused furans by gas-phase pyrolysis of 2-allyloxyarylpropenic esters. // J. Chem. Soc., Perkin. Trans. 1. 1997. -N 17. -P. 2483−2493.

36. Shaikh Y.A. and Trivedi K.N. Studies in synthesis of coumarino-a-pyrones and furocoumarins. Part XVII. Synthesis of psoralen derivatives. // J. Indian Chem. Soc. 1974. — Vol. 51, N 8. — P. 755−756.

37. Pardanani N.H., Trivedi K.N. Synthesis of furocoumarins: Part VIII. Synthesis of alkylpsoralens. // J. Indian Chem. Soc. 1971. — Vol. 48, N 4. — P. 339−343.

38. Singh K., Banerjee S.K. and Atal C.K. Synthesis of some difuranocoumarins. // Indian J. Chem., Sect. B. 1981. — Vol. 20, N 2. — P. 108−110.

39. Shah R.R. and Trivedi K.N. Studies on the synthesis of furocoumarins. // J. Indian Chem. Soc. 1981. — Vol. 58, N 3. — P. 302−305.

40. Rabindra M.C. and Kalyanmays K. Angular furocoumarins. I. Synthesis of 2', 3'-dihydro-2'-methylfuro54':7,8.coumarin derivatives. // J. Indian Chem. Soc. 1967. — Vol. 44, N 2. — P. 140−144.

41. Prashant A., Krupadanam G.L.D. and Srimannarayana G. DDQ oxidation of 6-ore 8-allyl-7-hydroxycoumarins. A new synthesis of benzodieyrandions and furobenzopyranones. // Bull. Chem. Soc. Japan. 1992. — Vol. 65, N 4. — P. 1191−1193.

42. Trivedi K.N., Chandratre S.P. Studies in synthesis of furocoumarins. XXVIII. Synthesis difuranocoumarins. // Indian J. Chem., Sect. B. 1987. — Vol. 26, N 12.-P. 1148−1150.

43. Kumar R.J., Krupadanam G.L.D. and Srimannarayana G. Facile synthesis of linear and angular a-methylfurocoumarins. // Indian J. Chem., Sect. B. 1987. -Vol. 26, N 11. — P. 1078−1079.

44. Rao C.P., Krupadanam G.L.D. and Srimannarayana G. Claisen rearrangement of 7-propargyloxycoumarins: formation of pyrano and furanocoumarins. // Indian J. Chem., Sect. B. 1991. — Vol. 30, N 7. — P. 666−671.

45. Bender D.R., Hearst J.I. and Rapoport H. Psoralen synthesis: improvements in furano ring formation, application to the synthesis of 4,5', 8-trimethyl psoralen. // J. Org. Chem. 1979. — Vol. 44, N 13. — P. 2176−2180.

46. Kaufman K.D. Synthetic furocoumarins. I. A new synthesis of methylsubstituted psoralens and isopsoralens. // J. Org. Chem. 1961. — Vol. 26, N 1. — P. 117 121.

47. Kaufman K.D., Russey W.E., Worden L.R. Synthetic furocoumarins. V. Preparation and reactions of 8-amino-4,5'-dimethyl psoralen. // J. Org. Chem. -1962. -Vol. 27, N 1, — P. 875−879.

48. Caffieri S., Moor A., van Henegouwen G.B.B., Dall’Acqua F., Guiotto A., Chilin A., Rodighiero P. Difurocoumarins, psoralen analogs: synthesis and DNA photobinding. // Z. Naturforsch. 1995. — Vol. 50b. — P. 1257−1264.

49. Mali R.S., Pandhare N.A. and Sindkhedkar M.D. Convenient two-step synthesis of seselin and angelicin derivatives. // Tetrahedron Lett. 1995. — Vol. 36, N 39. -P. 7109−7110.

50. Soman S.S. and Trivedi K.N. Synthesis of linear and angular fiirocoumarins using intramolecular Wittig reaction. Part XXXI. // Indian J. Chem., Sect. B. -1992. Vol. 31, N 8. — P. 532−534.

51. Lee Y.R. A concise new synthesis of angular fiirocoumarins: angelicin, oroselone and oroselol. // Tetrahedron. 1995. — Vol. 51, N 11. — P. 3087−3094.

52. MacLeod J.K., Worth B.R. Synthesis of benzofuranoid systems. I. Furocoumarins, benzofurans and dibenzofurans. // Tetrahedron Lett. 1972. — N 3. — P. 237−240.

