Synthesis and Antimicrobial Activity of Some New Thiadiazoles, Thioamides, 5-Arylazothiazoles and Pyrimido[4,5-d][1,2,4]triazolo[4,3-a]pyrimidines

A novel series of 1,3,4-thiadiazoles, 5-arylazothiazoles and hexahydropyrimido-[4,5-d][1,2,4]triazolo[4,3-a]pyrimidines were synthesized via reaction of hydrazonoyl halides with each of alkyl carbothioates, carbothioamides and 7-thioxo-5,6,7,8-tetrahydropyrimido-[4,5-d]pyrimidine-2,4(1H,3H)-diones in the presence of triethylamine. The structures of the newly synthesized compounds were established based on their spectral data, elemental analyses and alternative synthetic routes whenever possible. Also, the newly synthesized compounds were screened for their antimicrobial activity against various microorganisms.

[1]  A. Abdelhamid,et al.  Utility of N-aryl 2-aroylhydrazono-propanehydrazonoyl chlorides as precursors for synthesis of new functionalized 1,3,4-thiadiazoles with potential antimicrobial activity , 2014, Journal of advanced research.

[2]  Jianquan Weng,et al.  Microwave Assistant One Pot Synthesis, Crystal Structure, Antifungal Activities and 3D‐QSAR of Novel 1,2,4‐Triazolo[4,3‐a]pyridines , 2014, Chemical biology & drug design.

[3]  Mohamed Fares,et al.  Synthesis and antitumor activity of pyrido [2,3-d]pyrimidine and pyrido[2,3-d] [1,2,4]triazolo[4,3-a]pyrimidine derivatives that induce apoptosis through G1 cell-cycle arrest. , 2014, European journal of medicinal chemistry.

[4]  V. M. Chernyshev,et al.  Molecular Structure of 3-Amino[1,2,4]Triazolo-[4,3-A]Pyrimidin-5-One in Various Tautomeric Forms: Investigation by DFT and QTAIM Methods , 2014, Chemistry of Heterocyclic Compounds.

[5]  K. Dawood,et al.  Synthesis of some new pyrazole-based 1,3-thiazoles and 1,3,4-thiadiazoles as anticancer agents. , 2013, European journal of medicinal chemistry.

[6]  M. G. Badrey,et al.  Ecofriendly regioselective one-pot synthesis of chromeno[4,3-d][1,2,4]triazolo[4,3-a]pyrimidine derivatives , 2013 .

[7]  K. Mohana,et al.  Synthesis of indazole substituted-1,3,4- thiadiazoles and their anticonvulsant activity , 2013 .

[8]  Paweł Szymański,et al.  Synthesis and biological evaluation of 1,3,4-thiadiazole analogues as novel AChE and BuChE inhibitors. , 2013, European journal of medicinal chemistry.

[9]  T. Farghaly,et al.  Synthesis of pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidin-5-ones as potential antimicrobial agents , 2013, Archives of pharmacal research.

[10]  A. Abdelhamid.  Synthesis of Spiro-heterocycles via 1,3-Dipolar Cycloadditions of Nitrilimines to Exoheterocyclic Enones. Site-, Regio- and Stereo-Selectivities Overview , 2012 .

[11]  W. Rzeski,et al.  2-Amino-1,3,4-thiadiazole derivative (FABT) inhibits the extracellular signal-regulated kinase pathway and induces cell cycle arrest in human non-small lung carcinoma cells. , 2012, Bioorganic & medicinal chemistry letters.

[12]  P. Dhanabal,et al.  Synthesis, antidepressant and antimicrobial activities of some novel stearic acid analogues. , 2012, European journal of medicinal chemistry.

[13]  Hideki Matsui,et al.  Identification of benzoxazin-3-one derivatives as novel, potent, and selective nonsteroidal mineralocorticoid receptor antagonists. , 2011, Journal of medicinal chemistry.

[14]  Zhen-Hua Chen,et al.  Synthesis and Anti‐Bacterial Activity of Some Heterocyclic Chalcone Derivatives Bearing Thiofuran, Furan, and Quinoline Moieties , 2011, Archiv der Pharmazie.

[15]  M. Al-Amin,et al.  Microwave-assisted Efficient Synthesis of Chalcones as Probes for Antimicrobial Activities , 2011 .

[16]  J. Turnidge,et al.  Susceptibility Test Methods: General Considerations , 2011 .

[17]  R. Uddin,et al.  Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. , 2010, European journal of medicinal chemistry.

[18]  Abdullah M. Asiri,et al.  Ethyl (Z)-2-chloro-2-(2-phenylhydrazin-1-ylidene)acetate , 2010, Acta Crystallographica Section E.

[19]  P. Sharma,et al.  Synthesis and biological evaluation of some pyrazolylpyrazolines as anti-inflammatory-antimicrobial agents. , 2010, European journal of medicinal chemistry.

