Conclusions
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1.
6-Mercaptopurine derivatives containing amino acid residues at the nitrogen of the imidazole ring (N-9) were obtained.
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2.
A single-stage method involving the action of the appropriate N-bromoacetylamino acid esters on 6-benzylmercaptopurine (in dimethyl sulfoxide and in the presence of potassium carbonate) was proposed for the preparation of N-(6-benzylthio-9H-9-purinyl)acetylamino esters. Ethyl and benzyl esters of N-(6-benzylthio-9H-9-purinyl)acetylglycine and the corresponding alanine, valine, leucine, and phenylalanine derivatives (VIII a-e and VIII a1-e1) and also the ethyl esters of N-(6-benzylthio-9H-9-purinyl)acetylsarcolysine (VIII f) and the corresponding L-valine derivatives were obtained.
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3.
The corresponding N-(6-benzylthio-9H-9-purinyl)acetylamino acids (IX a-f) were obtained from the ethyl esters.
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4.
N-(6- Benzylthio-9H-9-purinyl)acetylvaline (IX c) and N-(6-benzylthio-9H-9-purinyl)acetylglycine ethyl ester were obtained from 6-benzylmercaptopurine by the multirange method A through the ethyl ester, hydrazide, and azide of 6-benzylthio-9H-9-purinylacetic acid. A by-product of the reaction (6-benzylthio-9H-9-purinylacetic acid) was isolated.
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5.
The ethyl and benzyl esters of N-bromoacetylglycine and the corresponding alanine, valine, leucine, and phenylalanine compounds and the ethyl esters of N-bromoacetylsarcolysine and the corresponding L-valine compounds were obtained as initial products.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2295–2304, October, 1970.
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Kaverzneva, E.D., Zvorykina, V.K. & Kiseleva, V.V. Synthesis of N-(6-benzylthio-9H-9-purinyl)acetylamino acids. Russ Chem Bull 19, 2157–2166 (1970). https://doi.org/10.1007/BF00861489
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DOI: https://doi.org/10.1007/BF00861489