53. Antonello C., Magno S.M., Gia O., Baessato O. 3-Amino and 3-oxyderivatives of psoralen: preparation and interactions with DNA. // Farmaco, Ed. Sc. 1981. -Vol. 36, N7.-P. 565−584.

54. Gia O., Anselemo A., Conconi M.T., Antonello C., Uriarte E., CafFieri S. 4'-Methyl derivatives of 5-MOP and 5-MOA: synthesis, photoreactivity and photobiological activity. // J. Med. Chem. 1996. — Vol. 39, N 22. — P. 44 894 496.

55. Gia O., Uriarte E., Zagotto G., Baccichetti F., Antonello C. and Magno S.M. Synthesis and photobiological activity of new methylpsoralen derivatives. // J. Photochem. Photobiol., B: Biology. 1992. — Vol. 14, N 1. — P. 95−104.

56. MacLeod J.K., Worth B.R., Wells R.T. Synthesis of benzofuranoid systems V. Alternative totals synthesis of cyperaquinone. // Aust. J. Chem. 1978. — Vol. 31, N 7. — P. 1545−1552.

57. MacLeod J.K., Worth B.R., Wells R.T. Synthesis of benzofuranoid systems IV. Total synthesis of cyperaquinone and conicaquinone. // Aust. J. Chem. 1978. -Vol. 31, N7. — P. 1533−1544.

58. Abu-Shady H.A., Safwat H.M., Abdel Zaher Y.A. Synthesis of some 9-allyl-5-methyl-7H-furo3,2-g. l]benzopyran-7-one derivatives of potential photodynamic activity. // Egypt. J. Pharm. Sci. 1983. — Vol. 24, N 1−4. — P. 7580.

59. Abu-Shady H.A., Sonia H.T., Amin K.M., Farag A.E. Synthesis of some methylpsoralen of potential photosensitizing activity. // Egypt. J. Pharm. Sci. -1990. Vol. 31, N 1−4. — P. 453−461.

60. Rajitha B., Geetanjali Y., Rao M.K., Somayajulu V.V. and Atal C.K. Antifertility agents synthesis and activity. // Proc. Indian Acad. Sci., Ser.: Chem. Sci. — 1981. — Vol. 90, N 4. — P. 291−296.

61. Rajitha B., Geetanjali Y., Rao M.K., Somayajulu V.V. Synthesis and antiimplantation study of furanobenzopyrones. // Indian J. Pharm. Sci. 1985. -Vol. 47, N6.-P. 222−224.

62. Ray J.N., Silooja S.S. and Vaid R.V. Experiments on the synthesis of bergapten and its derivatives. Part I. Furocoumarins. // J. Chem. Soc. 1935. — P. 813−816.

63. Antonello C., Zagotto G., Mobilo S., Marzano C., Gia O., Uriarte E. Synthesis and characterization of new methylpsoralens as potential photochemotherapeutic agents. // Farmaco. 1994. — Vol. 49, N 4. — P. 277−80.

64. Rao M.K., Pillai K.K., Rajagopal S. Furano compounds. XXIV. Synthesis of linear diphenyl furanocoumarins. // Proc. Indian Acad. Sci., Sect. A. 1976. -Vol. 84, N5.-P. 210−213.

65. Rao B.V., Somayajulu V.V., Atal C.K. and Chandhoke N. Synthesis of 2,6-diphenyl-3-(p-substituted phenyl)-5-methyl-7-oxo-7H-furo3,2-g. l]benzopy-rans. // Indian J. Chem., Sect. B. 1980. — Vol. 19, N 3. — P. 220−221.

66. Rao B.V., Somayajulu V.V. and Harish C. Synthesis of 2,3-diphenyl-6-(p-substituted phenyl)-5H/methyl-7(H)-oxofuro3,2-g. l]benzopyrans as possible antifertility agents. // Indian J. Chem., Sect. B. 1980. — Vol. 19, N 3. — P. 232 234.

67. Gia O., Anselemo A., Pozzan A., Antonello C., Marciani M.S., Uriarte E. Some new methyl-8-methoxypsoralens: synthesis, photobinding to DNA, photobiological properties and molecular modeling. // Farmaco. Vol. 52, N 6−7.-P. 389−397.

68. Singh R. and Malik O.P. A facile synthesis of alkyl substituted angular benzofurocoumarins. // Indian J. Chem., Sect. B. 1992. — Vol. 31, N 8. — P. 529−531.

69. Пат. 7 245 350 Япония, CI C07d A61k. 4-Hydroxyfuro2,3-h.-coumarins. C. A. Vol. 78, 72095t.

