- 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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- Synthesis, characterization and cytotoxicity of new 2-isonicotinoyl-N-phenylhydrazine-1-carbothioamide and its metal complexes
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The reaction of the newly synthesized ligand, 2-isonicotinoyl-N-phenylhydrazine-1-carbothioamide (H3L), with acetate salt of Co (II), Cu (II),Ni (II) and Zn (II) led to isolation of four solid complexes. The ligand and complexes structure elucidation were based on elemental analyses, spectral analyses (IR, UV–Visible, 1H and13C-NMR, MS and ESR), TGA, molar conductivity and magnetic moments measurements. The results indicated that the ligand exists in the thioketo form, while on coordination to the metal ions; it behaves as mono-negative bidentate chelate and exists in enol form. The optical band gap measurements of the ligand and its metal complexes are in the range 3.83–4.48?eV indicating their semi-conducting character. The cytotoxicity examination of H3L and its Zn (II) complex showed that the ligand have very strong cytotoxicity against both HCT-116 and HEPG-2 cell lines while, Zn (II) complex has moderate activity.
- Hosny, Nasser M.,Hassan, Nader Y.,Mahmoud, Heba M.,Abdel-Rhman, Mohamed H.
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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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- Synthetic nicotinic/isonicotinic thiosemicarbazides: In vitro urease inhibitory activities and molecular docking studies
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Nicotinic and isonicotinic thiosemicarbazide or hydrazine carbothioamides 3–27 were synthesized and the structures of synthetic compounds were elucidated by various spectroscopic techniques such as EI-MS, 1H-, and 13C NMR. Synthetic derivatives were evaluated for their urease inhibitory activity which revealed that except few all derivatives demonstrated excellent inhibition in the range of IC50 values of 1.21–51.42 μM as compared to the standard thiourea (IC50 = 21.25 ± 0.13 μM). Among the twenty-five synthetic derivatives nineteen 1–5, 7, 8, 10, 12, 14–18, 20–22, 24–27 were found to be more active showing IC50 values between 1.13 and 19.74 μM showing superior activity than the standard. Limited structure-activity relationship demonstrated that the positions of substituent as well as position of nitrogen in pyridine ring are very important for inhibitory activity of this class of compound. To verify these interpretations, in silico study was also performed. A good correlation was obtained between the biological evaluation of active compounds and docking study.
- Ali, Basharat,Mohammed Khan, Khalid,Arshia,Kanwal,Hussain, Shafqat,Hussain, Safdar,Ashraf, Muhammad,Riaz, Muhammad,Wadood, Abdul,Perveen, Shahnaz
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- Synthesis and molecular docking studies of glucose-linked isonicotinoyl- 1, 3, 4-thiadiazolidines as antitubercular agents
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Background: The recent emergence of multidrug-resistant strains of M. tuberculosis that are resistant to two major effective drugs, viz. isoniazid and rifampicin, stimulated us to make an attempt for the development of a new class of potent antitubercular
- Chavan, Snehal A.,Ulhe, Avinash G.,Berad, Baliram N.,Chikhale, Rupesh V.
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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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- Novel 1,3,4-oxadiazole motifs bearing a quinoline nucleus: Synthesis, characterization and biological evaluation of their antimicrobial, antitubercular, antimalarial and cytotoxic activities
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A series of quinoline based 1,3,4-oxadiazole derivatives (8a-l) were synthesized by a chloro-amine coupling reaction approach with different catalysts and solvents. Substituted 1,3,4-oxadiazole intermediates 7a-c were obtained from 2-substituted-N-phenylh
- Ladani, Gaurav G.,Patel, Manish P.
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p. 9848 - 9857
(2015/12/01)
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- Synthesis and anti-Candidal activity of N-(4-aryl/cyclohexyl)-2-(pyridine- 4-yl carbonyl) hydrazinecarbothioamide
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Eighteen N-(4-aryl/cyclohexyl)-2-(pyridine-4-yl carbonyl) hydrazinecarbothioamide derivatives were synthesized, evaluated against ten clinical isolates of Candida spp. and compared with itraconazole. Introduction of p-chloro (2c), p-iodo (2q), m-chloro (2
- Bhat, Mashooq Ahmad,Khan, Abdul Arif,Khan, Shahanavaj,Al-Omar, Mohamed A.,Parvez, Mohammad Khalid,Al-Dosari, Mohammed Salem,Al-Dhfyan, Abdullah
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p. 1299 - 1302
(2014/03/21)
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- 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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p. 2083 - 2085
(2014/06/09)
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- Efficient and mild synthesis of substituted 2-amino-1,3,4-oxadiazoles mediated by (tosylimino)phenyl-γ3-iodane
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A simple and convenient one-pot protocol for the synthesis of substituted 2-amino-1,3,4-oxadiazoles mediated by (tosylimino)phenyl-γ3- iodane has been described. Acylthiosemicarbazides prepared from the corresponding acylhydrazides undergo effi
- Prabhu, Girish,Madhu, Chilakapathi,Sureshbabu, Vommina V.
