Selective formation of a phenathridine derivative by photodegradation of azilsartan

Takahiro Yoshikawa; Naoto Hayashi; Naoya Hatta; Masayuki Yokota

doi:10.1016/j.bmcl.2021.128011

Selective formation of a phenathridine derivative by photodegradation of azilsartan

Takahiro Yoshikawa^*, Naoto Hayashi, Naoya Hatta, Masayuki Yokota

^*Corresponding author for this work

Program of Chemistry

Research output: Contribution to journal › Article › peer-review

1 Scopus citations

Abstract

Photodegradation of azilsartan produces a phenanthridine derivative, with its molecular structure determined by ¹H and ¹³C NMR spectroscopy. This structure is confirmed by single-crystal X-ray diffraction and alternative synthesis. The phenanthridine ring formation is explained through the ring closure of an imidoylnitrene intermediate produced by decarboxylation of the 5-oxo-1,2,4-oxadiazole ring (oxadiazolone).

Original language	English
Article number	128011
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	41
DOIs	https://doi.org/10.1016/j.bmcl.2021.128011
State	Published - 2021/06/01

Keywords

Azilsartan
Imidoylnitrene
Intramolecular cyclization
Phenanthridine
Photolysis

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2021.128011

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title = "Selective formation of a phenathridine derivative by photodegradation of azilsartan",

abstract = "Photodegradation of azilsartan produces a phenanthridine derivative, with its molecular structure determined by 1H and 13C NMR spectroscopy. This structure is confirmed by single-crystal X-ray diffraction and alternative synthesis. The phenanthridine ring formation is explained through the ring closure of an imidoylnitrene intermediate produced by decarboxylation of the 5-oxo-1,2,4-oxadiazole ring (oxadiazolone).",

keywords = "Azilsartan, Imidoylnitrene, Intramolecular cyclization, Phenanthridine, Photolysis",

author = "Takahiro Yoshikawa and Naoto Hayashi and Naoya Hatta and Masayuki Yokota",

note = "Publisher Copyright: {\textcopyright} 2021 Elsevier Ltd",

year = "2021",

month = jun,

day = "1",

doi = "10.1016/j.bmcl.2021.128011",

language = "英語",

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journal = "Bioorganic and Medicinal Chemistry Letters",

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TY - JOUR

T1 - Selective formation of a phenathridine derivative by photodegradation of azilsartan

AU - Yoshikawa, Takahiro

AU - Hayashi, Naoto

AU - Hatta, Naoya

AU - Yokota, Masayuki

PY - 2021/6/1

Y1 - 2021/6/1

N2 - Photodegradation of azilsartan produces a phenanthridine derivative, with its molecular structure determined by 1H and 13C NMR spectroscopy. This structure is confirmed by single-crystal X-ray diffraction and alternative synthesis. The phenanthridine ring formation is explained through the ring closure of an imidoylnitrene intermediate produced by decarboxylation of the 5-oxo-1,2,4-oxadiazole ring (oxadiazolone).

AB - Photodegradation of azilsartan produces a phenanthridine derivative, with its molecular structure determined by 1H and 13C NMR spectroscopy. This structure is confirmed by single-crystal X-ray diffraction and alternative synthesis. The phenanthridine ring formation is explained through the ring closure of an imidoylnitrene intermediate produced by decarboxylation of the 5-oxo-1,2,4-oxadiazole ring (oxadiazolone).

KW - Azilsartan

KW - Imidoylnitrene

KW - Intramolecular cyclization

KW - Phenanthridine

KW - Photolysis

UR - http://www.scopus.com/inward/record.url?scp=85104358195&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2021.128011

DO - 10.1016/j.bmcl.2021.128011

M3 - 学術論文

C2 - 33811993

AN - SCOPUS:85104358195

SN - 0960-894X

VL - 41

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

M1 - 128011

ER -

Selective formation of a phenathridine derivative by photodegradation of azilsartan

Abstract

Keywords

ASJC Scopus subject areas

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