SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF AZOL SUBSTITUTED DERIVATIVES

Authors

  • Ashutosh Barve Oriental College of Pharmacy, Indore, Madhya Pradesh, India
  • Ankur Joshi Rishiraj College of Pharmacy, Indore, Madhya Pradesh, India 3
  • Rajesh Kumar Nema Rishiraj College of Pharmacy, Indore, Madhya Pradesh, India 3
  • Sonia Gehlot Rishiraj College of Pharmacy, Indore, Madhya Pradesh, India
  • Niharika Subhedar Smiriti College of Pharmaceutical Studies, Indore, Madhya Pradesh, India
  • Vivek Daniel Mandsaur Institute of Pharmacy, Indore, , Madhya Pradesh, India
  • Pramod Singh Mandsaur Institute of Pharmacy, Indore, , Madhya Pradesh, India

Abstract

A series of dichlorides (Ia-h) followed by 1, 3, 4-Thiadiazol-2-Amine (II a-h) were synthesized by using various dicarboxylic acids(a-h), the further reaction of (I) was carried out with thiosemicarbazide in presence of sulphuric acid to converted into corresponding 1, 3, 4-Thiadiazol-2-Amine (II a-h) The structures of these compounds were confirmed by IR, NMR and Mass spectral analysis. The newly synthesized compounds were evaluated for the antibacterial and antifungal activity. The results show that compound (IIa), (IIe), (IIf) and (IIh) exhibited moderate to good antibacterial and antifungal activity at 5-100 mcg/ml.

Keywords:

Antimicrobial activity, Thionyl chloride, Gresiofluvin, thiosemicarbazide

DOI

https://doi.org/10.25004/IJPSDR.2009.010315

References

Varvarason A, Tantili-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. Arzneim. Forsch. 2000; 50: 48-54.

Gokce M, Cakir B, Earl K, Sahin M. Synthesis and antimicrobial activity of [(2-oxabenzothiazolin-3-yl)-methyl]-4-alkyl/aryl-1, 2, 4-triazoline-5-thiones. Arch. Pharm. 2001; 334: 279-283.

Pintilie O, Profire L, Sunel V, Popa M, Pui A. Synthesis and antimicrobial activity of some new 1, 3, 4-thiadiazole and 1, 2, 4-triazole compounds having a D,L-methionine moiety. Molecules 2007; 12: 103-113.

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

Mamolo MG, Falagiani V, Zanpier D, Vio L, Banfi F. Synthesis and antimycobacterial activity of [5-(pyridin-2-1, 3, 4-thiadiazol-2-yl-thio)]-acetic acid arylidene-hydrazide derivatives. Farmaco 2001; 56: 587-592.

Zamani K, Faghifi K, Tefighi I, Sharlatzadeh 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.

Zan XI, Lai LH, Jin GY, Zhong ZX. Synthesis, fungicide activity and 3D- QSAR of 1, 3, 4-oxadiazoles and 1, 3, 4-thiadiazoles. J. Agric. Food Chem. 2002; 50: 3757-3760.

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

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

Onkol T, Cakir B, Sahin MF. Synthesis and antinociceptive activity of 2-[(2-oxabenzothiazolin-3-yl)-methyl]-5-aminoalkyl/aryl-1, 3, 4-thiadiazole. Turk. J. Chem. 2004; 28: 461-466.

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

Labanauskas L, Kalcas V, Uderenaite 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.

Palaska E, Sahin G, Kelincen P, Durlu NT, Altionax G. Synthesis and anti-inflammatory activity of 1-acyl thiosemicarbazides, 1, 3, 4-oxadiazoles, 1,3,4-thiadiazoles and 1, 2, 4-triazole-3-thiones. Farmaco 2002; 57: 101-107.

Sunel V, Lionte C, Popa M, Pintilie O, Mungiu P, Teleman S. Synthesis of new methionine derivatives for the treatment of paracetamol-inducet hepatic injury. Eur. Chem. Tech. J. 2002; 4: 201-205.

