Skip to main content
Log in

Indole and Isatin Oximes: Synthesis, Reactions, and Biological Activity. (Review)

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Data on methods for the production of isatin and indole aldoximes, ketoximes, and amidoximes and their reactions are reviewed. Individual syntheses of new heterocycles from indole and isatin oximes are discussed. The principal results from investigation of the biological activity of derivatives of the oximes are also presented.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

REFERENCES

  1. E. H. Gordeev, V. N. Buyanov, and V. E. Zhigachev, Khim. Geterotsikl. Soedin., 46 (1992).

  2. F. M. Albini,R. Oberti, and P. Caramella, J. Chem. Res. Synop., 4 (1983).

  3. Y. Ergun,N. Bayraktar,S. Patir, and G. Okay, J. Heterocycl. Chem., 37, 11 (2000).

    Google Scholar 

  4. P. Nantka-Namirski and Z. Ozdowska, Pol. Pat. 65813; Chem. Abstr., 78, 136068 (1973).

    Google Scholar 

  5. A. Ahmad,I. Eelnurme, and I. D. Spencer, Can. J. Chem., 38, 2523 (1960).

    Google Scholar 

  6. J. Schallenberg and E. Meyer, Z. Naturforsch., 38B, 108 (1983).

    Google Scholar 

  7. M. Prudhomme,M. Sancelme,A. Bonnefoy,D. Fabbro, and T. Meyer, Eur. J. Med. Chem., 34, 161 (1999).

    Google Scholar 

  8. K. M. Biswas and H. Mallik, Indian J. Chem., 22B, 927 (1983).

    Google Scholar 

  9. S. V. Zhavrid,M. N. Shashikhina,N. V. Gribkova,N. F. Kazak,A. I. Mikhaleva,B. A. Trofimov,A. N. Vasil'ev,G. I. Zhungietu,M. A. Rekhter,O. M. Radul,L. A. Vlad,S. M. Bukhanyuk, and L. M. Zorin, Khim.-Farm. Zh., No. 17, 153 (1983).

  10. N. N. Bulatova and N. N. Suvorov, Khim. Geterotsikl. Soedin., 813 (1969).

  11. G. E. Ficken and R. P. Linstead, J. Chem. Soc., 3525 (1955).

  12. J. Schmitt,C. Perrin,M. Langlois, and M. Suquet, Bull. Soc. Chim. France, 1227 (1969).

  13. Sh. A. Samsoniya,I. Sh. Chikvaidze,T. G. Narindoshvili, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 899 (2001).

  14. S. P. Hiremath,S. S. Kaddargi,B. H. M. Mruthyunjayaswamy, and M. G. purohit, Indian J. Chem., 19B, 767 (1980).

    Google Scholar 

  15. L. A. Savel'eva,M. N. Preobrazhenskaya,K. G. Zhirnova, and N. N. Suvorov, Trudy Mosk. Khim. Tekhn. Inst., 119 (1972).

  16. M. Matsui and Y. Yamada, Jpn. Patent 7207390; Chem. Abstr., 77, 5326 (1972).

    Google Scholar 

  17. G. Tacconi, Farmaco. Ed. Sci., 20, 902 (1965); Chem. Abstr., 64, 8121 (1966).

    Google Scholar 

  18. H. F. Hodsonand G. F. Smith, J. Chem. Soc., 3544 (1957).

  19. G. La Parola, Gazz. Chim. Ital., 75, 157 (1945).

    Google Scholar 

  20. L. B. Shagalov,T. A. Tkachenko,A. M. Vasil'ev,V. N. Eraskina,T. A. Babushkina, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 940 (1974).

  21. A. Gonzalez and C. Galvez, Synthesis, 212 (1983).

  22. M. Colonna and P. Bruni, Gazz. Chim. Ital., 95, 857 (1965).

    Google Scholar 

  23. L. Cardellini,L. Greci, and P. Stipa, Synth. Commun., 24, 677 (1994).

    Google Scholar 

  24. H. C. J. Ottenheijm,R. Plate,J. H. Noordik, and J. D. M. Herscheid, J. Org. Chem., 47, 2147 (1982).

    Google Scholar 

  25. R. Plate,H. C. J. Ottenheijm, and R. J. F. Nivard, J. Org. Chem., 49, 540 (1984).

    Google Scholar 

  26. R. Plate,P. H. H. Hermkens,J. M. M. Smits, and H. C. J. Ottenheijm, J. Org. Chem., 51, 309 (1986).

    Google Scholar 

  27. R. R. Webb II,M. C. Venuti, and C. Eigenbrot, J. Org. Chem., 56, 4706 (1991).

    Google Scholar 

  28. Y. Maki,T. Furuta, and M. Suzuki, Chem. Pharm. Bull., 27, 1917 (1979).

    Google Scholar 

  29. H. Takechi and M. Machida, Synthesis, 206 (1989).

  30. R. G. Glushkov,I. M. Zasosova,I. M. Ovcharova,N. P. Solov'eva, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., 954 (1979).

