- Discovery of Novel Triazolothiadiazines as Fungicidal Leads Targeting Pyruvate Kinase
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Pyruvate kinase (PK) was discovered as a potent new target for novel fungicide development. A series of novel triazolothiadiazine derivatives were rationally designed and synthesized by a ring expansion strategy and computer-aided pesticide design using the 3D structure of Rhizoctonia solani PK (RsPK) obtained by homology modeling as a receptor and our previously discovered lead YZK-C22 as a ligand. The in vitro bioassay results indicated that compounds 4g, 6h, 6m, 6n, 6o, and 6p exhibited good activity against R. solani with the EC50 values falling between 10.99 and 72.76 μM. Especially, 6m showed similar potency to YZK-C22 (10.99 vs 11.97 μM of the EC50 value, respectively). The in vivo bioassay results suggested that 6m against R. solani at a concentration of 200 μg/mL displayed a numerically higher inhibition than YZK-C22 (70 vs 60%, respectively). A field experiment validated that 6m at an application rate of 120 g ai/ha showed comparable efficacy against R. solani to thifluzamide at an application rate of 80 g ai/ha (77.80 vs 84.5%, respectively). Enzymatic inhibition suggested that the potency of 6m was about twofold lower than that of YZK-C22 (67.30 vs 32.64 μM of IC50, respectively). Fluorescence quenching studies validated that RsPK was quenched by both 6m and YZK-C22, implying that they both might act at the same target site of PK. A possible binding conformation of 6m in the RsPK active site was depicted by molecular docking. Our studies suggest that 6m could be a fungicidal lead targeting PK.
- Chen, Hongyu,Chen, Lai,Chen, Lei,Fan, Zhijin,Gao, Wei,Liu, Xiaoyu,Qi, Xin,Tang, Liangfu,Ye, Rong,Zhang, Yue
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p. 1047 - 1057
(2022/02/14)
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- Electrocatalytic oxygen evolution and antiproliferative activity of Co(III) complexes stabilized by in situ generated bis(5-furan/phenyl-1,2,4-triazole)-3-sulfinamide
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Electrocatalytic water oxidation by transition metal complexes is an emerging area of research. Here, two cobalt(III) complexes [Co(ftsm)NH3(o-phen)]·H2O (1) {ftsm?= bis(5-furan-1,2,4-triazole)-3-sulfinamide} and [Co(ptsm)NH3/s
- Bharty, Manoj Kumar,Singh, Aarti,Bharati, Pooja,Pandey, Shivendra Kumar,Singh, Devesh Kumar,Ganesan, Vellaichamy,Verma, Praveen Kumar,Acharya, Arvind,Bharti, Akhilesh,Butcher, Ray J.
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- Anionic ligands tune the structural and catalytic properties of quinoxaline-based copper(II) complexes as mimetics of copper-containing oxidase protein
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The hexadentate ligand containing quinoxaline backbone along with its Cu(II) -based complexes with various anionic ligands were synthesized and their structures were determined. Molecular formulae were assigned based on the data of both elemental analysis
- Fathy, Ahmed M.,Hessien, Mahmoud M.,Ibrahim, Mohamed M.,Ramadan, Abd El-Motaleb M.
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- Design, Synthesis, and Evaluation of Novel Strobilurins Derivatives as Potential Fungicidal Agents
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To find new strobilurin analogs with high activity against resistant pathogens, a series of new strobilurin derivatives containing 1, 2, 4-triazole Schiff base side chain were designed and synthesized. Their structures were confirmed by IR, 1H
- Liu, Xin,Pang, Yanping,Wang, Xianyou,Wu, Guangchen,Zhao, Xin,Zhao, Zhilei,Zheng, Jiayan
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p. 613 - 619
(2022/01/26)
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- SYNTHESIS AND BIOLOGICAL ACTIVITIES OF SOME NOVEL STROBILURIN DERIVATIVES CONTAINING 1, 2, 4-TRIAZOLE MOIETY
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In this study, a series of strobilurin derivatives containing 1, 2, 4-triazole Schiff base side chain were designed and synthesized. Their structures were confirmed by IR,1H NMR,13C NMR, and HRMS. The antifungal tests indicated that compounds 6d′ displayed modest antifungal activity against Rhizoctonia solani, Botrytis cinereapers, and Fusarium graminearum. In addition, compounds 6g′, 6f′, 6e, and 6e′ exhibited better fungicidal activities against Blumeria graminis at a concentration of 50 μg/mL, with the inhibitory rates of 83.20%, 85.85%, 92.09%, and 100%, respectively.