70. Kawase Y., Yamaguchi S., Aoyama K. and Matsuda M. The Fries rearrangement of benzoyloxybenzofuran derivatives and the synthesis of the furo derivatives of 4-phenyl-2H-chromen-2-one. // Bull. Chem. Soc. Japan. -1978. Vol. 51, N 6. — P. 1907;1908.

71. Rao M.K., Rajagopal S. Furano compounds. XXIII. Synthesis of phenyl substituted furanobenzopyrones. // Proc. Indian Acad. Sci., Sect. A. 1975. -Vol. 81, N 1. — P. 38−41.

72. Spath E. and Pailer M. Uber eine neue synthese des angelicins (aus angelica archangelica). // Ber. 1934. — Bd. 67, N 2. — S. 1212−1213.

73. Dall’Acqua F., Vedaldi D., Bordin F., Baccichetti F., Carlassare F., Tamaro M., Rodighiero P., Pastorini G., Guiotto A., Reccia G. and Cristofolini M. 4'.

74. Methylangelicins: new potential agents for the photochemotherapy of psoriasis. // J. Med. Chem. 1983. — Vol. 26, N 6. — P. 870−876.

75. Kubaj Z. Structure and properties of 4,4'-dimethylangelicin derivatives I. // Roczn. Chem. 1968. — Vol. 42, N 7. — P. 675−684.

76. Zawadowski T., Mazur J. Synthesis of 4,4'-dimethylsphondin. // Acta Pol. Pharm. 1980. — Vol. 37, N 3. — P. 289−291.

77. Mehta R.H. Synthesis of some new furocoumarins. // Indian J. Chem. 1965. -Vol. 3, N 12. -P. 574−575.

78. Shah D.N. and Shah N.M. Furocoumarins and coumarino-a-and-y-pyrones. // J. Org. Chem. 1954. — Vol. 19, N 12. — P. 1938;1943.

79. Limaye D.V., Munje R.H., Shenolicar G.S. and Talwalkar S.S. Synthesis in the flirocoumarin group. Various angular and linear furocoumarins VI. // Rasayanam.- 1939.-Vol. 1, N1.-P. 187−189.

80. Jesthi P.K. and Rout M.K. Synthesis of furocoumarins. // J. Indian Chem. Soc. -1970.-Vol. 47, N 12.-P. 1211−1212.

81. Kum N.H., Pardanani M.G., Parekh and Trivedi K.N. Studies in synthesis of coumarino-a-pyrones and furocoumarins. Part IV. Synthesis of alkylpsoralens. //J. Indian Chem. Soc. 1969. Vol. 46, N 11.-P. 1014−1018.

82. Amin K.M. and Michael A.N. New derivatives of furocoumarins as potential photochemotherapeutic agents. // Egypt. J. Pharm. Sci. 1987. — Vol. 28, N 1−4. — P.425−435.

83. Pardanani N.H., Trivedi K.N., Kunjbihari N. Synthesis of coumarino-a-pyrones and furocoumarins. VI. Synthesis of alkylpsoralens. // J. Inst. Chem. Calcutta. -1970. Vol. 42, N 4. — P. 153−157.

84. Howell W.N. and Robertson A. Furanocompounds. Part I. A synthesis of bergapten. // J. Chem. Soc. 1937. — N 1. P. 293−294.

85. Antonello C. Sintesi di metilxantotoxine. // Gazz. Chim. Ital. 1958. — Vol. 88, N4.-P. 415−429.

86. Rodighiero G. and Antonello C. Nuova sintesi della xantotoxina. // Ann. Chim. (Roma). 1956. — Vol. 46, N 11. — P. 960−967.

87. Naik R.M. and Thakor V.M. Synthetic experiments in furocoumarin series. // J. Org. Chem. 1957. — Vol. 22, N 12. — P. 1696−1697.

88. Antonello C. Sintesi della 4-metilangelicina. // Gazz. Chim. Ital. 1958. — Vol. 88, N4.-P. 430−433.

89. Kawase Y., Nakayama M., Tamatsukuri H. Synthetic studies on the benzofiiran derivatives. VII. A new synthesis of angelicin and 4-methylangelicin. // Bull. Chem. Soc. Japan. 1962,-Vol. 35, N l.-P. 149−151.

