- Synthesis and crystal structure of 4-phenyl-3-(pyridin-4-yl)-1H-1,2,4- triazole-5(4H)-thione
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A triazole derivative i.e., 4-phenyl-3-(pyridin-4-yl)-1H-1,2,4-triazole- 5(4H)-thione was synthesized and its structure was studied by X-ray diffraction. The crystals are orthorhombic, space group pbcn with a = 11.337 (2), b = 12.789 (3), c = 17.625 (4) ?
- Gao, Wei,Guo, Feng-Peng,Yang, Jing
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- Discovery of antiproliferative and anti-FAK inhibitory activity of 1,2,4-triazole derivatives containing acetamido carboxylic acid skeleton
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Small molecule inhibitors of the focal adhesion kinase are regarded as promising tools in our armamentarium for treating cancer. Here, we identified four 1,2,4-triazole derivatives that inhibit FAK kinase significantly and evaluated their therapeutic pote
- Mustafa, Muhamad,Abuo-Rahma, Gamal El-Din A.,Abd El-Hafeez, Amer Ali,Ahmed, Esam R.,Abdelhamid, Dalia,Ghosh, Pradipta,Hayallah, Alaa M.
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- A first-in-class anticancer dual HDAC2/FAK inhibitors bearing hydroxamates/benzamides capped by pyridinyl-1,2,4-triazoles
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Novel 5-pyridinyl-1,2,4-triazoles were designed as dual inhibitors of histone deacetylase 2 (HDAC2) and focal adhesion kinase (FAK). Compounds 5d, 6a, 7c, and 11c were determined as potential inhibitors of both HDAC2 (IC50 = 0.09–1.40 μM) and F
- Mustafa, Muhamad,Abd El-Hafeez, Amer Ali,Abdelhamid, Dalia,Katkar, Gajanan D.,Mostafa, Yaser A.,Ghosh, Pradipta,Hayallah, Alaa M.,Abuo-Rahma, Gamal El-Din A.
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- Is Bismuth Really the "green" Metal? Exploring the Antimicrobial Activity and Cytotoxicity of Organobismuth Thiolate Complexes
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Antimicrobial resistance is becoming an ever-increasing threat for human health. Metal complexes and, in particular, those that incorporate bismuth offer an attractive alternative to the typically used organic compounds to which bacteria are often able to develop resistance determinants. Herein we report the synthesis, characterization, and biological evaluation of a series of homo- and heteroleptic bismuth(III) thiolates incorporating either one (BiPh2L), two (BiPhL2), or three (BiL3) sulfur-containing azole ligands where LH = tetrazolethiols or triazolethiols (thiones). Despite bismuth typically being considered a nontoxic heavy metal, we demonstrate that the environment surrounding the metal center has a clear influence on the safety of bismuth-containing complexes. In particular, heteroleptic thiolate complexes (BiPh2L and BiPhL2) display strong antibacterial activity yet are also nonselectively cytotoxic to mammalian cells. Interestingly, the homoleptic thiolate complexes (BiL3) were shown to be completely inactive toward both bacterial and mammalian cells. Further biological analysis of the complexes revealed the first insights into the biological mode of action of these particular bismuth thiolates. Scanning electron microscopy images of methicillin-resistant Staphylococcus aureus (MRSA) cells have revealed that the cell membrane is the likely target site of action for bismuth thiolates against bacterial cells. This points toward a nonspecific mode of action that is likely to contribute to the poor selectivity's demonstrated by the bismuth thiolate complexes in vitro. Uptake studies suggest that reduced cellular uptake could explain the marked difference in activity between the homo- and heteroleptic complexes.
- Stephens, Liam J.,Munuganti, Sarmishta,Duffin, Rebekah N.,Werrett, Melissa V.,Andrews, Philip C.