  31. N. W. Oilman,J. F. Blount, and L. H. Sternbach, J. Org. Chem., 37, 3201 (1972).

    Google Scholar 

  32. P. A. Wade and M. K. Pillay, Gazz. Chim. Ital., 114, 239 (1984).

    Google Scholar 

  33. G. A. Shvekhgeimer,V. I. Kelarev, and L. A. D'yankova, Khim. Geterotsikl. Soedin., 1609 (1984).

  34. V. I. Kelarev,S. Sh. Gasanov,R. A. Karakhanov,Yu. N. Polivin,K. P. Kuatbekova, and M. E. Panina, Zh. Org. Khim., 28, 2561 (1992).

    Google Scholar 

  35. G. I. Zhungietu and M. A. Rekhter, Isatin and its Derivatives [in Russian], Shtiintsa, Kishinev (1977), p. 92.

    Google Scholar 

  36. S. Gabriel, Berichte, 16, 517 (1883).

    Google Scholar 

  37. W. Borsche and W. Sander, Berichte, 47, 2815 (1914).

    Google Scholar 

  38. P. Stefanescu, Rev. Chim. (Bucharest), 20, 353 (1969).

    Google Scholar 

  39. C. Moises Perales, Anales Fac. Farm. y Bioquim., Univ. Nad. Mayor San Marcos (Lima), 7, 559 (1956); Chem. Abstr., 53, 7225 (1959).

    Google Scholar 

  40. G. Heller, Berichte, 40, 1296 (1905).

    Google Scholar 

  41. M. Takahashi, Bull. Chem. Soc. Japan, 43, 2986 (1970).

    Google Scholar 

  42. F. Watjen,C. F. Bigge,L. H. Jensen,P. A. Boxer,L. J. Lescosky,E. O. Nielsen,T. C. Malone,G. W. Campbell,L. L. Coughenour,D. M. Rock,J. Drejer, and F. W. Marcoux, Bioorg. Med. Chem. Lett., 4, 371 (1994).

    Google Scholar 

  43. A. Etienne, Bull. Soc. Chim. France, 651 (1948).

  44. E. Giovannini and P. Portmann, Helv. Chim. Acta, 31, 1375 (1948).

    Google Scholar 

  45. M. Colonna, Boll. Sci. Facolta Chim. Ind. Bologna, 89 (1941); Chem. Abstr., 37, 3096 (1943).

  46. K. Wiechert,H. H. Heilmann, and W. Jacob, Z. Chem., 1, 191 (1961).

    Google Scholar 

  47. F. Buscarons and L. Sanchez Moreno, Inform. Quim. Anal., 21, No. 6, 191 (1967); Chem. Abstr., 69, 27160 (1968).

    Google Scholar 

  48. T. Kearney,P. A. Harris,A. Jackson, and J. A. Joule, Synthesis, 769 (1992).

  49. T. Kearney,J. A. Joule,A. Jackson, Heterocycles, 33, 757 (1992).

    Google Scholar 

  50. C. O. Kappe,G. Kollenz, and C. Wentrup, J. Chem. Soc., Chem. Commun., 485 (1992).

  51. F. Piozzi, Atti Accad. Nazi. Lincei, Rend., Classe Sci. Fis., Mat. e Nat., 22, 629 (1957); Chem. Abstr., 52, 7278 (1958).

    Google Scholar 

  52. N. P.Kostyuchenko,K. G. Zhirnova,M. N. Preobrazhenskaya,Yu. N. Sheinker, and N. N. Suvorov, Zh. Org. Khim., 8, 2422 (1972).

    Google Scholar 

  53. M. A. Yurovskaya,V. V. Druzhinina,V. A. Budylin,Yu. G. Bundel',D. S. Yufit, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 226 (1983).

  54. D. S. Yufit and Yu. T. Struchkov, Zh. Strukt. Khim., 26, No. 2, 185 (1985).

    Google Scholar 

  55. R. W. Janes,B. S. Porter,M. A. Naylor,A. C. Ferguson,K. B. Patel,M. R. L. Stratford,P. Wardman, and S. A. Everett, Acta Crystallogr., C57, 58 (2001).

    Google Scholar 

  56. W. P. Bosman,P. T. Beurskens,J. M. M. Smits,R. Plate, and H. C. J. Ottenheijm, Recl. Trav. Chim. Pays-Bas, 105, 559 (1986).