90. Salvi V.S. and Sethna S. Studies in furan derivatives. // J. Indian Chem. Soc. -1968. Vol. 45, N 5. — P. 439−445.

91. Zawadowski T. and Checinski M. Synthesis of new derivatives of angelicin of expected pharmacological activity. // Roczn. Chem. 1977. — Vol. 51, N 7−8. -P.1511−1514.

92. Gia O., Baccichetti F., Pastorini G., Rodighiero P., Palumbo M. Photobiological and DNA binding properties of 4,8-dimethyl-5'-carboxypsoralen amides. // Med., Biol., Environ. 1986.-Vol. 14, N l.-P. 115−119.

93. Kobertz W.R. and Essigmann J.M. Total synthesis of cis-syn-2-carbomethoxypsoralen furan-side thymidine monoadduct. // J. Am. Chem. Soc. 1996. Vol. 118, N 30. — P. 7101−7107.

94. Kobertz W.R. and Essigmann J.M. An efficient synthesis of furan-side furocoumarin thymidine monoadduct. // J. Org. Chem. 1997. Vol. 62, N 8. — P. 2630−2632.

95. Zubia E., Luis F.R., Massanet G., Collado I. An efficient synthesis of furocoumarins. // Tetrahedron. 1992. — Vol. 48, N 20. — P. 4239−4246.

96. Bhayani R.J. and Thakor V.M. Furocoumarin studies. Part I. New synthesis of 4-methylangelicin and angelicin. // J. Indian Chem. Soc. 1990. — Vol. 67, N 1. -P. 71−72.

97. Dholakia V.N. and Trived K.N. Studies in the synthesis of coumarino-a-pyrones and furocoumarins: Part X. Synthesis 3-phenyl-4-oxo-4H-furo 2,3-е. benzopyrones. // J. Indian Chem. Soc. 1971. — Vol. 48, N 4. — P. 348−350.

98. Patell J. and Usgaonkar R.N. 3,4-Coumarin-pyrones: Part IV. Bromination of coumarino-(3', 4', 5,6)-4-methyl-a-pyrones and synthesis of coumarino-(3', 4', 4,5)-3-methyl-furans. // J. Indian Chem. Soc. 1967. — Vol. 44, N 9. — P. 747−751.

99. Несмеянов A.H., Вомпе А. Ф., Заревич Т. С., Смолин Д. Д. Из области синтеза в ряду производных 7-окси-кумарина. // Ж.О.Х. 1937. Т. 7, Вып. 22.-С. 2767−2771.

100. Malhotra U. and Joshi S.S. Some furocoumarins. // J. Indian Chem. Soc. 1967. -Vol. 44, N l.-P. 80−81.

101. Mazur J., Grabowska M., Zawadowski Т., Balicka E. Synthesis of aminoalkahol derivatives of 8-acetyl-4,9-dimethyl-6-hydroxy-2H-furo2,3-h. [ 1 ]benzopyran-2-one. // Acta Pol. Pharm. 1989. — Vol. 46, N 1. — P. 1−4.1. C. A.-Vol. 112, 21 6626n.

102. Geetanjali Y., Rajitha B. and Rao M.K. Synthesis of 2-aroyl-3-phenylfuranobenzopyrones. // Indian J. Chem., Sect. B. 1983. — Vol. 22, N 2. -P. 164−165.

103. Geetanjali Y., Rajitha B. and Rao M.K. Linear furanocompounds: synthesis of 7H-fiiro3,2-g. l]benzopyran-7-ones. // Bull. Chem. Soc. Japan. 1986. — Vol. 59, N4.-P. 1299−1301.

104. Rao P. S., Reddy K.V., Ashok D. A facile synthesis of 2-benzoyl-3-methyl-6-phenyl-5-(substituted styryl)-7H-furo-3,3-g. l]benzopyran-7-ones and their antifeedant activity. // Synth. Commun. 1997. — Vol. 27, N 18. — P. 31 813 189.

105. Valenti P., Montanari P. and Da Re P. Studies on the angelicin group. Synthesis of some coronary dilators. // Atti Accad. Sci. 1st. Bologna, CI. Sci. Fis. 1978. -Vol. 5, N2.-P. 189−193.1. C. A. -Vol. 92,22410k.

106. Valenti P., Montanari P. and Da Re P. Studies on the angelicin group. Synthesis of some possible (3-blocking antiadrenergic agents. // Atti Accad. Sci. 1st. Bologna, CI. Sci. Fis. 1978. — Vol. 5, N 2. — P. 195−198.1. C. A.-Vol. 92, 22411m.

