European Journal of Medicinal Chemistry 2011-11-01

Novel natural product-based cinnamates and their thio and thiono analogs as potent inhibitors of cell adhesion molecules on human endothelial cells.

Sarvesh Kumar, Brajendra K Singh, Pragya Arya, Shashwat Malhotra, Rajesh Thimmulappa, Ashok K Prasad, Erik Van der Eycken, Carl E Olsen, Anthony L DePass, Shyam Biswal, Virinder S Parmar, Balaram Ghosh

Index: Eur. J. Med. Chem. 46 , 5498-511, (2011)

Full Text: HTML

Abstract

In the present study, we report the design and synthesis of novel analogs of cinnamates, thiocinnamates and thionocinnamates and evaluated the potencies of these analogs to inhibit TNF-α induced ICAM-1 expression on human endothelial cells. By using whole cell-ELISA, our screening data demonstrated that ethyl 3',4',5'-trimethoxythionocinnamate (ETMTC) is the most potent inhibitor of TNF-α induced ICAM-1, VCAM-1 and E-selectin. As functional consequences, ETMTC abrogated TNF-α induced adhesion of neutrophils to the endothelial monolayer. Structure-activity relationship studies revealed the critical role of the chain-length of the alkyl group in the alcohol moiety, number of methoxy groups in the aromatic ring of the cinnamoyl moiety and the presence of the α, β- C-C double bond in the thiocinnamates and thionocinnamates.Copyright © 2011 Elsevier Masson SAS. All rights reserved.


Related Compounds

Related Articles:

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

2010-01-01

[Chem. Res. Toxicol. 23 , 171-83, (2010)]

Translating clinical findings into knowledge in drug safety evaluation--drug induced liver injury prediction system (DILIps).

2011-12-01

[J. Sci. Ind. Res. 65(10) , 808, (2006)]

Development and validation of an LC-MS/MS method for the determination of mesalazine in beagle dog plasma and its application to a pharmacokinetic study.

2015-02-01

[Biomed. Chromatogr. 29(2) , 261-7, (2015)]

A new approach for automated liquid-liquid extraction in a sequential injection manifold.

2015-01-01

[Anal. Bioanal. Chem 407(2) , 521-8, (2015)]

Prediction and identification of drug interactions with the human ATP-binding cassette transporter multidrug-resistance associated protein 2 (MRP2; ABCC2).

2008-06-12

[J. Med. Chem. 51 , 3275-87, (2008)]

More Articles...