Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines

Hsueh Yun Lee; Lin Wen Lee; Chih Ying Nien; Ching Chuan Kuo; Pen Yuan Lin; Chi Yen Chang; Jang Yang Chang; Jing Ping Liou

doi:10.1039/c2ob26614h

Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines

Hsueh Yun Lee
, Lin Wen Lee
, Chih Ying Nien
, Ching Chuan Kuo
, Pen Yuan Lin
, Chi Yen Chang
, Jang Yang Chang
, Jing Ping Liou

Department of Oncology

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

6 Citations (Scopus)

Abstract

A variety of functionalities were introduced at 2-aroylquinoline's C5 position, which is considered equivalent to C-3′ of the B-ring of CA4, via Suzuki arylation, Sonogashira ethynylation, and Rosenmund-von Braun cyanation. These substitutions are rarely utilized in the modification of 3′-OH of CA4. The resulting products 6 and 7 having cyano and ethynyl groups exhibited comparable antiproliferative and tubulin inhibitory activities to colchicine.

Original language	English
Pages (from-to)	9593-9600
Number of pages	8
Journal	Organic and Biomolecular Chemistry
Volume	10
Issue number	48
DOIs	https://doi.org/10.1039/c2ob26614h
Publication status	Published - 2012

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c2ob26614h

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Lee, H. Y., Lee, L. W., Nien, C. Y., Kuo, C. C., Lin, P. Y., Chang, C. Y., Chang, J. Y., & Liou, J. P. (2012). Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines. Organic and Biomolecular Chemistry, 10(48), 9593-9600. https://doi.org/10.1039/c2ob26614h

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title = "Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines",

abstract = "A variety of functionalities were introduced at 2-aroylquinoline's C5 position, which is considered equivalent to C-3′ of the B-ring of CA4, via Suzuki arylation, Sonogashira ethynylation, and Rosenmund-von Braun cyanation. These substitutions are rarely utilized in the modification of 3′-OH of CA4. The resulting products 6 and 7 having cyano and ethynyl groups exhibited comparable antiproliferative and tubulin inhibitory activities to colchicine.",

author = "Lee, \{Hsueh Yun\} and Lee, \{Lin Wen\} and Nien, \{Chih Ying\} and Kuo, \{Ching Chuan\} and Lin, \{Pen Yuan\} and Chang, \{Chi Yen\} and Chang, \{Jang Yang\} and Liou, \{Jing Ping\}",

year = "2012",

doi = "10.1039/c2ob26614h",

language = "English",

volume = "10",

pages = "9593--9600",

journal = "Organic and Biomolecular Chemistry",

issn = "1477-0520",

publisher = "Royal Society of Chemistry",

number = "48",

}

Lee, HY, Lee, LW, Nien, CY, Kuo, CC, Lin, PY, Chang, CY, Chang, JY & Liou, JP 2012, 'Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines', Organic and Biomolecular Chemistry, vol. 10, no. 48, pp. 9593-9600. https://doi.org/10.1039/c2ob26614h

Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines. / Lee, Hsueh Yun; Lee, Lin Wen; Nien, Chih Ying et al.
In: Organic and Biomolecular Chemistry, Vol. 10, No. 48, 2012, p. 9593-9600.

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

TY - JOUR

T1 - Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines

AU - Lee, Hsueh Yun

AU - Lee, Lin Wen

AU - Nien, Chih Ying

AU - Kuo, Ching Chuan

AU - Lin, Pen Yuan

AU - Chang, Chi Yen

AU - Chang, Jang Yang

AU - Liou, Jing Ping

PY - 2012

Y1 - 2012

N2 - A variety of functionalities were introduced at 2-aroylquinoline's C5 position, which is considered equivalent to C-3′ of the B-ring of CA4, via Suzuki arylation, Sonogashira ethynylation, and Rosenmund-von Braun cyanation. These substitutions are rarely utilized in the modification of 3′-OH of CA4. The resulting products 6 and 7 having cyano and ethynyl groups exhibited comparable antiproliferative and tubulin inhibitory activities to colchicine.

AB - A variety of functionalities were introduced at 2-aroylquinoline's C5 position, which is considered equivalent to C-3′ of the B-ring of CA4, via Suzuki arylation, Sonogashira ethynylation, and Rosenmund-von Braun cyanation. These substitutions are rarely utilized in the modification of 3′-OH of CA4. The resulting products 6 and 7 having cyano and ethynyl groups exhibited comparable antiproliferative and tubulin inhibitory activities to colchicine.

UR - https://www.scopus.com/pages/publications/84870050029

UR - https://www.scopus.com/pages/publications/84870050029#tab=citedBy

U2 - 10.1039/c2ob26614h

DO - 10.1039/c2ob26614h

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AN - SCOPUS:84870050029

SN - 1477-0520

VL - 10

SP - 9593

EP - 9600

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

IS - 48

ER -

Application of Suzuki arylation, Sonogashira ethynylation and Rosenmund-von Braun cyanation in the exploration of substitution effects on the anticancer activity of 2-aroylquinolines

Abstract

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