161975-87-7

Upstream product

• 119139-27-4 1-benzyl-5-(2,2-diethoxyethylamino)-1H-imidazole-4-carboxamide 
• 119139-25-2 1-benzyl-5-(2,2-diethoxyethylamino)-N'-ethoxy-1H-imidazole-4-carboxamidine 
• 119139-24-1 1-benzyl-5--N'-ethoxy-1H-imidazole-4-carboxamidine 
• 119139-26-3 1-Benzyl-5-(2,2-diethoxy-ethylamino)-1H-imidazole-4-carboxamidine 

Relevant academic research and scientific papers

Purines. LXIII. Syntheses of azepinomycin, an antitumor antibiotic from Streptomyces species, and its 3-β-D-ribofuranoside and their 8-imino analogues

Three variants of a synthetic route to the antitumor antibiotic azepinomycin (3) from 1-substituted N'-alkoxy-5-formamidoimidazole-4- carboxamidine (type 10) are described. The synthesis started with the monocycles 10a-c and proceeded through the intermediates 11a-c, 12a-c, 13a- c, 14a-c, and 4a, b and 3-β-D-ribofuranosylazepinomycin (4c). The benzyl version (series a), including the permutation 14a → 15 → 3, was found to produce the antibiotic (3) most efficiently. The starting materials 10a-c were readily prepared from the 9-substituted adenines 7a-c via the N-oxides 8a-c and the 1-alkoxy derivatives 9a-c. The 8-imino analogues (17 and 18) of 3 and 4c were also synthesized from 12a and 12c, respectively.

ALTERNATIVE SYNTHESES OF AZEPINOMYCIN

Three alternative syntheses of the antibiotic azepinomycin (XI) have now become feasible through a route starting from the monocycles Va-c and proceeding through the intermediates VIa-c, VIIa-c, VIIIa-c, IXa-c, and XIIa,b and 3-β-D-ribofuranosylazepinomycin (XIIc). The permutation IXa-Xa-XI was also found to be feasible. The starting materials Va-c were readily prepared from IIa-c through IIIa-c and IVa-c.