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p. 3494 - 3508
(2020/03/23)
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- Identification of 1,2,4-triazoles as new thymidine phosphorylase inhibitors: Future anti-tumor drugs
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Thymidine phosphorylase (TP) is over expressed in several solid tumors and its inhibition can offer unique target suitable for drug discovery in cancer. A series of 1,2,4-triazoles 3a–3l has been synthesized in good yields and subsequently inhibitory potential of synthesized triazoles 3a–3l against thymidine phosphorylase enzyme was evaluated. Out of these twelve analogs five analogues 3b, 3c, 3f, 3l and 3l exhibited a good inhibitory potential against thymidine phosphorylase. Inhibitory potential in term of IC50 values were found in the range of 61.98 ± 0.43 to 273.43 ± 0.96 μM and 7-Deazaxanthine was taken as a standard inhibitor with IC50 = 38.68 ± 4.42 μM. Encouraged by these results, more analogues 1,2,4-triazole-3-mercaptocarboxylic acids 4a–4g were synthesized and their inhibitory potential against thymidine phosphorylase was evaluated. In this series, six analogues 4b–4g exhibited a good inhibitory potential in the range of 43.86 ± 1.11–163.43 ± 2.03 μM. Angiogenic response of 1,2,4-triazole acid 4d was estimated using the chick chorionic allantoic membrane (CAM) assay. In the light of these findings, structure activity relationship and molecular docking studies of selected triazoles to determine the key binding interactions was discussed. Docking studies demonstrate that synthesized analogues interacted with active site residues of thymidine phosphorylase enzyme through π-π stacking, thiolate and hydrogen bonding interactions.
- Shahzad, Sohail Anjum,Yar, Muhammad,Khan, Zulfiqar Ali,Shahzadi, Lubna,Naqvi, Syed Ali Raza,Mahmood, Adeem,Ullah, Sami,Shaikh, Ahson Jabbar,Sherazi, Tauqir Ali,Bale, Adebayo Tajudeen,Kuku?owicz, J?drzej,Bajda, Marek
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p. 209 - 220
(2019/01/10)
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- Design, Synthesis and Antibacterial Evaluation of 1-[(1R,2S)-2-Fluorocyclopropyl]ciprofloxacin-1,2,4-triazole-5(4H)-thione Hybrids
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A new class of 1-[(1R,2S)-2-fluorocyclopropyl]ciprofloxacin (CPFX)-1,2,4-triazole-5(4H)-thione hybrids 6a?–?6o was designed, synthesized and evaluated for their in?vitro antibacterial activities against a panel of clinically important drug-sensitive and d
- Gao, Yang,Na, Lu-Xin,Xu, Zhi,Zhang, Shu,Wang, A-Peng,Kai,Guo, Hui-Yuan,Liu, Ming-Liang
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- Synthesis and antitumor activity of 4-cyclohexyl/aryl-5-(pyridin-4-yl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones
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The reaction of 2-isonicotinoyl-N-cyclohexyl/arylhydrazinecarbothioamide (2a-r) with sodium hydroxide, in each case, a single product was obtained. The structures of the compounds were confirmed on the basis of their elemental analysis and spectral data.
- Bhat, Mashooq Ahmad,Al-Omar, Mohamed A.,Naglah, Ahmed M.,Abdulla, Mohamed M.,Fun, Hoong-Kun
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p. 1558 - 1567
(2015/04/21)
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- Narrow SAR in odorant sensing Orco receptor agonists
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The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification.
- Romaine, Ian M.,Taylor, Robert W.,Saidu, Samsudeen P.,Kim, Kwangho,Sulikowski, Gary A.,Zwiebel, Laurence J.,Waterson, Alex G.
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p. 2613 - 2616
(2015/02/19)
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- Design, synthesis, and herbicidal activities of 3-aryl-4-substituted-5-[3- (trifluoromethyl)phenoxy]-1,2,4-triazoles
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In order to find novel bleaching herbicide lead compounds, a series of novel 3-aryl-4-substituted-5-[3-(trifluoromethyl)phenoxy]-1,2,4-triazoles were designed and synthesized by the multi-step reactions. N-(Arylformamido) phenylthioureas undergo ring clos
- Liu, Man-Yun,Shi, De-Qing
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p. E335-E339
(2014/11/07)
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- Narrow SAR in odorant sensing Orco receptor agonists
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The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification.
- Romaine, Ian M.,Taylor, Robert W.,Saidu, Samsudeen P.,Kim, Kwangho,Sulikowski, Gary A.,Zwiebel, Laurence J.,Waterson, Alex G.
