Synthesis, Characterization and Antimicrobial Activity of pyrimidothionyl - [Triazolo-thiadiazole] Fused Heterocycles
Keywords:
Pyrimidinthione, Triazole-Thiadiazole, Spectral Study, Antibacterial And Antifungal Activities.Abstract
The reaction of 6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidone carbo hydrazides (1) with CS2 in presence of KOH yielded 5-(4-amino-3-mercapto-4,5-dihydro-1H-1,2,4-triazol-5-yl)-6-methyl-4-phenyl-3,4-dihydropyrimidin-2(1H)-thione (2). The compound (2) on reaction with various aromatic acids afforded 5-[6-aryl-2,3-dihydro-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-3-yl]-6-methyl-4-phenyl-3,4-dihydro pyrimidin-2(1H)-thiones (3a-e). The structures of fused heterocycles compounds were confirmed by elemental contents and spectral features. The antimicrobial activities of all compounds have also been monitored against plant pathogens.
References
- Patil, B. and Saha, P. ,Synthesis, characterization and antimicrobial activity of novel sulphapiperazine containing arylazopyrazoles,Journal of Saudi Chemical Society, 2013;17(3):307-313.
- Kuettel, S., Zambon,A., Kaiser, M., Brun, R., Scapozza L.and Perozzo, R.,Synthesis and Evaluation of Antiparasitic Activities of New 4-[5-(4-Phenoxyphenyl)-2H-pyrazol-3-yl]morpholine Derivatives, J Med. Chem., 2017;50:5833.
- İlkay, K., Esra, T., Güniz, K., Sevim, R., Erik, D., Synthesis of some novel thiourea derivatives obtained from 5-[(4-aminophenoxy)methyl]-4-alkyl/aryl-2, 4-dihydro-3H-1, 2, 4-triazole-3-thiones and evaluation asantiviral/anti-HIV and antituberculosis agents. Eur J Med Chem,2016;43:381-92.
- Al-Omar, M.A., Al-Abdullah, E.S,. Shehata, I.A., Habib, E.E., Ibrahim, T.M., El-Emam, A.A., Synthesis, antimicrobial and anti-inflammatory activities of novel 5-(1-adamantyl)-4-arylideneamino-3-mercapto-1, 2, 4-triazoles and related derivatives,Molecules 2012; 15:2526-50.
- Sumangala, V., Poojary, B., Chidananda, N., Arulmoli, T., Shenoy, S.,Synthesis and biological evaluation of some Schiffs bases of 4-amino-5-(4-methylsulfonyl)benzyl-2, 4-dihydro-3H-[1, 2, 4]-triazole-3-thione,Med Chem Res.,2013;22:2921-8.
- Ilkay, K., Güniz, K., Sevim, R., Muammer, K., Some 3-thioxo/alkylthio-1, 2, 4-triazoles with a substituted thiourea moiety as possible antimycobacterials.,Bioorg Med Chem Lett., 2011;11:1703-7.
- Shalini, K., Kumar, N., Drabu, S., Sharma, P.K., Advances in synthetic approach to and antifungal activity of triazoles,Beilstein J. Org. Chem.,2011;7:66877.
- Koçyigit-Kaymakçioğlu, B., Çelen, A.O., Tabanca, N., Ali,A.,Khan,S.I., Khan, A.I., Synthesis and biological activity of substituted urea and thiourea derivatives containing 1, 2, 4-triazole moieties,Molecules,2013;18:3562-76.
- Yang, J.G. and Pan, F.Y., New 3-[(4-hydroxy-6-methly-2(1H)-pyridinones)-3-yl]-4-substituted - (1H)-1, 2, 4-triazole-5-thiones: efficient synthesis, X-ray crystallographic analysis and antitumor activity,Lett Org. Chem.,2017;4:137-41.
- Siddiqui, N., Alam, M.S., Ahsan, W., Synthesis, anticonvulsant and toxicity evaluation of 2-1H-indol-3-yl)acetyl-N-(substituted phenyl)hydrazine carbothioamides and their related heterocyclic derivatives, Acta Pharm,2016;58:445-54.
- Palaska, E., Sahin, G., Kelicen, P., Durlu, N.T., Altinok, G., Synthesis andanti-inflammatory activity of 1-acylthiosemicarbazides, 1, 3, 4-oxadiazoles, 1, 3, 4-thiadiazole and 1, 2, 4-triazole-3-thiones,Farmaco, 2012;57:101-7.
- Amir, M., Kumar, S., Anti-inflammatory and gastro sparing activity of some new indomethacin derivatives,Arch Pharm, 2015;338:24-31.
- Patil,M.M., Rajput, S.S., Succinimides: Synthesis, reaction and biological activity, Int J Pharm Pharm Sci,2014;6:8-14.
- Aswathanarayanappa, C., Bheemappa, E., Bodke, Y.D., Krishnegowda, P.S., Venkata, S.P., Ningegowda, R., Synthesis and evaluation of antioxidant properties of novel 1, 2, 4-triazole based Schiffs base heterocycles, Arch Pharm, 2013;346:922-30.
- Sandhu,S. and Sandhu,J.S.Past, Present and Future of the Biginelli reaction: A critical prospertive,ARKIVOC,2012;1:66-133.
- Daur,R., Chaudhary,S. Kumar,K.,Gupta,M.K.,Rawal,R.K.,Recent synthestic and medicinal perspectives of dihydropyrimidinones-A review,Eur.J.Med. Chem., 2017; 132: 108-134.
- Essid,I, Latibib,K., Kaminsky,W., Nasr,C.B.,Touil,S.,5-phosphonato-3,4-dihydro pyrimidin- 2(1H)-ones,Zinc triflate-catalysed one pot multi component synthesis , X-ray crystral structures and anti-inflammatory activity,J.Mol.Struct., 2017; 1142: 130-138.
- Nora,P.T., Adam,J., Evelyn,H. and Erika,B.,synthesis of 3,4-dihydropyrimidin-2(1H)-one phosphonates by the microwave Assisted Biginelli reaction, Catalysts, 2021;11:45.
- Bhoi, M.N., Board, M.A., Pithawala, E.A., Modi, S. Patel and H.D.,Synthesis of N'-(7-Chloroquinolin-4-yl)-6-Methyl-2-Oxo-4-Phenyl-1, 2, 3, 4-Tetrahydropyrimidine-5-Carbohydrazide Derivatives As Potent Antibacterial Agents, Int. Latters of Chem. Physics and Astronomy, 2015;56:82-90.
- Barry, A.L., The Antimicrobial Susceptibility Test:Principal and Practices,4th ed., edited by Illuslea and Feger,Philadelphia,1976;180.
- Nweze, E.I. , Mukherjee P.K. and Ohannoum, M.A., Agar-based disk diffusion assay for susceptibility testing of dermatophytes, J.Clin.Microbiology, 2019;48 (10): 3750-3752.
Downloads
Published
Issue
Section
License
Copyright (c) IJSRST

This work is licensed under a Creative Commons Attribution 4.0 International License.