87239-94-9Relevant academic research and scientific papers
Efficient formation of C–S bond using heterocyclic thiones and arynes
An, Yu,Xu, Gang,Cai, Menglu,Wang, Shihui,Wang, Xiao zhong,Chen, Yingqi,Dai, Liyan
, (2020/12/23)
Phenylthio heterocyclic compounds are widely used because of their diverse biological activities and medicinal prospects. Here, a facile method was reported. An arylation of 1,3,4-oxa(thia)diazol-2-thiones reacting with arynes to build C(aryl)-S bonds in the presence of CsF had good yields and excellent selectivity. The reaction was completed in short time without using expensive reagents and catalysts. Present reaction system is an efficient procedure to process phenylthio heterocyclic compounds and reveals a sustainable method and better application prospects in future organic synthesis.
Synthesis, Antimicrobial, and Antioxidant Screening of Aryl Acetic Acid Incorporated 1,2,4-Triazolo-1,3,4-Thiadiazole Derivatives
Kamboj, Vipan Kumar,Kapoor, Archana,Jain, Sandeep
, p. 1376 - 1382 (2019/02/20)
Some novel [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives were synthesized from aryl acetic acids. All the synthesized derivatives were selected for the screening of antibacterial potential against Gram-positive bacteria [Staphylococcus aureus (MTCC 3160) and Micrococcus luteus (MTCC 1538)] and Gram-negative bacteria [Escherichia coli (MTCC 1652) and Pseudomonas aeruginosa (MTCC 424)] and antifungal potential against Aspergillus niger (MTCC 8652) and Candida albicans (MTCC 227), and free radical scavenging activity through 2,2-diphenyl-2-picrylhydrazyl hydrate method. The compounds TH-4, TH-13, and TH-19 were found to be more potent antimicrobial agents compared to standard drugs. The compounds TH-3, TH-9, and TH-18 also showed significant antimicrobial activity. The compound TH-13 showed antioxidant activity with IC50 value better than the standard compound. The structures of all the synthesized compounds were confirmed by Fourier transform infrared, 1H-NMR, liquid chromatography–mass spectrometry, and CHN analyzer.
Dithiocarbamate as a valuable scaffold for the inhibition of metallo-β-lactmases
Ge, Ying,Xu, Li-Wei,Liu, Ya,Sun, Le-Yun,Gao, Han,Li, Jia-Qi,Yang, Kewu
, (2019/11/20)
The ‘superbug’ infection caused by metallo-β-lactamases (MβLs) has grown into an emergent health threat. Given the clinical importance of MβLs, a novel scaffold, dithiocarbamate, was constructed. The obtained molecules, DC1, DC8 and DC10, inhibited MβLs NDM-1, VIM-2, IMP-1, ImiS and L1 from all three subclasses, exhibiting an IC50 50 0.22 μM). DC1-2, DC4, DC8 and DC10 restored antimicrobial effects of cefazolin and imipenem against E. coli-BL21, producing NDM-1, ImiS or L1, and DC1 showed the best inhibition of E. coli cells, expressing the three MβLs, resulting in a 2-16-fold reduction in the minimum inhibitory concentrations (MICs) of both antibiotics. Kinetics and isothermal titration calorimetry (ITC) assays showed that DC1 exhibited a reversible, and partially mixed inhibition, of NDM-1, ImiS and L1, with Ki values of 0.29, 0.14 and 5.06 μM, respectively. Docking studies suggest that the hydroxyl and carbonyl groups of DC1 form coordinate bonds with the Zn (II) ions, in the active center of NDM-1, ImiS and L1, thereby inhibiting the activity of the enzymes. Cytotoxicity assays showed that DC1, DC3, DC7 and DC9 have low toxicity in L929 mouse fibroblastic cells, at a dose of up to 250 μM. These studies revealed that the dithiocarbamate is a valuable scaffold for the development of MβLs inhibitors.
Synthesis of Novel 1,2,4-Triazole-3-thione Derivatives as Influenza Neuraminidase Inhibitors
Liu, Ling,Ye, Jiao,Xiao, Mengwu,Yuan, Keyang,He, Mei,Hu, Aixi,Jia, Hao,Liu, Ailin
, p. 2192 - 2201 (2019/07/03)
A series of 1,2,4-triazole-3-thione derivatives (6a–6t) were synthesized and evaluated against influenza viruses (H1N1) neuraminidase (NA) in vitro. Eighteen compounds exhibited inhibitory potency with IC50 values ranging from 14.68?±?0.49 to 39.85?±?4.23?μg/mL. Among them, compounds 6e and 6h showed significant inhibitory activity with IC50 values of 14.97?±?0.70 and 14.68?±?0.49?μg/mL, respectively. Structure activity relationships were established. Molecular docking studies were performed to understand the binding interaction between active compounds and NA.
Antibacterial drug for targeted therapy of staphylococcal infection by synergizing with antibiotic as well as synthesis method and application of antibacterial drug
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Paragraph 0033; 0034, (2018/12/05)
The invention designs and synthesizes a novel antibacterial drug ASC for staphylococcus aureus based on a beta-lactam ring of a parent nucleus structure of beta-lactam antibiotic molecules, wherein the ASC is an antibacterial reagent and is also a broad-spectrum inhibitor of beta-lactam antibiotic drug-resistant target protein metal beta-lactamase; the ASC can synergize with three kinds of 7 to 8antibiotics such as beta-lactams, aminoglycosides and tetracyclines to carry out targeted therapy on the staphylococcal infection. The vitality of the antibiotics is increased by 4 to 128 times by combining with 1 [mu]g/ml dosage of ASC.
