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.
Similar content being viewed by others
REFERENCES
E. H. Gordeev, V. N. Buyanov, and V. E. Zhigachev, Khim. Geterotsikl. Soedin., 46 (1992).
F. M. Albini,R. Oberti, and P. Caramella, J. Chem. Res. Synop., 4 (1983).
Y. Ergun,N. Bayraktar,S. Patir, and G. Okay, J. Heterocycl. Chem., 37, 11 (2000).
P. Nantka-Namirski and Z. Ozdowska, Pol. Pat. 65813; Chem. Abstr., 78, 136068 (1973).
A. Ahmad,I. Eelnurme, and I. D. Spencer, Can. J. Chem., 38, 2523 (1960).
J. Schallenberg and E. Meyer, Z. Naturforsch., 38B, 108 (1983).
M. Prudhomme,M. Sancelme,A. Bonnefoy,D. Fabbro, and T. Meyer, Eur. J. Med. Chem., 34, 161 (1999).
K. M. Biswas and H. Mallik, Indian J. Chem., 22B, 927 (1983).
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).
N. N. Bulatova and N. N. Suvorov, Khim. Geterotsikl. Soedin., 813 (1969).
G. E. Ficken and R. P. Linstead, J. Chem. Soc., 3525 (1955).
J. Schmitt,C. Perrin,M. Langlois, and M. Suquet, Bull. Soc. Chim. France, 1227 (1969).
Sh. A. Samsoniya,I. Sh. Chikvaidze,T. G. Narindoshvili, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 899 (2001).
S. P. Hiremath,S. S. Kaddargi,B. H. M. Mruthyunjayaswamy, and M. G. purohit, Indian J. Chem., 19B, 767 (1980).
L. A. Savel'eva,M. N. Preobrazhenskaya,K. G. Zhirnova, and N. N. Suvorov, Trudy Mosk. Khim. Tekhn. Inst., 119 (1972).
M. Matsui and Y. Yamada, Jpn. Patent 7207390; Chem. Abstr., 77, 5326 (1972).
G. Tacconi, Farmaco. Ed. Sci., 20, 902 (1965); Chem. Abstr., 64, 8121 (1966).
H. F. Hodsonand G. F. Smith, J. Chem. Soc., 3544 (1957).
G. La Parola, Gazz. Chim. Ital., 75, 157 (1945).
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).
A. Gonzalez and C. Galvez, Synthesis, 212 (1983).
M. Colonna and P. Bruni, Gazz. Chim. Ital., 95, 857 (1965).
L. Cardellini,L. Greci, and P. Stipa, Synth. Commun., 24, 677 (1994).
H. C. J. Ottenheijm,R. Plate,J. H. Noordik, and J. D. M. Herscheid, J. Org. Chem., 47, 2147 (1982).
R. Plate,H. C. J. Ottenheijm, and R. J. F. Nivard, J. Org. Chem., 49, 540 (1984).
R. Plate,P. H. H. Hermkens,J. M. M. Smits, and H. C. J. Ottenheijm, J. Org. Chem., 51, 309 (1986).
R. R. Webb II,M. C. Venuti, and C. Eigenbrot, J. Org. Chem., 56, 4706 (1991).
Y. Maki,T. Furuta, and M. Suzuki, Chem. Pharm. Bull., 27, 1917 (1979).
H. Takechi and M. Machida, Synthesis, 206 (1989).
R. G. Glushkov,I. M. Zasosova,I. M. Ovcharova,N. P. Solov'eva, and Yu. N. Sheinker, Khim. Geterotsikl. Soedin., 954 (1979).
N. W. Oilman,J. F. Blount, and L. H. Sternbach, J. Org. Chem., 37, 3201 (1972).
P. A. Wade and M. K. Pillay, Gazz. Chim. Ital., 114, 239 (1984).
G. A. Shvekhgeimer,V. I. Kelarev, and L. A. D'yankova, Khim. Geterotsikl. Soedin., 1609 (1984).
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).
G. I. Zhungietu and M. A. Rekhter, Isatin and its Derivatives [in Russian], Shtiintsa, Kishinev (1977), p. 92.
S. Gabriel, Berichte, 16, 517 (1883).
W. Borsche and W. Sander, Berichte, 47, 2815 (1914).
P. Stefanescu, Rev. Chim. (Bucharest), 20, 353 (1969).
C. Moises Perales, Anales Fac. Farm. y Bioquim., Univ. Nad. Mayor San Marcos (Lima), 7, 559 (1956); Chem. Abstr., 53, 7225 (1959).
