Polycyclic N-Heterocyclic Compounds. Part 62: Reaction of N-(Quinazolin-4-yl)amidine Derivatives with Hydroxylamine Hydrochloride and Anti-platelet Aggregation Activity of the Products

Kensuke Okuda; Ying-Xue Zhang; Hiromi Ohtomo; Takashi Hirota; Kenji Sasaki

doi:10.1248/cpb.58.369

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Polycyclic N-Heterocyclic Compounds. Part 62: Reaction of N-(Quinazolin-4-yl)amidine Derivatives with Hydroxylamine Hydrochloride and Anti-platelet Aggregation Activity of the Products

Kensuke Okuda, Ying-Xue Zhang, Hiromi Ohtomo, Takashi Hirota, Kenji Sasaki

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Keywords: rearrangement, 1,2,4-oxadiazole, anti-platelet aggregation, N-(quinazolin-4-yl)amidine, amide oxime, hydroxylamine hydrochloride

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2010 Volume 58 Issue 3 Pages 369-374

DOI https://doi.org/10.1248/cpb.58.369

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Abstract

The reactions of N-(5,6,7,8-tetrahydroquinazolin-4-yl)amidines and their amide oximes with hydroxylamine hydrochloride gave abnormal cyclization products via a ring cleavage of pyrimidine component accompanied with a ring closure of 1,2,4-oxadiazole to give N-[2-([1,2,4]oxadiazol-5-yl)cyclohexen-1-yl]formamide oximes. Similarly, N-(quinazolin-4-yl)amidines reacted with hydroxylamine hydrochloride gave the same results. The evaluation of inhibitory activities against platelet aggregation in vitro is also described to show one derivative has potent activity.

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