1, 2, 4-TRIAZOLES: AS BIOLOGICALLY IMPORTANT AGENTS
HTML Full Text1, 2, 4-TRIAZOLES: AS BIOLOGICALLY IMPORTANT AGENTS
D. Kumudha*1, R. R. Reddy 1 and T. Kalavathi 2
Arya College of Pharmacy 1, Kandi, Sangareddy, Medak- 85, Andra Pradesh, India
Nirmala College of Pharmacy 2, Kadapa, Andra Pradesh, India
ABSTRACT
The chemistry of heterocyclic compounds containing five membered 1, 2, 4-triazole nucleus has been an intresting field of study for past few decades. The five membered 1, 2, 4-triazole ring exists in two tautomeric forms i.e., 1H-1, 2, 4-triazole, 4H-1, 2, 4-triazole collectively known as s-triazoles. The s-triazole derivatives possess extensive spectrum of biological activities such as antibacterial, antifungal, antitubercular, anxiolytic, anticonvulsant, anti-inflammatory, analgesic, anticancer, antioxidant activities. The present review provides a broad view of pharmacological activity of compounds bearing 1, 2, 4-triazole nucleus. It can be useful for medicinal chemists to design and develop novel compounds consisting 1, 2, 4-triazole nucleus to get better agents in terms of efficacy and safety.
Keywords: |
1, 2, 4-triazole derivatives, Antimicrobial, Anticonvulsant, Anticancer Activities
INTRODUCTION: The 1, 2, 4-triazole is a five membered heterocyclic compound containing two carbons and three nitrogens with a molecular formula of C2H3N3. It exists in two tautomeric forms. 1H and 4H-1, 2, 4-triazole is considered to be pharmacologically important nucleus.
The literature review shows that 1, 2, 4-triazole possess wide spectrum of biological activities. In particular compounds having 1, 2, 4-triazole nucleus are known to have excellent antibacterial, antifungal, antitubercular, antioxidant, anticancer, anti-inflammatory, analgesic, anticonvulsant, anxiolytic activities 1.
Biological Activities of 1, 2, 4-Triazoles:
As Antibacterial and Antifungal agents: Xin-Ping Hui et al, prepared variety of 5-(5-methylisoxazol-3-yl)-1,3,4-thiadiazoles, 1,2,4-triazoles and 1,3,4-oxadiazoles and evaluated for their antibacterial potency 2.
- Shivarama Holla et al, prepared variety of diaryloxy-methyl-substituted-1,2,4-triazolo [3,4-b]-1,3,4-thiadi-azoles and evaluated for antibacterial activity 3.
- Shivarama Holla et al, prepared a series of 6-(5-aryl-2-furyl)-1,2,4-triazolo [3,4-b]-1,3,4-thiadiazoles and investigated for antibacterial potency 4.
- Shivarama Holla et al, reported the synthesis of N-bridged heterocycles such as triazolothiadiazoles, bis-triazolothiadiazoles, triazolothiadiazines, triazolothiadi-azinones derived from 3-aryloxymethyl-4-amino-5-mercapto-1,2,4-triazoles and evaluated for their antibacterial activity 5.
- Shivarama Holla et al, reported the synthesis of various bis–(4-amino-5-mercapto-triazol-3-yl)alkanes, their schiffs bases and bis-(1,2,4-triazolo[3,4-b]-1,3,4-thiadiazol-4-yl]alkanes and investigated as potent antibacterial agents6.
- Mogilaiah et al, prepared a series of 1-arylazetidino [2,3-b][1,8]napthyridin2-(1H)-ones and 1-aryl-4-carbethoxy-1,2,4-triazolo[4,3-a][1,8] naphthyridines and tested for antibacterial potency7.
- S. Sudha et al, reported the synthesis of 5-[(4-aroyl) aryloxymethyl]-2-(4-methylphenylamino)-1,3,4-thiadiazoles and 5-[(4-aroyl)aryloxymethyl]-4-(4-methyl)-3-mercapto-4H-1,2,4-triazoles and investigated as antibacterial agents8.
- K. Ravi et al, reported the synthesis of 1,2,4-triazoles derivatives of anthranalic acid and for their antibacterial activity 9.
- V. Mulwad et al, had reported the synthesis of a series of oxadiazolo(1,3,5)-triazines, 1,2,4-triazoles and thiadiazolo 1,3,4-oxadiazole analogues and investigated for their antibacterial activity 10.
Umesh Kumar et al, reported the synthesis of 4-amino-5-aryl-1,2,4-triazoles and screened for their antibacterial activity 11.
Nizamuddin et al, reported the synthesis of 2-Aryl/aryloxy methyl-1,3,4-oxa/thiadiazolo[4,5-b]1,2,4-triazolo[5,4-c]thiazolo-spiro-7-cyclohexanes and investigated as fungicidal agents 12.
Anees A Siddiqui et al, reported the synthesis of a series of 3-(p-substituted anilinoethyl)-4-(p-substituted phenyl)-5-thioxo-1,2,4-triazoles and investigated as active antifungal agents 13.
Qing-Yan Sun et al, prepared various 1,2,4-triazol-1-yl)-2-(2,4-difluorophenyl)-3-[(4-substitutedphenyl)-piperazin-1-yl)-propan-2-ols and investigated for their antifungal potency 14.
Yong Sun et al, synthesized 2-alkylamino-3-aryl-6-(1H)-1,2,4-triazol-1-yl)-thieno (2,3-d)-pyrimidin-4(3H)-ones and evaluated for fungicidal activity. Compound 6h showed excellent activity 15.
Jag Mohan et al, synthesized s-triazolo[3,4 b)[1,3,4] thiadizoles, s-triazolo(3,4 – b)[1,3,4]thiadiazines and s-triazolo(3’,4’-2,3)[1,3,4-thiadizino[5,6-b]quinoxalines and evaluated for antimicrobial potency 16.
