Abstract
Thecis- andtrans-diastereomers of the 7,8-dihydro-7-deazapurine derivatives were synthesized from the corresponding diastereomers of 4-trans-cyano-2-methyl-3-phenyl-5-oxopyrrolidine (5), which were reduced from the 2-cis- and 2-trans-diastereomers of 4-trans-cyano-2-hydroxymethyl-3-phenyl-5-oxopyrrolidine (2)via tosylation, iodination and following elimination, respectively. The preparedcis- andtrans-diastereomers of 6-amino-2-mercapto-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (8) were transferred to the corresponding 2-methylthio-diastereomers9 and following desulfurization with Raney-nickel leaded to thecis-andtrans-diastereomers of 6-amino-8-methyl-7-phenyl-7,8-dihydro-7(9H)-deazapurine (10), respectively. The synthesized 7-deazapurine derivatives were tested for their antibiotic activity by the serial two-fold dilution method.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References Cited
Anzai, K., Nakamura G. and Suzuki, S., Antibiotic substance produced in the culture broth of streptomyces tubercidus.J. Antibiotics (Tokyo) 10A, 201 (1957).
Becker, H. G. O., Domschke, G., Berger W., Faust J, Schwetlick, K.,et al., Organikum, Deutscher Verlag der Wissenschaften, Berlin 1990.
Cottam H. B., Kazimierczuk, Z., Geary, S., Mckernan P., Revankar, G. R. and Robins, R. K., Synthesis of 2,6-disubstituted 2′-deoxytubercidine prepared via the stereospecific sodium salt glycosylation procedure.J. Med. Chem., 28, 1461 (1985).
Girgis. N., Joergensen A., and Pedersen E. B., Phsophorous pentoxide in organic synthesis. XI, A new synthesis apporach to 7-deazahypoxanthines.Synthesis, 101 (1985).
Joergensen A., El-bayouki, and Khairy A. M., Phosphorous pentoxide in organic synthesis. XXI, Synthesis of 7H-pyrrolo[2,3-d]pyrimidin-4(3H)-ones and N-aryl-7H-pyrrolo.[2,3-d]pyrimidine-4-amines.Chem. Scr., 25, 222 (1985).
Morita T., Okamoto Y., and Sakurai, H., Chlorotrimethylsilane/Sodium iodide/Zn as a simple and convenient reducing system; One-pot deoxygenation of alcohols and ethers.Synthesis, 32 (1981).
Nishimura H., Katakiri, K., Sato, K., Mayama, M., and Shimaoka N., Antibiotic substance extrated from the culture filtrate and mycelium ofStreptomyces toyocaensis.J. Antibiotics (Tokyo) 9A, 60 (1956).
Pachaly, P., Kang, H. S. and Wahl, D., LDA-katalysierte diastereoselective Michael addition mit glycinderivativen: Synthese von 4-substituierten 3-Aryl-2-ethoxycarbonyl-5-oxo-pyrrolidine.Arch. Pharm. (Weinhein) 324, 989 (1991).
Perrin, D. D., Armarego W. L. F.,Purification of laboratory chemicals, 4th edition, Butter-worth-Heinemann, Oxford, 1996.
Pichler H., Folkers G., Roth H. J., and Eger K., Synthesis of 7-unsubstituted 7-H-pyrrolo[2,3-d]pyrimidines.Liebigs Ann. Chem., 1486 (1986).
Schick W., Pachaly, P., Kang H. S. and Wahl, D., Synthese von 7-Deazapurinen als potentielle purinanaloga.Arch. Pharm. (Weinheim) 326, 641 (1993).
Seela, F. and H. D. Winkeler, 4-Amino-7-(β-D-arabiofuranosyl)pyrrolo[2,3-d]pyrimidin-the synthesis of ara tubercidin by phase transfer cataysis.Chem. Ber. 113, 2069–2080 (1980).
Seela F., and Muth H. P., Synthesis of 7-deaza-2′,3′-d 9deoxyhuanosine by deoxygenation of its 2′-deoxy-β-D-ribofuranoside.Liebigs Ann. Chem., 215 (1988).
Sin K. S., Nam, J. U., Lee C. K. and Jun, J. G., Synthesis of 7-deazapurine.J. Pharm. Soc. Korea, 37, 228 (1993).
Sin K. S., Kim N. H., Lee J. H., Sung S. T. and Pachaly P., Synthesis of 7-deazahypoxanthine and 7-deazaadenine derivatives.J. Pharm. Soc. Korea, 41, 181–186 (1997).
Sinambela, J. M., Zimmermann W., Roth H. J., and Eger K., Amino acids as bifuntional synthons of pyrrol[1,2-a]- and-[2,3-d]annelate heterocycles.J. Heterocycl. Chem., 23, 393 (1986).
Tolman R. L., Robinson R. K. and Townsend L. B., Pyrrole[2,3-d]pyrimidine nucleoside antibiotics. Total synthesis and structure of toyocamycin, unamycin B, vengicide, antibiotic E-212, and sangivamycin (BA-90912).J. Am. Chem. Soc., 90, 524 (1968).
Tolman, R. L., Robinson, R. K., and Townsend, L. B., Pyrrolepyrimidine nucleosides III. The total synthesis and structure of toyocamycin, sangimycin, tubercidin and related derivatives.J. Am. Chem. Soc., 91, 2102 (1969).
Ueno, Y. and Omura S.,Microbial Chemistry, 127–129, Nankodo, Tokyo, Japan (1995).
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sung, S.Y., Sin, K.S. Synthesis of the 7,8-dihydro-7-deazapurine derivatives and their antibiotic activity. Arch. Pharm. Res. 21, 187–192 (1998). https://doi.org/10.1007/BF02974026
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02974026