Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

Takashi Nishiyama; Noriyuki Hatae; Teruki Yoshimura; Sawa Takaki; Takumi Abe; Minoru Ishikura; Satoshi Hibino; Tominari Choshi

doi:10.1016/j.ejmech.2016.05.065

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

Takashi Nishiyama, Noriyuki Hatae, Teruki Yoshimura, Sawa Takaki, Takumi Abe, Minoru Ishikura, Satoshi Hibino, Tominari Choshi

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

22 Citations (Scopus)

Abstract

We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O₂ atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

Original language	English
Pages (from-to)	561-577
Number of pages	17
Journal	European Journal of Medicinal Chemistry
Volume	121
DOIs	https://doi.org/10.1016/j.ejmech.2016.05.065
Publication status	Published - Oct 4 2016
Externally published	Yes

Keywords

Antiproliferative activity
Carbazole-1,4-quinone
Koeniginequinone A
Koeniginequinone B

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.ejmech.2016.05.065

Cite this

@article{005ef1d2bbfd429b9e7fabef50613a6d,

title = "Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells",

abstract = "We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.",

keywords = "Antiproliferative activity, Carbazole-1,4-quinone, Koeniginequinone A, Koeniginequinone B",

author = "Takashi Nishiyama and Noriyuki Hatae and Teruki Yoshimura and Sawa Takaki and Takumi Abe and Minoru Ishikura and Satoshi Hibino and Tominari Choshi",

note = "Funding Information: This work was partly supported by Fukuyama University Grant for Academic Research Projects (Grant Number: GARP2014-209 (T.N.)). Publisher Copyright: {\textcopyright} 2016 Elsevier Masson SAS.",

year = "2016",

month = oct,

day = "4",

doi = "10.1016/j.ejmech.2016.05.065",

language = "English",

volume = "121",

pages = "561--577",

journal = "CHIM.THER.",

issn = "0223-5234",

publisher = "Elsevier Masson SAS",

}

TY - JOUR

T1 - Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

AU - Nishiyama, Takashi

AU - Hatae, Noriyuki

AU - Yoshimura, Teruki

AU - Takaki, Sawa

AU - Abe, Takumi

AU - Ishikura, Minoru

AU - Hibino, Satoshi

AU - Choshi, Tominari

N1 - Funding Information: This work was partly supported by Fukuyama University Grant for Academic Research Projects (Grant Number: GARP2014-209 (T.N.)). Publisher Copyright: © 2016 Elsevier Masson SAS.

PY - 2016/10/4

Y1 - 2016/10/4

N2 - We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

AB - We report a convenient synthesis of carbazole-1,4-quinone alkaloid koeniginequinones A and B using a tandem ring-closing metathesis with the dehydrogenation reaction sequence under an O2 atmosphere as an important step. Using this method, carbazole-1,4-quinones substituted at the 5-, 6-, 7-, and/or 8-positions have been synthesized. Moreover, 24 compounds, including koeniginequinones A and B, have been evaluated for their antiproliferative activity against HCT-116 and HL-60 cells, and the 6-nitro analog exhibited the most potent activity against both tumor cell types.

KW - Antiproliferative activity

KW - Carbazole-1,4-quinone

KW - Koeniginequinone A

KW - Koeniginequinone B

UR - http://www.scopus.com/inward/record.url?scp=84975144885&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84975144885&partnerID=8YFLogxK

U2 - 10.1016/j.ejmech.2016.05.065

DO - 10.1016/j.ejmech.2016.05.065

M3 - Article

C2 - 27318980

AN - SCOPUS:84975144885

SN - 0223-5234

VL - 121

SP - 561

EP - 577

JO - CHIM.THER.

JF - CHIM.THER.

ER -

Concise synthesis of carbazole-1,4-quinones and evaluation of their antiproliferative activity against HCT-116 and HL-60 cells

Abstract

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this