SYNTHESIS AND ANTIMICROBIAL EVALUATION OF 2-[(SUBSTITUEDPHENYL)-5-(1-PHENYL-3-(PIPERAZINYL)PYRIDO[3,2-f]QUINAZOLIN-4(1H)-YL]-1,3,4-THIADIAZOLES

Tilak Ram, Ranjana Dubey, Nidhi Chaudhary

Abstract


Several novel 2-[(substitutedphenyl)-5-(1-phenyl-3-(piperazinyl)pyrido[3,2-f] quinazolin-4(1H)-yl]-1,3,4 thiadiazole derivatives have been designed and synthesised by incorporating  four  known moieties  such  as  2-methylquinolin-5-ol, acetophenone, urea and 3-substitutedphenyl-4-amino-5-mercapto triazoles by using multi-step conventional reaction strategy. The synthesized derivatives were characterized by IR, 1H-NMR, Mass and elemental analysis (C, H, N). Furthermore the synthesized 2-[(substitutedphenyl)-5-(1-phenyl-3-(piperazinyl)pyrido[3,2-f]quinazolin-4(1H)-yl]-1,3,4-thiadiazoles 4a-g were screened for antibacterial and antifungal activities. The bacterial panel consisted of Staphylococcus aureus, Escherichia coli, Klabsiella pneumoniae, Proteus vulgaris while fungal panel included of Aspergillus fumigatus (plant isolate), Candida glabrata, Candida albacans, Candida krusei. Ampicillin trihydrate and fluconazole were used as reference drugs for antibacterial and antifungal activity respectively. Bacterial and fungal inhibition determined by disk diffusion and serial plate dilution method respectively. Pathogenic inhibitions were determined by measuring the diameter of the inhibition zone in mm. Compound 4c demonstrated significant antibacterial and antifungal spectrum against all the tested microbes.

Keywords- antibacterial, antifungal and substituted 1,3,4-thiadiazoles.


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References


Anderith, L. F.; Scott, E. S.; Kipper, P. S.; J. Org. Chem., 1954, 733.

antimycotic activity of 4-substituted-3-(thiophene-2-yl-methyl)-Delta2-1,2,4-triazoline-5-thiones, Acta Pharm. 2004, 54, 251-260.

Baldwin, J. J.; Engelhardt, E. L.; Hirschmann, R.; Ponticello, G. S.; Atkinson, J. G.; Wasson, B.K.; Sweet, C. S.; Scriabine, A. Heterocyclic analogues of the antihypertensive beta-adrenergic blocking agents (S)-2-[3-(ter-butylamino)-2-hydroxypropoxy]-3-cyanopyridine, J. Med. Chem. 1980, 23, 65-70.

Chen, H.; Li, Z.; Han, Y. Synthesis and fungicidal activity against Rhizoctonia solani of 2-alkyl(Alkylthio)-5-pyrazolyl-1,3,4-oxadiazoles, J. Agric. Food Chem. 2000, 48, 5312-5315.

Clerici, F.; Pocar, D.; Guido, M.; Loche, A.; Perlini, V.; Brufani, M. Synthesis of 2-amino-5-sulfanyl-1,3,4-thiadiazole derivatives and evaluation of their antidepressant and anxiolytic activity, J. Med. Chem. 2001, 44, 931-936.

Collins, A.H. 1976. Microbiological Methods, (2nd ed.), Butterworth, London, UK.

Cruickshank, R.; Duguid, J.P., Marion, BP.; Swain, R.H. 1975. In: Medicinal Microbiology, Churchill Livingstone, London, U.K. 12.

El-Sayed, O. A.; Al-Turki, T. M.; Al-Daffiri, H.M.; Al-Bassam, B. A.; Hussein, M. E.; Tetrazolo[1,5-a]quinoline derivatives as anti-inflammatory and antimicrobial agents, Boll Chim Farm., 2004, 143(6), 227-238.

Foroumadi, A.; Mirzaei, M.; Shafiee, A. Antituberculosis agents:Synthesis and antituberculosis activity of 2-aryl-1,3,4-thiadiazole derivatives, Pharmazie 2001, 56, 610-612.

