105576-60-1Relevant academic research and scientific papers
Synthesis and antimicrobial evaluation of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety
Li, Chao,Liu, Jia-Chun,Li, Ya-Ru,Gou, Cheng,Zhang, Mei-Ling,Liu, Hong-Yan,Li, Xiao-Zhen,Zheng, Chang-Ji,Piao, Hu-Ri
, p. 3052 - 3056 (2015)
Three series of 5-aryl-1,2,4-triazole-3-thione derivatives containing a rhodanine moiety (5a-k, 6a-i, and 7a-i) have been synthesized, characterized and evaluated for their antibacterial activity. Some of these displayed potent antibacterial activity against several Gram-positive and Gram-negative bacterial strains (including multidrug-resistant clinical isolates) with minimum inhibitory concentration (MIC) values in the range of 4-64 μg/mL and minimum bactericidal concentration (MBC) values in the range of 8-256 μg/mL. Compared with previously reported rhodanine derivatives, these compounds exhibited a broad spectrum of antibacterial activity by means of introducing 4-amino-5-aryl-1,2,4-triazole-3-thione moiety. Notably, compound 5f exhibited good antibacterial activity against Staphylococcus aureus RN 4220, S. aureus 209, S. aureus 503, Gram-negative bacteria (Escherichia coli 1924), and Candida albicans 7535 with MBC values of 8 or 16 μg/ml. All of the compounds synthesized in the current Letter were characterized by 1H NMR, 13C NMR, infrared and mass spectroscopy.
Design, synthesis, and urease inhibition studies of a series of 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones
Khan, Mahmood-Ul-Hassan,Hameed, Shahid,Yasin, Khawaja A.,Akhtar, Tashfeen,Khan, Khalid M.
, p. 479 - 484 (2010)
A series of 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones was synthesized by reaction of aryl hydrazides with CS2 and hydrazine hydrate. The synthesized compounds were characterized by spectroanalytical techniques, and their urease inhibition activity was evaluated using jack bean urease. All but one of the synthesized compounds were active, and two of them were found to be more potent than the standard, with 50% inhibition concentration (IC 50) values of 17.5 ± 0.52 and 4.3 ± 0.169 μM, respectively (standard IC 50 = 21.0 ± 0.11 μM). Tentative statements regarding the role of different functional groups in binding to the enzyme active site are also presented.
Synthesis, anti-HIV activity and Molecular modeling study of 3-aryl-6-adamantylmethyl-[1,2,4] triazolo[3,4-b][1,3,4]thiadiazole derivatives
Khan, Mahmood-Ul-Hassan,Hameed, Shahid,Farman, Muhammad,Al-Masoudia, Najim A.,Stoeckli-Evans, Helen
, p. 609 - 616 (2015)
A series of novel 3-aryl-6-adamantylmethyl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 6a-l were synthesized by a simple method with the aim of developing novel HIV non-nucleoside reverse transcriptase inhibitors. All the synthesized compounds were structurally confirmed by spectral analyses. The structure of 6a was unambiguously verified by X-ray structure determination. The synthesized compounds were evaluated for their anti-HIV activity and four analogs displayed moderate inhibitory activity with EC50 values ranging from 10.10 to 12.40 μg mL-1. Molecular docking of 6g with HIV-1 reverse transcriptase was studied to rationalize some structureactivity relationships (SARs).
Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4-triazole as Potent Tyrosinase Inhibitors
Xie, Wenlin,Zhang, Jingai,Ma, Xiaojing,Yang, Wenqian,Zhou, Ying,Tang, Xufu,Zou, Yan,Li, Hui,He, Jingjing,Xie, Shimin,Zhao, Yunhui,Liu, Fengping
, p. 1087 - 1092 (2015)
A series of 5-substituted-3-[5-hydroxy-4-pyrone-2-yl-methymercapto]-4-amino-1,2,4-triazole derivatives were synthesized by nucleophilic substitution reaction of 5-hydroxy-2-chloromethyl -4H-pyran-4-one with 5-substituted-3-mercapto-4-amino-1,2,4-triazole,
Synthesis of 1,3-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl] benzenes
Li, Dejiang,Long, Deqing,Fu, Heqing
, p. 519 - 526 (2006)
1,3-bis[(3-aryl)-s-triazolo[3,4-b]-[1,3,4]thiadiazole-6-yl]benzenes 2 were synthesized in high yields by the reaction of 3-aryl 4-amino-5-mercapto-1,2,4- triazole 1 with m-phthalic acid. Copyright Taylor & Francis Group, LLC.
