146397-67-3

Upstream product

• 16420-13-6 N,N-Dimethylthiocarbamoyl chloride 
• 621-59-0 isovanillin 

Downstream Products

• 146397-69-5 S-(5-formyl-2-methoxyphenyl)-N,N-dimethylthiocarbamate 
• 151792-90-4 2-<3-N,N-(Dimethylcarbamoylthio)-4-methoxyphenyl>-4H-3,1-benzoxathiine 

Relevant academic research and scientific papers

Synthesis and crystal structures of cis- and trans-1-(3′-N,N- dimethylthiocarbamoyl-4′-methoxy)-2-(3″, 4″, 5″-trimethoxyphenyl) ethene

The combretastatin A-4 analogue cis-1-(3′-N,N-dimethylthiocarbamoyl- 4′-methoxy)-2-(3″,4″,5″-trimethoxyphenyl) ethene (1) and its trans stereoisomer (2) were synthesized. The molecular structures of these compounds were obtained by single-crystal X-ray di

Design, synthesis, and biological evaluation of novel combretastatin A-4 thio derivatives as microtubule targeting agents

A series of novel combretastatin A-4 (CA-4) thio derivatives containing different molecular cores, namely α-phenylcinnamic acids (core 1), (Z)-stilbenes (core 2), 4,5-disubstituted oxazoles (core 3), and 4,5-disubstituted N-methylimidazoles (core 4), as cis-restricted analogues were designed and synthesized. They were selected with the use of a parallel virtual screening protocol including the generation of a virtual combinatorial library based on an elaborated synthesis protocol of CA-4 analogues. The selected compounds were evaluated for antiproliferative activity against a panel of six human cancer cell lines (A431, HeLa, MCF7, MDA-MB-231, A549 and SKOV) and two human non-cancer cell lines (HaCaT and CCD39Lu). Moreover, the effect of the test compounds on the inhibition of tubulin polymerization in vitro was estimated. In the series studied here, oxazole-bridged analogues exhibited the most potent antiproliferative activity. Compounds 23a, 23e, and 23i efficiently inhibited tubulin polymerization with IC50 values of 0.86, 1.05, and 0.85 μM, respectively. Thio derivative 23i, when compared to its oxygen analogue 23j, showed a 5-fold higher inhibitory impact on tubulin polymerization. Compounds 23e and 23i, which showed both best cytotoxic and antitubulin activity, were further studied in terms of their effect on cell cycle distribution and proapoptotic activity. Compound 23e induced a statistically significant block of the cell cycle at the G2/M phase in A431, HaCaT, HeLa, MCF-7, MDA-MB-231, and SKOV-3 cells to an extent comparable to that observed in CA-4. In HeLa and SKOV-3 cells incubated with 23i, a concentration-dependent block of the G2/M phase was observed. The proapoptotic effect of 23e and 23i in A431, HaCaT, MCF-7, MDA-MB-231, and SKOV-3 was demonstrated with ELISA assay and double staining with Annexin V-FITC/PI. The results indicated that compound 23e and 23i may serve as novel lead compounds in research on more effective anticancer agents.

Ambient-Temperature Newman-Kwart Rearrangement Mediated by Organic Photoredox Catalysis

The Newman-Kwart rearrangement is perhaps the quintessential method for the synthesis of thiophenols from the corresponding phenol. However, the high thermal conditions required for the rearrangement of the requisite O-aryl carbamothioates often leads to decomposition. Herein, we present a general strategy for catalysis of O-aryl carbamothioates to S-aryl carbamothioates using catalytic quantities of a commercially available organic single-electron photooxidant. Importantly, this reaction is facilitated at ambient temperatures.

Isovanillyl Sweeteners. Synthesis and Sweet Taste of Sulfur Heterocycles

As part of an investigation into the structure-sweetness relationship in isovanillyl sweeteners, 15 compounds containing sulfur atoms either in the heterocyclic or the isovanillyl ring have been synthesized and tasted.In general the replacement of oxygen