Azolylthioacetamides as a potent scaffold for the development of metallo-β-lactamase inhibitors
Xiang, Yang,Chang, Ya-Nan,Ge, Ying,Kang, Joon S.,Zhang, Yi-Lin,Liu, Xiao-Long,Oelschlaeger, Peter,Yang, Ke-Wu
, p. 5225 - 5229 (2017/11/13)
In an effort to develop new inhibitors of metallo-β-lactamases (MβLs), twenty-eight azolylthioacetamides were synthesized and assayed against MβLs. The obtained benzimidazolyl and benzioxazolyl substituted 1–19 specifically inhibited the enzyme ImiS, and 10 was found to be the most potent inhibitor of ImiS with an IC50 value of 15 nM. The nitrobenzimidazolyl substituted 20–28 specifically inhibited NDM-1, with 27 being the most potent inhibitor with an IC50 value of 170 nM. Further studies with 10, 11, and 27 revealed a mixed inhibition mode with competitive and uncompetitive inhibition constants in a similar range as the IC50 values. These inhibitors resulted in a 2–4-fold decrease in imipenem MIC values using E. coli cells producing ImiS or NDM-1. While the source of uncompetitive (possibly allosteric) inhibition remains unclear, docking studies indicate that 10 and 11 may interact orthosterically with Zn2 in the active site of CphA, while 27 could bridge the two Zn(II) ions in the active site of NDM-1 via its nitro group.
Synthesis and antihyperlipidemic activity of some novel 4-(substitutedamino)-5-substituted-3-mercapto-(4H)-1,2,4-triazoles
Chhabria, Mahesh T.,Suhagia, Bhanubhai N.,Brahmkshatriya, Pathik S.,Raval, Priyesha M.
, p. 452 - 457 (2012/06/16)
Hyperlipidemia is considered one of the key factors for cardiovascular diseases. Based on earlier work on a series of 5-alkyl-4-aryl-3-mercapto-(4H)-1, 2,4-triazoles, for further lead modification, a series of 4-(substituted)amino- 5-substituted-3-mercapto-(4H)-1,2,4-triazoles was designed. Target compounds were synthesized by the well known Hoggarth synthesis of substituted 1,2,4-triazoles. Synthesized compounds were screened for lipid lowering activity using the "Poloxamer 407 induced hyperlipidemia in rats" model at a dose of 100 mg/kg p. o. Compounds were found to alter serum lipid levels significantly. Most of the compounds significantly reduced serum cholesterol and triglyceride levels. Some of the compounds were found to reduce triglycerides and elevate high density lipoprotein (HDL) levels more than the standard drug atorvastatin (CAS 134523-03-8). Compounds with chloro substitution on aryl rings were found more active in reducing serum lipid levels than other substitutions. ECV ? Editio Cantor Verlag.
Studies on fused heterocyclic 3,6-disubstituted-1,2, 4-triazolo-1,3,4- thiadiazoles: Synthesis and biological evaluation
Husain, Asif,Naseer, Md. Arif
experimental part, p. 47 - 54 (2012/02/04)
In this study, a series of 3,6-disubstituted-1,2, 4-triazolo-[3,4-b]-1,3,4- thiadiazoles (5a-t) were synthesized by condensing 4-amino-3-mercapto-(4H)-1,2, 4-triazoles (4a-c) with different aromatic or aroyl acids through one-pot reaction. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic, and lipid peroxidation actions. Some of the newly synthesized compounds showed very good anti-inflammatory activity with low GI toxicity and reduced lipid peroxidation. These compounds also showed interesting profile of analgesic activity in acetic acid-induced writhing test. The findings of the study indicate that the synthesized compounds have superior GI safety profile along with reduction in lipid peroxidation as compared to that of the standard. Springer Science+Business Media, LLC 2010.
Thiadiazole-based Thioglycosides as Sodium-glucose Co-transporter 2 (SGLT2) Inhibitors
Gao, Yunlong,Zhao, Guilong,Liu, Wei,Wang, Yuli,Xu, Weiren,Wang, Jianwu
scheme or table, p. 605 - 612 (2010/10/19)
A series of thiadiazole-based thioglycosides were synthesized as SGLT2 inhibitors from D-glucose, D-galactose and a variety of phenylacetic acids via a convenient protocol in 8 steps and evaluated in vivo with an oral glucose tolerance test (OGTT), and 5-benzyl-1,3,4-thiadiazol-2-yl 1-thio-β-D-glucopyranoside (1a) was the most efficacious to suppress the blood glucose excursion during OGTT.
Synthesis of 3-substituted (6-[(e)-2-(1-benzofuran-2-yl)ethenyl][1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles
Obushak, Mykola D.,Pokhodylo, Nazariy T.,Ostapiuk, Yuri V.,Matiychuk, Vasyl S.
, p. 136 - 143 (2008/12/23)
The reaction of (2E)-3-(1-benzofuran-2-yl)-2-propenoic acid with 4-amino-5-R-1,2,4-triazole-3-thioles has been investigated. It has been established, that 6-[(E)-2-(1-benzofuran-2-yl)ethenyl][1,2,4]triazolo[3,4-b][1, 3,4] thiadiazole were formed as the result of heterocyclization.
