729-46-4Relevant academic research and scientific papers
Carbonic anhydrase inhibitors: Synthesis of N-morpholylthiocarbonylsulfenylamino aromatic/heterocyclic sulfonamides and their interaction with isozymes I, II and IV
Scozzafava, Andrea,Supuran, Claudiu T.
, p. 1117 - 1120 (2000)
Several aromatic/heterocyclic sulfonamides possessing free amino, imino or hydrazino moieties were transformed into the corresponding N-morpholylthiocarbonylsulfenyl derivatives, by reaction with N-morpholyldithiocarbamate in the presence of oxidizing age
Continuous-flow step-economical synthesis of thiuram disulfidesviavisible-light photocatalytic aerobic oxidation
Xu, Hao-Xing,Zhao, Ze-Run,Patehebieke, Yeersen,Chen, Qian-Qian,Fu, Shun-Guo,Chang, Shuai-Jun,Zhang, Xu-Xu,Zhang, Zhi-Liang,Wang, Xiao
supporting information, p. 1280 - 1285 (2021/02/26)
A continuous-flow photocatalytic synthesis of the industrially important thiuram disulfides has been developed, utilizing O2as the oxidant and Eosin Y as the photoredox catalyst. This highly atom- and step-economical method features much reduced reaction time as well as excellent product yield and purity, making it a sustainable and potentially scalable process for industrial production.
Disulfiram as a potent metallo-β-lactamase inhibitor with dual functional mechanisms
Chen, Cheng,Li, Jia-Qi,Sun, Le-Yun,Wu, Lin-Yu,Yang, Ke-Wu
supporting information, p. 2755 - 2758 (2020/03/17)
We report a promising NDM-1 inhibitor, disulfiram, which can covalently bind to NDM-1 by forming an S-S bond with the Cys208 residue. Its copper-containing metabolite in vivo, Cu(DTC)2, also inactivated NDM-1 through oxidizing the Zn(ii) thiolate site of the enzyme, therefore exhibiting dual functional inhibitory potential against B1 and B2 subclass MβLs.
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.
Thiuram disulfide compound and synthesis process thereof
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Paragraph 0039-0043, (2019/03/25)
The invention belongs to the field of rubber additives and particularly relates to a thiuram disulfide compound and a synthesis process thereof. The synthesis process comprises the following steps: (1) mixing secondary amine with alkaline liquid, then dropwise adding carbon disulfide, wherein the molar ratio of the secondary amine to the alkaline liquid to the carbon disulfide is 1 to (1-2) to (1-2), and reacting at the temperature of 30-60 DEG C to obtain a sodium dithioformate intermediate; (2) mixing and stirring the sodium dithioformate intermediate obtained in the step (1), dimethylsulfoxide and a dispersant, dropwise adding a strong acid catalyst and reacting at the temperature of 30-80 DEG C, wherein the molar ratio of the sodium dithioformate intermediate to the dimethylsulfoxide to the strong acid catalyst is 2 to (1-1.8) to (2-4), and the molar amount of the catalyst is metered by hydrogen ions; and generating a target product. The product yield of the reaction can reach 95%or above; through HPLC test of the product, the purity can reach up to 96%.
Pyruvate dehydrogenase kinase inhibitor and application thereof
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Paragraph 0107; 0108; 0109; 0110; 0122; 0123; 0124; 0125, (2017/08/28)
The invention provides a pyruvate dehydrogenase kinase inhibitor and an application thereof, specifically a compound as shown in a formula I described in the specification or pharmaceutically acceptable salts thereof. The compound has excellent effects of inhibiting pyruvate dehydrogenase kinase activity and resisting tumors. The invention also provides a pharmaceutical composition containing the compound provided by the invention and the application thereof in the aspect of inhibiting pyruvate dehydrogenase kinase.
Role of disulfide linkage in action of bis(dialkylaminethiocarbonyl)disulfides as potent double-Edged microbicidal spermicide: Design, synthesis and biology
Lal, Nand,Jangir, Santosh,Bala, Veenu,Mandalapu, Dhanaraju,Sarswat, Amit,Kumar, Lalit,Jain, Ashish,Kumar, Lokesh,Kushwaha, Bhavana,Pandey, Atindra K.,Krishna, Shagun,Rawat, Tara,Shukla, Praveen K.,Maikhuri, Jagdamba P.,Siddiqi, Mohammad I.,Gupta, Gopal,Sharma, Vishnu L.
, p. 275 - 290 (2016/04/26)
Trichomoniasis and candidiasis are amongst the most common morbidity-causing reproductive tract infections, generally treated by Metronidazole and Fluconazole respectively. Poor vaginal efficacy, drug-resistance and non-spermicidal nature limit their use as topical microbicidal contraceptives. Bis(dialkylaminethiocarbonyl)disulfides (4-38) were designed as dually active, non-surfactant molecules capable of eliminating Trichomonas vaginalis and Candida strains as well as irreversibly immobilizing 100% human sperm instantly, at doses non-cytotoxic to human cervical epithelial cells and vaginal microflora in vitro. Compounds 12, 16, 17 were fifty times more active than nonoxynol-9, OTC vaginal spermicide, and compounds 12 and 17 have shown remarkable in vivo activity in rabbit model. Most promising compound 17 has shown promise for further development as a double-edged vaginal microbicide due to their improved activity and safety along with notable in vivo trichomonicidal activity. Role of disulfide group was established by loss of spermicidal activity on chemical modifications (39-56). These disulfides might be targeting thiol groups present over cell membrane of human sperm and Trichomonas as shown by fluorescence labeling of free thiols.
Reduced graphene oxide as recyclable catalyst for synthesis of Bis(aminothiocarbonyl)disulfides from secondary amines and carbon disulfide
Wang, Meishuang,Song, Xianghai,Ma, Ning
, p. 1233 - 1239 (2014/07/21)
The reaction of secondary amines with CS2 under mild conditions using reduced graphene oxide (rGO) as a green catalyst was reported, which provided an efficient access to the one-pot synthesis of bis(aminothiocarbonyl) disulfides. The rGO can be recycled at least four times without any loss of catalytic activity. A plausible mechanism was proposed.
Bis(dialkylaminethiocarbonyl)disulfides as potent and selective monoglyceride lipase inhibitors
Kapanda, Coco N.,Muccioli, Giulio G.,Labar, Geoffray,Poupaert, Jacques H.,Lambert, Didier M.
experimental part, p. 7310 - 7314 (2010/07/14)
Monoglyceride lipase (MGL) inhibition may offer an approach in treating diseases in which higher 2-arachidonoyglycerol activity would be beneficial. We report here the synthesis and pharmacological evaluation of bis(dialkylaminethiocarbonyl)disulfide derivatives as irreversible MGL inhibitors. Inhibition occurs through interactions with MGL C208 and C242 residues, and these derivatives exhibit high inhibition selectivity over fatty acid amide hydrolase, another endocannabinoid-hydrolyzing enzyme. 2009 American Chemical Society.
Carbon tetrabromide promoted reaction of amines with carbon disulfide: Facile and efficient synthesis of thioureas and thiuram disulfides
Liang, Fushun,Tan, Jing,Piao, Chengri,Liu, Qun
experimental part, p. 3579 - 3584 (2009/07/04)
A novel carbon tetrabromide promoted one-pot reaction of amines and carbon disulfide under mild conditions has been developed, which provides a straightforward and efficient access to thioureas and thiuram disufides, depending on the nature of the amines employed. The promotion effect is explained as the transient formation of a sulfenyl bromide intermediate from dithiocarbamate and carbon tetrabromide during the reaction. Georg Thieme Verlag Stuttgart · New York.
