Green Synthesis and Evaluation of 5-(4-Aminophenyl)-4-Aryl-4H-1, 2, 4-Triazole-3-Thiol Derivatives Green synthesis and evaluation of 5-(4-aminophenyl)-4-aryl-4H-1, 2, 4-triazole-3-thiol derivatives
Iranian Journal of Pharmaceutical Sciences,
Vol. 13 No. 2 (2017),
1 April 2017
,
Page 37-50
https://doi.org/10.22037/ijps.v13.40695
Abstract
The green synthesis of 5-(4-aminophenyl)-4-aryl-4H-1,2,4-triazole-3-thiol was achieved in four steps. In the first step, 4-amino benzoic acid was refluxed in ethanol along with catalyst Conc. Sulphuric acid to produce ethyl-4-amino benzoate I. Further compound I was refluxed with hydrazine hydrate in ethanol to produce 4-amino benzohydrazide II. Compound II was refluxed in ethanolic potassium hydroxide with carbon disulfide to produce 5-(4-aminophenyl)-1, 3, 4-oxadiazole-2-thiol III. Compound III refluxed in ethanol with different substituted primary aryl amine gave title compounds 5-(4-aminophenyl)-4-aryl-4H-1, 2, 4-triazole-3-thiol IVa-o. The compounds obtained were identified by FT-IR, 1H-NMR, GC- mass spectroscopy data, and elemental analysis and also screened for in-vivo antimicrobial activity. In vitro antibacterial activity was carried out against organisms like E.coli. K.pneumonia, S.aureus, and B.subtilis as well as in vitro antifungal activity were carried out against organisms like A.niger and S.cerevisiae. In vitro antimicrobial evaluation, the most potent broad spectrum compound IVc, IVd, and IVf were found significant agent against standard drug Norfloxacin and Ketoconazole.
Keywords:
- Triazole
- Antimicrobial
- MIC
- FT-IR
- H-NMR
- GC-MS
How to Cite
Vikas Gopalrao Rajurkar, & Sagar M. Shirsath. (2017). Green Synthesis and Evaluation of 5-(4-Aminophenyl)-4-Aryl-4H-1, 2, 4-Triazole-3-Thiol Derivatives: Green synthesis and evaluation of 5-(4-aminophenyl)-4-aryl-4H-1, 2, 4-triazole-3-thiol derivatives. Iranian Journal of Pharmaceutical Sciences, 13(2), 37–50. https://doi.org/10.22037/ijps.v13.40695
References
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[28] Sarah A, Othman AA (2012) A convenient new synthesis, characterization and antibacterial activity of double headed acyclo-C-nucleosides from unprotected D-glucose. Arabian J Chem. In Press.
[29] Kiran S, Yogender K, Parvesh P, Chetan S, Kamal Rai A (2013) Antimicrobial, spectral and thermal studies of divalent cobalt, nickel, copper and zinc complexes with triazole Schiff bases. Arabian J Chem. In Press.
[30] Brahimi FT, Belkadi M, Othman AA (2013) Synthesis of nonionic surfactants with azole ring bearing N-glycosides and their antibacterial activity. Arabian J Chem. In Press.
[31] Sunil D, Isloor AM, Shetty P, Nayak PG, Pai KSR (2013) In vivo anticancer and histopathology studies of Schiff bases on Ehrlich ascitic carcinoma cells: 1st Cancer Update Arabian J Chem. 6(1):25-33.
[32] Hunashal RD, Ronad PM, Maddi VS, Satyanarayana D, Kamadod MA (2014) Synthesis, anti-inflammatory and analgesic activity of 2-[4-(substituted benzylideneamino)-5-(substituted phenoxymethyl)-4H-1,2,4-triazol-3-yl thio] acetic acid derivatives. Arabian J Chem. 7:1070-1078.
[33] Bhanojirao ME, Rajurkar VG (2009) Synthesis and biological evaluation of 5-pyridine-4- (arylidine amino)-3-mercapto-4(H)-1, 2, 4-triazoles. Asian J of Chem. 21 (6), 4733-4736.
[34] Rajurkar VG, Bhanojirao ME (2011) Synthesis and biological studies of N-phenyl substituted 2-(-5-(pyridine-4-yl)-1, 3, 4-oxadiazole-2-yl thio) acetamides. Asian J of Chem. 23 (6), 2648-2652.
[35] Farghaly AR, Erik DC, Hussein EK (2006) Synthesis and antiviral activity of novel [1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles, [1,2,4]triazolo[3,4-b] [1,3,4] thiadiazines and [1,2,4] triazolo[3,4-b][1,3,4] thiadiazepines. ARKIVOC. (x):137-151.
[2] Serap B, Meltem Y, Ahmet D, Hakan B, Rza A, Neslihan D (2012) Synthesis of linezolid- like molecules and evaluation of their antimicrobial activities.Turk. J. Chem. 36:37-53.
