Synthesis and evaluation of 9-benzylideneamino derivatives of homocamptothecin as potent inhibitors of DNA topoisomerase I

被引：17

作者：

Guo, Wei ^{[1
]}

Miao, Zhenyuan ^{[1
]}

Sheng, Chunquan ^{[1
]}

Yao, Jianzhong ^{[1
]}

Feng, Hao ^{[1
]}

Zhang, Wannian ^{[1
]}

Zhu, Lingjian ^{[1
]}

Liu, Wenfeng ^{[1
]}

Cheng, Pengfei ^{[1
]}

Zhang, Jing ^{[1
]}

Che, Xiaoying ^{[1
]}

Wang, Wenya ^{[1
]}

Luo, Chuan ^{[1
]}

Xu, Yulan ^{[1
]}

机构：

[1] Second Mil Med Univ, Sch Pharm, Shanghai 200433, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 06期

基金：

中国国家自然科学基金;

关键词：

Homocamptothecin; 9-Benzylideneamino; Antitumor activity; Synthesis; RING-MODIFIED CAMPTOTHECIN; ANTITUMOR-ACTIVITY; PHASE-I; ANALOGS; DRUGS;

D O I：

10.1016/j.ejmech.2010.01.063

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of novel 9-benzylideneamino derivatives of homocamptothecin were synthesized via Friedlaender cyclization from our obtained intermediate 5. All the compounds were evaluated for in vitro cytotoxicity against three cancer cell lines (A549, LOVO and MDA-MB-435). Most of these derivatives possessed potent growth inhibitory effect on all the tested cell lines and four compounds (6d, 6f, 6i, 6k) showed higher inhibitory activities with the IC50 values of 2.3 nM-9.8 nM against breast cancer cell than topotecan. As compared to CPT, compound 61 revealed higher topoisomerase I inhibitory activity.

引用

页码：2223 / 2228

页数：6

共 50 条

[31] Heterocyclic bibenzimidazole derivatives as topoisomerase I inhibitors
Jin, S
Kim, JS
Sim, SP
Liu, A
Pilch, DS
Liu, LF
LaVoie, EJ
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (08) : 719 - 723
[32] Anthracycline antibiotics and their derivatives, inhibitors of topoisomerase I
Dezhenkova, L. G.
Tevyashova, A. N.
Sureva, E. N.
Treshchalin, I. A.
Shfil, A. A.
Preobrazhenskaya, M. N.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY, 2008, 34 (03) : 387 - 389
[33] Anthracycline antibiotics and their derivatives, inhibitors of topoisomerase I
L. G. Dezhenkova
A. N. Tevyashova
E. N. Olsuf’eva
I. D. Treshchalin
A. A. Shtil
M. N. Preobrazhenskaya
Russian Journal of Bioorganic Chemistry, 2008, 34 : 387 - 389
[34] Novel camptothecin derivatives as topoisomerase I inhibitors
Basili, Serena
Moro, Stefano
EXPERT OPINION ON THERAPEUTIC PATENTS, 2009, 19 (05) : 555 - 574
[35] Synthesis of 9-(Heteroarylmethylidene)amino Derivatives of Homocamptothecin with Biological Activities
Guo, Wei
Miao, Zhenyuan
Sheng, Chunquan
Yao, Jianzhong
Liu, Wenfeng
Zhu, Lingjian
Zhang, Yongqiang
Cheng, Pengfei
Dong, Guoqiang
Zhuang, Chunlin
Zhang, Wannian
CHEMISTRY & BIODIVERSITY, 2011, 8 (07) : 1266 - 1273
[36] Design, synthesis and evaluation of flavonoid derivatives as potent AChE inhibitors
Sheng, Rong
Lin, Xiao
Zhang, Jing
Chol, Kim Sun
Huang, Wenhai
Yang, Bo
He, Qiaojun
Hu, Yongzhou
BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (18) : 6692 - 6698
[37] Synthesis and Evaluation of Novel Xanthone Derivatives as Potent AChE Inhibitors
Qu, Falin
Bai, Guojing
Dong, Wenshen
Yang, Yan
Jin, Yongsheng
Meng, Qingguo
Wu, Qiuye
Guo, Wei
Yu, Shichong
ASIAN JOURNAL OF CHEMISTRY, 2014, 26 (12) : 3496 - 3498
[38] Design, Synthesis and Biological Evaluation of Novel 9H Purine Derivatives as Potent CDK9 Inhibitors
Tang, Chunlei
Wang, Dong
Wang, Huabing
Cui, Shengkai
Fan, Weizheng
Zhang, Yan
CHEMICAL BIOLOGY & DRUG DESIGN, 2025, 105 (02)
[39] Synthesis and evaluation of indenoisoquinoline topoisomerase I inhibitors substituted with nitrogen heterocycles
Nagarajan, Muthukaman
Morrell, Andrew
Ioanoviciu, Alexandra
Antony, Smitha
Kohlhagen, Glenda
Agama, Keli
Hollingshead, Melinda
Pommier, Yves
Cushman, Mark
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (21) : 6283 - 6289
[40] A new scaffold of topoisomerase I inhibitors: Design, synthesis and biological evaluation
Mazza, Alberto
Beccalli, Egle M.
Contini, Alessandro
Garcia-Argaez, Aida Nelly
Via, Lisa Dalla
Gelmi, Maria Luisa
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2016, 124 : 326 - 339

← 1 2 3 4 5 →