G. Heller, Berichte, 40, 1296 (1905).
M. Takahashi, Bull. Chem. Soc. Japan, 43, 2986 (1970).
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).
A. Etienne, Bull. Soc. Chim. France, 651 (1948).
E. Giovannini and P. Portmann, Helv. Chim. Acta, 31, 1375 (1948).
M. Colonna, Boll. Sci. Facolta Chim. Ind. Bologna, 89 (1941); Chem. Abstr., 37, 3096 (1943).
K. Wiechert,H. H. Heilmann, and W. Jacob, Z. Chem., 1, 191 (1961).
F. Buscarons and L. Sanchez Moreno, Inform. Quim. Anal., 21, No. 6, 191 (1967); Chem. Abstr., 69, 27160 (1968).
T. Kearney,P. A. Harris,A. Jackson, and J. A. Joule, Synthesis, 769 (1992).
T. Kearney,J. A. Joule,A. Jackson, Heterocycles, 33, 757 (1992).
C. O. Kappe,G. Kollenz, and C. Wentrup, J. Chem. Soc., Chem. Commun., 485 (1992).
F. Piozzi, Atti Accad. Nazi. Lincei, Rend., Classe Sci. Fis., Mat. e Nat., 22, 629 (1957); Chem. Abstr., 52, 7278 (1958).
N. P.Kostyuchenko,K. G. Zhirnova,M. N. Preobrazhenskaya,Yu. N. Sheinker, and N. N. Suvorov, Zh. Org. Khim., 8, 2422 (1972).
M. A. Yurovskaya,V. V. Druzhinina,V. A. Budylin,Yu. G. Bundel',D. S. Yufit, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 226 (1983).
D. S. Yufit and Yu. T. Struchkov, Zh. Strukt. Khim., 26, No. 2, 185 (1985).
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).
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).
M. A. Yurovskaya,V. V. Druzhinina,M. A. Tyurekhodzhaeva,A. K. Shestakova,V. A. Chertkov, and Yu. T. Struchkov, Khim. Geterotsikl. Soedin., 65 (1984).
P. B. Terent'ev,V. V. Druzhinina, and M. A. Yurovskaya, Khim. Geterotsikl. Soedin., 790 (1983).
D. G. O'Sullivan and P. W. Sadler, J. Chem. Soc., 876 (1959).
T. Sasaki and M. Takahashi, Yuki Gosei Kagaku Kyokai Shi, 26, 899 (1968); Chem. Abstr., 70, 28746 (1969).
W. Holzer and Z. Gyorgydeak, J. Heterocycl. Chem., 33, 675 (1996).
M. Bugeanu, Rev. Chim. (Bucharest), 30, 1193 (1979).
M. Alam and A. Mohammad, Proc. Pak. Acad. Sci., 24, 337 (1987); Chem. Abstr., 110, 134570 (1989).
M. A. Ghandour,I. M. Issa,M. R. Mahmoud, and R. A. Abou-Doma, J. Indian Chem. Soc., 53, 258 (1976).
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).
L. S. Malowan, Ciencia, 19, 119 (1959); Chem. Abstr., 54, 7412 (1960).
L. Divis, Sb. Vys. Sk. Chem.-Technol. Praze, Anal. Chem., No. 5, 21 (1969); Chem. Abstr., 73, 126626 (1970).
V. Hovorka and L. Divis, Coll. Czech. Chem. Commun., 14, 116 (1949).
F. Watjen,J. Drejer, and L.H. Jensen, Eur. Pat. 432,648; Chem. Abstr., 115, 183089 (1991).
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).
