- Efficient formation of C–S bond using heterocyclic thiones and arynes
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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.
- An, Yu,Xu, Gang,Cai, Menglu,Wang, Shihui,Wang, Xiao zhong,Chen, Yingqi,Dai, Liyan
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- Efficient Synthesis of Fluorinated [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazoles
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Abstract: An efficient synthesis of fluorinated [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives has been achievedby cyclocondensation of 5-substituted 4-amino-1,2,4-triazole-3-thiols withfluoro-substituted aromatic acids using phosphoryl chloride as a cyclizingagent. The synthesized compounds were characterized by spectroscopic techniques,including IR, 1H NMR, and mass spectra.
- Dhotre, B. K.,Jagrut, V. B.,Pathan, M. A.,Patharia, M. A.,Raut, S. V.
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p. 1135 - 1140
(2021/09/08)
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- 1,2,4-Triazole-conjugated 1,3,4-thiadiazole hybrid scaffolds: A potent ameliorant of carrageenan-induced inflammation by lessening proinflammatory mediators
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Inflammation acts as an alarming signal for the progression of various biological complications. Various reports in the literature have revealed that heterocycle-containing synthetic compounds have a restorative capability against acute and chronic inflammatory stages. In the current study, we synthesized a series of 1,2,4-triazole-conjugated 1,3,4-thiadiazole hybrid scaffolds and evaluated their impacts against carrageenan-induced paw edema and proinflammatory markers in Wistar rats. Further, 3D QSAR study (three-dimensional quantitative structure–activity relationships), ADMET (absorption, distribution, metabolism, and excretion) profiling, and docking studies were performed to determine the possible mechanism of the action of the derivatives. The study shows that the most active derivatives, 13f and 13g, have optimal logP, a higher anti-inflammatory activity score, and poor metabolism at various sites of cytochrome P450. The docking studies recommended that the synthesized compounds have a similar affinity as the ligands A307, 63X, and S58 to interact with tumor necrosis factor-α, COX-1, and COX-2. So, these molecules will definitely hold a promise for the future drug development initiative.
- Pathak, Prateek,Shukla, Parjanya K.,Naumovich, Vladislav,Grishina, Maria,Verma, Amita,Potemkin, Vladimir
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- Synthesis of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as potent antiproliferative agents via a hybrid pharmacophore approach
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Imiquimod (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-amine) is efficacious in topical therapy for certain types of skin cancers. Structurally similar EAPB0203 (N-methyl-1-(2-phenethyl)imidazo[1,2-a]quinoxalin-4-amine) has been shown higher in vitro potency than imiquimod. Besides, triazole, oxadiazole, and thiadiazole rings are privileged building blocks in drug design. A series of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole and [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-thiadiazole derivatives were therefore synthesized by incorporation of these rings into the structure of EAPB0203 and assessed their antiproliferative effects against various cancer cell lines. The 1,3,4-oxadiazole derivatives demonstrated the superior effectiveness compared to imiquimod and EAPB0203. Our findings highlight the excellent potential of [1,2,4]triazolo[4,3-a]quinoxaline-1,3,4-oxadiazole derivatives as anticancer agents.
- Kaneko, Daiki,Ninomiya, Masayuki,Yoshikawa, Rina,Ono, Yukari,Sonawane, Amol D.,Tanaka, Kaori,Nishina, Atsuyoshi,Koketsu, Mamoru
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- Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: Structure-activity relationship, in vitro and in vivo study
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Based on our prior work, we reported the design, synthesis, and biological evaluation of fifty-two new triazolothiadiazine-based analogues of CA-4 and their preliminary structure-activity relationship. Among synthesized compounds, Iab was found to be the most potent derivative possessing IC50 values ranging from single-to double-digit nanomolar in vitro, and also exhibited excellent selectivity over the normal human embryonic kidney HEK-293 cells (IC50 > 100 μM). Further mechanistic studies revealed that Iab significantly blocked tubulin polymerization and disrupted the intracellular microtubule network of A549 cells. Moreover, Iab induced G2/M cell cycle arrest by regulation of p-cdc2 and cyclin B1 expressions, and caused cell apoptosis through up-regulating cleaved PARP and cleaved caspase-3 expressions, and down-regulating of Bcl-2. Importantly, in vivo, Iab effectively suppressed tumor growth of A549 lung cancers in a xenograft mouse model without obvious signs of toxicity, confirming its potential as a promising candidate for cancer treatment.
