Design, Synthesis, Antimicrobial, and Antioxidant Activities of Novel-{4, 5-(substituted diphenyl)-4H-1, 2, 4-triazol-3-ylthio} Acetyl Chloride

Prabhakar Kumar VERMA, Mukesh KUMAR, Nelam MALIK, Priyanka DHIMAN, Anurag KHATAHAR


A series of 20 new biologically active derivatives of 2-{4, 5-(substituted diphenyl)-4H-1,2,4-triazol-3-ylthio}acetyl chloride has been synthesized, with the aim to investigate antimicrobial, free radical scavenging activity. All the synthesized compounds were characterized by spectroscopic data and elemental analysis. The final compounds were tested for antibacterial activity against Gram-positive bacteria: Staphylococcus aureus MTCC 3160, Bacillus subtilis MTCC 441; Gram-negative bacteria: Escherichia coli MTCC 443, and, for antifungal activity, against Candida albicans MTCC 227 and Aspergillus niger MTCC 281, taking ciprofloxacin as antibacterial and fluconazole as antifungal standard drugs. Compound 7a6 was found to be the most effective antibacterial (MIC = 3.12 µg/ml), and compounds 7a2 and 7d1 (MIC = 3.12 and 6.25 µg/ml) had the most effective antifungal effects on the selected strains, as compared to the standard drugs. The results of antioxidant studies revealed that compound 7b1 was found to be most active antioxidant, with 40.4±0.687 µg/ml, and compounds 7b3, 7d7, and 7d4 also showed promising free radical scavenging activity, as compared with the standard drug ascorbic acid.


Antibacteria, antifungus, MIC, antioxidant,structure activity relationship triazole

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NM Khalifa, AH Adel, SI Abd-Elmoez, OA Fathalla and AAA El-Gwaad. Antimicrobial activity of newly synthesized imidazolones, their oxadiazolyl and acyclic C-nucleosides. Res. Chem. Intermediat. 2015; 41 1-11.

Z Chen, R Bertin and G Froldi. Evaluation of anogeissus acuminata (Roxb. ex DC.) in diabetes mellitus and its complications Food. Chem. 2013; 138, 414-20.

M Aufort, J Herscovici, P Bouhours, N Moreau and C Girard. Synthesis and antibiotic activity of a small molecules library of 1,2,3-triazole derivatives. Bioorg. Med. Chem. Lett. 2008; 18, 1195-8.

SMI Badr and RM Barwa. Synthesis of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines and [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles starting from 5-nitro-2-furoic acid and evaluation of their antimicrobial activity. Bioorg. Med. Chem. Lett. 2013; 19, 4506-12.

GL Almajan, SF Barbuceanu, ER Almajan, C Draghici and G Saramet. Synthesis, characterization and antibacterial activity of some triazole Mannich bases carrying diphenylsulfone moieties. Eur. J. Med. Chem. 2009; 44, 3083-9.

H Yuksek, Z Ocak, M Alkan, S Behceci and M Ozdemir. Synthesis and determination of pKa values of some new 3,4-disubstituted-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives in non-aqueous solvents. Molecules 2004; 9, 232-40.

V Padmavathi, RG Sudhakar, A Padmaja, P Kondaiah and A Shazia. Synthesis and antimicrobial studies of novel methylene bridged benzisoxazolyl imidazo[2,1-b][1,3,4]thiadiazole derivatives. Eur. J. Med. Chem. 2012; 44, 2106-12.

P Selvam, M Chandramohan, ED Clercq and M Witvrouw. Synthesis and anti-HIV activity of 4-[(1,2-dihydro-2-oxo-3H-indol-3-ylidene) amino]-N (4,6-dimethyl-2-pyrimidinyl)-benzenesulphonamide and its derivatives. Eur. J. Pharm. Sci. 2001; 14, 313-6.

SP Aytac, B Tozkoparan, F Betu, B Kaynak, G Aktay, O Goktas and S Unuvar. Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as anti-inflammatory and analgesic agents. Eur. J. Med. Chem. 2009; 44, 4528-38.

M Dhooghe, S Vandekerckhove, K Mollet, K Vervisch, S Dekeukeleire and L Lehoucq. Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity. Beil. J. Org. Chem. 2011; 7, 1745-52.

MS Costa, N Boechat, EA Rangel, FD Silva, AM Souza and CR Rodrigues Synthesis, tuberculosis inhibitory activity, and SAR study of N-substituted-phenyl-1,2,3-triazole derivatives. Bioorg. Med. Chem. Lett. 2006; 14, 8644-53.