    Google Scholar 

  57. M. A. Yurovskaya,V. V. Druzhinina,M. A. Tyurekhodzhaeva,A. K. Shestakova,V. A. Chertkov, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 65 (1984).

  58. P. B. Terent'ev,V. V. Druzhinina, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 790 (1983).

  59. D. G. O'Sullivan and P. W. Sadler, J. Chem. Soc., 876 (1959).

  60. T. Sasaki and M. Takahashi, Yuki Gosei Kagaku Kyokai Shi, 26, 899 (1968); Chem. Abstr., 70, 28746 (1969).

    Google Scholar 

  61. W. Holzer and Z. Gyorgydeak, J. Heterocycl. Chem., 33, 675 (1996).

    Google Scholar 

  62. M. Bugeanu, Rev. Chim. (Bucharest), 30, 1193 (1979).

    Google Scholar 

  63. M. Alam and A. Mohammad, Proc. Pak. Acad. Sci., 24, 337 (1987); Chem. Abstr., 110, 134570 (1989).

    Google Scholar 

  64. M. A. Ghandour,I. M. Issa,M. R. Mahmoud, and R. A. Abou-Doma, J. Indian Chem. Soc., 53, 258 (1976).

    Google Scholar 

  65. C. Calzolari, Boll. Soc. Adriat. Sci. Nat., (Trieste), 45, 109 (1949-1950); Pubbl. Facolla Sci. Ing.-Univ. Trieste, Ser. B, 81, 1; 82, 3; 83, 3 (1950); Chem. Abstr., 46, 3423 (1952).

    Google Scholar 

  66. L. S. Malowan, Ciencia, 19, 119 (1959); Chem. Abstr., 54, 7412 (1960).

    Google Scholar 

  67. L. Divis, Sb. Vys. Sk. Chem.-Technol. Praze, Anal. Chem., No. 5, 21 (1969); Chem. Abstr., 73, 126626 (1970).

  68. V. Hovorka and L. Divis, Coll. Czech. Chem. Commun., 14, 116 (1949).

    Google Scholar 

  69. F. Watjen,J. Drejer, and L.H. Jensen, Eur. Pat. 432,648; Chem. Abstr., 115, 183089 (1991).

    Google Scholar 

  70. K. W. Woods,C. D. W. Brooks,R. G. Maki,K. E. Rodrigues,J. B. Bouska,P. Young,R. L. Bell, and G. W. Carter, Bioorg. Med. Chem. Lett., 6, 1547 (1996).

    Google Scholar 

  71. H. C. J. Ottenheijm,R. Plate,J. H. Noordik, and J. D. M. Herscheid, J. Org. Chem., 47, 2147 (1982).

    Google Scholar 

  72. C. W. Holzapfel and M. S. Van Dyk, Synth. Commun., 17, 1349 (1987).

    Google Scholar 

  73. A. Andreani and M. Rambaldi, J. Heterocycl. Chem., 25, 1519 (1988).

    Google Scholar 

  74. A. K. Padhy,P. K. Panda,S. K. Sahu, and P. K. Misro, Indian J. Chem., 40B, 258 (2001).

    Google Scholar 

  75. E. Abele,O. Dzenitis,S. Grinberga,P. Arsenjans, and E. Lukevics, Latv. J. Chem., 349 (2001).

  76. M. A. Yurovskaya,V. V. Druzhinina,M. A. Tyurekhodzhaeva, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., 69 (1984).

