Rational design, synthesis and structure-activity relationships of antitumor (E)-2-benzylidene-1-tetralones and (E)-2-benzylidene-1-indanones

H Shih; L Deng; C J Carrera; S Adachi; H B Cottam; D A Carson

doi:10.1016/s0960-894x(00)00032-9

Rational design, synthesis and structure-activity relationships of antitumor (E)-2-benzylidene-1-tetralones and (E)-2-benzylidene-1-indanones

Bioorg Med Chem Lett. 2000 Mar 6;10(5):487-90. doi: 10.1016/s0960-894x(00)00032-9.

Authors

H Shih¹, L Deng, C J Carrera, S Adachi, H B Cottam, D A Carson

Affiliation

¹ The Sam and Rose Stein Institute for Research on Aging and Department of Medicine, University of California San Diego, La Jolla 92093-0663, USA. hshih@ucsd.edu

PMID: 10743954
DOI: 10.1016/s0960-894x(00)00032-9

Abstract

Novel substituted 6,7-dimethoxy-1-tetralones and 5,6-dimethoxy-1-indanones have been synthesized and evaluated for their cytotoxicity. Compounds with 3'-lipophilic, 3',5'-dilipophilic, or 3',5'-dilipophilic-4'-hydrophilic substituents on (E)-2-benzylidene moiety showed highly cytotoxic effects. The unique structure of 42 possibly matches the pharmacophore features for these cytotoxic compounds.

MeSH terms

Antineoplastic Agents / chemical synthesis*
Antineoplastic Agents / pharmacology
Benzylidene Compounds / chemical synthesis*
Benzylidene Compounds / pharmacology
Drug Screening Assays, Antitumor
Humans
Jurkat Cells
Magnetic Resonance Spectroscopy
Molecular Conformation
Structure-Activity Relationship
Tetrazolium Salts
Thiazoles
Tumor Cells, Cultured

Substances

Antineoplastic Agents
Benzylidene Compounds
Tetrazolium Salts
Thiazoles
thiazolyl blue