- Ma, Weifeng,Chen, Peng,Huo, Xiansen,Ma, Yufeng,Li, Yanhong,Diao, Pengcheng,Yang, Fang,Zheng, Shengquan,Hu, Mengjin,You, Wenwei,Zhao, Peiliang
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- Synthesis and antimicrobial activity of piperine analogues containing 1,2,4-triazole ring
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A series 1,2,4-triazole piperine analogues (TP1-TP6) were designed and synthesized. The structures were confirmed using 1H NMR and 13C NMR. Antibacterial study was done using Gram-positive (Staphylococcus aureus and Bacillus cereus) and Gram-negative microorganisms (E. coli and Pseudomonas aeruginosa) by disc diffusion method. Compound containing chloro substitution (TP6) showed the highest effect, while compound TP1, TP3, TP4, TP5 showed the moderate activity.
- Kumar, Kottakki Naveen,Amperayani, Karteek Rao,Ummdi, V. Ravi Sankar,Parimi, Uma Devi
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p. 1077 - 1080
(2019/04/05)
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- Synthesis and antitumor evaluation of novel fused heterocyclic 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives
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In this study, twenty three 3,6-disubstituted 1,2,4-triazolo[3,4-b]-1,3,4-thiadiazole derivatives were synthesized and their antiproliferative activities in vitro were studied against SMMC-7721, HeLa, A549, and L929 by the CCK-8 assay. The bioassay results demonstrated that all tested compounds 8(a–w) exhibited antiproliferation with different degrees, and some compounds showed better effects than reference drug 5-fluorouracil. Among these screened compounds, compounds 8a, 8d, and 8l displayed significant antitumor activities in inhibiting SMMC-7721cell proliferation with IC50 values of 1.64, 1.74, and 1.61 μM, respectively. Compounds 8d and 8l were manifested highly effective biological activity versus HeLa cells with IC50 values of 2.23 and 2.84 μM, respectively. Compound 8l was found to have the highest antitumor potency against A549 cells with IC50 value of 2.67 μM. Furthermore, all compounds exhibited weaker cytotoxic effects than 5-fluorouracil on normal cell lines L929.
- Liu, Xiao-Jia,Liu, Hai-Ying,Wang, Hai-Xin,Shi, Yan-Ping,Tang, Rui,Zhang, Shuai,Chen, Bao-Quan
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p. 1718 - 1725
(2019/08/02)
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- Design, Synthesis, and Antifungal Activities of Novel 1,2,4-Triazole Schiff Base Derivatives
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With the aim to find new compounds with high antifungal activity, 21 4-amino-5-substituted-1,2,4-triazole Schiff bases (2a?–?2g, 3a?–?3g, and 4a?–?4g) were designed and synthesized. Their antifungal activities against Pythium solani, Gibberlla nicotiancola, Fusarium oxysporium f. sp. niveum, Gibberlla saubinetii, Alternaria iycopersici, Phytophthora capsici, Physalospora piricola, Cercospora arachidicola hori, and Fusarium oxysporium f. sp. cucumber were tested, parts of the compounds exhibited excellent antifungal activity. This research provides useful information for further study of antifungal agents.
- Jin, Ruyi,Liu, Jingli,Zhang, Guanghui,Li, Jiajia,Zhang, Shuan,Guo, Hui
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- Triazolothiadiazines as a new class of efficient DNA intercalating agents
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A new series of N-bridged heterocycles 1,2,4-triazolo[3,4-b][1,3,4]thiadiazine derivatives (6a-e) have been synthesized by the condensation of 4-amino-5-(4-methoxyphenyl)-4H-1,2,4-triazole-3-thiol and various substituted phenacyl bromides in absolute ethanol in high yields. Cyclic voltammetric and molecular docking methods have been used to investigate the interaction of potential binding affinities of 6a-e with DNA. The change in peak potential and peak current is used to probe the mode of interaction, formation constant Kf, free binding energy and irreversible nature of system. The DNA-binding potency of 6a (Kf = 5.00 105 M-1) and 6c (Kf = 4.80 105 M-1) are found to be greater than epirubicin (Kf = 4.1 105 M-1), the clinically used anticancer drug. The positive shift in peak potential revealed the intercalative mode of interactions. The high negative value of ?G signifies the spontaneity and high conformational stability of compound-DNA adduct. A molecular docking study of all the compounds using Auto-Dock 4.2 confirmed additional specificity and insight of the interaction with the DNA. Free energies by theoretical studies had much resemblance and almost completely satisfied the experimental results. From results investigation, it is revealed that the examined compounds exhibit intercalation mode.
