66560-19-8Relevant academic research and scientific papers
Continuous Flow Synthesis of 2H-Thiopyrans via thia-Diels–Alder Reactions of Photochemically Generated Thioaldehydes
Sachse, Florian,Gebauer, Konrad,Schneider, Christoph
supporting information, p. 64 - 71 (2020/11/30)
Herein, we report a novel protocol for the photochemical generation of thioaldehydes in a continuous flow process which were in situ reacted with electron rich 1,3-butadienes in thia-Diels–Alder reactions. A broad range of 3,6-dihydro-2H-thiopyrans were formed as products in much higher yields and productivities as compared to classical batch processes. Moreover, greatly reduced reaction times and a facile large-scale preparation of products were achieved by fully exploiting the advantages of continuous flow technology.
An umpolung oxa-[2,3] sigmatropic rearrangement employing arynes for the synthesis of functionalized enol ethers
Gaykar, Rahul N.,George, Malini,Guin, Avishek,Bhattacharjee, Subrata,Biju, Akkattu T.
, p. 3447 - 3452 (2021/05/04)
An oxa-[2,3] sigmatropic rearrangement involving arynes is reported featuring the umpolung of ketones, where the C=O bond polarity is reversed. The in situ-generated sulfur ylides from β-keto thioethers and arynes undergo efficient rearrangement allowing the facile and robust synthesis of functionalized enol ethers in high yields and excellent functional group compatibility. Preliminary mechanistic studies rule out the possibility of Pummerer-type rearrangement operating in this case.
Dichloroacetophenone Derivatives: A Class of Bioconjugation Reagents for Disulfide Bridging
Wu, Liu-Hai,Zhou, Shuguang,Luo, Qun-Feng,Tian, Jie-Sheng,Loh, Teck-Peng
supporting information, p. 8193 - 8197 (2020/11/18)
A mild and biocompatible method for the construction of disulfide bridging in peptides using dichloroacetophenone derivatives is developed. This method is highly selective (chemo, diastereo, regio, etc.) and atom economic and works under biocompatible reaction conditions (metal-free, water, pH 7, rt, etc.).
Macromolecular surface design: Photopatterning of functional stable nitrile oxides
Altintas, Ozcan,Glassner, Mathias,Rodriguez-Emmenegger, Cesar,Welle, Alexander,Trouillet, Vanessa,Barner-Kowollik, Christopher
supporting information, p. 5777 - 5783 (2015/05/20)
The efficient trapping of photogenerated thioaldehydes with functional shelf-stable nitrile oxides in a 1,3-dipolar cycloaddition is a novel and versatile photochemical strategy for polymer end-group functionalization and surface modification under mild a
1,2,3-Thiadiazole thioacetanilides as a novel class of potent HIV-1 non-nucleoside reverse transcriptase inhibitors
Zhan, Peng,Liu, Xinyong,Cao, Yuan,Wang, Yan,Pannecouque, Christophe,De Clercq, Erik
scheme or table, p. 5368 - 5371 (2009/06/18)
A novel series of 1,2,3-thiadiazole thioacetanilide (TTA) derivatives have been designed, synthesized and evaluated for its anti-HIV activities in MT-4 cells. Some derivatives proved to be highly effective in inhibiting HIV-1 replication at nanomolar concentrations. Among them, 2-[4-(2,4-dichlorophenyl)-1,2,3-thiadiazol-5-ylthio]-N-(2-nitrophenyl)acetamide 7d2 was identified as the most promising compound (EC50 = 0.059 ± 0.02 μM, CC50 > 283.25 μM, SI > 4883). The structure-activity relationship (SAR) of these novel structural congeners is discussed. Crown Copyright
ACAT inhibitors derived from hetero-Diels-Alder cycloadducts of thioaldehydes
Wilde, Richard G.,Billheimer, Jeffrey T.,Germain, Sandie J.,Hausner, Elizabeth A.,Meunier, Paul C.,Munzer, Deborah A.,Stoltenborg, Janet K.,Gillies, Peter J.,Burcham, Deborah L.,Huang, Shiew-Mai,Klaczkiewicz, John D.,Ko, Soo S.,Wexler, Ruth R.
, p. 1493 - 1513 (2007/10/03)
Acyl-CoA:cholesterol acyltransferase (ACAT) is the enzyme largely responsible for intracellular cholesteror esterification. A systemic inhibitor of ACAT is believed to be able to slow or even reverse the atherosclerotic process. Towards that goal, a series of cyclic sulfides, derived from the hetero-Diels-Alder reaction of thioaldehydes with 1,3-dienes, and bearing carboxamide substituents, were prepared and evaluated for in vitro (in several tissues and species) and ex vivo ACAT inhibition. Minor changes in subsequent structure were found to have a significant effect in optimization of the biological activity of this series of compounds.
Derivatives of cyclic ethers and sulfides for the treatment of atherosclerosis
-
, (2008/06/13)
The present invention provides compounds of Formula I, STR1 or a pharmaceutically acceptable salt forms thereof, which are inhibitors of acyl-Coenzyme A: cholesterol O-acyltransferase (ACAT), pharmaceutical compositions containing such compounds, processes for the preparation of such compounds, and the use of such compounds as antihypercholesterolemic and/or antiatherosclerotic agents.
Phenacylthio/sulfonyl acetates as synthons: Synthesis and conformational aspects of some 1,4-thiomorpholines Part III
Reddy, D. Bhaskar,Reddy, M. Muralidhar,Reddy, P. V. Ramana
, p. 1018 - 1023 (2007/10/02)
The synthons, phenacylthio/sulfonyl acetates (III and IV) for the synthesis of title compounds VI, VII and VIII have been obtained by two different methods starting from phenacylbromide (I) and thioglycollic acid or from I and thioglycollates.The cyclocon
Synthesis of Unsymmetrical Functionalised Organic Sulphides
Singh, Harjit,Batra, Manohar S.,Singh, Paramjit
, p. 131 - 136 (2007/10/02)
Acyclic thioiminium salts and the condensed thiazolium salts in the presence of aqueous sodium hydroxide as such or under base catalyzed phase transfer catalysis conditions react with appropiate organic halides to provide corresponding unsymmetrical functionalized organic sulphides.With aqueous sodium hydroxide, thioiminium salts provide the disulphides corresponding to incipient thiol.
Synthesis of Unsymmetrical Thioethers Using Solid-Liquid Phase-transfer Catalysis
Singh, Paramjit,Batra, Manohar S.,Singh, Harjit
, p. 484 (2007/10/02)
The title compounds have been synthesised from appropriate organic halides and thioimminium salts (1) in moderate to good yields under solid-liquid phase-transfer catalysis using Triethylbenzylammonium chloride (TEBA) as a catalyst, solid KOH as a base in chloroform.
