A novel, broad-spectrum antitumor compound containing the 1-hydroxycyclohexa-2,5-dien-4-one group: the disclosure of a new antitumor pharmacophore in protoapigenone 1

Qianying Yuan; Ziwei Liu; Chaomei Xiong; Liqian Wu; Jianping Wang; Jinlan Ruan

doi:10.1016/j.bmcl.2011.03.108

A novel, broad-spectrum antitumor compound containing the 1-hydroxycyclohexa-2,5-dien-4-one group: the disclosure of a new antitumor pharmacophore in protoapigenone 1

Bioorg Med Chem Lett. 2011 Jun 1;21(11):3427-30. doi: 10.1016/j.bmcl.2011.03.108. Epub 2011 Apr 5.

Authors

Qianying Yuan¹, Ziwei Liu, Chaomei Xiong, Liqian Wu, Jianping Wang, Jinlan Ruan

Affiliation

¹ Key Laboratory of Natural Medicinal Chemistry and Resources Evaluation of Hubei Province, College of Pharmacy, Tongji Medical Center of Huazhong University of Science and Technology, Wuhan 430030, China.

PMID: 21515048
DOI: 10.1016/j.bmcl.2011.03.108

Abstract

The synthesis of a new compound 9 containing the 4-hydroxy-2,5-cyclohexadien-1-one system, a key elements toward elucidation of the protoapigenone 1 antitumor pharmacophore, was described. The compound showed potent in vitro antitumor potency with low micromolar IC(50)'s against breast, ovarian, prostate, liver, pancreas, and blood cancer cell lines tested and could inhibit tumor growth in vivo but no significant impairment of hematopoiesis or immune function was observed. The minimum structural pharmacophore of 1 has now been refined.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / chemistry
Antineoplastic Agents / pharmacology*
Cell Line, Tumor
Cell Proliferation / drug effects
Cyclohexanones / chemical synthesis*
Cyclohexanones / chemistry
Cyclohexanones / pharmacology*
Female
Flavones / chemical synthesis*
Flavones / chemistry
Flavones / pharmacology*
Humans
Inhibitory Concentration 50
Male
Neoplasms / drug therapy

Substances

Antineoplastic Agents
Cyclohexanones
Flavones
protoapigenone