- Ibrar, Aliya,Nawazish, Shamyla,Khan, Imtiaz,Noor, Tayyaba,Uzair, Bushra,Bukhari, Syed Majid,Khan, Farhan A.,Zaidi, Asma
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p. 1405 - 1411
(2017/10/23)
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- Preliminary SAR and biological evaluation of antitubercular triazolothiadiazine derivatives against drug-susceptible and drug-resistant Mtb strains
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Following up the SAR study of triazolothiadiazoles for their antitubercular activities targeting Mt SD in our previous study, on the principle of scaffold hopping, the C3 and C6 positions of triazolothiadiazine were examined systematically to define a preliminary structure–activity relationship (SAR) with respect to biological activity. This study herein highlights the potential of two highly potent advanced leads 6c-3, 6g-3 and several other compounds with comparable potencies as promising new candidates for the treatment of TB (6c-3, MIC-H37Rv?=?0.25?μg/mL; MIC-MDRTB?=?2.0?μg/mL; MIC-RDRTB?=?0.25?μg/mL; Mt SD-IC50?=?86.39?μg/mL; and 6g-3, MIC-H37Rv?=?1.0?μg/mL; MIC-MDRTB?=?4.0?μg/mL; MIC-RDRTB?=?2.0?μg/mL; Mt SD-IC50?=?73.57?μg/mL). Compounds 6c-3 and 6g-3 possessed a para-nitro phenyl at the 6 position showed low Vero and HepG2 cells toxicity, turning out to be two excellent lead candidates for preclinical trials. In addition, in vitro Mt SD inhibitory assay indicates that Mt SD is at least one of the targets for their antitubercular activity. Thus, they may turn out to be promising multidrug-resistance-reversing agents.
- Li, Ziqiang,Bai, Xiaoguang,Deng, Qi,Zhang, Guoning,Zhou, Lei,Liu, Yishuang,Wang, Juxian,Wang, Yucheng
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p. 213 - 220
(2016/12/18)
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- Facile synthesis, biological evaluation and molecular docking studies of novel substituted azole derivatives
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In this study, we synthesized the series of novel azole derivatives and evaluated for enzyme inhibition assays, corresponding kinetic analysis and molecular modeling. Among the investigated bioassays, the oxadiazole derivatives 4a-k were found potent α-glucosidase inhibitors while the Schiff base derivatives 7a-k exhibited considerable potential toward urease inhibition. The inhibition kinetics for the most active compounds were analyzed by the Lineweaver–Burk plots to investigate the possible binding modes of the synthesized compounds toward the tested proteins. Moreover, the detailed docking studies were performed on the synthesized library of 4a-k and 7a-k to study the molecular interaction and binding mode in the active site of the modeled yeast α-glucosidase and Jack Bean Urease, respectively. It could be inferred from docking results that theoretical studies are in close agreement to that of the experimental results. The structure of one of the compound 7k was characterized by the single crystal X-ray diffraction analysis in order to find out the predominant conformation of the molecules.
