1950-65-8Relevant academic research and scientific papers
Synthesis and Dopamine Antagonist Activity of 2-Thioether Derivatives of the Ergoline Ring System
Tupper, David E.,Pullar, Ian A.,Clemens, James A.,Fairhurst, John,Risius, Francesca C.,et al.
, p. 912 - 918 (1993)
A series of 2-thioether derivatives of a number of clavine alkaloid (ergoline) ring systems have been synthesized and tested for dopamine antagonist activity.Of the compounds tested 2-(methylthio)agroclavine (8,9-didehydro-6,8-dimethyl-2-(methylthio)ergoline) (6) was the most potent and had a profile of activity in animal models indicative of potential antipsychotic activity.The synthesis and biological activity of a number of metabolites of 6, including the 13-hydroxy derivative, are also reported.
Rhodium(I)-catalyzed cycloisomerization of allene-allenylcyclopropanes
Kawamura, Takamasa,Kawaguchi, Yasuaki,Sugikubo, Katsuya,Inagaki, Fuyuhiko,Mukai, Chisato
, p. 719 - 722 (2015)
The RhI-catalyzed intramolecular [5+2-2]-type cycloisomerization of allene-allenylcyclopropanes was developed. In this reaction, ethylene was liberated from the cyclopropane ring to afford the 1,5,6,7-tetrahydroazulene skeletons.
Synthesis of 4-chalcogenyl pyrazoles via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones
Cheng, Yu-Fei,Gao, Wen-Chao,Niu, Yulan,Shang, Yu-Zhu,Tian, Jun,Yu, Xinzhang
, p. 1806 - 1811 (2020)
A facile method for the synthesis of 4-chalcogenylated pyrazoles has been developed via electrophilic chalcogenation/cyclization of α,β-alkynic hydrazones. The cyclization of α,β-alkynic aldehyde hydrazones could be induced by using either sulfenyl chloride or the S-electrophiles generated in situ from the reaction of NCS and arythiol. The developed method was successfully applied to the synthesis of the sulfenyl analogue of celecoxib.
Indole derivatives containing disulfide alkyl heterocyclic structure or stereoisomer, salt or solvate of the indole derivatives
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Paragraph 0035; 0050; 0057-0058, (2020/07/06)
The invention relates to a preparation method and application of indole derivatives containing a disulfide alkyl heterocyclic structure. The compounds have a general structure as shown in a general formula (I) shown in the specification. Indole compounds
Development of disulfide-derived fructose-1,6-bisphosphatase (FBPase) covalent inhibitors for the treatment of type 2 diabetes
Xu, Yi-xiang,Huang, Yun-yuan,Song, Rong-rong,Ren, Yan-liang,Chen, Xin,Zhang, Chao,Mao, Fei,Li, Xiao-kang,Zhu, Jin,Ni, Shuai-shuai,Wan, Jian,Li, Jian
, (2020/07/25)
Fructose-1,6-bisphosphatase (FBPase), as a key rate-limiting enzyme in the gluconeogenesis (GNG) pathway, represents a practical therapeutic strategy for type 2 diabetes (T2D). Our previous work first identified cysteine residue 128 (C128) was an important allosteric site in the structure of FBPase, while pharmacologically targeting C128 attenuated the catalytic ability of FBPase. Herein, ten approved cysteine covalent drugs were selected for exploring FBPase inhibitory activities, and the alcohol deterrent disulfiram displayed superior inhibitory efficacy among those drugs. Based on the structure of lead compound disulfiram, 58 disulfide-derived compounds were designed and synthesized for investigating FBPase inhibitory activities. Optimal compound 3a exhibited significant FBPase inhibition and glucose-lowering efficacy in vitro and in vivo. Furthermore, 3a covalently modified the C128 site, and then regulated the N125–S124–S123 allosteric pathway of FBPase in mechanism. In summary, 3a has the potential to be a novel FBPase inhibitor for T2D therapy.
Trichloroisocyanuric acid-promoted thiolation of phosphites by thiols
Chen, Yingying,Li, Meichao,Gong, Zhangshui,Shen, Zhenlu
, p. 19 - 27 (2020/08/06)
A simple and convenient method for the synthesis of thiophosphates by coupling of phosphites with thiols under mild conditions has been developed. The reactions were promoted by trichloroisocyanuric acid (TCCA) and were carried out at room temperature in
Synthesis of unsymmetrical disulfides: Via PPh3-mediated reductive coupling of thiophenols with sulfonyl chlorides
Liang, Xiao,Pan, Yuanjiang,Wang, Dungai,Xiong, Mingteng,Zhou, Yifeng,Zhu, Heping
supporting information, p. 4447 - 4451 (2020/10/20)
A facile and rapid synthesis of unsymmetrical aryl disulfides using PPh3-mediated reductive coupling of thiophenols with aryl sulfonyl chlorides was described. Good functional group tolerance and scalability were achieved in this strategy. More importantl
Increasing Scope of Clickable Fluorophores: Electrophilic Substitution of Ylidenemalononitriles
De Souza, Juliana M.,Abdiaj, Irini,Chen, Jiaqi,Hanson, Kenneth,De Oliveira, Kleber T.,McQuade, D. Tyler
, p. 11822 - 11834 (2020/10/23)
Recently, we demonstrated that ylidenemalononitriles (YMs) react with amines to form cyclic amidines and that the starting linear YMs are nonemissive in solution and the cyclic amidines are fluorescent. These turn-on systems were of interest to us because of their potential as biosensors and synthons for accessing functionalized pyridines. While our original method was promising, several limitations persisted, including access to more functionalized and polar-solvent-soluble structures as well as increased control over the rate of cyclization. Herein, we report a new approach that allows the electrophilic substitution of YMs. These substituted YMs exhibit faster turn-on rates, color tunability, access to polar-solvent-soluble species, and increased control over cyclization rate. This allowed us to significantly expand the fluorophore's chemical space.
Melanoma-targeted delivery system (part 1): Design, synthesis and evaluation of releasable disulfide drug by glutathione
El Aissi, Radhia,Chezal, Jean-Michel,Tarrit, Sébastien,Chavignon, Olivier,Moreau, Emmanuel
, p. 668 - 680 (2015/08/03)
Abstract Here we describe the design and synthesis of a prodrug developed for pigmented melanoma therapy, consisting of a Melanin-Targeting Probe (MTP) conjugated to 5-iodo-2′-deoxyuridine (IUdR) with a reduction-sensitive pre-determined breaking point. C
A metal free chlorothiolation strategy for synthesis of vinyl sulfides from internal alkynoates
Surineni, Naresh,Buragohain, Pori,Saikia, Bishwajit,Barua, Nabin C.,Baruah, Rajani K.
supporting information, p. 6965 - 6969 (2015/11/27)
A metal free chlorothiolation approach has been developed for conversion of internal alkynoates to vinyl sulfides and also utilized mild PIDA mediated oxidation to yield the corresponding sulfoxides.