107. Worden L.R., Kaufman K.D., Weis J.A., Schaaf T.K. A new synthetic route to psoralen. //J. Org. Chem. 1969. — Vol. 34, N 8. — P. 2311−2313.

108. Norre P. and Honkanen E. A new synthesis of methoxalen. // J. Heterocycl. Chem. 1980. — Vol. 17, N 5. — P. 985−987.

109. Pecori V.L., Auzzi G., Papini P., Bruni F. Synthesis of 4,9-dimethoxy-5-metyl-7H-furo3,2-g.-l-benzopyran-7-one-6-carboxylic acid derivatives. // Farmaco, Ed. Sci. 1975. Vol. 30, N 9. — P. 754−760.1. C. A. Vol. 84, 43896y.

110. Magno S.M., Rodighiero P., Gia O., Bordin F., Baccichetti F. and Guiotto A. Carbomethoxyderivatives of psoralens: interaction with DNA and photobiological properties. // Farmaco, Ed. Sci. 1981. — Vol. 36, N 7. — P. 629 647.

111. Пат. 2 837 295 США, CI. C07D493/04. Monofimctional psoralen derivatives. C. A. Vol. 91, P20481q.

112. Пат. CH 638 978 Швейцария, CI. A61k31/35. Monofimctional psoralen derivatives for treating skin disorder.1. C. A.-Vol. 100, P26040w.

113. Hishmat O.H., Abdel-Rahman A.H., Khalil K.M.A., Moawad M.I., Atalla M.M. Synthesis of some benzofuran and fiirocoumarin derivatives for possible biological activity. // J. Pharm. Sci. 1982. Vol. 71, N 9. — P. 1046−1049.

114. Hishmat O.H., Abdel Rahman A., Abdel Rahman H. Reactions of substituted hydroxy benzofurans. III. Acylation of 5- and 6-methoxy-2,3-diphenylbenzofurans. // Aust. J. Chem. 1974. — Vol. 27, N 11. — P. 2499−2503.

115. Queval P., Bisagni E. New synthesis of psoralen and related compounds. // Eur. J. Med. Chem. Chim. Ther. — 1974. — Vol. 9, N 3. — P. 335−340.

116. Пат. 0482 Европа, CI. C07D493/04. 8-Methoxypsoralen and intermediate products in its synthesis.1. C. A.-Vol. 91, P211253b.

117. Yu-Ying Liu, Thorn E. and Liebman A.A. Coumarins via Wittig reaction. Synthesis of methoxalen-5−14C. // J. Heterocycl. Chem. 1979. — Vol. 16, N 4. -P. 799−801.

118. Hishmat O.H., Zohair M.M.Y. and Miky J.A.A. A new approach for the synthesis of some pyridine and pyridone derivatives. // Z. Naturforsch. 1983. -Vol. 38b.-P. 1690−1694.

119. Пат. 4 107 182 США, CI. C07D493/04. 7-Oxo-9-methoxy-7H-foro3,2-g. [ 1 ]benzopyran-6-carboxylic acid.1. С. А. Vol. 90, Р72 165р.

120. Rene L., Buisson J.P., Royer R., Averbeck D. Difiirobenzene and fiirochromone analogs of angelicin and other angular furocoumarins. // Eur. J. Med. Chem. -Chim. Ther. 1978. — Vol. 13, N 5. — P. 435−439.

121. Bastian G., Rene L., Averbeck S. Study on nitro derivatives of biological interest. XXIV. Synthesis and photobiological study of nitrofurocoumarins. // Eur. J. Med. Chem. Chim. Ther. — 1981. — Vol. 16, N 6. — P. 563−568.

122. Duffley R.P. and Stevenson R. Synthesis of oroselol. // Synth. Commun. 1978. — Vol. 8, N 3. — P. 175−180.

123. Schreiber F.G. and Stevenson R. Synthesis of the angular furocoumarin oroselone and the linear analogue 2'-isopropenylpsoralen. // J. Chem. Research. (S). 1978.-N3.-P. 92.

124. Isaacs S.T., Shen C.K.J., Hearst J.E. and Rapoport H. Synthesis and characterization of new psoralen derivatives with superior photoreactivity with DNA and RNA. // Biochemistry. 1977. — Vol. 16, N 6. — P. 1058−1064.

125. Пат. 2 746 942 США, CI. C07D407/10. Psoralen derivatives. C. A. Vol. 89, 24284j.

126. Пат. 4 124 589 США, CI. 260−343.21- C07D493/04. Psoralens. C. A. Vol. 90, 12 1567g.