  77. E. Abele, O. Dzenitis, and E. Lukevics, Latv. J. Chem., in press.

  78. E. S. H. El Ashry, Sci. Pharm., 47, 5 (1979); Chem. Abstr., 91, 74403 (1979).

    Google Scholar 

  79. C. Fauran,M. Turin,G. Raynaud, and N. Dorme, French Patent 2244499; Chem. Abstr., 83, 206097 (1975).

    Google Scholar 

  80. M. Giannella and M. Pigini, Farmaco. Ed. Sci., 28, 157 (1973).

    Google Scholar 

  81. M. Colonna,L. Greci, and M. Poloni, Gazz. Chim. Ital., 104, 231 (1974).

    Google Scholar 

  82. W. Dehaen and A. Hassner, J. Org. Chem., 114, 896 (1991).

    Google Scholar 

  83. H. Plieninger,K. Suhr,G. Werst, and B. Kiefer, Chem. Ber., 89, 270 (1956).

    Google Scholar 

  84. F. Hofmann,T. Rausch, and W. Hilgenberg, J. Labelled Compounds Radiopharm., 18, 1491 (1981).

    Google Scholar 

  85. M. A. Khan and E. K. Rocha, Chem. Pharm. Bull., 27, 528 (1979).

    Google Scholar 

  86. S. T. Hilton,T. C. T. Ho,G. Pljevaljcic, and K. Jones, Org. Lett., 2, 2639 (2000).

    Google Scholar 

  87. M. A. Kira and Y. M. Shaker, Egypt. J. Chem., 16, 551 (1973); Chem. Abstr., 82, 169982 (1975).

    Google Scholar 

  88. Z. Zhang,G. Jin,H. Chen, and Z. Qiu, Wuji Huaxue, 4, 112 (1988); Chem. Abstr., 111, 133736 (1989).

    Google Scholar 

  89. G. Rosini,G. Baccolini, and S. Cacchi, J. Org. Chem., 38, 1060 (1973).

    Google Scholar 

  90. S. A. Kumar and S. Mahadevan, Arch. Biochem. Biophys., 103, 516 (1963); Chem. Abstr., 60, 5826 (1964).

    Google Scholar 

  91. S. Mahadevan, Arch. Biochem. Biophys., 100, 557 (1963); Chem. Abstr., 58, 13062 (1963).

    Google Scholar 

  92. J. Helmlinger,T. Rausch, and W. Hilgenberg, Phytochemistry, 26, 615 (1987); Chem. Abstr., 107, 3008 (1987).

    Google Scholar 

  93. J. Ludwig-Mueller and W. Hilgenberg, Physiol. Plant., 79, 311 (1990); Chem. Abstr., 113, 111349 (1990).

    Google Scholar 

  94. A. Kasahara, Jpn. Patent 0383969; Chem. Abstr., 115, 183088 (1991).

    Google Scholar 

  95. T. Sasaki and H. Yanai, Jpn. Patent 01100157; Chem. Abstr., 111, 153626 (1989).

    Google Scholar 

  96. R. M. Acheson,P. G. Hunt,D. M. Littlewood,B. A. Murrer, and H. E. Rosenberg, J. Chem. Soc., Perkin Trans. 1, 1117 (1978).

    Google Scholar 

  97. A. Ahmad and I. D. Spencer, Can. J. Chem., 38, 1625 (1960).

    Google Scholar 

  98. K. Freter, J. Org. Chem., 37, 2010 (1972).

    Google Scholar 

  99. H. Fritz,M. Soleymani-Jamarani,J. W. Bats, and H.-J. Teuber, Liebigs Ann. Chem., 705 (1993).

  100. J. Schmitt,M. Langlois, and C. Perrin, Bull. Soc. Chim. France, 1234 (1969).

  101. E. Wenkert,B. S. Bernstein, and J. H. Udelhofen, J. Am. Chem. Soc., 80, 4899 (1958).

    Google Scholar 

  102. P. Kutschy,M. Dzurilla,M. Takasugi,M. Torok,I. Achbergerova,R. Homzova, and M. Racova, Tetrahedron, 54, 3549 (1998).

    Google Scholar 

  103. H. Feuer and D. M. Braunstein, J. Org. Chem., 34, 1817 (1969).

    Google Scholar 

  104. M. N. Preobrazhenskaya,G. K. Zhirnova,N. P. Kostyuchenko,O. S. Anisimova, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 778 (1971).

  105. J. Szmuszkovicz, J. Org. Chem., 29, 843 (1964).

    Google Scholar 

  106. S. V. Tolkunov,M. N. Kal'nitskii,A. I. Khizhan,S. Yu. Suikov,M. Yu. Zubritskii, and V. I. Dulenko, Khim. Geterotsikl. Soedin., 1124 (1995).

  107. P. H. Gotz,J. W. Bats, and H. Fritz, Liebigs Ann. Chem., 2065 (1986).

  108. A. N. Grinev,S. Yu. Ryabova,G. N. Kuriolo, and K. F. Turchin, Khim. Geterotsikl. Soedin., 1068 (1980).

  109. L. Greci,M. Rossetti,R. Galeazzi,P. Stipa,P. Sgarabotto, and P. Cozzini, J. Chem. Soc., Perkin Trans. 2, 2683 (1998).

    Google Scholar 

  110. E. Abele and E. Lukevics, Heterocycles, 53, 2285 (2000).

    Google Scholar 

  111. B. A. Trofimov, Adv. Heterocycl. Chem., 51, 177 (1990).

    Google Scholar 

  112. B. A. Trofimov and A. I. Mikhaleva, Heterocycles, 37, 1193 (1994).

    Google Scholar 

  113. B. A. Trofimov and A. I. Mikhaleva, Zh. Org. Khim., 32, 1127 (1996).

    Google Scholar 

  114. B. A. Trofimov, in: R. A. Jones (editor), The Chemistry of Heterocyclic Compounds, Vol. 48, Pyrroles, Part 2, p.131.