- Rafiq, Muhammad,Saleem, Muhammad,Jabeen, Farukh,Hanif, Muhammad,Seo, Sung-Yum,Kang, Sung Kwon,Lee, Ki Hwan
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p. 177 - 191
(2017/03/15)
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- Triazole-based compound and composition for detecting carbonate or bicarbonate ion comprising the same
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The present invention refers to compounds of formula 1 to a number under public affairs substrate. [Formula 1] The present invention according to setting of triazole compound including composition ion detection time, the ion concentration can be grasp for hereinafter, can be between of the first and second number morning fair, convenient for detecting various conditions not requiring the carbonate and bicarbonate ion detection can be useful. (by machine translation)
- -
-
Paragraph 0103-0104
(2017/07/31)
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- Design, synthesis and bioevaluation of antitubulin agents carrying diaryl-5,5-fused-heterocycle scaffold
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A series of 3,6-diaryl-1H-pyrazolo[5,1-c][1,2,4]triazoles (I) and 3,6-diaryl-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles (II) as antitubulin agents were designed, synthesized and bioevaluated. Compounds (II) 4a, 4d, 4f, 4j, 4l and 4n showed potent antiproli
- Xu, Qile,Sun, Maolin,Bai, Zhaoshi,Wang, Yueting,Wu, Yue,Tian, Haiqiu,Zuo, Daiying,Guan, Qi,Bao, Kai,Wu, Yingliang,Zhang, Weige
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p. 242 - 249
(2017/08/14)
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- Development of 3,5-Dinitrobenzylsulfanyl-1,3,4-oxadiazoles and Thiadiazoles as Selective Antitubercular Agents Active Against Replicating and Nonreplicating Mycobacterium tuberculosis
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Herein, we report the discovery and structure-activity relationships of 5-substituted-2-[(3,5-dinitrobenzyl)sulfanyl]-1,3,4-oxadiazoles and 1,3,4-thiadiazoles as a new class of antituberculosis agents. The majority of these compounds exhibited outstanding in vitro activity against Mycobacterium tuberculosis CNCTC My 331/88 and six multidrug-resistant clinically isolated strains of M. tuberculosis, with minimum inhibitory concentration values as low as 0.03 μM (0.011-0.026 μg/mL). The investigated compounds had a highly selective antimycobacterial effect because they showed no activity against the other bacteria or fungi tested in this study. Furthermore, the investigated compounds exhibited low in vitro toxicities in four proliferating mammalian cell lines and in isolated primary human hepatocytes. Several in vitro genotoxicity assays indicated that the selected compounds have no mutagenic activity. The oxadiazole and thiadiazole derivatives with the most favorable activity/toxicity profiles also showed potency comparable to that of rifampicin against the nonreplicating streptomycin-starved M. tuberculosis 18b-Lux strain, and therefore, these derivatives, are of particular interest.
- Karabanovich, Galina,Zemanová, Júlia,Smutny, Tomá?,Székely, Rita,?arkan, Michal,Centárová, Ivana,Vocat, Anthony,Pávková, Ivona,?onka, Patrik,Něme?ek, Jan,Stola?íková, Ji?ina,Vejsová, Marcela,Vávrová, Kate?ina,Klime?ová, Věra,Hrabálek, Alexandr,Pávek, Petr,Cole, Stewart T.,Miku?ová, Katarína,Roh, Jaroslav
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p. 2362 - 2380
(2016/04/09)
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- Synthesis, Antimicrobial, and Antioxidant Activities of Some Fused Heterocyclic [1,2,4]Triazolo[3,4-b][1,3,4]thiadiazole Derivatives
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In the present work, we synthesized a series of [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives (6a, 6b, 6c, 6d, 6e, 6f and 7a, 7b, 7c, 7d, 7e, 7f) by using simple starting materials, namely, β-amino acids and different aromatic acid hydrazides. The
- Seelolla, Gangadhara,Ponneri, Venkateswarlu
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p. 929 - 936
(2016/05/19)
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- SAR studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of Mtb shikimate dehydrogenase for the development of novel antitubercular agents
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Shikimate dehydrogenase, an essential protein for the biosynthesis of the chorismate end product, is a highly promising therapeutic target, especially for the discovery and development of new-generation anti-TB agents. Following up the identification of one lead 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole (1), targeting Mt SD in our previous study, an extensive SAR study for optimization of the lead compound was performed through systematic modification of the 3 and 6 positions. This study has successfully led to the discovery of two highly potent advanced leads 6d-4, 6c-4 and several other compounds with comparable potencies (6d-4, MIC-H37Rv = 0.5 μg mL-1; MIC-MDRTB = 4.0 μg mL-1; MIC-RDRTB = 0.5 μg mL-1; Mt SD-IC50 = 14.20 μg mL-1; and 6c-4, MIC-H37Rv = 0.5 μg mL-1; MIC-MDRTB = 4.0 μg mL-1; MIC-RDRTB = 1.0 μg mL-1; Mt SD-IC50 = 6.82 μg mL-1). These advanced lead compounds possess a para-halogen phenyl at the 3 position. In vitro Mt SD inhibitory assay indicates that Mt SD is the target for their antitubercular activity. Moreover, the BacT/ALERT 3D liquid culture technology and in vitro Mt SD inhibitory assay were initially applied.