- Liu, Xin,Pang, Yan-Ping,Wang, Wei,Wang, Xian-You,Wu, Guang-Chen,Zhao, Xin,Zheng, Jia-Yan,Zhou, Zhao-Xi
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p. 347 - 353
(2022/02/23)
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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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- 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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- Methoxy acrylate compound containing 1, 2, 4-triazole Schiff base and preparation method and application thereof
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The invention provides a methoxy acrylate compound containing 1, 2, 4-triazole Schiff base and preparation method and application thereof, the compound has a structure as shown in a general formula I,in the general formula I, a substituent R1 is independe
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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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- 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, characterization, and anticancer activity of some azole-heterocyclic complexes with gold(III), palladium(II), nickel(II), and copper(II) metal ions
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Four new complexes of Au(III), Pd(II), Ni(II), and Cu(II) ions were synthesized, derived from a novel heterocyclic ligand (L) that has both triazole and tetrazole rings. The ligand synthesis was through successive steps to achieve both heterocyclic rings.
- Abdnoor, Zahraa M.,Alabdali, Ammar J.
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p. 1474 - 1483
(2019/04/13)
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- Dithiocarbamate as a valuable scaffold for the inhibition of metallo-β-lactmases
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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.
- Ge, Ying,Xu, Li-Wei,Liu, Ya,Sun, Le-Yun,Gao, Han,Li, Jia-Qi,Yang, Kewu
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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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- Synthesis and characterization of Mn(II) complexes of 4-phenyl(phenyl-acetyl)-3-thiosemicarbazide, 4-amino-5-phenyl-1,2,4-triazole-3-thiolate, and their application towards electrochemical oxygen reduction reaction
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Two new complexes, [Mn(ppt)2(o-phen)] (1) and [Mn(aptt)(Cl)(o-phen)2]·2Haptt·H2O (2) with 4-phenyl (phenyl-acetyl)-3-thiosemicarbazide (Hppt) and 4-amino-5-phenyl-1,2,4-triazole-3-thiolate (Haptt) have been synthesized containing o-phenanthroline (o-phen) as a coligand. These complexes have been characterized by elemental analyses, IR and UV–Vis spectroscopic techniques, thermogravimetric analysis (TGA), magnetic susceptibility and single crystal X-ray diffraction data. The complexes are paramagnetic and have a distorted octahedral geometry. In complex 2, two molecules of Haptt and one water molecule are cocrystalized outside the coordination sphere. Complexes 1 and 2 are fluorescent and upon their excitation at 38 167 cm?1, exhibit emissions at 27 173 and 32 894 cm?1, respectively. TGA of complexes 1 and 2 indicate that the metal is converted into metal oxide at very high temperature. In the solid state, the crystal structure of both complexes are stabilized by various inter and intramolecular interactions. To explore the possible electrochemical applications of the complexes 1 and 2, they are immobilized on glassy carbon electrode using Nafion?. Cyclic voltammetry technique is used to characterize the metal complex immobilized electrodes in basic medium. Both complexes demonstrate excellent electrocatalytic activity towards electrochemical oxygen reduction. Since the electrocatalytic materials for oxygen reduction can dramatically increase the efficiency of the fuel cells and metal-air batteries, these metal complexes can be used as cathodic catalyst material in fuel cells and in metal-air batteries.
- Bharti, A.,Bharty, M. K.,Butcher, R. J.,Chaudhari, U. K.,Chaurasia, R.,Ganesan, V.,Kushawaha, S. K.,Sonkar, P. K.