  115. N. Shoji,Y. Kondo, and T. Takemoto, Heterocycles, 1, 251 (1973).

    Google Scholar 

  116. G. B. Jones,C. J. Moody,A. Padwa, and J. M. Kassir, J. Chem. Soc., Perkin Trans. 1, 1721 (1991).

    Google Scholar 

  117. E. Malamidou-Xenikaki,X. N. Stampelos, and E. Coutouli-Argyropoulou, J. Heterocycl. Chem., 33, 563 (1996).

    Google Scholar 

  118. E. Malamidou-Xenikaki,X.N. Stampelos,T.A. Charalambis, and C. C. Karapostolou, Tetrahedron, 53, 747 (1997).

    Google Scholar 

  119. A. S. Bailey,C. J. Barnes, and P. A. Wilkinson, J. Chem. Soc., Perkin Trans. 1, 1321 (1974).

    Google Scholar 

  120. K. Shanmugasundaram and K. J. R. Prasad, Z. Naturforsch., 54B, 1202 (1999).

    Google Scholar 

  121. C. Kavitha and K. J. R. Prasad, Heterocycl. Commun., 5, 481 (1999).

    Google Scholar 

  122. K. M. Devries and A. Villalobos, PCT Int. Appl. WO Pat. 9613505; Chem. Abstr., 125, 114591 (1996).

    Google Scholar 

  123. S. P. Hiremath,S. B. Thakar, and M. G. Purohit, Indian J. Chem., 23B, 926 (1984).

    Google Scholar 

  124. K. C. Joshi,A. Dandia, and S. Sanan, J. Indian Chem. Soc., 67, 404 (1990).

    Google Scholar 

  125. V. P. Gorbunova and N. N. Suvorov, Khim. Geterotsikl. Soedin., 936 (1978).

  126. M. S. Morales-Rios,L. Gerardo Zepeda,O. R. Suarez-Castillo, and P. Joseph-Nathan, Heterocycles, 43, 1483 (1996).

    Google Scholar 

  127. V. N. Komissarov, Zh. Org. Khim., 31, 1060 (1995).

    Google Scholar 

  128. M. Devys and M. Barbier, Synthesis, 214 (1990).

  129. J. N. Coker,W. L. Kohlhase,T. F. Martens,A. O. Rogers, and G. G. Allan, J. Org. Chem., 27, 3201 (1962).

    Google Scholar 

  130. J. N. Coker,M. Fields, and A. O. Rodgers, US Patent 292 941; Chem. Abstr., 54, 8853 (1960).

    Google Scholar 

  131. R. Baker,A. J. Reeve, and L. J. Street, US Patent 5317103; Chem. Abstr., 123, 9441 (1995).

    Google Scholar 

  132. R. Baker,J. Saunders, and C. Swain, Eur. Patent 328200; Chem. Abstr., 112, 139035 (1990).

    Google Scholar 

  133. A. Ono and K. Narasaka, Chem. Lett., 146 (2001).

  134. A. A. Semenov,I. V. Terent'eva, and E. P. Styngach, in: Chemistry of Heterocyclic Compounds. 1. Nitrogen-Containing Heterocycles [in Russian], Zinatne, Riga (1967), p. 38.

    Google Scholar 

  135. K. I. Kuchkova and A. A. Semenov, Khim. Geterotsikl. Soedin., 1131 (1967).

  136. K. I. Kuchkova,A. A. Semenov, and I. V. Terent'eva, Khim. Geterotsikl. Soedin., 197 (1970).

  137. K. I. Kuchkova,E. P. Styngach,F. Sh. Rivilis,N. M. Frolova, and A. A. Semenov, Khim. Geterotsikl. Soedin., 386 (1976).

  138. A. A. Semenov, in: Chemistry of Heterocyclic Compounds. 1. Nitrogen-Containing Heterocycles [in Russian], Zinatne, Riga (1967), p. 44.

    Google Scholar 

  139. T. Choshi,Y. Matsuya,M. Okita,K. Inada,E. Sugino, and S. Hibino, Tetrahedron Lett., 39, 2341 (1998).

    Google Scholar 

  140. N. Kanekiyo,T. Choshi,T. Kuwada,E. Sugino, and S. Hibino, Heterocycles, 53, 1877 (2000).

    Google Scholar 

  141. U. C. Mashelkar and R. N. Usgaonkar, Indian J. Chem., 16B, 782 (1978).

    Google Scholar 

  142. F. Sori,M. Incze,Z. Kardos-Bologh,M. Kajtar-Peredy, and C. Szantay, Arch. Pharm., 326, 227 (1993).

    Google Scholar 

  143. S. A. Snyder,D. A. Vosburg,M. G. Jarvis, and J. H. Markgraf, Tetrahedron, 56, 5329 (2000).

    Google Scholar 

  144. S. Hibino,E. Sugino,T. Kuwada,N. Ogura,K. Sato, and T. Choshi, J. Org. Chem., 57, 5917 (1992).

    Google Scholar 

  145. A. Nemes,J. Kreidl,L. Czibula,K. Nogradi,M. Farkas,C. Szantay Jr.,G. Tarkanyi,G. Balogh,I. Juhasz,A. Kalman, and L. Parkanyi, Heterocycles, 53, 1697 (2000).