[3] Rajurkar VG, Gadekar K, Deshmukh VK (2014) Synthesis, Characterization and Study of Some N-Substituted Aryl-2- ({4-[(Substituted Aryl Carbamoyl) Methyl]-5-(Pyridin-4-yl)- 4H-1, 2, 4-Triazol-3-yl} Sulfanyl) Acetamide. Iranian J.Pharma. Sci. 10(2):21-34.
[4] Katrijn B, Arthur Van A (2009) Antimicrobial resistance in bacteria. Cent. Eur. J. Med. 4(2):141-155.
[5] Aly HM (2011) Novel pyrrolidinone and pyrazolo[1,5-a][1,3,5]triazine derivatives bearing a biologically active sulfamoyl moiety as a new class of antitumor agents. Monatsh Chem 142: 935-941.
[6] Sarkate AP, Pansare DN, Karnik KS, Kale IA, Bahekar SS, Shinde DB (2017) Microwave assisted copper-catalyzed synthesis of substituted benzamides through decarboxylative C-N cross coupling. Current Microwave Chemistry. 4:163-167.
[7] Sarkate AP, Pansare DN, Kale IA, Shinde DB (2017) Microwave and conventional method assisted synthesis of 2-(substituted) -3-(4-methoxybenzyl) thiazolidin-4-ones using ZrOCl2∙8H2O as a catalyst.Current Microwave Chemistry. 4:139-145.
[8] Bahekar SS, Sarkate AP, Kale IA, Wakte PS (2016) Catalyst free microwave assisted synthesis of sulfides in aqueous media. Current Microwave Chemistry. 3(3):233-237.
[9] Nerkar AG, Pawale D, Ghante MR, Sawant SD (2013) Microwave assisted organic synthesis of some traditional and named reactions: a practical approach of green chemistry. Int J Pharm Pharm Sci. 5(3):564-566.
[10]Agalave SG, Maujan SR, Pore VS (2011) Click chemistry: 1, 2, 3-triazoles as pharmacophores. Chem. Asian J. 6:2696-2718.
[11] Shaikh MH, Subhedar DD, Arkile M, Khedkar VM, Jadhav N, Sarkar D, Shingate BB (2016) Facile Synthesis of 1,3-Thiazolidin-4-ones as Antitubercular Agents. Bioorg. Med. Chem. Lett. 26:561.
[12]Rao PS, Kurumurthy C, Veeraswamy B, Kumar GS, Poornachandra Y, Kumar CG, Vasamsetti SB, Kotamraju S, Narsaiah B (2014) Synthesis of novel 1,2,3-triazole substituted-N-alkyl/aryl nitrone derivatives, their anti-inflammatory and anticancer activity. Eur. J. Med. Chem. 80:184-191.
[13] Dofe VS, Sarkate AP, Shaikh ZM, Charansingh HG (2017) Ultrasound-Mediated Synthesis of Novel 1,2, 3-Triazole-Based Pyrazole and Pyrimidine Derivatives as Antimicrobial Agents. J. Hetero. Chem. DOI: 10.1002/jhet.2935
[14] Dofe VS, Sarkate AP, Lokwani DK, Kathwate SH, Gill CH (2017) Synthesis, antimicrobial evaluation, and molecular docking Studies of novel chromone based 1,2,3-triazoles. Research on Chemical Intermediates. 43 (1):15-28.
[15] Sangshetti JN, Lokwani DK, Sarkate AP, Shinde DB (2011) Synthesis, Anti-Fungal Activity and Docking Study of Some New 1,2,4-triazole analogues. Chem. Bio. & Drug Design. 78 (5): 800-809.
[16] Sheremet EA, Tomanov RI, Trukhin EV, Berestovitskaya VM (2004) Synthesis of 4-Aryl-5-nitro-1, 2, 3-triazoles.Russ. J. Org. Chem. 40(4):594-595.
[17]Holla BS, Mahalinga M, Karthikeyan MS, Poojary B, Akberali PM, Kumari NS (2005) Synthesis, characterization and antimicrobial activity of some substituted 1,2,3-triazoles.Eur. J. Med. Chem. 40:1173-1178. [18]Gavara L, Saugues E, Alves G, Debiton E, Anizon F, Moreau PG, Moreau P (2010) Synthesis and biological activities of pyrazolo [3,4-g]quinoxaline derivatives. Eur. J. Med. Chem. 45(11):5520-6. doi: 10.1016/j.ejmech.2010.08.067.
[19] G1owacka IE, Balzarini J, Wróblewski AE (2013) The synthesis, antiviral, cytostatic and cytotoxic evaluation of a new series of acyclonucleotide analogues with a 1,2,3-triazole linker. Eur. J. Med. Chem. 70: 703-722.