- Li, Ziqiang,Liu, Yishuang,Bai, Xiaoguang,Deng, Qi,Wang, Juxian,Zhang, Guoning,Xiao, Chunling,Mei, Yaning,Wang, Yucheng
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p. 97089 - 97101
(2015/12/01)
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- Syntheses, structural and thermal studies on Zn(II) complexes of 5-aryl-1,3,4-oxadiazole-2-thione and dithiocarbamates: Antibacterial activity and DFT calculations
-
The new complexes [Zn(pyot)2(en)2] (1), [Zn(mphot)2(en)2] (2), [Zn(bhpzdtc)2(py)] (3), [Zn(bhpzdtc)2(4-pic)] (4) and [Zn(ecpzdtc)(bpy)(Cl)] (5) {pyot = 5-(4-pyridyl)-1,3,4-oxadiazole-2-thio
- Bharty,Dani,Nath,Bharti,Singh,Prakash, Om,Singh, Ranjan K.,Butcher
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- Synthesis and Biological Evaluation of Kojic Acid Derivatives Containing 1,2,4-triazole as Potent Tyrosinase Inhibitors
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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,
- Xie, Wenlin,Zhang, Jingai,Ma, Xiaojing,Yang, Wenqian,Zhou, Ying,Tang, Xufu,Zou, Yan,Li, Hui,He, Jingjing,Xie, Shimin,Zhao, Yunhui,Liu, Fengping
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p. 1087 - 1092
(2015/10/28)
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- Ultrasound-assisted, one-pot, three-component synthesis and antibacterial activities of novel indole derivatives containing 1,3,4-oxadiazole and 1,2,4-triazole moieties
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Thirteen novel indole derivatives were efficiently synthesized through ultrasound irradiation by using 4-amino-5-(1H-indol-3-yl)-4H-[1,2,4]triazole-3-thiol (8) and 2-mercapto-5-substituted-1,3,4-oxadiazoles (5a-m). Compared with conventional and microwave methods, yields increased to 82-93%, and reaction times decreased to 15-35 min. The structures of these novel compounds were characterized by spectral data and elemental analysis. Two out of the synthesized compounds (10f and 10l) exhibited excellent activity against Staphylococcus aureus and Escherichia coli, and thus warrant further research.
- Shi, Zhichuan,Zhao, Zhigang,Huang, Meiwei,Fu, Xiaolin
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p. 1320 - 1327
(2015/12/11)
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- Synthesis and evaluation of novel azoles as potent antifungal agents
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Using a rational approach to the design of antifungal agents, a series of azole agents with 1,3,4-oxadiazole side chains were designed and synthesized. The results of preliminary in vitro antifungal tests with eight human pathogenic compounds showed that all of the title compounds exhibited excellent activities against all of the tested fungi except Aspergillus fumigatus. Compounds 11e and 11f were found to be the most effective, with a minimum inhibitory concentration of 0.0039 μg/mL, followed by voriconazole, which has a MIC of 0.0625 μg/mL. The 1,3,4-oxadiazole side chain is not the major contributor but plays a role in eliciting the observed antifungal activity.
- Li, Liangjing,Ding, Hao,Wang, Baogang,Yu, Shichong,Zou, Yan,Chai, Xiaoyun,Wu, Qiuye
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supporting information
p. 192 - 194
(2014/01/17)
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- Synthesis, docking and evaluation of antioxidant and antimicrobial activities of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3- d]pyrimidines
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A series of 1,2,4-(triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d] pyrimidines (10a-j) were synthesized with various substituted anilines and benzoic acids. Structures of newly synthesized compounds were established by IR, 1H & 13C NMR and LC-MS spectral data. The antioxidant activity of the synthesized compounds was evaluated by DPPH, NO and H 2O2 radical scavenging methods. The newly synthesized compounds were evaluated for their antimicrobial activity against Gram +ve and Gram -ve bacteria and antifungal activity by well diffusion method. Compounds 10d, 10h and 10i showed promising antioxidant, antibacterial as well as antifungal activity and these were found to be the most potent activity molecules when compared with that of standard drugs. Molecules docking studies have been performed on Staphylococcus aureus (SA) of Gram +ve bacteria.