[20]  H. F. Zohdi,et al.  Atom-Efficient, Solvent-Free, Green Synthesis of Chalcones by Grinding , 2009 .

[21]  Kamala K Vasu,et al.  Synthesis of 4-benzyl-1,3-thiazole derivatives as potential anti-inflammatory agents: An analogue-based drug design approach , 2009, Journal of enzyme inhibition and medicinal chemistry.

[22]  P. Kondaiah,et al.  Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles. , 2009, European journal of medicinal chemistry.

[23]  S. M. Gomha,et al.  A facile one-pot synthesis of 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones , 2009 .

[24]  K. Dawood,et al.  Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles. , 2006, Bioorganic & medicinal chemistry.

[25]  D. Secci,et al.  Synthesis, molecular modeling studies, and selective inhibitory activity against monoamine oxidase of 1-thiocarbamoyl-3,5-diaryl-4,5-dihydro-(1H)- pyrazole derivatives. , 2005, Journal of medicinal chemistry.

[26]  Y. Joshi,et al.  Solvent Free Synthesis of Chalcones and their Antibacterial Activities , 2005 .

[27]  M. N. Nasr,et al.  Novel 3, 3a, 4, 5, 6, 7‐Hexahydroindazole and Arylthiazolylpyrazoline derivatives as Anti‐inflammatory Agents , 2003, Archiv der Pharmazie.

[28]  M. Mosselhi.  A Convenient Synthesis of Novel Derivatives of Pyrido[2,3‐d][1,2,4]triazolo[4,3‐a]pyrimidine‐5,6‐dione. , 2003 .

[29]  M. Mosselhi.  A Convenient Synthesis of NovelDerivatives of Pyrido[2,3-d][1,2,4]triazolo[4,3-a]pyrimidine-5,6-dione , 2002 .

[30]  J. Rudolph,et al.  seco-Cyclothialidines: new concise synthesis, inhibitory activity toward bacterial and human DNA topoisomerases, and antibacterial properties. , 2001, Journal of medicinal chemistry.

[31]  G. Çapan,et al.  Synthesis and Hypnotic Activity of New 4‐Thiazolidinone and 2‐Thioxo‐4,5‐imidazolidinedione Derivatives , 1999, Archiv der Pharmazie.

[32]  C. Koboldt,et al.  Synthesis and activity of sulfonamide-substituted 4,5-diaryl thiazoles as selective cyclooxygenase-2 inhibitors. , 1999, Bioorganic & medicinal chemistry letters.

[33]  A. Abdelhamid,et al.  Reactions with Hydrazonoyl Halides. Part 21. Reinvestigation of the Reactions of Hydrazonoyl Bromides with 1,1-Dicyanothioacetanilide , 1999 .

[34]  A. Smânia,et al.  Antibacterial Activity of Steroidal Compounds Isolated from Ganoderma applanatum (Pers.) Pat. (Aphyllophoromycetideae) Fruit Body , 1999 .

[35]  J. Herbert,et al.  New orally active non-peptide fibrinogen receptor (GpIIb-IIIa) antagonists: identification of ethyl 3-[N-[4-[4-[amino[(ethoxycarbonyl) imino]methyl]phenyl]-1,3-thiazol-2-yl]-N-[1-[(ethoxycarbonyl)methyl]pip erid -4-yl]amino]propionate (SR 121787) as a potent and long-acting antithrombotic agent. , 1997, Journal of medicinal chemistry.

[36]  Alan R. Katritzky,et al.  Comprehensive Heterocyclic Chemistry IV , 1996 .

[37]  J M Morin,et al.  Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure-activity relationship studies of PETT analogs. , 1995, Journal of medicinal chemistry.

[38]  H. Ishikawa,et al.  Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7 , 1994 .

[39]  A. Doherty,et al.  Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors. , 1992, Journal of medicinal chemistry.

[40]  T. Heffner,et al.  4-(1,2,5,6-Tetrahydro-1-alkyl-3-pyridinyl)-2-thiazolamines: a novel class of compounds with central dopamine agonist properties. , 1990, Journal of medicinal chemistry.

[41]  N. Eweiss,et al.  Synthesis of heterocycles. Part II. New routes to acetylthiadiazolines and alkylazothiazoles , 1980 .

[42]  S. A. Sami,et al.  Reaction of dimethylphenacylsulfonium bromide with N-nitrosoacetarylamides and reactions of the products with nucleophiles. , 1976 .

[43]  A. S. Shawali,et al.  Synthesis and reactions of phenylcarbamoylarylhydrazidic chlorides , 1971 .

[44]  R. Schmidt,et al.  1.3‐Dipolare Additionen, III. Umsetzungen des Diphenylnitrilimins mit Carbonyl und Thiocarbonyl‐Verbindungen , 1962 .