Nucleosides and Nucleotides. 143. Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives.

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Nucleosides and Nucleotides. 143. Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives.

1996; Pharmaceutical Society of Japan; Volume: 44; Issue: 2 Linguagem: Inglês

10.1248/cpb.44.288

ISSN

1347-5223

Autores

Noriaki Minakawa, Yoshimasa Sasabuchi, Arihiro Kiyosue, Naoshi Kojima, Akira Matsuda,

Tópico(s)

HIV/AIDS drug development and treatment

Resumo

An efficient and large scale chamical synthesis of 5-aminoimidazole-4-carboxamide (AICA) 2'-deoxyriboside (5a) and its 3'-deoxyriboside 5b is described. Treatment of 3', 5'-di-O-acetyl-N1-triphenylmethyl-2'-deoxyinosine (3a) with 5 N NaOH in EtOH, followed by anhydrous trifluoroacetic acid gave 5a in 59% yield from 2'-deoxyinosine (1a). AICA 3'-deoxyriboside (5b) was also obtained in a similar manner as for 5a in 73% yield from 3'-deoxyinosine (1b). Conversion of these AICA derivatives (5a, b) into 3-deazapurine derivatives (9a, b, 15a, b, 20a, b) is also described.

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Nucleosides and Nucleotides. 143. Synthesis of 5-Amino-4-imidazolecarboxamide (AICA) Deoxyribosides from Deoxyinosines and Their Conversion into 3-Deazapurine Derivatives.