    Google Scholar 

  146. A. Nemes,L. Czibula,G. Visky,M. Farkas, and J. Kreidl, Heterocycles, 32, 2329 (1991).

    Google Scholar 

  147. J. Kreidl,K. Nogradi,L. Czibula,J. Farkas,G. Visky,J. I. Deutsch, and J. Meszaros, Hung. Pat. 59928; Chem. Abstr., 118, 39241 (1993).

    Google Scholar 

  148. I. Moldvai,C. Szantay Jr., and C. Szantay, Heterocycles, 55, 2147 (2001).

    Google Scholar 

  149. K. Shinhama,K. Matoba,Y. Torisawa, and J. Minamikawa, Tetrahedron, 56, 7427 (2000).

    Google Scholar 

  150. K. Matoba,H. Tone,F. Goto,K. Niihama,M. Saka,K. Abe,J. Namikawa,T. Tanaka, and T. Nishi, Jpn. Patent 07157481; Chem. Abstr., 123, 256434 (1995).

    Google Scholar 

  151. K. Matoba,H. Tone,K. Shinhama,F. Goto,M. Sakai, and J. Minamikawa, J. Synth. Org. Chem. Japan, 57, 401 (1999).

    Google Scholar 

  152. S. S. Klioze,F. J. Ehrgott Jr., and E. J. Glamkowski, J. Heterocycl. Chem., 21, 1257 (1984).

    Google Scholar 

  153. C. Papamicael,G. Queguiner,J. Bourguignon, and G. Dupas, Tetrahedron, 57, 5385 (2001).

    Google Scholar 

  154. A. P. Terent'ev,M. N. Preobrazhenskaya, and G. M. Sorokina, Zh. Obshch. Khim., 29, 2875 (1959).

    Google Scholar 

  155. J. B. Kyziol and A. Kyzniak, Tetrahedron, 36, 3017 (1980).

    Google Scholar 

  156. F. Piozzi,M. Dubini, and M. Cecere, Gazz. Chim. Ital., 89, 2342 (1959).

    Google Scholar 

  157. J. B. Hester Jr., J. Org. Chem., 35, 875 (1970).

    Google Scholar 

  158. J. Bergman,S. Bergman, and T. Brimert, Tetrahedron, 55, 10447 (1999).

    Google Scholar 

  159. E. Giovannini and T. Lorenz, Helv. Chim. Acta, 40, 2287 (1957).

    Google Scholar 

  160. B. Eistert,R. Mueller,H. Selzer, and E. A. Hackmann, Chem. Ber., 97, 2469 (1964).

    Google Scholar 

  161. J. B. Campbell, Jr., and T. W. Davenport, Synth. Commun., 19, 2255 (1989).

    Google Scholar 

  162. M. D. Khidre, Egypt. J. Chem., 40, 327 (1997); Chem. Abstr., 127, 262753 (1997).

    Google Scholar 

  163. O. E. Nasakin,A. V. Sukhobokov,I. A. Abramov,E. L. Gefter,A. Ya. Chernikov,M. N. Yakovlev, and N. N. Shmagina, USSR Inventor's Certificate 10286665; Chem. Abstr., 100, 6106 (1984).

    Google Scholar 

  164. N. N. Shmagina,G. A. Gulyaeva,E. L. Gefter,E. S. Botvinnik,E. L. Zaitseva,A. N. Pravednikov,E. N. Teleshov, and A. N. Frelova, USSR Inventor's Certificate 550382; Chem. Abstr., 87, 22813 (1977).