- Kotaiah,Nagaraju,Harikrishna,Venkata Rao,Yamini,Vijjulatha
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p. 195 - 202
(2014/03/21)
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- Synthesis and X-ray structural studies of Cd(II) and Ni(II) complexes of 5-(4-methoxy phenyl), 5-(2-pyridyl) and 5-(2-methoxy phenyl)-1,3,4-oxadiazole-2- thione
-
Three new mixed ligand complexes [Cd(en)2(4-mpot)2] (1) [Ni(2-pytone)2(en)2] (2) and [Ni(2-mpot) 2(en)2] (3) {4-mpot = 5-(4-methoxy-phenyl)-1,3,4- oxadiazole-2-thione, 2-pytone = 5-(2-pyrid
- Bharty,Bharti,Dani,Dulare,Bharati,Singh
-
experimental part
p. 34 - 41
(2012/03/22)
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- Synthesis using microwave irradiation, characterisation and antibacterial activity of Novel deoxycholic acid-triazole conjugates
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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.
- Yang, Jie,Zhao, Zhigang,Li, Hui
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scheme or table
p. 383 - 386
(2012/10/08)
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- In vitro antifungal activity of some new triazole compounds
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In the present study, the derivatives of 1,2,4-triazoles were synthesized and tested for antifungal activity against Candida tropicalis ATCC-4563, Candida albicans ATCC-2091, Cryptococcus neoformans ATCC-34664, Trichosporon beigelii NCIM-3404 and Aspergillus flavus NCIM-538 by disc diffusion method. 1,2,4-Triazoles were obtained by cyclization of the potassium salt of substituted dithiocarbazinic acid with hydrazine hydrate. The new synthesized compounds were characterized using IR, 1H NMR spectral data and Mass spectrometry together with elemental analysis. The inhibitory effect of the newly synthesized triazole compounds was compared to the standard antifungal agents. Minimum inhibitory concentration (MIC) was determined for those compounds which could inhibit all the tested fungal strains with maximum inhibition zone.
- Chanda, Sumitra,Baluja, Shipra,Parekh, Jigna
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p. 281 - 285
(2012/11/07)
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- Synthesis and biological activities of some new 3,6-disubstituted 1,2,4-triazolo[3,4-b]1,3,4-thiadiazole derivatives
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A series of aromatic hydrazides 3a-j were prepared by refluxing esters 2a-j with hydrazine hydrate in methanol, which were prepared by the esterification of 1a-j. Acetohydrazides 3a-j upon treatment with carbon disulfide and methanolic potassium hydroxide yielded potassium dithiocarbazate salts 4a-j, which on refluxing with hydrazine hydrate yielded substituted 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones 5a-j. The target compounds 6a-j were synthesized by condensing furan-3-carboxylic acid in the presence of polyphosphoric acid under reflux. The structures of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were screened for their urease, acetylcholine esterase inhibition, antioxidant and alkaline phosphatase inhibition activity. Almost all of the compounds 6a-j showed good to excellent activities against urease and acetylcholine esterase more than the reference drugs. Compounds 6f and 6g were more potent scavenger of free radicals than the reference n-propyl gallate. Compound 6b and 6h showed excellent activities of alkaline phosphatase as compare to the reference KH 2PO4.
- Rafiq, Muhammad,Saleem, Muhammad,Hanif, Muhammad,Maqsood, Muhammad Rizwan,Rama, Nasim Hasan,Lee, Ki-Hwan,Seo, Sung-Yum
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p. 3943 - 3949
(2013/08/23)
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- Some pyridyl- and thiophenyl- Substituted 1,2,4-triazolo[3,4-b]1,3,4- thiadiazole derivatives as potent antibacterial
-
The target compounds 6-11a-e were synthesized by condensing 4-amino-5-aryl-3H-1,2,4-triazole-3-thiones 5a-f with various aromatic carboxylic acids in the presence of phosphorous oxychloride. The structures of newly synthesized compounds were characterized by IR, 1H NMR, 13C NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were screened for their antibacterial activity. Almost all the tested compounds were potent against four different strains of bacteria when compared with that of reference drug ciprofloxacin. Compounds 6c, 6e, 8d, 9b, 9e, 11a and 11b showed nearly equal or lower MIC values than standard drug, against all four tested bacterial strains but rest of the compounds showed excellent antibacterial activities.
- Maqsood, Muhammad Rizwan,Hanif, Muhammad,Rafiq, Muhammad,Saleem, Muhammad,Zaib, Sumera,Khan, Aftab Ahmed,Iqbal, Mazhar,Iqbal, Jamshed,Rama, Nasim Hasan,Seo, Sung-Yum,Lee, Ki-Hwan
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p. 4180 - 4184
(2013/08/23)
-
- Synthesis and antihyperlipidemic activity of some novel 4-(substitutedamino)-5-substituted-3-mercapto-(4H)-1,2,4-triazoles
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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.