H. C. J. Ottenheijm,R. Plate,J. H. Noordik, and J. D. M. Herscheid, J. Org. Chem., 47, 2147 (1982).
C. W. Holzapfel and M. S. Van Dyk, Synth. Commun., 17, 1349 (1987).
A. Andreani and M. Rambaldi, J. Heterocycl. Chem., 25, 1519 (1988).
A. K. Padhy,P. K. Panda,S. K. Sahu, and P. K. Misro, Indian J. Chem., 40B, 258 (2001).
E. Abele,O. Dzenitis,S. Grinberga,P. Arsenjans, and E. Lukevics, Latv. J. Chem., 349 (2001).
M. A. Yurovskaya,V. V. Druzhinina,M. A. Tyurekhodzhaeva, and Yu. G. Bundel', Khim. Geterotsikl. Soedin., 69 (1984).
E. Abele, O. Dzenitis, and E. Lukevics, Latv. J. Chem., in press.
E. S. H. El Ashry, Sci. Pharm., 47, 5 (1979); Chem. Abstr., 91, 74403 (1979).
C. Fauran,M. Turin,G. Raynaud, and N. Dorme, French Patent 2244499; Chem. Abstr., 83, 206097 (1975).
M. Giannella and M. Pigini, Farmaco. Ed. Sci., 28, 157 (1973).
M. Colonna,L. Greci, and M. Poloni, Gazz. Chim. Ital., 104, 231 (1974).
W. Dehaen and A. Hassner, J. Org. Chem., 114, 896 (1991).
H. Plieninger,K. Suhr,G. Werst, and B. Kiefer, Chem. Ber., 89, 270 (1956).
F. Hofmann,T. Rausch, and W. Hilgenberg, J. Labelled Compounds Radiopharm., 18, 1491 (1981).
M. A. Khan and E. K. Rocha, Chem. Pharm. Bull., 27, 528 (1979).
S. T. Hilton,T. C. T. Ho,G. Pljevaljcic, and K. Jones, Org. Lett., 2, 2639 (2000).
M. A. Kira and Y. M. Shaker, Egypt. J. Chem., 16, 551 (1973); Chem. Abstr., 82, 169982 (1975).
Z. Zhang,G. Jin,H. Chen, and Z. Qiu, Wuji Huaxue, 4, 112 (1988); Chem. Abstr., 111, 133736 (1989).
G. Rosini,G. Baccolini, and S. Cacchi, J. Org. Chem., 38, 1060 (1973).
S. A. Kumar and S. Mahadevan, Arch. Biochem. Biophys., 103, 516 (1963); Chem. Abstr., 60, 5826 (1964).
S. Mahadevan, Arch. Biochem. Biophys., 100, 557 (1963); Chem. Abstr., 58, 13062 (1963).
J. Helmlinger,T. Rausch, and W. Hilgenberg, Phytochemistry, 26, 615 (1987); Chem. Abstr., 107, 3008 (1987).
J. Ludwig-Mueller and W. Hilgenberg, Physiol. Plant., 79, 311 (1990); Chem. Abstr., 113, 111349 (1990).
A. Kasahara, Jpn. Patent 0383969; Chem. Abstr., 115, 183088 (1991).
T. Sasaki and H. Yanai, Jpn. Patent 01100157; Chem. Abstr., 111, 153626 (1989).
R. M. Acheson,P. G. Hunt,D. M. Littlewood,B. A. Murrer, and H. E. Rosenberg, J. Chem. Soc., Perkin Trans. 1, 1117 (1978).
A. Ahmad and I. D. Spencer, Can. J. Chem., 38, 1625 (1960).
K. Freter, J. Org. Chem., 37, 2010 (1972).
H. Fritz,M. Soleymani-Jamarani,J. W. Bats, and H.-J. Teuber, Liebigs Ann. Chem., 705 (1993).
J. Schmitt,M. Langlois, and C. Perrin, Bull. Soc. Chim. France, 1234 (1969).
E. Wenkert,B. S. Bernstein, and J. H. Udelhofen, J. Am. Chem. Soc., 80, 4899 (1958).
P. Kutschy,M. Dzurilla,M. Takasugi,M. Torok,I. Achbergerova,R. Homzova, and M. Racova, Tetrahedron, 54, 3549 (1998).
H. Feuer and D. M. Braunstein, J. Org. Chem., 34, 1817 (1969).
M. N. Preobrazhenskaya,G. K. Zhirnova,N. P. Kostyuchenko,O. S. Anisimova, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 778 (1971).
J. Szmuszkovicz, J. Org. Chem., 29, 843 (1964).
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).