    Google Scholar 

  165. P. Pazdera and E. Novacek, Czech. Pat. 273404; Chem. Abstr., 117, 171217 (1992).

    Google Scholar 

  166. G. Bargellini and C. J. Turi, Gazz. Chim. Ital., 84, 157 (1954).

    Google Scholar 

  167. G. R. Bedford and M. W. Partridge, J. Chem. Soc., 1633 (1959).

  168. D. Sicker,F. Fiebig, and G. Mann, Ger. (East) Patent 263756; Chem. Abstr., 111, 194321 (1989).

    Google Scholar 

  169. D. Sicker,F. Fiebig, and G. Mann, Org. Prep. Proced. Int., 21, 514 (1989).

    Google Scholar 

  170. P. I. Abramenko, Zh. Fiz. Khim. Obshch., 16, 231 (1971).

    Google Scholar 

  171. M. N. Deshpande and S. Seshadri, Indian J. Chem., 11, 538 (1973).

    Google Scholar 

  172. F. J. Lalor and F. G. Scott, J. Chem. Soc. (C), 1034 (1969).

  173. B. S. Jensen,T. D. Jorgensen,P. K. Ahring,P. Christophersen,D. Strobaek,L. Teuber, and S. P. Olesen, PCT Int. Appl. WO 0033834; Chem. Abstr., 133, 43434 (2000).

    Google Scholar 

  174. R. Lattrell,W. Bartmann,J. Musil, and E. Grancer, Ger. Patent 2707268; Chem. Abstr., 89, 179858 (1978).

    Google Scholar 

  175. E. Magnien and J. Cabilio, US Patent 3838135; Chem. Abstr., 82, 4121 (1975).

    Google Scholar 

  176. J. Schmitt, US Patent 2930798; Chem. Abstr., 54, 21130 (1960).

    Google Scholar 

  177. F. Manna,F. Chimenti,A. Bolasco,R. Lena,A. Filippelli,M. Falciani, and M. Fontana, Farmaco, 51, 699 (1996).

    Google Scholar 

  178. E. Lubisch,B. Behl, and H. P. Hofmann, Ger. Patent 4242675; Chem. Abstr., 121, 108514 (1994).

    Google Scholar 

  179. G. Johnson, US Patent 5 1927 92; Chem. Abstr., 119, 95330 (1993).

    Google Scholar 

  180. F. Watjen,J. Drejer, and L. H. Jensen, Eur. Patent 522494; Chem. Abstr., 118, 254746 (1993).

    Google Scholar 

  181. F. Watjen,B. H. Dahl,J. Drejer, and L. H. Jensen, US Patent 5436250; Chem. Abstr., 123, 340088 (1995).

    Google Scholar 

  182. F. Watjen,B.H. Dahl,J. Drejer, and L. H. Jensen, Eur. Patent 633262; Chem. Abstr., 122, 187559 (1995).

    Google Scholar 

  183. F. Waetjen and J. Drejer, PCT Int. Appl. WO Pat. 9426747; Chem. Abstr., 122, 105928 (1995).

    Google Scholar 

  184. P. Moldt and F. Watjen, PCT Int. Appl. WO Pat. 9608494; Chem. Abstr., 125, 114582 (1996).

    Google Scholar 

  185. P. Moldt and F. Watjen, PCT Int. Appl. WO Pat. 9608495; Chem. Abstr., 125, 86681 (1996).

    Google Scholar 

  186. F. Watjenand J. Drejer, PCT Int. Appl. WO Pat. 9814447; Chem. Abstr., 128, 270536 (1998).

    Google Scholar 

  187. F. Watjen and J. Drejer, PCT Int. Appl. WO Pat. 9949864; Chem. Abstr., 131, 257553 (1999).

    Google Scholar 

  188. W. Fischer,E. Schilling,R. Schmiedel, and M. Mueller, Pharmazie, 37, 858 (1982).

    Google Scholar 

  189. F. Watjen,E. 0. Nielsen,J. Drejer, and L. H. Jensen, Bioorg. Med. Chem. Lett., 3, 105 (1993).

    Google Scholar 

  190. H. Demarne, French Patent 217 937; Chem. Abstr., 80, 59863 (1974).

    Google Scholar 

  191. H. Najer,D. Obitz, and J. P. Kaplan, French Patent 2506764; Chem. Abstr., 99, 38360 (1983).

    Google Scholar 

  192. G. Neef,U. Eder,R. Schmiechen,A. Huth,D. Rathz,D. Seidelmann,W. Kehr,D. Palenschat, and C. T. Braestrup, European Patent 54507; Chem. Abstr., 98, 16663 (1983).

