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Your search keyword '"4-Butyrolactone chemistry"' showing total 2 results
Start Over Descriptor "4-Butyrolactone chemistry" Region indian ocean
2 results on '"4-Butyrolactone chemistry"'

1. Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors.

Author

Hassan HM, Sallam AA, Mohammed R, Hifnawy MS, Youssef DT, and El Sayed KA

Subjects
4-Butyrolactone chemistry, 4-Butyrolactone pharmacology, 4-Butyrolactone therapeutic use, Animals, Anthozoa chemistry, Antineoplastic Agents pharmacology, Antineoplastic Agents therapeutic use, Cell Line, Tumor, Cell Migration Assays, Diterpenes chemical synthesis, Diterpenes chemistry, Diterpenes pharmacology, Diterpenes therapeutic use, Drug Screening Assays, Antitumor, Female, Humans, Indian Ocean, Male, Structure-Activity Relationship, 4-Butyrolactone analogs & derivatives, Antineoplastic Agents chemistry, Breast Neoplasms drug therapy, Cell Migration Inhibition drug effects, Cell Proliferation drug effects, Prostatic Neoplasms drug therapy
Abstract

Sarcophine (1) is a bioactive cembranoid diterpene isolated from the Red Sea soft coral Sarcophyton glaucum. Previous semisynthesis attempts resulted in decreased or complete loss of 1's anticancer activity. Sarcophine and analogues showed antimigratory activity against breast and prostate cancer cell lines. This encouraged further semisynthestic optimizations to improve its activity and establish a preliminary structure-activity relationship. Eight new and five known semisynthetic analogues were generated. These compounds were evaluated for their ability to inhibit growth, proliferation, and migration of the prostate and breast metastatic cancer cell lines PC-3 and MDA-MB-231, respectively. Most analogues exhibited enhanced antimigratory activity., (Copyright © 2011 Elsevier Ltd. All rights reserved.)

Published
2011
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2. Semisynthesis of new sarcophine derivatives with chemopreventive activity.

Author

Katsuyama I, Fahmy H, Zjawiony JK, Khalifa SI, Kilada RW, Konoshima T, Takasaki M, and Tokuda H

Subjects
4-Butyrolactone chemistry, 4-Butyrolactone pharmacology, Animals, Anthozoa, Anticarcinogenic Agents chemistry, Anticarcinogenic Agents classification, Anticarcinogenic Agents pharmacology, Antigens, Viral metabolism, Chemoprevention methods, Dose-Response Relationship, Drug, Egypt, Hydroxylation, Indian Ocean, Models, Molecular, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, Oxidation-Reduction, Selenium Compounds, Selenium Oxides, Stereoisomerism, Structure-Activity Relationship, 4-Butyrolactone analogs & derivatives, 4-Butyrolactone chemical synthesis, Anticarcinogenic Agents isolation & purification
Abstract

The natural cembranolide sarcophine (3) and its lactone ring-opened analogue (10) were oxidized using selenium dioxide under different reaction temperatures to prepare hydroxylated derivatives. Nine new compounds were obtained, six of them targeted hydroxylated derivatives. The determination of regio- and stereochemistry as well as the mechanistic considerations on the selectivity observed in these reactions are discussed on the basis of 2D NMR and molecular modeling. In preliminary in vitro tests on inhibition of EBV-EA activation, compounds 10 and 12-15 have shown higher activity than the known chemopreventive agent sarcophytol A.

Published
2002
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