P. H. Gotz,J. W. Bats, and H. Fritz, Liebigs Ann. Chem., 2065 (1986).
A. N. Grinev,S. Yu. Ryabova,G. N. Kuriolo, and K. F. Turchin, Khim. Geterotsikl. Soedin., 1068 (1980).
L. Greci,M. Rossetti,R. Galeazzi,P. Stipa,P. Sgarabotto, and P. Cozzini, J. Chem. Soc., Perkin Trans. 2, 2683 (1998).
E. Abele and E. Lukevics, Heterocycles, 53, 2285 (2000).
B. A. Trofimov, Adv. Heterocycl. Chem., 51, 177 (1990).
B. A. Trofimov and A. I. Mikhaleva, Heterocycles, 37, 1193 (1994).
B. A. Trofimov and A. I. Mikhaleva, Zh. Org. Khim., 32, 1127 (1996).
B. A. Trofimov, in: R. A. Jones (editor), The Chemistry of Heterocyclic Compounds, Vol. 48, Pyrroles, Part 2, p.131.
N. Shoji,Y. Kondo, and T. Takemoto, Heterocycles, 1, 251 (1973).
G. B. Jones,C. J. Moody,A. Padwa, and J. M. Kassir, J. Chem. Soc., Perkin Trans. 1, 1721 (1991).
E. Malamidou-Xenikaki,X. N. Stampelos, and E. Coutouli-Argyropoulou, J. Heterocycl. Chem., 33, 563 (1996).
E. Malamidou-Xenikaki,X.N. Stampelos,T.A. Charalambis, and C. C. Karapostolou, Tetrahedron, 53, 747 (1997).
A. S. Bailey,C. J. Barnes, and P. A. Wilkinson, J. Chem. Soc., Perkin Trans. 1, 1321 (1974).
K. Shanmugasundaram and K. J. R. Prasad, Z. Naturforsch., 54B, 1202 (1999).
C. Kavitha and K. J. R. Prasad, Heterocycl. Commun., 5, 481 (1999).
K. M. Devries and A. Villalobos, PCT Int. Appl. WO Pat. 9613505; Chem. Abstr., 125, 114591 (1996).
S. P. Hiremath,S. B. Thakar, and M. G. Purohit, Indian J. Chem., 23B, 926 (1984).
K. C. Joshi,A. Dandia, and S. Sanan, J. Indian Chem. Soc., 67, 404 (1990).
V. P. Gorbunova and N. N. Suvorov, Khim. Geterotsikl. Soedin., 936 (1978).
M. S. Morales-Rios,L. Gerardo Zepeda,O. R. Suarez-Castillo, and P. Joseph-Nathan, Heterocycles, 43, 1483 (1996).
V. N. Komissarov, Zh. Org. Khim., 31, 1060 (1995).
M. Devys and M. Barbier, Synthesis, 214 (1990).
J. N. Coker,W. L. Kohlhase,T. F. Martens,A. O. Rogers, and G. G. Allan, J. Org. Chem., 27, 3201 (1962).
J. N. Coker,M. Fields, and A. O. Rodgers, US Patent 292 941; Chem. Abstr., 54, 8853 (1960).
R. Baker,A. J. Reeve, and L. J. Street, US Patent 5317103; Chem. Abstr., 123, 9441 (1995).
R. Baker,J. Saunders, and C. Swain, Eur. Patent 328200; Chem. Abstr., 112, 139035 (1990).
A. Ono and K. Narasaka, Chem. Lett., 146 (2001).
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.
K. I. Kuchkova and A. A. Semenov, Khim. Geterotsikl. Soedin., 1131 (1967).
K. I. Kuchkova,A. A. Semenov, and I. V. Terent'eva, Khim. Geterotsikl. Soedin., 197 (1970).
K. I. Kuchkova,E. P. Styngach,F. Sh. Rivilis,N. M. Frolova, and A. A. Semenov, Khim. Geterotsikl. Soedin., 386 (1976).
A. A. Semenov, in: Chemistry of Heterocyclic Compounds. 1. Nitrogen-Containing Heterocycles [in Russian], Zinatne, Riga (1967), p. 44.
T. Choshi,Y. Matsuya,M. Okita,K. Inada,E. Sugino, and S. Hibino, Tetrahedron Lett., 39, 2341 (1998).
N. Kanekiyo,T. Choshi,T. Kuwada,E. Sugino, and S. Hibino, Heterocycles, 53, 1877 (2000).
U. C. Mashelkar and R. N. Usgaonkar, Indian J. Chem., 16B, 782 (1978).
F. Sori,M. Incze,Z. Kardos-Bologh,M. Kajtar-Peredy, and C. Szantay, Arch. Pharm., 326, 227 (1993).
S. A. Snyder,D. A. Vosburg,M. G. Jarvis, and J. H. Markgraf, Tetrahedron, 56, 5329 (2000).
S. Hibino,E. Sugino,T. Kuwada,N. Ogura,K. Sato, and T. Choshi, J. Org. Chem., 57, 5917 (1992).
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).