    Google Scholar 

  193. S. Yoshina and A. Tanaka, Jpn. Patent 7663196; Chem. Abstr., 86, 29786 (1977).

    Google Scholar 

  194. N. R. Banna and C. W. T. Pilcher, Neuropharmacology, 19, 103 (1980); Chem. Abstr., 92, 208910(1980).

    Google Scholar 

  195. E. Bouchara, French Patent 2244501; Chem. Abstr., 83, 206098 (1975).

    Google Scholar 

  196. M. R. Bell, Eur. Patent 171037; Chem. Abstr., 105, 78832 (1986).

    Google Scholar 

  197. D. W. Brooks and P. Bhatia, US Patent 5420282; Chem. Abstr., 123, 143874 (1995).

    Google Scholar 

  198. T. Kolasa,P. Bhatia, and D. W. Brooks, US Patent 5399699; Chem. Abstr., 123, 227986 (1995).

    Google Scholar 

  199. C. D. W. Brooks,R. A. Craig,D. E. Gunn,T. Kolasa,J. L. Moore, and A. O. Stewart, PCT Int. Appl. WO Pat. 9741100; Chem. Abstr., 128, 13200 (1998).

    Google Scholar 

  200. C. D. W. Brooks,T. Kolasa,W. Lee, and A. O. Stewart, US Patent 5750558; Chem. Abstr., 129, 4576 (1998).

    Google Scholar 

  201. N. Shih,G. A. Reichard, and R. G. Aslanian, PCT Int. Appl. WO Pat. 98 2001 0; Chem. Abstr., 129, 16060 (1998).

    Google Scholar 

  202. N. Shih,G. A. Reichard, and R. G. Aslanian, US Patent 5945428; Chem. Abstr., 131, 170343 (1999).

    Google Scholar 

  203. G. A. Reichard,N. Shih, and D. Wang, PCT Int. Appl. WO Pat. 0039114; Chem. Abstr., 133, 74037 (2000).

    Google Scholar 

  204. F. G. Salituro,G. W. Bemis,S. Wilke,J. Green,J. Cao,H. Gao, and E. M. Harrington, PCT Int. Appl. WO Pat. 0064872; Chem. Abstr., 133, 335157 (2000).

    Google Scholar 

  205. C. Li,Y. Go,Z. Mao,K. Koyano,Y. Kai,N. Kanahisa,Q. Zhu,Z. Zhou, and S. Wu, Bull. Chem. Soc. Jpn., 69, 1621 (1996).

    Google Scholar 

  206. F. C. A. Gaeta,A. A. Galan, and E. A. Kraynack, PCT Int. Appl. WO Pat. 9965875; Chem. Abstr., 132, 35611 (2000).

    Google Scholar 

  207. A. W. Czarnik,D. P. Mack,H.-Y. Mei, and D.W. Moreland, PCT Int. Appl. WO Pat. 9925327; Chem. Abstr., 131, 689 (1999).

    Google Scholar 

  208. M. Sy,M. Maillet, and J. Pages, Chim. Ther., 5, 216 (1970); Chem. Abstr., 73, 95728 (1970).

    Google Scholar 

  209. G. R. Alien, Jr.,J. F. Poletto, and M. J. Weiss, J. Med. Chem., 10, 14 (1966).

    Google Scholar 

  210. A. A. El-Gendy and A. M. Ahmedy, Arch. Pharm. Res., 23, 310 (2000).

    Google Scholar 

  211. S. Koshimura,A. Hamada,T. Otaki, and K. Deguchi, Ann. Rept. Research Inst. Tuberc., Kanazawa Univ., 12, No. 2, 9 (1954); Chem. Abstr., 49, 9160 (1955).

    Google Scholar 

  212. H.-P. Wang and I.-H. Lui, Chin. Pharm. J. (Taipei), 46, 269 (1994).

    Google Scholar 

  213. T. Iihama and C. Sano, Jpn. Patent 0812648; Chem. Abstr., 124, 316984 (1996).

    Google Scholar 

  214. A. Widdig,E. Urbschat,F. Grewe, and H. Kaspers, Ger. Patent 2408897; Chem. Abstr., 84, 30883 (1976).

    Google Scholar 

  215. B. Boehlendorf,E. Forche,N. Bedorf,K. Gerth,H. Irschik,R. Jansen,B. Kunze,W. Trowitzsch-Kienast,H. Reichenbach, and G. Hoefle, Liebigs Ann. Chem., 49 (1996).

  216. C. H. Fawcett, Nature, 204, 1200 (1964).

    Google Scholar 

  217. N. Nishizono,K. Oda,K. Ohno,M. Minami, and M. Machida, Heterocycles, 55, 1897 (2001).

    Google Scholar 

  218. A. F Childs,D. R. Davies,A. L. Green, and J. P. Ruland, Brit. J. Pharmacol., 10, 462 (1955); Chem. Abstr., 52, 7533 (1958).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Abele, E., Abele, R., Dzenitis, O. et al. Indole and Isatin Oximes: Synthesis, Reactions, and Biological Activity. (Review). Chemistry of Heterocyclic Compounds 39, 3–35 (2003). https://doi.org/10.1023/A:1023008422464

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1023008422464

Navigation