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p. 865 - 870
(2014/08/05)
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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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- Studies on phenylmercury(II) complexes of nitrogen-sulfur ligands: Synthesis, spectral, structural characterization, TD-DFT and photoluminescent properties
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The reactions of phenylmercury(II) acetate with N-phenyl-5-(pyridin-4-yl)- 1,3,4-thiadiazol-2-amine (Hppt) (1) and potassium N(4-methylpiperazine)-1- carbodithioate [K(mpcdt)] yielded [PhHg(ppt)] (2) and [PhHg(mpcdt)] (3). The complexes have been characte
- Bharti,Bharati,Dulare, Ram,Bharty,Singh, Dheeraj K.,Singh
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p. 170 - 180
(2013/10/01)
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- A new and efficient synthesis of 1,3,4-oxadiazole derivatives using TBTU
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An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from isothiocyanates and hydrazides through cyclodesulfurization in the presence of (O-(benzotriazol-1-yl)-N,N,N′, N′-tetramethyluronium tetrafluoroborate) TBTU as an uronium cou
- Maghari, Shokoofeh,Ramezanpour, Sorour,Darvish, Fatemeh,Balalaie, Saeed,Rominger, Frank,Bijanzadeh, Hamid Reza
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p. 2075 - 2080
(2013/03/13)
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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 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, 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 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 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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- Hypervalent iodine(V) mediated mild and convenient synthesis of substituted 2-amino-1,3,4-oxadiazoles
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A simple protocol for the synthesis of 2-amino-1,3,4-oxadiazoles starting from the corresponding acylhydrazides by cyclodesulfurization of intermediate acylthiosemicarbazides mediated by o-iodoxybenzoic acid in good yields has been described. The protocol
- Prabhu, Girish,Sureshbabu
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experimental part
p. 4232 - 4234
(2012/09/07)
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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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scheme or table
p. 703 - 710
(2012/09/22)
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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 anticonvulsant activity of substituted oxadiazole and thiadiazole derivatives
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A series of five membered heterocyclics was synthesized by the reaction between isoniazid and various substituted isothiocyanates and was tested for their anticonvulsant activity by determining their ability to provide protection against convulsions induc
- Yar, Mohammad Shahar,Akhter, Mohammad Wasim
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experimental part
p. 393 - 397
(2010/01/13)
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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
-
body text
p. 834 - 841
(2009/12/01)
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- Isonicotinoylhydrazothiazoles and isonicotinoyl-N4-substituted thiosemicarbazides: Synthesis, characterization, and anti-mycobacterial activity
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Differently substituted isonicotinoylhydrazothiazoles and isonicotinoyl-N4-substituted thiosemicaibazides have been prepared and characterized by means of elemental analysis, 1H-NMR, 13C-NMR, and Mass spectrometry. All the
- Cardia, Maria Cristina,Distinto, Simona,Maccioni, Elias,Plumitallo, Antonio,Saddi, Manuela,Sanna, Maria Luisa,DeLogu, Alessandro
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p. 1337 - 1342
(2007/10/03)
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- 1,3,4-Thiadiazole derivatives. Synthesis, structure elucidation, and structure-antituberculosis activity relationship investigation
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A series of 2,5-disubstituted-1,3,4-thiadiazoles were synthesized, the compounds structures were elucidated and screened for the antituberculosis activity against Mycobacterium tuberculosis H37Rv using the BACTEC 460 radiometric system. Among the tested compounds, 2-phenylamino-5-(4-fluorophenyl) -1,3,4-thiadiazole 22 showed the highest inhibitory activity. The relationships between the structures of compounds and their antituberculosis activity were investigated by the Electronic-Topological Method (ETM) and feed forward neural networks (FFNNs) trained with the back-propagation algorithm. As a result of the approach, a system of pharmacophores and anti-pharmacophores has been found that effectively separates compounds of the examination set into groups of active and inactive compounds. The system can be applied to the screening and design of new active compounds possessing skeletons similar to those used in the present study.
- Oru?, El?in E.,Rollas, Sevim,Kandemirli, Fatma,Shvets, Nathaly,Dimoglo, Anatholy S.
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p. 6760 - 6767
(2007/10/03)
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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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- Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives
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A series of substituted 1,3,4-oxadiazole derivatives 19-34 were synthesized as antiinflammatory agents. The target compounds were obtained by cyclodesulfurization of the corresponding thiosemicarbazides 3-18 using either dicyclohexylcarbodiimide DCC, or I
- Omar,Mahfouz,Rahman
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p. 819 - 825
(2007/10/03)
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- Synthesis and characterization of palladium(II) complexes derived from aromatic thiosemicarbazide derivatives
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The reaction of aromatic thiosemicarbazides with palladium(II) ions give three type of complexes having the composition PdLCl2, Pd(L-H)2 and Pd(L-2H) .Elemental analyses, molar conductivities, magnetic measurements and spe
- Bekheit, M. M.,Elewady, Y. A.,Taha, F. I.,Mostafa, S. I.
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p. 178 - 183
(2007/10/02)
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