Investigation on 4-amino-5-substituent-1,2,4-triazole-3-thione Schiff bases an antifungal drug by characterization (spectroscopic, XRD), biological activities, molecular docking studies and electrostatic potential (ESP)
Wu, Shaojie,Zhang, Wenhui,Qi, Le,Ren, Yinghui,Ma, Haixia
, p. 171 - 182 (2019/07/19)
Four novel Schiff bases 4-(2,4-dinitrobenzylideneamino)-5-m-tolyl-2H-1,2,4-triazole-3(4H)-thione) (F1), 4-(2,4-dinitrobenzylideneamino)-5-(2-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione) (F2), 4-(2,4-dinitrobenzylideneamino)-5-(3-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione) (F3) and 4-(2,4-dinitrobenzylideneamino)-5-(4-methoxyphenyl)-2H-1,2,4-triazole-3(4H)-thione) (F4) were prepared as new antifungal compounds contributing 4-Amino-5-Substituent-1,2,4-Triazole-3-Thione and 2,4-dinitrobenzaldehyde via a condensation reaction under the mild conditions with excellent yields. The structures of compounds were characterized by elemental analysis (EA), FT-IR, 1H NMR, 13C NMR spectra and X-ray analysis. In addition, the compounds were screened for in vitro biological activity, and the bioassay results indicated that the newly synthesized compounds showed different in vitro antifungal activities against five plant fungi. Particularly, compound F3 (EC50 = 11.16 mg/L) was found to be the most active respectively against Wheat gibberellic, even more effective than Fluconazole (EC50 = 16.03 mg/L). The active compounds were further evaluated for enzyme inhibition efficacy against the receptor CYP51 by docking. Meanwhile, an explicit surface analysis on compounds were carried out theoretically using the wave function analyzer (Multiwfn 3.4.1 software) in order to study the reactivity of the compounds.
A process for preparing 3 - substituted - 6 - ferrocenyl methylene - 1, 2, 4 - triazolo [3.4 - b] - 1, 3, 4 - thiadiazole method
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Paragraph 0070, (2017/11/21)
The invention relates to a method for preparing 3-substituted-6-ferrocenylmethylene-1,2,4-triazolo[3.4-b]-1,3,4-thiadiazole. The method comprises the following steps: 1) adding A mmol of ferrocenyl acetic acid, B mmol of 3-substituted-4-amino-5-sulfhydryl
Synthesis using microwave irradiation, characterisation and antibacterial activity of Novel deoxycholic acid-triazole conjugates
Yang, Jie,Zhao, Zhigang,Li, Hui
, p. 383 - 386 (2012/10/08)
Novel deoxycholic acid 3α-triazole conjugates based on methyl 3α-chloroacetoxy-12α-hydroxy-cholanate have been synthesised. The synthesis is accelerated by microwave irradiation under solvent free conditions in the presence of K2CO3. Some of these compounds were tested for antibacterial activity against B.subtilis, P.aeruginosa and S.aureus. The preliminary results indicated that these deoxycholic acid-triazole conjugates have good inhibitory effect against B.subtilis. All of the compounds were characterised by 1H NMR, IR, ESI-MS spectra and elemental analyses.
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.
experimental part, 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.
Synthesis, crystal structure and antiproliferative activity of 6-adamantyl-3-aryl[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles
Khan, Mahmood-Ul-Hassan,Akhtar, Tashfeen,Yasin, Khawaja A.,Al-Masoudi, Najim A.,Jones, Peter G.,Hameed, Shahid
scheme or table, p. 178 - 184 (2010/08/22)
A series of 3,6-disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles 5a - l bearing an adamantyl moiety were synthesized by condensation of 4-amino-5-aryl-2H-1,2,4-triazole-3(4H)-thiones 4a - l with adamantyl-1- carboxylic acid in the presence of POCl3. The structures of the newly synthesized compounds were established using spectroanalytical techniques and verified further by the crystal structure determination of compounds 5a and 5j. The compounds were screened for their antiproliferative activity against a large panel of human cell lines.