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- Triazolbenzothiazole derivative and preparation method and application thereof
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The invention relates to a triazolbenzothiazole derivative, the chemical formula I of which is as shown in the following: wherein R1 is hydrogen, halogen and alkyl; R2 is hydrogen and halogen. Meanwhile, the invention also discloses a method for synthesizing the derivative. The method comprises the following steps: carrying out a reflux reaction in an ethylene glycol solution under the action of 2-aminobenzothiazole 1 and hydrazine hydrate by taking a 2-aminobenzothiazole derivative and an aryl hydrazide compound as initial raw materials to obtain a compound 2; further carrying out a reactionon the compound 2 and benzoyl chloride under the action of phosphorus oxychloride to obtain a compound 4, dissolving aromatic hydrazide and a proper amount of KOH in ethanol, carrying out a reaction with CS2 at normal temperature to obtain a compound 6, carrying out a reaction under the action of concentrated sulfuric acid to obtain a compound 7, and carrying out a reaction on the compound 4 and the compound 7 under the catalytic action of potassium carbonate in an acetonitrile solution to obtain a target product. The method provided by the invention is simple, easy to operate and liable to produce on a large scale, and the prepared compound I has relatively high antibacterial activity, and is widely applied to antibacterial pharmaceutical preparations through experimental verification.
- -
-
Paragraph 0020
(2018/05/16)
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- Synthesis and biological evaluation of disulfides bearing 1,2,4-triazole moiety as antiproliferative agents
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A series of novel nonsymmetrical disulfides bearing 1,2,4-triazole moiety were designed, synthesized, and evaluated for their in vitro antiproliferative activities against human cancer cell lines SMMC-7721, Hela, A549, and normal cell lines L929 by CCK-8 assay. The preliminary bioassay results demonstrated that most of the tested compounds 8a–r exhibited good antiproliferative activities, and some compounds showed better effects than positive control 5-fluorouracil against various cancer cell lines. Among these compounds, compound 8l showed significant antiproliferative activity against SMMC-7721 cells with IC50 value of 2.97 μM. Compound 8f displayed highly effective biological activity against Hela cells with IC50 value of 3.51 μM. Compound 8d exhibited the best inhibitory effect against A549 cells with IC50 value of 2.79 μM. Furthermore, some of the tested compounds showed weak cytotoxic effect against the normal cell lines L929. The pharmacological results suggest that the substituent groups are vital for improving the potency and selectivity of this class of compounds.
- Wang, Xue-Feng,Zhang, Shuai,Li, Bao-Lin,Zhao, Ji-Jun,Liu, Yu-Ming,Zhang, Rui-Lian,Li, Bo,Chen, Bao-Quan
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p. 3367 - 3374
(2017/11/16)
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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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- Pharmacological screening of some newly synthesized triazoles for H1 receptor antagonist activity
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The present work deals with the pharmacological screening of some newly synthesized triazoles. A series of 1,2,4-triazoles have been synthesized using benzoic acid or 4-chloro benzoic acid as the starting materials. The synthesized compounds were characterized by physical and spectral analysis viz., Fourier transform infrared spectroscopy, 1H nuclear magnetic resonance, 13C nuclear magnetic resonance, Gas Chromatography-Mass Spectrometry and elemental analysis Carbon, Hydrogen and Nitrogen analysis in order to confirm the structure. Acute toxicity studies were carried out in accordance with the Organization for Economic Co-operation and Development guideline 425. The compounds were not found to be lethal even at a dose level of 2000 mg/kg. Pharmacological evaluation was done following three intact animal experiments and one experiment on the isolated tissue. Results of the study indicated that the compound 7bi and 7bj protected up to 60% against histamine-induced dyspnea. Antihistaminic nature of the test compounds 7bi, 7bj, 7ai, and 7bk were also confirmed by the loss of catalepsy after the administration of clonidine (1%, s.c.). During experiments on isolated tissue, suppression of dose-response curve of histamine indicates a noteworthy denouement in favor of the said effect.
- Gupta, Jeetendra Kumar,Mishra, Pradeep
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p. 2260 - 2271
(2017/10/03)
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- Synthesis and biological evaluation of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives as acetylcholinesterase inhibitors
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An efficient protocol for the synthesis of novel glycosyl-containing 1,2,4-triazolo[3,4-b][1,3,4]thiadiazole derivatives starting from the commercially available d-glucosamine hydrochloride is described by reaction of glycosyl isothiocyanate with various aminotriazoles in DMF. Glycosyl isothiocyanate is an important intermediate and synthetic methods are discussed. The acetylcholinesterase inhibitory activity of these compounds was tested by Ellman’s method. It was found that most compounds exhibited over 90% inhibition and they were subsequently evaluated for their IC50values.