127. Пат. 3 033 896 США, CI. C07D407/10. 4'-Substituted-4,5', 8-tri-lower alkylpsoralens.1. C. A. Vol. 95, P43079m.

128. Пат. 3 033 897 США, CI. C07D407/10. 5'-Primary amino lower alkyl -4,4'-di-lower alkyl psoralens.1. C. A. Vol. 95, P25038t.

129. Bender D.R., Kanne D., Frazier J.D. and Rapoport H. Synthesis and derivitization of 8-acetylpsoralens. Acetyl migrations during Claisen rearrangement. // J. Org. Chem. 1983. — Vol. 48, N 16. P. 2709−2719.

130. Shaikh Y.A., Trivedi K.N. Synthesis of coumarino-a-pyrones and furocoumarins. XVI. Synthesis of 4-hydroxy-4', 8-dimethylpsoralen derivatives. // J. Indian Chem. Soc. 1972. — Vol. 49, N 9. — P. 877−881.

131. Hishmat O.H., Soliman F.M., Klialil Kli.M.A. Synthesis of substituted linear furo3,2-g.benzopyrones. // Indian J. Chem. 1975. — Vol. 13, N 5. — P. 479 481.

132. Bhanu S., Saroja Т., Seshadri T.R., Mukerjee S.K. New synthesis of halkendin and isohalkendin. // Indian J. Chem. 1972. — Vol. 10, N 1. -P. 16−18.

133. Kawase Y., Nanbu M., Yanagihara H. The synthesis of 4-hydroxyfuro2', 3':7,8.coumarins and 5H-benzofuro[3,2-c]furo[2,3-h][ 1 ]benzopyran-5-one. // Bull. Chem. Soc. Japan. 1968. — Vol. 41, N 5. — P. 1201−1208.

134. Kawase Y., Nanbu M., Miyoshi F., Kawamura H. The syntheses of dimethylfuro derivatives of 4-hydroxycoumarins and benzofurol.benzopyranones. // Bull. Chem. Soc. Japan. 1968. — Vol. 41, N 11. — P. 2683−2689.

135. Пат. 7 245 349 Япония, CI. C07DA61k. 4-Hydroxyfuro-2,3-h.-coumarins. C. A. Vol. 78, 58 387.

136. Bhanu S., Seshadri T.R. and Mukerjee S.K. Ring isomeric change in furanocoumarins: synthesis of angular isomers of bergapten and halfordin. // Indian J. Chem.- 1975.-Vol. 13, N1.-P. 15−17.

137. Pardanani N.H., Shaikh Y.A., Trivedi K.N. Synthesis of coumarino-a-pyrones and furocoumarins. XIX. Synthesis of 4-hydroxy-3-phenyl-5'8-dimethylpsoralens. // J. Indian Chem. Soc. 1975. — Vol. 52, N 1. — P. 45−46.

138. Ahluwalia V.K., Prakash C. New synthesis of isohalkendin and study of 3,4-dioxygenated coumarins. // Indian J. Chem. 1975. — Vol. 13, N 8. — P. 791 794.

139. Ahluwalia V.K., Prakash C., Singh R.P. Removal of 4-hydroxyl group in 4-hydroxy-3-methoxycoumarins: synthesis of 3-methoxyangelicin and partial methyl ethers of 3-methoxycoumarins. // Indian J. Chem., Sect. B. 1978. -Vol. 16, N7.-P. 587−590.

140. Madhavarao S.S. and Trivedi K. N. Studies in the synthesis of furocoumarins. Part 29: Synthesis of aminomethyl psoralen and angelicin derivatives as potential photochemotherapeutic agents. // Pharmazie. 1991. — Vol. 46, N 9. -P. 644−646.

141. Пат. 4 328 239 США, CI. 424−279- C07D493/04. 8-Aminoalkylpsoralens. C. A.-Vol. 97, P109985d.

142. Пат. 4 169 204 США, CI. 546−270- C07D403/14. Psoralens. C. A. Vol. 92, P94372x.

143. Пат. 4 294 822 США, CI. 429−59- C07D493/02. 5'-Aminoalkyl-4,4', 8-trialkylpsoralens.1. C. A. Vol. 96, P35224k.

144. Пат. 4 370 344 США, CI. 424−279- C07D493/04. 5'-Aminoalkyl-4'-alkylpsoralens.1. C. A.-Vol. 98, P198189h.

145. Isaac W. Photochemotherapy: a new promising chemical derivative. // Arch. Dermatol. Res. 1982. — Vol. 272, N 3−4. — P. 251−256.

