Polycyclic N-heterocyclic compounds. Part 621

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

Research output: Contribution to journalArticle

12 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)369-374
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume58
Issue number3
DOIs
Publication statusPublished - Mar 2010

Fingerprint

Heterocyclic Compounds
Hydroxylamine
Oximes
Platelets
Platelet Aggregation
Agglomeration
Oxadiazoles
Derivatives
Cyclization
Amides
N-(quinazolin-4-yl)-amidine
formamide
pyrimidine
N-(5,6,7,8-tetrahydroquinazolin-4-yl)amidine
In Vitro Techniques

Keywords

  • 1,2,4-oxadiazole
  • Amide oxime
  • Anti-platelet aggregation
  • Hydroxylamine hydrochloride
  • N-(quinazolin-4-yl)amidine
  • Rearrangement

ASJC Scopus subject areas

  • Drug Discovery
  • Chemistry(all)

Cite this

Polycyclic N-heterocyclic compounds. Part 621 : Reaction of N-(quinazolin-4-yl)amidine derivatives with hydroxylamine hydrochloride and anti-platelet aggregation activity of the products. / Okuda, Kensuke; Zhang, Ying Xue; Ohtomo, Hiromi; Hirota, Takashi; Sasaki, Kenji.

In: Chemical and Pharmaceutical Bulletin, Vol. 58, No. 3, 03.2010, p. 369-374.

Research output: Contribution to journalArticle

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