- Liu, Xiu-Jian,Wang, Lei,Yin, Long,Cheng, Feng-Chang,Sun, Hui-Min,Liu, Wei-Wei,Shia, Da-Hua,Caoa, Zhi-Ling
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p. 571 - 575
(2017/11/14)
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- Impact of inclusion complex formation on absorption and emission characteristics of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols
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The inclusion complexes of a series of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols have been synthesized with β-cyclodextrin. The compounds and their inclusion complexes have been characterized by studying their physical and spectral properties. The thermodynamic stability constant and free energy of activation have been determined to know the stability of inclusion complexes and type of host-guest relation. Finally, the absorption, excitation and emission spectra of the compounds and their inclusion complexes have been taken to examine whether the inclusion complex formation has any impact on absoption and emission characteristics of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols. It is found that inclusion complex formation brings about a drastic change in absorption, excitation and emission spectra of newly synthesized compounds.
- Panda, Sunakar,Nayak, Sashikanta,Das,Singh
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p. 981 - 986
(2016/03/01)
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- Impact of inclusion complex formation on antibacterial, antioxidant and anthelmintic activities of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols
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Three different 4-arylidenamino-5-phenyl-4H-l,2,4-triazole-3-thiols have been synthesized and their inclusion complexes are prepared with β-cyclodextrin. The compounds and their inclusion complexes have been characterized by studying their physical and spectral properties. The determination of thermodynamic stability constant and standard free energy change indicates that inclusion complexes of the newly synthesized compounds are stable and their formation is thermodynamically allowed. Finally, the compounds and their inclusion complexes are screened for antibacterial, antioxidant and anthelmintic activities. It is found that inclusion complex formation increases the antibacterial, antioxidant and anthelmintic activities significantly as compared to naked compounds. The higher pharmacological activities have been explained in terms of enhanced solubility in the systemic circulation which makes them more available to specific tissues for better therapeutic efficacy.
- Nayak, Sashikanta,Panda, Sunakar
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p. 1144 - 1150
(2017/04/28)
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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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- 1, 2, 4- triazoles[3, 4-b]-1, 3, 4-thiadiazole derivative containing glucosamine, and preparation method and application thereof
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The invention relates to a 1, 2, 4- triazoles[3, 4-b]-1, 3, 4-thiadiazole derivative containing glucosamine. Theinvention also relates to a synthetic method of the 1, 2, 4- triazoles[3, 4-b]-1, 3, 4-thiadiazole derivative containing glucosamine. The method comprises the following steps of: reacting substituted hydrazine with potassium hydroxide and carbon disulfide to obtain potassium salt; conducting cyclization on the potassium salt under the action of hydrazine hydrate to obtain 3-substituted-4-amino-5- sulfydryl-1,2,4-triazole, reacting the 3-substituted-4-amino-5- sulfydryl-1,2,4 -triazole with 2-deoxy-2-isothiocyanate-1,3,4,6-quaternary-O-benzyl-beta-D-glucopyranose for direct synthesis of N- (1,3,4, 6- quaternary-O-benzyl-beta-D-glucopyranose-2-yl) -6-amino-3- substituted-1,2,4-triazole[3,4-b]-1,3,4- thiadiazole. The synthesis method of the invention is simple, has small environmental pollution and simple posttreatment; and the synthesized material has strong inhibiting effect on acetylcholinesterase has broad application prospects in preparing anti-acetylcholinesterase drugs.
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Paragraph 0046
(2017/01/17)
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- Synthesis of novel (E)-α-(methoxyimino) benzeneacetate derivatives and their fungicidal activities
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In order to find novel strobilurin derivatives with good fungicidal activities, a series of (E)-α-(methoxyimino)benzeneacetate analogues containing 1,2,4-triazole Schiff base moiety were designed and synthesized. Their structures were confirmed by IR,sup
- Wang, Xianyou,Wang, Hua,Chen, Peiyun,Pang, Yanping,Zhao, Zhilei,Wu, Guangchen
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p. 502 - 510
(2015/08/04)
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- Antibacterial, antioxidant and anthelmintic studies of inclusion complexes of some 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols
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A series of 4-arylidenamino-5-phenyl-4H-1,2,4-triazole-3-thiols have been synthesised and their inclusion complexes have been prepared with β-cyclodextrin. The compounds and their inclusion complexes have been characterised by studying their physical and
- Panda, Sunakar,Nayak, Sashikanta
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p. 679 - 689
(2015/11/03)
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- Facile synthesis of new 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones
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The reaction of 2-bromo-1,4-naphthoquinone with 4-amino-5-aryl-4H-1,2,4-triazole-3-thiols in ethanol at 50 °C gave the corresponding 2-[(4-amino-5-aryl-4H-1,2,4-triazol-3-yl)thio]naphthalene-1,4-diones. Their treatment with EtOH/HCl under reflux conditions produced 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones through intramolecular cyclization.
