Synthesis and properties of analogs of 5(4)-aminoimidazole-4(5)-carboxamide and purines. 14. Acylation of 5(4)-aminoimidazole derivatives / Mokrushin V.S., Pospelova T.A., Bakulev V.A., Golovina E.F., Nikolaeva S.L., Pushkareva Z.V. // Chemistry of Heterocyclic Compounds. - 1984. - V. 20, l. 2. - P. 204-209.

ISSN:
00093122
Type:
Article
Abstract:
The acylation of 5(4)-aminoimidazole derivatives was studied. It is shown that acylation by means of carboxylic acid anhydrides and chlorides takes place at the amino group, whereas acylation by means of chlorocarbonic acid esters takes place at the nitrogen atoms of the imidazole ring. Methods for the selective introduction of a carbomethoxy group in the 1, 3, and 5 positions of the 5(4)-aminoimidazole-4(5)-carboxamide molecule were developed. © 1984 Plenum Publishing Corporation.
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DOI:
10.1007/BF00506294
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Affiliations S. M. Kirov Ural Polytechnic Institute, Sverdlovsk, 620002, Russian Federation
References Mokrushin, V.S., Golovina, E.F., Nifontov, V.I., Bakulev, V.A., Pospelova, T.A., Usova, V.K., (1983) Khim. Geterotsikl. Soedin., 11, p. 1552; S. Hashimoto, A. Nakada, S. Kano, and S. Takahashi, US Patent No. 3983241; Ref. Zh. Khim., 140344P (1977); A. T. Ainsworth and C. J. Rose, British Patent No. 1421787; Ref. Zh. Khim., 18083P (1976); Hoshi, A., Kanzawa, F., Kumagei, K., Kuretani, K., Studies on antitumor agents. II. Antitumor activity of 5-amino-4-imidazolethiocarboxamide derivatives on a variety of animal tumors. (1969) Cancer Chemother Rep, 53, p. 165; Itoh, M., Genta, Y., (1978) Chem. Abstr., 88, p. 170142; Fidler, Shibanova, E.F., Makerov, P.V., Kalikhman, I.D., Zhulunova, P.M., Sarapulova, G.I., Klyba, L.V., Voronkov, M.G., (1980) Khim. Geterotsikl. Soedin., 10, p. 1414; Bennett, L.L., Baker, H.T., Synthesis of Potential Anticancer Agents. IV. 4-Nitro- and 4-Amino-5-imidazole Sulfones (1957) Journal of the American Chemical Society, 79, p. 2188; Shaw, E., A new synthesis of the purines adenine, hypoxanthine, xanthine, and isoguanine. (1950) J Biol Chem, 185, p. 439; Enoki, K., Sawabe, S., Yamamoto, T., Masuyama, K., Genda, Y., (1975) Chem. Abstr., 83, p. 43319; Shevelev, S.A., (1970) usp. Khim., 39, p. 1773; Matlews, H.B., Rapoport, H., (1973) J. Am. Chem. Soc., 95, p. 2297; Kalinin, F.L., Lobov, V.P., Zhidkov, V.A., (1971) Handbook of Biochemistry [in Russian], p. 1012. , Naukova Dumka, Kiev; V. S. Mokrushin, T. A. Pospelova, and Z. V. Pushkareva, USSR Inventor's Certificate No. 891662; Byull. Izobret., No. 47, 107 (1981); Rubtsov, V.M., Baichikov, A.G., (1971) Synthetic Pharmochemical Preparations [in Russian], p. 328. , Meditsina, Moscow; K. Aida, T. Tagagi, H. Segawa, and H. Nigai, US Patent No. 3915982; Ref. Zh. Khim., 150103P (1976)
Correspondence Address Mokrushin, V.S.; S. M. Kirov Ural Polytechnic Institute, Sverdlovsk, 620002, Russian Federation
Publisher Kluwer Academic Publishers-Plenum Publishers
CODEN CHCCA
Language of Original Document English
Abbreviated Source Title Chem Heterocycl Compd
Source Scopus