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p. 2613 - 2616
(2014/06/09)
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- Synthesis and in-silico studies of some diaryltriazole derivatives as potential cyclooxygenase inhibitors
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The synthesis of several 4-phenyl-5-pyridin-4-yl-2,3-dihydro-3H-1,2,4- triazole-3-thiones possessing N-2 Mannich bases or S-alkyl substituents, is reported. Several of them exhibited a low nanomolar COX enzyme inhibition activity. Most of the compounds sh
- Radwan, Awwad A.,Eltahir, Kamal E. H.
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p. 553 - 563
(2013/07/28)
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- Synthesis, molecular modeling, and biological evaluation of 1,2,4-triazole derivatives containing pyridine as potential anti-tumor agents
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There is an accumulating body of experimental evidences validating focal adhesion kinase (FAK) as a therapeutic target and offering opportunities for anti-tumor drug development. In present study, we sought to synthesize twenty-eight potential FAK inhibit
- Zhang, Yan-Bin,Liu, Wen,Yang, Yu-Shun,Wang, Xiao-Liang,Zhu, Hai-Liang,Bai, Li-Fei,Qiu, Xiao-Yang
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p. 3193 - 3203
(2013/07/19)
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- Synthesis and antiviral activity of benzimidazolyl-and triazolyl-1,3,5- triazines
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A novel series of 1,3,5-triazine analogs was successfully synthesized through conjugation with benzimidazole or 1,2,4-triazole derivatives via a methylenethio linker. The new analogs were in vitro evaluated against HSV-1 in Vero cells; among these analogs, two compounds exhibited good effect in inhibiting HSV-1 replication (for compound 5p: EC50 = 3.5 μg/ml, SI = 358; for compound 5r: EC50 = 5.0 μg/ml, SI = 300) in comparison to acyclovir. Springer Science+Business Media, LLC 2011.
- Maarouf, Azza R.,Farahat, Abdelbasset A.,Selim, Khalid B.,Eisa, Hassan M.
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p. 703 - 710
(2012/09/22)
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- Synthesis and evaluation of antimicrobial activity of some new hetaryl-azoles derivatives obtained from 2-aryl-4-methylthiazol-5- carbohydrazides and isonicotinic acid hydrazide
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A series of new 1,3,4-oxadiazole/thiadiazole and 1,2,4-triazole derivatives have been synthesized starting from 2-aryl-4-methylthiazol-5-carbohydrazides and isonicotinic acid hydrazide. All the newly synthesized compounds were characterized by IR, 1
- Tiperciuc, Brindusa,Zaharia, Valentin,Colosi, Ioana,Moldovan, Cristina,Crisan, Ovidiu,Pirnau, Adrian,Vlase, Laurian,Duma, Mihaela,Oniga, Ovidiu
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p. 1407 - 1414
(2013/02/22)
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- Synthesis and antimicrobial evaluation of 2-amino-6-[(5-pyridin-4-yl-1,2,4- triazol-4(h)-phenyl-3-ylthio) methyl]-4-substituted phenylnicotinonitriles
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A series of novel 2-amino-6-f(5-pyridin-4-yl-1,2,4-triazoM(W)-phenyl-3- ylthio) methylJ-4-substitutedphenylnicotinonitriles were (7a-e) prepared by one-pot synthesis from malononitrile, aromatic aldehydes, ketone derivative and ammonium acetate under micr
- Mahajan, Niranjan S.,Dhavale, Shashikant C.,Jawarkar, Rahul D.,Manikrao, Anil M.,Chaple, Dinesh R.
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p. 361 - 364
(2013/09/24)
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- Synthesis, characterization and antiamoebic activity of some hydrazone and azole derivatives bearing pyridyl moiety as a promising heterocyclic scaffold
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In an effort to develop effective antiamoebic agents, some hydrazones and azoles containing pyridyl moiety were synthesized and screened for in vitro antiamoebic activity against HM1:IMSS strain of Entamoeba histolytica. Among all the compounds, only five compounds (1, 3, 5, 9 and 11) were found to be better inhibitors of growth of E. histolytica than the reference drug metronidazole. The cytotoxic studies of these compounds on human breast cancer MCF-7 cell line revealed that all the compounds were low-cytotoxic in the concentration range of 2.5-250 μM.