- Khalafy, Jabbar,Mohammadlou, Mahsa,Mahmoody, Miri,Salami, Fatemeh,Poursattar Marjani, Ahmad
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p. 1528 - 1530
(2015/03/14)
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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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- 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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- 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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- Synthesis and Biological Activities of Some Novel (E)-Alpha-(methoxyimino)benzeneacetate Derivatives with Modified 1,2,4-Triazole Moiety
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To find new strobilurin analogues with high activity against resistant pathogens, a series of (E)-α-(methoxyimino)benzeneacetate derivatives containing 1,2,4-triazole Schiff base side chain were designed and synthesized. Their structures were confirmed by
- Wang, Xianyou,Wang, Hua,Chen, Peiyun,Pang, Yanping,Zhao, Zhilei,Wu, Guangchen
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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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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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- Syntheses, spectral and structural characterization of Ni(II) complexes of 4-amino-5-phenyl/3-pyridyl/thiophen-2H-1,2,4-triazole-3-thione
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New mixed ligand complexes [Ni(aptt)2(en)2] (1), [Ni(apytt)2(en)2]×CHCl3 (2) and [Ni(athtt)2(en)2] (3) with 4-amino-5-phenyl-2H-1,2,4- triazole-3-thione (Haptt), 4-amino-5-(pyridin-3-yl)-4,5-dihydro-3H-1,2,4- triazole-3-thione (Hapytt) and 4-amino-5-thiophen-2H-1,2,4-triazole-3-thione (Hathtt) have been prepared containing en as the secondary ligand. The metal complexes have been characterized with the aid of elemental analyses, IR, magnetic susceptibility and single crystal X-ray data. All the complexes are bonded through two nitrogen atoms of two triazole ligands and four nitrogens of two ethylenediamine and the resulting complexes have distorted octahedral geometry. The triazole ligands behave as uninegative monodentate, bonding through triazole nitrogen due to the hard character of the nickel(II). The complexes contain extended hydrogen bonding providing supramolecular framework. The course of the thermal degradation of complex 2 has been investigated by TG-DTA which suggest the loss of CHCl3 molecule around 200 C and finally a residue of NiS is left behind.
- Bharty,Bharati, Pooja,Bharti,Singh,Singh, Sanjay,Singh
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p. 326 - 332
(2013/12/04)
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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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p. 383 - 386
(2012/10/08)
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- Synthesis and crystal structures of Zn(II)/Co(II) complexes with condensed heterocyclic based 1,2,4-triazole
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Three Zn(II)/Co(II) coordination compounds with condensed heterocyclic based 1,2,4-triazole 8H-4, 7-diphenyl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (L1), and 8H-4-phenyl-7-(pyridine-2-yl)-1,2,4-triazolo[3,4-b]-1,3, 4-thiadiazines (L2), Co(L1)2Cl2 (1), Zn(L1)2Cl2 (2). and Co(L2) 2Cl2 (3) were synthesized and structurally characterized by elemental analyses, IR spectroscopy and single-crystal X-ray diffraction. Complexes 1, 2 and 3 have mononuclear structure, the mononuclear structures of 1 and 2 were further assembled by the C-H...Cl and C-H...N weak interactions into an infinite 2-D supramolecular sheet. Springer Science+Business Media, LLC 2012.
