- Mn(II) complexes of N0-(2-methoxybenzoyl)hydrazine carbodithioic acid ethyl ester: Synthesis, spectral and structural characterization
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Two new Mn(II) complexes [Mn(Hmbhce)2- (o-phen)] (1) and [Mn(Hmbhce) 2(bpy)] (2) based on N0-(2- methoxybenzoyl)hydrazine carbodithioic acid ethyl ester (H2mbhce) have been synthesized by reacting Mn(OAc)2- 4H2O with H2mbhce in the presence of
- Singh, Mamata,Bharty, Manoj K.,Singh, Aarti,Kashyap, Sujata,Singh, Udai P.,Singh, Nand K.
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- Design, synthesis, biological activity, crystal structure and theoretical calculations of novel 1,2,4-triazole derivatives
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Series of 1,2,4-triazole Schiff base (Ia-f) were designed and synthesized. Their in-vitro antifungal activity to pythium solani, gibberlla nicotiancola, fusarium oxysporium fs.p. niveum and gibberlla saubinetii were evaluated. The results showed compound If exhibited good activity with tested fungi, which indicated that 1,2,4-triazole scaffold with introduction of imidazole phenyl could keep the antifungal activity. In order to further research the compound If, the crystal structure was detected by X-ray diffraction. Meanwhile, the FT-IR, FT-Raman, natural bond orbital (NBO), HOMO-LUMO and MEP were calculated at B3LYP/6-311G+(d,p) level. All the results will be helpful for further drug design in 1,2,4-triazole analogues.
- Jin, Ruyi,Wang, Yanyan,Guo, Hui,Long, Xu,Li, Jiajia,Yue, Shijun,Zhang, Shuan,Zhang, Guanghui,Meng, Qinghua,Wang, Chuan,Yan, Hao,Tang, Yuping,Zhou, Sha
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- 5-substituent-1, 2, 4-triazole-thioketone Schiff base compound as well as preparation method and application thereof
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The invention belongs to the technical field of chemical medicines, and relates to a 5-substituent 1, 2, 4-triazole thioketone Schiff base compound as well as a preparation method and application thereof. An intermediate (I) or an intermediate (II) is subjected to reflux reaction with 3, 5-dimethyl 4-hydroxy benzaldehyde in glacial acetic acid respectively, filtering and drying are performed to obtain the 5-substituent -1, 2, 4-triazole thioketone Schiff base compound. According to the 5-substituent-1, 2, 4-triazole-thioketone Schiff base compound as well as the preparation method and application thereof of the invention, an active group-- imino is introduced into a triazole ring matrix to prepare and synthesize a series of triazole Schiff base compounds with multiple active sites, and thetriazole Schiff base compounds have the advantages of good activity, small dosage, small toxic and side effects, safety and environmental protection; meanwhile, the compounds can be used as crop antifungal agents and can influence the synthesis of fungal cell walls, so that the growth and proliferation of fungi are inhibited, and finally, an antibacterial or bactericidal effect is achieved.
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Paragraph 0100; 0105
(2021/01/04)
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- Design, synthesis, biological activities and DFT calculation of novel 1,2,4-triazole Schiff base derivatives
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Series of 1,2,4-triazole Schiff bases (2a-2d, 2f-2h and 3a-3h) have been designed and synthesized. The structure of title compounds was confirmed on the basis of their spectral data and elemental analysis. All the target compounds were screened for their in vitro antifungal activity and antibacterial activity. Two of the tested compounds (2a and 2b) exhibited significant antifungal activity against most fungi, especially compound 2a showed better antifungal activity than triadimefon. Meanwhile, the antibacterial activity assay also indicated compound 2a exhibited excellent antibacterial activities comparable to chloramphenicol. The SAR manifested no substitution at position 5 of the triazole ring caused an increase in activity, and 3-phenoxy phenyl group introduced in 1,2,4-triazole scaffold can enhance the antibacterial activity. The DFT calculation indicated triazole ring, S atom and benzene ring in both of the 2a and 3a make a major contribution to the activity.
- Jin, Ru-Yi,Zeng, Chu-Yue,Liang, Xu-Hua,Sun, Xiao-Hong,Liu, Yuan-Fa,Wang, Yan-Yan,Zhou, Sha
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p. 253 - 260
(2018/07/06)
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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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- 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 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 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 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
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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
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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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- 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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- 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 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)
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- Exploration and optimization of substituted triazolothiadiazines and triazolopyridazines as PDE4 inhibitors
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An expansion of structure-activity studies on a series of substituted 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine PDE4 inhibitors and the introduction of a related [1,2,4]triazolo[4,3-b]pyridazine based inhibitor of PDE4 is presented. The development of SAR included strategic incorporation of known substituents on the critical catachol diether moiety of the 6-phenyl appendage on each heterocyclic core. From these studies, (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine (10) and (R)-3-(2,5-dimethoxyphenyl)-6-(4-methoxy-3-(tetrahydrofuran-3-yloxy)phenyl)-[1,2,4]triazolo[4,3-b]pyridazine (18) were identified as highly potent PDE4A inhibitors. Each of these analogues was submitted across a panel of 21 PDE family members and was shown to be highly selective for PDE4 isoforms (PDE4A, PDE4B, PDE4C, PDE4D). Both 10 and 18 were then evaluated in divergent cell-based assays to assess their relevant use as probes of PDE4 activity. Finally, docking studies with selective ligands (including 10 and 18) were undertaken to better understand this chemotypes ability to bind and inhibit PDE4 selectively.
- Skoumbourdis, Amanda P.,LeClair, Christopher A.,Stefan, Eduard,Turjanski, Adrian G.,Maguire, William,Titus, Steven A.,Huang, Ruili,Auld, Douglas S.,Inglese, James,Austin, Christopher P.,Michnick, Stephen W.,Xia, Menghang,Thomas, Craig J.
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supporting information; experimental part
p. 3686 - 3692
(2010/03/24)
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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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