- Siddiqui, Shadab Miyan,Salahuddin, Attar,Azam, Amir
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experimental part
p. 411 - 416
(2012/04/04)
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- Synthesis of some new 1,2,4-triazoles, their Mannich and Schiff bases and evaluation of their antimicrobial activities
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4-Phenyl-5-pyridin-4-yl-4H-1,2,4-triazole-3-thiol (3) was obtained in basic media via the formation of 2-isonicotinoyl-N-phenylhydrazinecarbothioamide (2), and converted to some alkylated derivatives (4a,b) and Mannich base derivatives (5a-c). 2-[(4-Pheny
- Bayrak, Hacer,Demirbas, Ahmet,Karaoglu, Senguel Alpay,Demirbas, Neslihan
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experimental part
p. 1057 - 1066
(2009/08/14)
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- Synthesis and molecular structure of new S-nucleosides of 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols
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The synthesis of some new S-nucleosides of 5-(4-pyridyl)-4-aryl-4H-l,2,4- triazole-3-thiols (4a-n) is described. Direct glycosylation of (4a-n) with tetra-O-acetyl-α-D-glucopyranosyl bromide in the presence of potassium hydroxide followed by deacetylation using dry ammonia in methanol gave the corresponding 3-S-(β-D-glucopyranosyl)-5-(4-pyridyl)-4-aryl-4H-l,2,4- triazoles (6a-n) in good yields. All the compounds were fully characterized by means of 1H NMR, 13C NMR spectra and elemental analyses. To assist in the interpretation of the spectroscopic data, the crystal structure of 3-S-(2′,3′,4′,6′-tetra-O-acetyl-β-D- glucopyranosyl)-5-(4-pyridyl)-4-phenyl-4H-l,2,4-triazole (5a) was determined by X-ray diffraction.
- Zhang, Huan-Huan,Hu, Xiu-Qin,Fan, Gui-Fang,Xu, Peng-Fei
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body text
p. 834 - 841
(2009/12/01)
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- Novel anthelmintic and insecticidal compositions
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The present invention relates to novel anthelmintic and insecticidal compositions in general, and, more specifically, compositions containing triazole derivatives as active ingredients.
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Page/Page column 5
(2008/06/13)
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- Synthesis and structure elucidation of some new thioether derivatives of 1,2,4-triazoline-3-thiones and their antimicrobial activities.
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5-(4-Pyridinyl)-4-substituted-2.4-dihydro-3H-1,2,4-triazole-3-thiones and 5-(4-pyridinyl)-4-substituted-3-(benzoylmethyl)thio-4H-1,2,4-triazoles were synthesized. The structures of original nine compounds were confirmed by IR, 'H NMR, mass spectral methods and elemental analysis. The antibacterial, antifungal and antimycobacterial activities, together with those of known intermediate 1,4-disubstituted thiosemicarbazides, were reported.
- Guelerman,Dogan,Rollas,Johansson,Celik
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p. 953 - 958
(2007/10/03)
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- Synthesis and biological activity of bis-1,2,4-triazole and bis-1,3,4-thiadiazole derivatives
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Synthesis of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives via the condensation of N3-substituted amidrazones and p-phenylenediisothiocyanate (PPD) is presented. The reaction conditions are discussed. Results of a preliminary pharmacological screening are presented.
- Modzelewska-Banachiewicz, Bozena,Jagiello-Wojtowicz, Ewa,Tokarzewska-Wielosz, Ewa
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p. 199 - 204
(2007/10/03)
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- CYCLIZATION REACTION OF THIOSEMICARBAZONE-4-PICOLINAMIDE DERIVATIVES
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The ways of cyclization of thiosemicarbazone-4-picolinamide derivatives in different media such as ethanol, benzene, xylene and aqueous solution of sodium hydroxide were investigated.The reaction occured with liberation of primary amine from amide group of amidrazone or from isothiocyanate residue and led to formation of 1,2,4-triazoline-5-thione. - Keywords: thiosemicarbazone-4-picolinamide derivatives; cyclization
- Modzelewska, Bozena
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p. 425 - 427
(2007/10/03)
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- 4H-1,2,4-TRIAZOL-3-YL COMPOUNDS
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The present invention provides novel 4-phenyl-triazol-3-yl-and 3-phenyl-triazol-4-yl-piperidines which are useful as analgesics.
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