A. Nemes,L. Czibula,G. Visky,M. Farkas, and J. Kreidl, Heterocycles, 32, 2329 (1991).
J. Kreidl,K. Nogradi,L. Czibula,J. Farkas,G. Visky,J. I. Deutsch, and J. Meszaros, Hung. Pat. 59928; Chem. Abstr., 118, 39241 (1993).
I. Moldvai,C. Szantay Jr., and C. Szantay, Heterocycles, 55, 2147 (2001).
K. Shinhama,K. Matoba,Y. Torisawa, and J. Minamikawa, Tetrahedron, 56, 7427 (2000).
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).
K. Matoba,H. Tone,K. Shinhama,F. Goto,M. Sakai, and J. Minamikawa, J. Synth. Org. Chem. Japan, 57, 401 (1999).
S. S. Klioze,F. J. Ehrgott Jr., and E. J. Glamkowski, J. Heterocycl. Chem., 21, 1257 (1984).
C. Papamicael,G. Queguiner,J. Bourguignon, and G. Dupas, Tetrahedron, 57, 5385 (2001).
A. P. Terent'ev,M. N. Preobrazhenskaya, and G. M. Sorokina, Zh. Obshch. Khim., 29, 2875 (1959).
J. B. Kyziol and A. Kyzniak, Tetrahedron, 36, 3017 (1980).
F. Piozzi,M. Dubini, and M. Cecere, Gazz. Chim. Ital., 89, 2342 (1959).
J. B. Hester Jr., J. Org. Chem., 35, 875 (1970).
J. Bergman,S. Bergman, and T. Brimert, Tetrahedron, 55, 10447 (1999).
E. Giovannini and T. Lorenz, Helv. Chim. Acta, 40, 2287 (1957).
B. Eistert,R. Mueller,H. Selzer, and E. A. Hackmann, Chem. Ber., 97, 2469 (1964).
J. B. Campbell, Jr., and T. W. Davenport, Synth. Commun., 19, 2255 (1989).
M. D. Khidre, Egypt. J. Chem., 40, 327 (1997); Chem. Abstr., 127, 262753 (1997).
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).
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).
P. Pazdera and E. Novacek, Czech. Pat. 273404; Chem. Abstr., 117, 171217 (1992).
G. Bargellini and C. J. Turi, Gazz. Chim. Ital., 84, 157 (1954).
G. R. Bedford and M. W. Partridge, J. Chem. Soc., 1633 (1959).
D. Sicker,F. Fiebig, and G. Mann, Ger. (East) Patent 263756; Chem. Abstr., 111, 194321 (1989).
D. Sicker,F. Fiebig, and G. Mann, Org. Prep. Proced. Int., 21, 514 (1989).
P. I. Abramenko, Zh. Fiz. Khim. Obshch., 16, 231 (1971).
M. N. Deshpande and S. Seshadri, Indian J. Chem., 11, 538 (1973).
F. J. Lalor and F. G. Scott, J. Chem. Soc. (C), 1034 (1969).
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).
