Synthesis and antitumor activity of 7-ethyl-9-alkyl derivatives of camptothecin

Heyong Gao; Xiongwen Zhang; Yi Chen; Hongwu Shen; Jing Sun; Min Huang; Jian Ding; Chuan Li; Wei Lu

doi:10.1016/j.bmcl.2005.02.072

Synthesis and antitumor activity of 7-ethyl-9-alkyl derivatives of camptothecin

Heyong Gao
, Xiongwen Zhang
, Yi Chen
, Hongwu Shen
, Jing Sun
, Min Huang
, Jian Ding
, Chuan Li
, Wei Lu^*

^*Corresponding author for this work

CAS - Shanghai Institute of Materia Medica

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

14 Scopus citations

Abstract

A series of new camptothecin derivatives, as topoisomerase I inhibitor, were synthesized to identify potent antitumor agents. The synthesis method was based on the Claisen rearrangement of 10-allyloxy-7-ethylcamptothecin. All of the compounds were assayed for cytotoxicity against two human tumor cell lines, Bel7402, HCT116, and showed good potency in vitro. Compounds 2, 4, 9, were assessed for the stability of lactone in human plasma. And then compound 2 was tested for antitumor activity in vitro against mouse tumor sarcoma-180. The results suggested that the small alkyl groups in the both 7- and 9-positions of camptothecin could promote liposolubility, antitumor activity in vitro and vivo, though did not bring much increase of the stability of lactone.

Original language	English
Pages (from-to)	2003-2006
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	15
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2005.02.072
State	Published - 15 Apr 2005
Externally published	Yes

Keywords

Antitumor activity
Camptothecin
Topoisomerase I

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10.1016/j.bmcl.2005.02.072

Cite this

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title = "Synthesis and antitumor activity of 7-ethyl-9-alkyl derivatives of camptothecin",

abstract = "A series of new camptothecin derivatives, as topoisomerase I inhibitor, were synthesized to identify potent antitumor agents. The synthesis method was based on the Claisen rearrangement of 10-allyloxy-7-ethylcamptothecin. All of the compounds were assayed for cytotoxicity against two human tumor cell lines, Bel7402, HCT116, and showed good potency in vitro. Compounds 2, 4, 9, were assessed for the stability of lactone in human plasma. And then compound 2 was tested for antitumor activity in vitro against mouse tumor sarcoma-180. The results suggested that the small alkyl groups in the both 7- and 9-positions of camptothecin could promote liposolubility, antitumor activity in vitro and vivo, though did not bring much increase of the stability of lactone.",

keywords = "Antitumor activity, Camptothecin, Topoisomerase I",

author = "Heyong Gao and Xiongwen Zhang and Yi Chen and Hongwu Shen and Jing Sun and Min Huang and Jian Ding and Chuan Li and Wei Lu",

year = "2005",

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doi = "10.1016/j.bmcl.2005.02.072",

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TY - JOUR

T1 - Synthesis and antitumor activity of 7-ethyl-9-alkyl derivatives of camptothecin

AU - Gao, Heyong

AU - Zhang, Xiongwen

AU - Chen, Yi

AU - Shen, Hongwu

AU - Sun, Jing

AU - Huang, Min

AU - Ding, Jian

AU - Li, Chuan

AU - Lu, Wei

PY - 2005/4/15

Y1 - 2005/4/15

N2 - A series of new camptothecin derivatives, as topoisomerase I inhibitor, were synthesized to identify potent antitumor agents. The synthesis method was based on the Claisen rearrangement of 10-allyloxy-7-ethylcamptothecin. All of the compounds were assayed for cytotoxicity against two human tumor cell lines, Bel7402, HCT116, and showed good potency in vitro. Compounds 2, 4, 9, were assessed for the stability of lactone in human plasma. And then compound 2 was tested for antitumor activity in vitro against mouse tumor sarcoma-180. The results suggested that the small alkyl groups in the both 7- and 9-positions of camptothecin could promote liposolubility, antitumor activity in vitro and vivo, though did not bring much increase of the stability of lactone.

AB - A series of new camptothecin derivatives, as topoisomerase I inhibitor, were synthesized to identify potent antitumor agents. The synthesis method was based on the Claisen rearrangement of 10-allyloxy-7-ethylcamptothecin. All of the compounds were assayed for cytotoxicity against two human tumor cell lines, Bel7402, HCT116, and showed good potency in vitro. Compounds 2, 4, 9, were assessed for the stability of lactone in human plasma. And then compound 2 was tested for antitumor activity in vitro against mouse tumor sarcoma-180. The results suggested that the small alkyl groups in the both 7- and 9-positions of camptothecin could promote liposolubility, antitumor activity in vitro and vivo, though did not bring much increase of the stability of lactone.

KW - Antitumor activity

KW - Camptothecin

KW - Topoisomerase I

UR - https://www.scopus.com/pages/publications/15944380477

U2 - 10.1016/j.bmcl.2005.02.072

DO - 10.1016/j.bmcl.2005.02.072

M3 - 文章

C2 - 15808456

AN - SCOPUS:15944380477

SN - 0960-894X

VL - 15

SP - 2003

EP - 2006

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 8

ER -

Synthesis and antitumor activity of 7-ethyl-9-alkyl derivatives of camptothecin

Abstract

Keywords

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