Bioorganic and Medicinal Chemistry Letters p. 3364 - 3368 (2008)
Update date:2022-08-04
Topics:
Shi, Aibin
Nguyen, Thu A.
Battina, Srinivas K.
Rana, Sandeep
Takemoto, Dolores J.
Chiang, Peter K.
Hua, Duy H.
Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy)anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy)quinoline (14). The amino function of 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline, prepared from 14, was connected to various side chains via alkylation with N-(3-iodopropyl)phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC50 value of 6-methoxy-8-[(2-furanylmethyl)amino]-4-methyl-5-(3-trifluoromethylphenyl oxy)quinoline is 16 ± 3 nM, the lowest IC50 out of all the quinolines tested. IC50 values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing.
View MoreHangzhou Ocean Chemical Co., Ltd.
website:http://www.hzoceanchem.com
Contact:+86-571-88025872, 28272092, 28272096
Address:Room 623 ,Building No 1 , COFCO Radius Commercial Center Xiwen Road, Xiacheng District, Hangzhou, Zhejiang Province, China
Contact:+86-21-61318535
Address:Building 29,No.2139 Xizha Road, Fengxian District, Shanghai
QINGDAO NEW FLOURISH INTERNATIOANAL TRADE CO., LTD.
Contact:+86 532 80861829
Address:No. 1, Yinchuan East Road, 266061, Qingdao, China
Lianyungang Yunbo Chemical Co.,Ltd.
Contact:518-81066110
Address:B907,Dongsheng"Mingdu Square,21-2 East Chaoyang Road,Xinpu,(sale department)
Contact:(86) 731 88718666
Address:Room 1222, Unit 4, Building B, Shangcheng, No.47, Kaiyuan East Road.
Doi:10.1080/00397910801989600
(2008)Doi:10.1021/ol8011452
(2008)Doi:10.1021/acs.jmedchem.0c01345
(2020)Doi:10.1021/jo01281a005
(1967)Doi:10.1021/jo800932t
(2008)Doi:10.1246/bcsj.38.339
(1965)