Polycyclic N-heterocyclic compounds 76: Synthesis and antiplatelet evaluation of 2,4-disubstituted 5,6-Dihydro[1]benzofuro[3′,2′:2,3] oxepino[4,5-d]pyrimidines

Kensuke Okuda, Jun Ichi Takano, Takashi Hirota, Kenji Sasaki, Yuta Nishina, Hiroyuki Ishida

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Abstract

Reaction of several Vilsmeier reagents with 5-amino-2,3-dihydro[1] benzofuro[3,2-b]oxepin-4-carbonitrile gave tetracyclic 2-substituted 4-chloro-5,6-dihydro[1]benzofuro[3′,2′:2,3]oxepino[4,5-d] pyrimidines. The structure of one of these, the 4-chloro-2-phenyl derivative, was confirmed by X-ray crystallography. Treatment of the 4-chloro derivatives with simple amines as nucleophile afforded 2-substituted 4-amino derivatives. A pentacyclic compound was also obtained by dehydrative ring closure. These products were evaluated for antiplatelet activity, and some showed potency comparable with that of aspirin.

Original languageEnglish
Pages (from-to)661-668
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume51
Issue number3
DOIs
Publication statusPublished - 2014

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Heterocyclic Compounds
Pyrimidines
Derivatives
Oxepins
Nucleophiles
X ray crystallography
Aspirin
Amines

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Polycyclic N-heterocyclic compounds 76: Synthesis and antiplatelet evaluation of 2,4-disubstituted 5,6-Dihydro[1]benzofuro[3′,2′:2,3] oxepino[4,5-d]pyrimidines",
abstract = "Reaction of several Vilsmeier reagents with 5-amino-2,3-dihydro[1] benzofuro[3,2-b]oxepin-4-carbonitrile gave tetracyclic 2-substituted 4-chloro-5,6-dihydro[1]benzofuro[3′,2′:2,3]oxepino[4,5-d] pyrimidines. The structure of one of these, the 4-chloro-2-phenyl derivative, was confirmed by X-ray crystallography. Treatment of the 4-chloro derivatives with simple amines as nucleophile afforded 2-substituted 4-amino derivatives. A pentacyclic compound was also obtained by dehydrative ring closure. These products were evaluated for antiplatelet activity, and some showed potency comparable with that of aspirin.",
author = "Kensuke Okuda and Takano, {Jun Ichi} and Takashi Hirota and Kenji Sasaki and Yuta Nishina and Hiroyuki Ishida",
year = "2014",
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pages = "661--668",
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TY - JOUR

T1 - Polycyclic N-heterocyclic compounds 76

T2 - Synthesis and antiplatelet evaluation of 2,4-disubstituted 5,6-Dihydro[1]benzofuro[3′,2′:2,3] oxepino[4,5-d]pyrimidines

AU - Okuda, Kensuke

AU - Takano, Jun Ichi

AU - Hirota, Takashi

AU - Sasaki, Kenji

AU - Nishina, Yuta

AU - Ishida, Hiroyuki

PY - 2014

Y1 - 2014

N2 - Reaction of several Vilsmeier reagents with 5-amino-2,3-dihydro[1] benzofuro[3,2-b]oxepin-4-carbonitrile gave tetracyclic 2-substituted 4-chloro-5,6-dihydro[1]benzofuro[3′,2′:2,3]oxepino[4,5-d] pyrimidines. The structure of one of these, the 4-chloro-2-phenyl derivative, was confirmed by X-ray crystallography. Treatment of the 4-chloro derivatives with simple amines as nucleophile afforded 2-substituted 4-amino derivatives. A pentacyclic compound was also obtained by dehydrative ring closure. These products were evaluated for antiplatelet activity, and some showed potency comparable with that of aspirin.

AB - Reaction of several Vilsmeier reagents with 5-amino-2,3-dihydro[1] benzofuro[3,2-b]oxepin-4-carbonitrile gave tetracyclic 2-substituted 4-chloro-5,6-dihydro[1]benzofuro[3′,2′:2,3]oxepino[4,5-d] pyrimidines. The structure of one of these, the 4-chloro-2-phenyl derivative, was confirmed by X-ray crystallography. Treatment of the 4-chloro derivatives with simple amines as nucleophile afforded 2-substituted 4-amino derivatives. A pentacyclic compound was also obtained by dehydrative ring closure. These products were evaluated for antiplatelet activity, and some showed potency comparable with that of aspirin.

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