Polycyclic N-heterocyclic compounds. Part 80: Synthesis and evaluation of effects on in vitro pentosidine formation of 5,6-dihydro[1]benzothieno[3′, 2′:2,3]thiepino[4,5-d]pyrimidine and related compounds

Kensuke Okuda, Yutaka Itsuji, Takashi Hirota, Kenji Sasaki

Research output: Contribution to journalArticle

Abstract

Reaction of 3-(3-cyanopropylthio)[1]benzothiophene-2-carbonitrile with tert-BuONa gave 5-amino-1,2-dihydro[1]benzothieno[3,2-d]thieno[2,3-b]pyridine and 5-amino-2,3-dihydro[1]benzothieno[3,2-b]thiepin-4-carbonitrile. The latter compound served as a convenient scaffold for the synthesis of the new heterocycles, [1]benzothieno[3′,2′:2,3]thiepino[4,5-d]pyrimidines. All of our new tetracyclic products were evaluated for in vitro inhibitory activity on the formation of pentosidine, which is one of representative advanced glycation end products.

Original languageEnglish
Pages (from-to)891-898
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume51
Issue number4
DOIs
Publication statusPublished - 2014

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Thiepins
Heterocyclic Compounds
Pyrimidines
Advanced Glycosylation End Products
Scaffolds
pentosidine
benzothiophene
pyridine
pyrimidine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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title = "Polycyclic N-heterocyclic compounds. Part 80: Synthesis and evaluation of effects on in vitro pentosidine formation of 5,6-dihydro[1]benzothieno[3′, 2′:2,3]thiepino[4,5-d]pyrimidine and related compounds",
abstract = "Reaction of 3-(3-cyanopropylthio)[1]benzothiophene-2-carbonitrile with tert-BuONa gave 5-amino-1,2-dihydro[1]benzothieno[3,2-d]thieno[2,3-b]pyridine and 5-amino-2,3-dihydro[1]benzothieno[3,2-b]thiepin-4-carbonitrile. The latter compound served as a convenient scaffold for the synthesis of the new heterocycles, [1]benzothieno[3′,2′:2,3]thiepino[4,5-d]pyrimidines. All of our new tetracyclic products were evaluated for in vitro inhibitory activity on the formation of pentosidine, which is one of representative advanced glycation end products.",
author = "Kensuke Okuda and Yutaka Itsuji and Takashi Hirota and Kenji Sasaki",
year = "2014",
doi = "10.1002/jhet.1709",
language = "English",
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journal = "Journal of Heterocyclic Chemistry",
issn = "0022-152X",
publisher = "Heterocorporation",
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TY - JOUR

T1 - Polycyclic N-heterocyclic compounds. Part 80

T2 - Synthesis and evaluation of effects on in vitro pentosidine formation of 5,6-dihydro[1]benzothieno[3′, 2′:2,3]thiepino[4,5-d]pyrimidine and related compounds

AU - Okuda, Kensuke

AU - Itsuji, Yutaka

AU - Hirota, Takashi

AU - Sasaki, Kenji

PY - 2014

Y1 - 2014

N2 - Reaction of 3-(3-cyanopropylthio)[1]benzothiophene-2-carbonitrile with tert-BuONa gave 5-amino-1,2-dihydro[1]benzothieno[3,2-d]thieno[2,3-b]pyridine and 5-amino-2,3-dihydro[1]benzothieno[3,2-b]thiepin-4-carbonitrile. The latter compound served as a convenient scaffold for the synthesis of the new heterocycles, [1]benzothieno[3′,2′:2,3]thiepino[4,5-d]pyrimidines. All of our new tetracyclic products were evaluated for in vitro inhibitory activity on the formation of pentosidine, which is one of representative advanced glycation end products.

AB - Reaction of 3-(3-cyanopropylthio)[1]benzothiophene-2-carbonitrile with tert-BuONa gave 5-amino-1,2-dihydro[1]benzothieno[3,2-d]thieno[2,3-b]pyridine and 5-amino-2,3-dihydro[1]benzothieno[3,2-b]thiepin-4-carbonitrile. The latter compound served as a convenient scaffold for the synthesis of the new heterocycles, [1]benzothieno[3′,2′:2,3]thiepino[4,5-d]pyrimidines. All of our new tetracyclic products were evaluated for in vitro inhibitory activity on the formation of pentosidine, which is one of representative advanced glycation end products.

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