R. Lattrell,W. Bartmann,J. Musil, and E. Grancer, Ger. Patent 2707268; Chem. Abstr., 89, 179858 (1978).
E. Magnien and J. Cabilio, US Patent 3838135; Chem. Abstr., 82, 4121 (1975).
J. Schmitt, US Patent 2930798; Chem. Abstr., 54, 21130 (1960).
F. Manna,F. Chimenti,A. Bolasco,R. Lena,A. Filippelli,M. Falciani, and M. Fontana, Farmaco, 51, 699 (1996).
E. Lubisch,B. Behl, and H. P. Hofmann, Ger. Patent 4242675; Chem. Abstr., 121, 108514 (1994).
G. Johnson, US Patent 5 1927 92; Chem. Abstr., 119, 95330 (1993).
F. Watjen,J. Drejer, and L. H. Jensen, Eur. Patent 522494; Chem. Abstr., 118, 254746 (1993).
F. Watjen,B. H. Dahl,J. Drejer, and L. H. Jensen, US Patent 5436250; Chem. Abstr., 123, 340088 (1995).
F. Watjen,B.H. Dahl,J. Drejer, and L. H. Jensen, Eur. Patent 633262; Chem. Abstr., 122, 187559 (1995).
F. Waetjen and J. Drejer, PCT Int. Appl. WO Pat. 9426747; Chem. Abstr., 122, 105928 (1995).
P. Moldt and F. Watjen, PCT Int. Appl. WO Pat. 9608494; Chem. Abstr., 125, 114582 (1996).
P. Moldt and F. Watjen, PCT Int. Appl. WO Pat. 9608495; Chem. Abstr., 125, 86681 (1996).
F. Watjenand J. Drejer, PCT Int. Appl. WO Pat. 9814447; Chem. Abstr., 128, 270536 (1998).
F. Watjen and J. Drejer, PCT Int. Appl. WO Pat. 9949864; Chem. Abstr., 131, 257553 (1999).
W. Fischer,E. Schilling,R. Schmiedel, and M. Mueller, Pharmazie, 37, 858 (1982).
F. Watjen,E. 0. Nielsen,J. Drejer, and L. H. Jensen, Bioorg. Med. Chem. Lett., 3, 105 (1993).
H. Demarne, French Patent 217 937; Chem. Abstr., 80, 59863 (1974).
H. Najer,D. Obitz, and J. P. Kaplan, French Patent 2506764; Chem. Abstr., 99, 38360 (1983).
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).
S. Yoshina and A. Tanaka, Jpn. Patent 7663196; Chem. Abstr., 86, 29786 (1977).
N. R. Banna and C. W. T. Pilcher, Neuropharmacology, 19, 103 (1980); Chem. Abstr., 92, 208910(1980).
E. Bouchara, French Patent 2244501; Chem. Abstr., 83, 206098 (1975).
M. R. Bell, Eur. Patent 171037; Chem. Abstr., 105, 78832 (1986).
D. W. Brooks and P. Bhatia, US Patent 5420282; Chem. Abstr., 123, 143874 (1995).
T. Kolasa,P. Bhatia, and D. W. Brooks, US Patent 5399699; Chem. Abstr., 123, 227986 (1995).
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).
C. D. W. Brooks,T. Kolasa,W. Lee, and A. O. Stewart, US Patent 5750558; Chem. Abstr., 129, 4576 (1998).
N. Shih,G. A. Reichard, and R. G. Aslanian, PCT Int. Appl. WO Pat. 98 2001 0; Chem. Abstr., 129, 16060 (1998).
N. Shih,G. A. Reichard, and R. G. Aslanian, US Patent 5945428; Chem. Abstr., 131, 170343 (1999).
G. A. Reichard,N. Shih, and D. Wang, PCT Int. Appl. WO Pat. 0039114; Chem. Abstr., 133, 74037 (2000).
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).
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).
F. C. A. Gaeta,A. A. Galan, and E. A. Kraynack, PCT Int. Appl. WO Pat. 9965875; Chem. Abstr., 132, 35611 (2000).
A. W. Czarnik,D. P. Mack,H.-Y. Mei, and D.W. Moreland, PCT Int. Appl. WO Pat. 9925327; Chem. Abstr., 131, 689 (1999).
M. Sy,M. Maillet, and J. Pages, Chim. Ther., 5, 216 (1970); Chem. Abstr., 73, 95728 (1970).
G. R. Alien, Jr.,J. F. Poletto, and M. J. Weiss, J. Med. Chem., 10, 14 (1966).
A. A. El-Gendy and A. M. Ahmedy, Arch. Pharm. Res., 23, 310 (2000).
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).
H.-P. Wang and I.-H. Lui, Chin. Pharm. J. (Taipei), 46, 269 (1994).
T. Iihama and C. Sano, Jpn. Patent 0812648; Chem. Abstr., 124, 316984 (1996).
A. Widdig,E. Urbschat,F. Grewe, and H. Kaspers, Ger. Patent 2408897; Chem. Abstr., 84, 30883 (1976).
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).
C. H. Fawcett, Nature, 204, 1200 (1964).
N. Nishizono,K. Oda,K. Ohno,M. Minami, and M. Machida, Heterocycles, 55, 1897 (2001).
A. F Childs,D. R. Davies,A. L. Green, and J. P. Ruland, Brit. J. Pharmacol., 10, 462 (1955); Chem. Abstr., 52, 7533 (1958).
Author information
Authors and Affiliations
Rights 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
Issue Date:
DOI: https://doi.org/10.1023/A:1023008422464