P Shanmugavelan, S Nagarajan, MS Kumar, A Ponnuswamy, P Yogeeswari and D Sriram. Efficient synthesis and in vitro antitubercular activity of 1,2,3-triazoles as inhibitors of Mycobacterium tuberculosis.Bioorg. Med. Chem. Lett. 2011; 21, 7273-6.

HM Faidallah, AK Khalid and MA Abdullah. Synthesis and biological evaluation of new N,N′-bis(1-substituted-ethylidene)-ethane1,2-diamine and their acetyl and trifluoroacetyl derivatives as cytotoxic and antimicrobial agents. J. Fluorine. Chem. 2011; 132, 870-77.

S Oida, T Yawara, K Toshiyuki, N Yoshie, S Atsushi and T Teruo. Synthesis and antifungal activities of R-102557 and related dioxane-triazole derivatives. Chem. Pharm. Bull. 2000; 48, 694-707.

M Serwar, T Akhtar, S Hameed and KM Khan. Synthesis, urease inhibition and antimicrobial activities of some chiral 5-aryl-4-(1-phenylpropyl)-2H-1,2,4-triazole-3(4H)-thiones. Arch. Org. Chem. 2009; 7, 210-21.

RK Sharma, K Shrivastava, V Daniel, MS Panwar and S Goyal. Critical analysis of cell block versus smear examination in effusionsInt. J. Pharm. Sci. 2010; 2, 502-7.

N Siddiqui and W Ahsan. Triazole incorporated thiazoles as a new class of anticonvulsants: Design, synthesis and in vivo screening. Eur. J. Med. Chem. 2010; 45, 1536-43.

I Khan, S Ali, S Hameed, NH Rama and MT Hussain. Synthesis, antioxidant activities and urease inhibition of some new 1,2,4-triazole and 1,3,4-thiadiazole derivatives. Eur. J. Med. Chem. 2010; 45, 5200-7.

K Sancak, Y Unver, D Unluer, E Dugdu, G Kor, F Celik and E Birinci. Synthesis of 2-acylamino, 2-aroylamino and ethoxycarbonyl imino-1, 3, 4-thiadiazoles as antitumor agents. Turk. J. Chem. 2010; 36, 457-66.

B Tozkoparan, G Aktay and E Yesilada. Synthesis of some 1,2,4-triazolo[3,2-b]-1,3-thiazine-7-ones with potential analgesic and antiinflammatory activities. Farmaco 2002; 57, 145-52.

Pharmacopoeia of India Ministry of Health Department. Vol ІІ. Ministry of Health and Family Welfare. Nirman Bhavan, Government of India, New Delhi, 1996, p. A88.

JG Cappucino and N Sherman. Microbiology: A Laboratory Manual. Addison Wesley, California 1999, p. 263.

MS Blois. Antioxidant determinations by the use of a stable free radical. Nature 1958; 181, 1199-200.

V Bondet, W Brand-Williams and C Berset. Total antioxidant capacity of teas by the ferric reducing/antioxidant power assay. Food. Sci. Tech. 1997; 30, 609-15.

S Hussain, J Sharma and M Amir. Synthesis and antimicrobial activities of 1,2,4-triazole and 1,3,4-thiadiazole derivatives of 5-amino-2-hydroxybenzoic acid. Eur. J. Med. Chem. 2008; 5, 963-8.

TA Naik and KH Chikhalia. Studies on synthesis of pyrimidine derivatives and their pharmacological evaluation. J. Chem. 2007; 4, 60-6.

K Palrasu, A Duraikannu and B Thirunavukkarasu. Synthesis of 4-methyl-N'-(3-alkyl-2r,6c-diarylpiperidin-4-ylidene)-1,2,3-thiadiazole-5-carbohy drazides with antioxidant, antitumor and antimicrobial activities. Org. Biomol. Chem. 2014; 12, 5911-21.

P Mondal, S Jana and LK Kanthal. Synthesis of some new isoxazoline derivatives of chalconised indoline 2-one as a potential analgesic, antibacterial and anthelmimtic agents. T. Ph. Res. 2010; 3, 17-26.

M Trujillo, E Gallardo, A Madrona, L Bravo, B Sarria, JA Gonzaalez-Correa and JL Espartero. Synthesis and antioxidant activity of nitrohydroxytyrosol and its acyl derivatives J. Agr. Food Chem. 2014; 62, 10297-303.


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