- Ma, Peng-Yuan,Zhang, Jian-Bin,Bai, Mei,Wang, Duo-Zhi
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scheme or table
p. 803 - 808
(2012/09/22)
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- 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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p. 452 - 457
(2012/06/16)
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- Safety and Efficacy of New 3,6-diaryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine Analogs as Potential Phosphodiesterase-4 Inhibitors in NIH-3T3 Mouse Fibroblastic Cells
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A novel series of potential phosphodiesterase-4 (PDE-4) inhibitors, 6-(3-(cyclopentyloxy)-4-methoxyphenyl)-3-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, were developed. Different concentrations of the synthesized compounds were tested on cultured NIH-3T3 cells to determine their safety and efficacy in NIH-3T3 mouse fibroblastic cells in comparison with rolipram, a selective PDE-4 inhibitor. The viability of cells was determined by (3-(4,5-dimethylthiazol-2-yl)-2,5-di-phenyltetrazoliumbromide (MTT) assay. The PDE inhibition rate was measured indirectly by determination of concentrations of extracellular cyclic adenosine monophosphate (cAMP) and cyclic guanosine monophosphate (cGMP) using enzyme-linked immunoassay technique. The results showed that all tested compounds caused a marked increase in the concentration of cAMP, whereas the concentration of cGMP stayed approximately unchanged. The cytotoxic IC50 of all synthesized compounds was approximately twofold greater than their required concentration for inhibition of PDE-4 (in terms of elevation of cAMP), and thus, these structures could be used to develop potent and safe inhibitors of PDE-4 enzyme.
- Baeeri, Maryam,Foroumadi, Alireza,Motamedi, Maryam,Yahya-Meymandi, Azadeh,Firoozpour, Loghman,Ostad, Seyed N.,Shafiee, Abbas,Souzangarzadeh, Saeid,Abdollahi, Mohammad
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scheme or table
p. 438 - 444
(2012/04/04)
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- Synthesis, characterization and biological activity of some transition metals complexes with Schiff base derived from 4-amino-5-phenyl-4H-1,2,4- triazole-3-thiol and p-methoxysalicyldehyde
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The coordination behaviour of Schiff base with NOS donation sites, derived from condensation of 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol and p-methoxysalicyldehyde (H2L), transition metal ions namely Cr(III), Mn(II), Co(II) (Cl, ClO4/su
- Altalbawy, Farag M.A.,Mohamed, Gehad G.,Mohamed, Mohamed I.A.
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scheme or table
p. 7291 - 7307
(2012/07/14)
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- 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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- Spectral and equilibrium studies on some new derivatives of 4-amino-5-phenyl-3-mercapto-1,2,4-triazole
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4-Amino-5-phenyl-3-mercapto-1,2,4-triazole (APMT), 4-(4′-methoxy) benzylidineamino-5-phenyl-3-mercapto-1,2,4-triazole (PMBPMT), 4-benzylidineamino-5-phenyl-3-mcrcapto-1,2,4-triazole (BPMT), 4-(2′-hydroxy)benzylidineamino-5-phenyl-3-mercapto-1,2,4-triazole (HBPMT) and 4-amino-5-(4′-nitro)phenyl-3-mercapto-1,2,4-triazole (ANPMT) were synthesized and characterized by elemental analyses, IR, 1H NMR, 13C NMR, DEPT and Mass spectral studies. Proton dissociation constants of these compounds in 70% v/v dioxan water medium at 303 K. and 0.1 M (KNO3) ionic strength were measured. The order of the pKa corresponding to mercapto group follows the sequence : PMBPMT > BPMT > HBPMT > APMT > ANPMT.
- Sireesha, Aliya B.,Reddy, Ch. Venkata Ramana,Devi, Ch. Sarala
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scheme or table
p. 926 - 929
(2009/12/07)
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- Synthesis and in-vitro antimicrobial activity of new 1,2,4-triazoles
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We have described the synthesis of new 1,2,4-triazoles and have evaluated their antimicrobial profile. Antitubercular activity was determined in triplicate using the Lowenstein-Jensen medium. A loopful of Mycobacterium tuberculosis suspension was inoculated on the surface of each Lowenstein-Jensen media containing the test compounds (100, 10 or 1 μg mL-1). To evaluate in-vitro antibacterial activity, compounds (50, 5 or 0.5 μg) were evaluated against B. subtilis, Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Staphylococcus typhi by the disc diffusion method. To evaluate antifungal activity Sabourauds Dextrose agar medium was used. Some of the compounds (5, 0.5 or 0.05 μg mL-1) were screened for activity against Aspergillus niger 88 and Aspergillus niger 90 and others were screened for activity against T. rubrum TR1, T. rubrum R6, T. rubrum R7 and T. mentagrophyte M1, using the cup plate method. Our results show that the triazoles with a pyrazine moiety at position 3 were more active as antitubercular and antifungal agents compared with the triazoles which had a pyrazine moiety at position 4 of the molecule.
- Bhat,Bhat,Shenoy
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p. 267 - 272
(2007/10/03)
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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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