[20] Chinthala Y, Thakur S, Tirunagari S, Chinde S, Domatti AK, Arigari NK, Srinivas KVNS, Alam S, Jonnala KK, Khan F, Tiwari A, Grover P(2015) Synthesis, docking and ADMET studies of novel chalcone triazoles for anti-cancer and anti-diabetic activity. Eur. J. Med. Chem. 93:564-573.
[21] William D, Nikoletta A, Andrew K, Derek N, Joanna McG, Nikalje AP, Lokwani D, Sarkate A, Evans P (2017) Synthesis and Evaluation of 1,2,3-Triazole-Containing Vinyl and Allyl Sulfones as Anti-Trypanosomal Agents.Euro. J. Org. Chem.1:175-185.
[22] Altintop MD, Kaplancikli ZA, Turan-Zitouni G, Ozdemir A, Iscan G, Akalin G, Yildirım, SU (2011) Synthesis and anticandidal activity of new triazolothiadiazine derivatives. Eur. J. Med.Chem. 46:5562–5566.
[23] Narayana Rao DV, Raghavendra Guru Prasad A, Spoorthy YN, Raghunatha Rao D, Ravindranath LK (2014) Synthesis, characterization and pharmacological studies of sulphur containing 1,2,4-triazole derivatives. J Taibah University Medical Sciences 9(4):293-300.
[24] El Ashry El SH, EL-Rafey E, Rezki N, Abou-Elnaga HH, Bakry WMA, Boghdadi YM (2014) Evaluation of some functionalized imidazoles and 1,2,4-triazoles as antioxidant additives for industrial lubricating oils and correlating the results with the structures of additives using empirical am1 calculations. J Saudi Chem. Society 18: 443-449.
[25] Saeed A, Mumtaz A (2015) Novel isochroman-triazoles and thiadiazole hybrids: Design, synthesis and antimicrobial activity. Journal of Saudi Chemical Society In Press.
[26] Suresh M, Lavanya P, Venkata Rao C (2011) Synthesis and pharmacological evaluation of novel 2H/6H-thiazolo-[30,20:2,3][1,2,4]triazolo[1,5-a] pyridine-9-carbonitrile derivatives. Arabian J Chem. In Press.
[27] Abd El-Badih AGG, Moustafa HM, Elsayed AAH, Bahgat RMH(2012) Synthesis and antibacterial activity of some new 4-anilino-5-phenyl-4H-1,2,4-triazole-3-thiol derivatives. Arabian J Chem. In Press.
[28] Sarah A, Othman AA (2012) A convenient new synthesis, characterization and antibacterial activity of double headed acyclo-C-nucleosides from unprotected D-glucose. Arabian J Chem. In Press.
[29] Kiran S, Yogender K, Parvesh P, Chetan S, Kamal Rai A (2013) Antimicrobial, spectral and thermal studies of divalent cobalt, nickel, copper and zinc complexes with triazole Schiff bases. Arabian J Chem. In Press.
[30] Brahimi FT, Belkadi M, Othman AA (2013) Synthesis of nonionic surfactants with azole ring bearing N-glycosides and their antibacterial activity. Arabian J Chem. In Press.
[31] Sunil D, Isloor AM, Shetty P, Nayak PG, Pai KSR (2013) In vivo anticancer and histopathology studies of Schiff bases on Ehrlich ascitic carcinoma cells: 1st Cancer Update Arabian J Chem. 6(1):25-33.
[32] Hunashal RD, Ronad PM, Maddi VS, Satyanarayana D, Kamadod MA (2014) Synthesis, anti-inflammatory and analgesic activity of 2-[4-(substituted benzylideneamino)-5-(substituted phenoxymethyl)-4H-1,2,4-triazol-3-yl thio] acetic acid derivatives. Arabian J Chem. 7:1070-1078.
[33] Bhanojirao ME, Rajurkar VG (2009) Synthesis and biological evaluation of 5-pyridine-4- (arylidine amino)-3-mercapto-4(H)-1, 2, 4-triazoles. Asian J of Chem. 21 (6), 4733-4736.
[34] Rajurkar VG, Bhanojirao ME (2011) Synthesis and biological studies of N-phenyl substituted 2-(-5-(pyridine-4-yl)-1, 3, 4-oxadiazole-2-yl thio) acetamides. Asian J of Chem. 23 (6), 2648-2652.
[35] Farghaly AR, Erik DC, Hussein EK (2006) Synthesis and antiviral activity of novel [1,2,4] triazolo[3,4-b][1,3,4]thiadiazoles, [1,2,4]triazolo[3,4-b] [1,3,4] thiadiazines and [1,2,4] triazolo[3,4-b][1,3,4] thiadiazepines. ARKIVOC. (x):137-151.
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