54895-19-1Relevant academic research and scientific papers
ZrCl4/TMSCl as an efficient catalyst for synthesis of 4,6-substituted 2-alkylthio-6H-1,3-thiazines
Halimehjani,Airamlounezhad
, p. 1147 - 1150 (2014)
4,6-Substituted-2-alkylthio-6H-1,3-thiazines were synthesized by the reaction of S-alkyl dithiocarbamates and α, β-unsaturated ketones in the presence of ZrCl4/TMSCl. The procedure is simple and efficient and gives good to high yields of produc
Synthesis, cytotoxic evaluation, and molecular docking study of 4,5-diaryl-thiazole-2-thione analogs of combretastatin A-4 as microtubule-binding agents
Salehi, Marjan,Ostad, Seyed Nasser,Riazi, Gholam Hossein,Assadieskandar, Amir,Cheraghi-Shavi, Tayebeh,Shafiee, Abbas,Amini, Mohsen
, p. 1465 - 1473 (2014/03/21)
A series of combretastatin A-4 analogs in which cis-olefinic bond replaced by thiazole ring were prepared by reaction of α-bromo-1,2-(p-substituted) diaryl-1-ethanones and dithiocarbamate derivatives. The cytotoxicity of these compounds was determined against three cancer cell lines (HT-29), (MCF-7), (AGS) as well as fibroblastic cell line (NIH-3T3) using MTT assay. Inhibition of tubulin polymerization for some potent compounds was evaluated. These biological studies proved that 6j and 6o were the most potent compounds in this series. Furthermore 2-(methylthio)-substituted compounds show moderate or no activity. Docking studies involving 6j and 6o demonstrated that this analogs could be successfully docked in the colchicine binding site of α,β-tubulin.
Synthesis, cytotoxic evaluation and molecular docking study of 2-alkylthio-4-(2,3,4-trimethoxyphenyl)-5-aryl-thiazoles as tubulin polymerization inhibitors
Salehi, Marjan,Amini, Mohsen,Ostad, Seyed Nasser,Riazi, Gholam Hossein,Assadieskandar, Amir,Shafiei, Bentolhoda,Shafiee, Abbas
, p. 7648 - 7654 (2014/01/06)
A series of cis-restricted 2-alkylthio-4-(2,3,4-trimethoxyphenyl)-5-aryl- thiazole analogues of combretastatin A-4 were synthesized and investigated for inhibition of cell proliferation against three cancer cell lines, HT-29, MCF-7, and AGS, and a normal mouse fibroblastic cell line, NIH-3T3, using an MTT assay. The biological study showed that 2-(methylthio) substituted compounds showed little cytotoxic activity against the four cell lines. In contrast, the presence of the 2-(benzylthio) group on the thiazole ring resulted in a significant improvement in cytotoxic activity relative to the 2-(methylthio) substituted derivatives. Furthermore, the inhibition of tubulin polymerization by some potent compounds was evaluated. All the compounds studied were moderate tubulin polymerization inhibitors. The flow cytometry analysis confirmed that the synthesized compounds led to cell cycle arrest at the G2/M phase. Docking simulation was performed to insert these compounds into the crystal structure of tubulin at the colchicine binding site to determine a probable binding model.
Syntheses of 2-alkylthio-1,3-thiazine derivatives from S-alkyldithiocarbamates and α,β-unsaturated ketones
Koketsu, Mamoru,Okumura, Miki,Ishihara, Hideharu
, p. 377 - 379 (2007/10/03)
Various 2-alkylthio-1,3-thiazine derivatives were synthesized by the reactions of S-alkylthiocarbamates with α,β-unsaturated ketones in the presence of BF3 · Et2O. The thiazine was converted into two isomeric dehydrated products in t
THIA-1 AZA-3 BUTADIENES SUBSTITUES: ACTION DU CETENE ET DERIVES
Gokou, Celestin Tea,Chehna, Moustafa,Pradere, Jean-Paul,Duguay, Guy,Toupet, Loic
, p. 327 - 340 (2007/10/02)
Novel, diversely substituted 1-thia 3-aza butadienes have been prepared and reacted with ketene or its derivatives.Via a general (4+2) cycloaddition reaction, they afford functionalised 6H-1,3-thiazine 6-ones, the electrophilic properties of which are described.This cycloaddition gives rise to other reaction products resulting from the addition of two or three molecules of ketene according to the nature of the substituents.
Preparative Methods for Dialkyl Dithioseleno- and Thiodiselenocarbonates
Yokoyama, Masataka,Hatanaka, Hidekatsu
, p. 891 - 892 (2007/10/02)
Preparative scale synthesis for S,Se-, Se,Se'- and S,S'-dialkyl (di)thioselenocarbonates 1-4 are described.
