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

[1] Synthesis and Pharmacological Evaluation of Novel Homocamptothecin-Dihydropyridine Derivative Conjugates as Potent Topoisomerase I Inhibitors
Zhu, Ling-Jian
Zhuang, Chun-Lin
Lei, Ning
Sheng, Chun-Quan
Guo, Wei
Miao, Zhen-Yuan
Liu, Wen-Feng
Yao, Jian-Zhong
Zhang, Wan-Nian
AUSTRALIAN JOURNAL OF CHEMISTRY, 2011, 64 (10) : 1390 - 1396
[2] Synthesis and cytotoxicity of novel 20-O-linked homocamptothecin ester derivatives as potent topoisomerase I inhibitors
Li, Di-Zao
Wang, Cun-Ying
Liu, Rui-Hua
Wang, Yan-Ming
Ji, Teng-Fei
Li, Yu-Rong
Pan, Xian-Dao
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2013, 15 (11) : 1179 - 1188
[3] Synthesis and Biological Evaluation of Novel Homocamptothecins Conjugating with Dihydropyrimidine Derivatives as Potent Topoisomerase I Inhibitors
Zhu, Lingjian
Cheng, Pengfei
Lei, Ning
Yao, Jianzhong
Sheng, Chunquan
Zhuang, Chunlin
Guo, Wei
Liu, Wenfeng
Zhang, Yongqiang
Dong, Guoqiang
Wang, Shengzhang
Miao, Zhenyuan
Zhang, Wannian
ARCHIV DER PHARMAZIE, 2011, 344 (11) : 726 - 734
[4] The homocamptothecin, BN 80927, is a potent topoisomerase I poison and topoisomerase II catalytic inhibitor
Demarquay, D
Coulomb, H
Huchet, M
Lesueur-Ginot, L
Camara, J
Lavergne, O
Bigg, D
CAMPTOTHECINS: UNFOLDING THEIR ANTICANER POTENTIAL, 2000, 922 : 301 - 302
[5] Design, synthesis and evaluation of thiohydantoin derivatives as potent topoisomerase I (Top1) inhibitors with anticancer activity
Majumdar, Papiya
Bathula, Chandramohan
Basu, Suparna M.
Das, Subhendu K.
Agarwal, Rahul
Hati, Santanu
Singh, Ashutosh
Sen, Subhabrata
Das, Benu Brata
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 102 : 540 - 551
[6] SYNTHESIS AND KINETIC EVALUATION OF 1H-BENZIMIDAZOLE DERIVATIVES AS MAMMALIAN DNA TOPOISOMERASE I INHIBITORS
Zencir, Sevil
Alpan, Selcen A.
Alcil, Pinar
Coban, Gunes
Gunes, Semih
Topcu, Zeki
DRUG METABOLISM REVIEWS, 2007, 39 : 220 - 220
[7] Synthesis and Biological Evaluation of 7-Alkenyl Homocamptothecins as Potent Topoisomerase I Inhibitors
Zhu, Lingjian
Zhang, Xianghua
Lei, Ning
Liu, Wenfeng
Miao, Zhenyuan
Zhuang, Chunlin
Sheng, Chunquan
Guo, Wei
Dong, Guoqiang
Yao, Jianzhong
Cheng, Pengfei
Zhang, Wannian
CHEMISTRY & BIODIVERSITY, 2012, 9 (06) : 1084 - 1094
[8] Synthesis and identification of quinoline derivatives as topoisomerase I inhibitors with potent antipsoriasis activity in an animal model
Zhang, Wen-Jin
Li, Peng-Hui
Zhao, Min-Cong
Gu, Yao-Hao
Dong, Chang-Zhi
Chen, Hui-Xiong
Du, Zhi-Yun
BIOORGANIC CHEMISTRY, 2019, 88
[9] The homocamptothecin BN 80915 is a highly potent orally active topoisomerase I poison
Demarquay, D
Huchet, M
Coulomb, H
Lesueur-Ginot, L
Lavergne, O
Kasprzyk, PG
Bailly, C
Camara, J
Bigg, DCH
ANTI-CANCER DRUGS, 2001, 12 (01) : 9 - 19
[10] Synthesis and Biological Assays of 9-(Acylamino)homocamptothecins as DNA Topoisomerase I Inhibitors
Guo, Wei
Dong, Guoqiang
Zhu, Lingjian
Liu, Wenfeng
Zhuang, Chunlin
Guo, Zizhao
Yao, Jianzhong
Sheng, Chunquan
Zhang, Huojun
Miao, Zhenyuan
Zhang, Wannian
CHEMISTRY & BIODIVERSITY, 2013, 10 (10) : 1804 - 1815

← 1 2 3 4 5 →