Pintilie O, Sunel V, Profire L, Pui A. Synthesis and antimicrobial activity of some new (sulfonamidophenyl)-amides of N-(metanitrobenzoyl)-D,L-methionine. Farmacia 2007; 55: 345-251.

Moise M, Sunel V, Profire L, Popa M, Lionte C. Synthesis and antimicrobial activity of some new (sulfon-amidophenyl)-amide derivatives of N-(4-nitrobenzoyl)-phenylglycine and N-(4-nitrobenzoyl)-phenylalanine. Farmacia 2008; 56: 283-289.

Sunel V, Lionte C, Basu C, Cheptea C. New antitumour alkylating compounds with N-[m-(arylthiocarbamoyl)-aminobenzoyl]-asparagic acids support. Chem. Indian J. 2005; 2: 1-6.

Sunel V, Popa M, Desbrieres J, Profire L, Pintilie O, Lionte C. New di-(β-chloroethyl)-α-amides on N-(m-acylaminobenzoyl)-D, L-aminoacid supports with antitumoral activity.Molecules 2008; 13: 177-189.

Coleman K. Drug Discov. Today, Therapeutic Strategies 2004; 1: 455–460.

Smyth RD. Clinical analysis, Microbiology, Remington’s Pharmaceutical sciences 18th Edition, Mack Publishing Company Peninisilvenia, 1991, 524-27

Biological assay, Indian Pharmacopoeia published by Govt. of India 1996(2): A-88.

Pelczar, Reid and Cohn, Antibiotics and other chemotherapeutic agent Microbiology, TMH Edition, TATA-McGraw-Hill Publishing Houses, 1989, 466-93

Harry W, Antiseptic and Disinfectant action, Microbes in Action, A Laboratory manual in Microbiology 1982, 75-76.

Davis WW, Stout TR. Appl Environ Microbiol. 1971; 22(4): 666-670

Lalitha MK. Manual on Antimicrobial Susceptibility Testing (Under the auspices of Indian Association of Medical Microbiologists).

Microbial Assays, In Practical Microbiology, (S.R. Gaud), 4, Nirali Publication: 2006, 111-116.

Basics of Microbiology, Cooper and Gunn’s Tutorial Pharmacy, (S. J. Carter), 6, CBS Publishers and Distributors: 2005, 289-366.

Andrews JM. Jour. of Antimicro. Chemotherapy. 2001; 48: 5-11.

Phair JP, Watanakunakorn C, Bannister T. American Society for Microbiology, 1969; 18(3): 303-306.

Therese KL, Bagyalakshmi R, Madhavan HN, Deepa P. Indian Jour. of Med. Microbio. 2006; 24(4): 273-279.

Nature 158, 877 (14 December 1946) | doi:10.1038/158877a0; Action of Thionyl Chloride on Carboxylic Acids in Presence of Pyridine, J. P. E. HUMAN & JOHN A. MILLS.

Demirbas N, Demirbas A, Sancak K. Synthesis and Antimicrobial Activities of Some new 1-(5-phenylamino- [1, 3, 4] thiadiazol-2-yl) Methyl-5-oxo- [1, 2, 4] Triazole and 1-(4-phenyl-5-thioxo- [1, 2, 4] triazol-3-yl) methyl-5-oxo- [1, 2, 4] Triazole Derivatives. European Journal of Medicinal Chemistry, 2004; 39: 793–804.

Published

03-10-2009
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How to Cite

“SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF AZOL SUBSTITUTED DERIVATIVES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 1, no. 3, Oct. 2009, pp. 207-10, https://doi.org/10.25004/IJPSDR.2009.010315.

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Research Article

How to Cite

“SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL ACTIVITY OF AZOL SUBSTITUTED DERIVATIVES”. International Journal of Pharmaceutical Sciences and Drug Research, vol. 1, no. 3, Oct. 2009, pp. 207-10, https://doi.org/10.25004/IJPSDR.2009.010315.