Gokce. M.; Cakir, B.; Erol, K.; Sahin, M. F. Synthesis and antinociceptive activity of [(2-

Khan, Z.K. 1997. In vitro and vivo screening techniques for bioactivity screening and evaluation. In: Proceedings of the International Workshop on UNIDO-CDRI.

Labanauskas, L.; Kalcas, V.; Udrenaite, E.; Gaidelis, P.; Brukstus, A.; Dauksas, V. Synthesis of 3-(3,4-dimethoxyphenyl)-1H-1,2,4-triazole-5-thiol and 2-amino-5-(3,4-dimethoxyphenyl)-1,3,4-thiadiazole derivatives exhibiting anti-inflammatory activity, Pharmazie 2001, 56, 617-619.

Mamolo, M. G.; Falagiani, V.; Zanpieir, D.; Vio, L.; Banfi, F. Synthesis and antimycobacterial activity of [5-( yridine-2-yl)-1,3,4-thiadiazol-2-ylthio]acetic acid arylidene-hydrazide derivatives, Farmaco 2001, 56, 587-592.

Onkol, T.; Cakir, B.; Sahin, M. F. Synthesis and Antinociceptive Activity of 2-[(2-Oxobenzothiazolin-3-yl)methyl]-5-aminoalkyl / aryl-1,3,4-thiadiazole, Turk. J. Chem. 2004, 28,461-466.

oxobenzothiazolin-3-yl)methyl]-4-alkyl/aryl-1,2,4-triazoline-5-thiones, Arch. Pharm. 2001, 334, 279-283.

Padhy, A.K.; Nag, V.L.; Panda, C.S.; Indian J. Chem., 1999, 38B, 998-1001.

Palaska, E.; Sahin, G.; Kelicen, P.; Durlu, N. T.; Altinok, G. Synthesis and anti-inflammatory activity of 1-acylthiosemicarbazides, 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazole-3-thiones, Farmaco 2002, 57, 101-107.

pyridazino nethiadiazoles. J. Agric. Food Chem. 2002, 50, 1461-1454; (b) Zou, X. J.; Lai, L. H.; Jin, G. Y.; Zhang, Z. X. Synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles, J. Agric. Food Chem. 2002, 50, 3757-3760.

Schenone, S.; Bruno, O.; Ranise, A.; Bondavalli, F.; Filippeli, W.; Falcone, G.; Giordano, L.; Vitelli, M. R. 3-Arylsulphonyl-5-arylamino-1,3,4-thiadiazol-2(3H)ones as anti-inflammatory and analgesic agents, Bioorg. Med. Chem. 2001, 9, 2149-2153.

Shanker, K.; Aggarwal, V.K.; Selveraj, R.J.; Permar, S.; J. Med. Chem., 1969, 12(2), 324-326.

Varma, R.S. 1998. Antifungal Agents: Past, Present and Future Prospects. National Academy of Chemistry and Biology, Lucknow, India.

Varvaresou, A.; Tsantili-Kakoulidou, A.; Siatra-Papastasikoudi, T.; Tiligada, E. Synthesis and biological evaluation of indole containing derivatives of thiosemicarbazide and their cyclic 1,2,4-triazole and 1,3,4-thiadiazole analogs, Arzneimittelforschung 2000, 50, 48-54; (b) Varvaresou, A.; Siatra-Papastasikoudi, T.; Tsontinis, A.; Tsantili-Kakoulidou, A.; Vamvakides, A. Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2, 4-triazole, Farmaco 1998, 53, 320-326.

Vogel, A. I.; Text book of practical organic chemistry including qualitative organic analysis, 3rd ed., E.L.B.S. and Longman Group Ltd., London, 1973, 781.

Wujec, M.; Pitucha, M.; Dobosz, M.; Kosikowska, U.; Malm, A. Synthesis and potential

Zamani, K.; Faghifi, K.; Tefighi, I.; Sharlatzadeh, M. R. Synthesis and potential antimycotic activity of 4-substituted 3-(thiophene-2-yl-methyl)-Δ2-1,2,4-triazoline-5-thiones, Turk. J. Chem. 2004, 28, 95-101.

Zou, X. J.; Jin, G. Y.; Zhang, Z. X. Synthesis, fungicidal activity, and QSAR of




DOI: http://dx.doi.org/10.14499/indonesianjpharm27iss4pp183

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