146. Heindel N.D., Choundhuri M., Ressner J. and Foster N. Aminomethyl psoralens. Electrophilic substitution of hydroxymethylphthalimide on linear furocoumarins. // J. Heterocycl. Chem. -1985. Vol. 22, N 1. — P. 73−76.

147. Пат. 4 950 770 США, CI. 549−282- C07D493/04. Aminomethylation of psoralens by hydroxymethylamides.1. C. A.-Vol. 114, P45576v.

148. Schneiders G.E. and Stevenson R. Synthesis of the natural furanocoumarin prangosine. //J. Chem. Research (S). 1982. — Vol. 3. — P. 182.

149. Mazur J., Grabowska M., Zawadowski T. Synthesis of novel sfondine (angular furocoumarin) derivatives. // Acta Pol. Pharm. 1994. — Vol. 51, N 4−5. — P. 343−345.

150. Mazur J., Zawadowski T., Kawiak J., Miks B. Synthesis of novel 4,4'-dimethylsfondine derivatives with potential photochemotherapeutic and antileukemic activity. // Acta Pol. Pharm. 1994. — Vol. 51, N 6. — P. 475−477.

151. Mazur J., Zawadowski T. Synthesis of novel sfondine (angular furocoumarin) derivatives. // Acta Pol. Pharm. 1997. — Vol. 54, N 5. — P. 371−374.

152. Mazur J., Grabowska M., Zawadowski T. Synthesis of the aminoalkahol derivatives of 6-hydroxy-4,9-dimethyl-2H-furo2,3-h. l]benzopyran-2-one. // Acta Pol. Pharm. 1987. — Vol. 44, N 2. — P. 155−158.

153. Kubaj Z. The structure and properties of some 4,4'-dimethylangelicin derivatives. // Roczn. Chem. 1968. — Vol. 42, N 6. — P. 1029−1037.

154. Valenti P., Montanari P., Scapini G., Guisti P. and Cima L. Local anesthetic activity of some N-disubstituted 4,5'-dimethylangelicin glycinamides. // Arch. Pharm. 1980. — Vol. 313, N 5. — P. 449−453.

155. Mosti L., Schenone P., Menozzi G., Carlassare F., Baccichetti F. and Bordin F. Synthesis and photobiological activity of new N, N-disubstituted 4-amino-3-cloroangelicin. // Farmaco, Ed. Sci. 1988. — Vol. 43, N 10. — P. 775−792.

156. Блинов JI.M. Физические свойства и применение Лэнгмюровских монои мультимолекулярных структур. // Успехи химии. 1983. — Т. 52, Вып.8. -С. 1263−1300.

157. Блинов JI.M. Лэнгмюровские пленки // Успехи физических наук. 1988. -Т. 155, Вып. З.-С. 443−480.

158. Gnanaguru К., Ramasubbu N., Venkatesan К. and Ramamurthy V. A study on the photochemical dimerization of coumarins in the solid state. // J.Org. Chem. -1985. Vol. 50, N 13. — P. 2337−2346.

159. Besson Т., Coudert G. and Guillaumet G. Synthesis and fluorescent properties of some heterobifunctional and rigidized 7-aminocoumarin. // J. Heterocycl. Chem. 1991. — Vol. 28, N 6. — P. 1517−1524.

160. Bojilova A., Ivanov C. Two new routes to esters of 2-oxochroman-4-acetic acid. // Synthesis. 1976. — N 4. — P. 267−268.

161. Bojilova A., Kostadinova T. and Ivanov C. Interaction of nitromethane with esters and amides of 2-oxo-2H-l-benzopyrane-3-carboxylic acid. // Synth. Commun. 1989. — Vol. 19, N 17. — P. 2963−2975.

162. El-Farargy A.F., Soliman A.Y., El-Mobayed M. and El-Esser S. Synthesis and studies of 3-N-arylcarbamidocoumarins. // Rev. Roumaine Chim. 1987. — Vol. 32, N4.-P. 435−441.

163. Darbarwar M., Sundaramurthy V. Synthesis of coumarins with 3:4-fiised ring systems and their physiological activity. Reviews. // Synthesis. 1982. — N 5. -P. 337−388.

164. Wawzonek S. and Morreal C.E. The action of alkali on 3,4-phenacylidene-3-acetylcoumarin. //J. Am. Chem. Soc. 1960. Vol. 82, N 1. — P. 439−441.