- Chhabria, Mahesh T.,Suhagia, Bhanubhai N.,Brahmkshatriya, Pathik S.,Raval, Priyesha M.
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experimental part
p. 452 - 457
(2012/06/16)
-
- Green synthesis of 5-substituted-1,3,4-thiadiazole-2-thiols as new potent nitrification inhibitors [1]
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(Chemical Equation Presented) A fast, efficient synthesis of 5-substituted-1,3,4-thiadiazole-2-thiols was successfully developed, assessed using green chemistry matrices, and compounds were screened for their in vitro nitrification inhibitory activity. The greener method was superior with higher energy efficiency, E(nvironmental) factor, atom economy, atom efficiency, carbon efficiency, and reaction mass efficiency.
- Saha, Ajoy,Kumar, Rajesh,Kumar, Rajendra,Devakumar
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experimental part
p. 838 - 845
(2010/10/04)
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- Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity
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A new series of chiral 1,3,4-thiadiazoles derivatives possessing γ-substituted butenolide moiety were synthesized and evaluated for in vitro anticancer properties. All the compounds showed good anticancer activities against Hela cell lines. Of all the studied compounds, compound 9e exhibited the best inhibitory activity with an IC50 of 0.9 μM. After being treated with 0.1 μg/mL compound 9e for 24 h, the growth inhibition rate of Hela cell lines was 59.2%.
- Wei, Meng-Xue,Feng, Lei,Li, Xue-Qiang,Zhou, Xue-Zhang,Shao, Zhi-Hui
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scheme or table
p. 3340 - 3344
(2009/12/01)
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- Identification of a potent new chemotype for the selective inhibition of PDE4
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A series of substituted 3,6-diphenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines were prepared and analyzed as inhibitors of phosphodiesterase 4 (PDE4). Synthesis, structure-activity relationships, and the selectivity of a highly potent analogue against related phosphodiesterase isoforms are presented.
- Skoumbourdis, Amanda P.,Huang, Ruili,Southall, Noel,Leister, William,Guo, Vicky,Cho, Ming-Hsuang,Inglese, James,Nirenberg, Marshall,Austin, Christopher P.,Xia, Menghang,Thomas, Craig J.
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p. 1297 - 1303
(2008/09/20)
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- Investigation on the reaction of 4-anilino-5-mercapto-s-triazoles with pyrazolines and barbituric acids
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Synthesis of new 4-anilino-5-mercapto-3-substituted-1,2,4-triazoles (III) has been described.Reaction of III with 4,4-dibromo-substituted-pyrazolin-5-ones (VIII) affords 3,3'-substituted-5-phenyl-s-triazolothiadiazolidin-spiropyrazolin-5-ones
- Chande, Madhukar S.,Bhandari, Jayesh D.,Joshi, Vishwas R.
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p. 1218 - 1228
(2007/10/02)
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- THE ACIDITIES AND THE TAUTOMERIC STRUCTURE OF 5-ARYL-2-MERCAPTO-1,3,4-OXADIAZOLES
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The acidity constants of a series of substituted 5-phenyl-2-mercapto-1,3,4-oxadiazoles were determined by potentiometric and spectrophotometric methods in 80percent (vol.) ethanol-water at 25 deg C.The data obtained by the two methods are in good agreement.The pKa values correlate with the ?*XC6H4 constants of the substituted phenyl group (p = -0.985, r = 0.936), however, a better correlation of the pKa data with the Hammett substituent constants ?X (p = -0.983, r = 0.959) was obtained.These linear correlations exclude the possibility of the presence of the thiol tautomer 1 in eqiulibrium with the thioamide tautomer 2 and indicate that the ionization of the compounds takes place in the form of the thioamide tautomer 2.According to the results of the HMO calculations, the thioamide form 2 is more stable than the thiol tautomer 1.A satisfactory correlation between the observed pKa values and the difference between the ?-electronic energies (ΔE?) of the thioamide tautomer and of the common resonance-stabilized anion was obtained, thus supporting the assigned tautomeric structure 2 for the series under study.
- Shawali, Ahmad S.,Rizk, Mahmoud S.,Abdelhamid, Abdou O.,Abdalla, Magda A.,Parkanyi, Cyril,Wojciechowska, Magdalena E.
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p. 2211 - 2224
(2007/10/02)
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