165. Risinger G.E. and Timm G.E. On the mechanism of the Widman reaction. // Chem. Ind. (London). 1967. — N 2. — P. 158−159.

166. Fall Y., Santana L., Teijeira M. and Uriarte E. A convenient synthesis of benzofuran-3-acetic acids. / Heterocycles. 1995. — Vol. 41, N 4. — P. 647−650.

167. Дуленко В. И., Голяк B.M., Губарь В. И., Алексеев Н. Н. Новый метод синтеза бензофуран-3-уксусных кислот. // ХГС. 1979. — N 7. — С. 992.

168. Wade R.C. Catalyzed reduction of organofunctional groups with sodium borohydride. (Review). // J. Mol. Catal. 1983. — Vol. 18, N 2. P. 273−297.

169. March J. Advanced organic chemistry: reactions, mechanisms, and structure. 4th. ed. Wiley Interscience. New York. 1992. — P. 918−919, 1218−1220.

170. Rylander. Catalytic hydrogenation over platinum metals. Academic Press. New York.- 1967.-P. 123−138.

171. Boulton A.J., Epsztajn J., Katritzky A.R., Pai-Lin Nie. Allylic and benzylic deamination by thermal cleavage of 1-substituted l, 2-dyhydro-2,4,6-triphenylpyridines. // Tetrahedron Lett. 1976. — N 31. — P. 2689−2690.

172. Chatterjea J.N. and Singh K.R.R.P. Furano compounds: part IL solvolytic rearrangement of ketoximes in benzofliran series and PMR study of benzofuryl-2-alkyl (aryl) ketoximes. // J. Indian Chem., Sect. B. — 1981. — Vol. 20, N 12. -P. 1053−1056.

173. Сибирцев B.C., Гарабаджиу А. В., Иванов С. Д. Спектральные свойства красителей бисбензимидазольного ряда при взаимодействии с ДНК. // Биоорган, химия. 1997. — Т. 23, N 12. — С. 969−978.

174. Arima V.J. Ueber die konstitution des nodakenins, eines neuen glucosids von peucedanum decursivum maxim. // Bull. Chem. Soc. Japan. 1929. — Vol.4, N l.-P. 113−119.

175. Woods L.L. and Sapp J. A new one-step synthesis of substituted coumarins. // J. Org. Chem. 1962. — Vol. 27, N 20. — P. 3703−3705.

176. Chakravarti D. Synthesis of coumarins from phenols andketonic esters using phosphorus pentoxide. Part I. Coumarins from resorcinol and ethyl acetoacetates. // J. Indian Chem. Soc. 1931. — Vol. 8. — P. 129−136.

177. Зайцев И. А., Шестаева M.M., Загоревский В. А. Синтез некоторых 3-замещенных 4-метил-7-оксикумаринов. // ХГС. 1970. — N 2. — С. 150−154.

178. Buu-Hoi NG. Ph., Ekert В., Royer R. Bz-hydroxylated-3-aiyland 3,4-diaryl-coumarins. // J. Org. Chem. 1954. — Vol. 19, N 9. — P. 1548−1552.

179. Шамшурин А. А., Ревенко Ю. М. Синтез у-замещенных резорцинов. I. Синтез производных 2,6-дигидроксиацетофенона и пропиофенона, включая некоторые амины. // Изв. Акад. Наук Молд. ССР. Серия биол. и хим. наук. 1962. — Т. 10, N 1. — С. 86−97.

180. Shah D.N. and Shah N.M. The Fries isomerization of acetyl and benzoyl esters of umbelliferones. //J. Org. Chem. 1954. — Vol. 19, N 10. — P. 1681−1685.

181. Thakar K.A. and Bhawal B.M. Synthesis of isoxazolo (7,6-d)coumarins and izoxazolo (7,8-d)coumarins. // Curr. Sci. 1977. — Vol. 46, N 23. — P. 810−812.

182. Nes W.R. and Steele J.A. Influence of a 9 (11) double bond on the course and mechanism of alkyl-oxygen cleavage reactions of unsaturated steroids. // J. Org. Chem. 1957.-Vol. 22, N 11.-P. 1457−1465.

183. O’Connor G.L. and Nace H.R. Further studies on the Chugaev reaction and related reactions. //J. Am. Chem. Soc. 1953. — Vol. 75, N 9. — P. 2118−2122.

184. Massarani E., Nardi D., Barzaghi F., Bonacina F. a-Pyrones with coronary dilating activity. IV. // Farmaco, Ed. Sci. 1963. — Vol. 18, N 4. — P. 254−267.

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