Jagmohan et al, prepared s-triazolo[3,4-b][1,3,4] thiadiazoles and s-triazolo[3,4-b][1,3,4]thiadiazines and evaluated for antifungal and antibacterial activities 17.
- M. Hirpara et al, synthesized a series of 6-aryl-3-pyridin-4-yl-5,6-dihydro[1,2,4]-triazolo[3,4-b][1,3,4]-thiadiazoles and investigated for antimicrobial activity 18.
- M. Srinivasa et al, reported the synthesis of 8-fluoro-9-substituted(1,3)-benzothiazolo(5,1-b)-3-substituted triazoles and investigated for their antimicrobial activities 19.
Arun Kumar Wahi et al, prepared N-(substituted benzylidene)-2-(N-(4H-1,2,4-triazole-4-yl)benzamido) acetohydrazides and N-((5-substitutedaryl)-1,3,4-oxadiazole-2-yl)methyl-N-(4H-1,2,4-triazole-4-yl)benzamides and screened for antibacterial and antifungal activity 20.
Mudasir Rashid Banday et al, reported the synthesis of substituted triazoles and thiazolidinones from fatty acids and screened for antimicrobial activity 21.
- A. Baviskar et al, synthesized thiazolyltriazole substituted azetidinone derivatives and evaluated for their antimicrobial activity22.
Bahittin Kahveci et al, reported the synthesis of 3-alkyl-4-(arylmethyleneamino) 4,5-dihydro-1H-1,2,4-triazol-5-one derivatives and screened for the antimicrobial activity23.
- Shivakumar et al, synthesized 3-aryl-oxymethyl-4-[2-(benzimidazolyl thio)acetamide]-5-mercapto-1,2,4-triazoles and evaluated for their antimicrobial activities 24.
Jag Mohan prepared a series of s-triazolo(3,4-b)(1,3,4)thiadiazoles, s-triazolo (3,4-b)(1,3,4) thiadiazines and screened for their antibacterial and antifungal activities 25.
Chang –Hu Chu et al, prepared a series of ω-(5-arylamino-1,3,4-thiadiazol-2-thiol)-ω-(1H-1, 2, 4-triazol-yl)acetophenones and screened for antifungal and growth regulatory activities 26.
Balakrishna Kalluraya et al, prepared 3-alkyl-/aryl-9-substituted 1,2,4-triazolo[3,4-b][1,3,4]quinolino thiadiazipines and selected compounds were screened for their antibacterial and antifungal activities 27.
Nasser S. A. M. Kalil synthesized N-and S-α-L-arabinopyranosyl[1,2,4]triazolo[3,4-b][1,3,4]thiadi- azoles and investigated for antimicrobial potency 28.
- K. Swamy et al, synthesized 3-substituted(1,2,4)-triazolo[3,4-b]1,2-benzisoxazole derivatives and tested for their antimicrobial activity 29.
A.M. Manikaro et al, reported the synthesis of substituted 4-(N-pyridyl-5-4-amino-s-triazole-5-thiolate and evaluated for antimicrobial activity 30.
Harish Rajak et al, prepared 4-substituted piperizin-1yl)phenyl]-4-substituted 2,4-dihydro[1,2,4] triazole-3-thiones and evaluated for antimicrobial activity 31.
Rajkumar Agarwal et al, synthesized 5- aromatic substituted -4H-1,2,4-triazol-3-thiol and evaluated for antimicrobial activity 32.
Mrs. Arti Singh et al, reported the synthesis of N-(disubstituted amino)methyl(4H)-1,2,4-triazole-4-yl)benzamide and investigated for antimicrobial activity 33.
As diuretic agents: Jag Mohan reported the synthesis of 3-(2-thienyl)-s-triazolo[3,4-b][1,3,4]-thiadiazole, 2-(2-thienyl)thiazolo[3,2-b]-s-triazole and isomeric 3-(2-thienyl)-thiazolo(2,3-c)-s-triazole and screened for their diuretic, antibacterial and antifungal activities 34.
As anti-inflammatoty agents: Arun K. Wahi et al, synthesized the series of N-substituted benzylidene)-2-N-(4H-1,2,4-triazole-4yl)benzamido acetohydrazides and evaluated for antimicrobial and anti-inflammatory activities 35.
Rajive Gupta et al, synthesized a series of 3-alkyl/aryl-6-(2-chloro-2- substituted-phenylethenyl)-5-b-dihydro-s-trizolo[3,4-b][1,3,4].thiadiazoles and evaluated for anti-inflammatory, antibacterial and antifungal activities 36.
Rohini Diwedi et al, synthesized several 5,5’-Methylene bis(4-substituted phenyl/alkyl)-4H-1,2,4-triazole-3-thiol and investigated for their antioxidant, anti-inflammatory activities37.
Mario Di Braccio et al, prepared 5-(alkylamino)-N-N-diethyl[1,2,4]triazolo[4,3-a][1,8]napthyridine carboxamide and its derivatives and screened for their anti-inflammatory activity 38.
Ram Janam Singh et al, synthesized 1,2,4-triazolothiadiazines, 1,2,4-triazolothiadiazinones and evaluated for anti-inflammatory activity 39.
As anticancer agents: S. B. Hipara et al, reported the synthesis of 2-aryl 5-(2’-methoxy-5’-methylphenylamino)-1,3,4-thiadiazoles and 2-Phenyl-4-arylidine-1-(2’-methoxy-5’-methylphenyl thiourido-5-oxo-imidazolines and investigated for their antibacterial, antifungal and anticancer activities40.
Olcay Bekircan et al, reported the synthesis of various 4-arylidenamino-4H-1,2,4-triazoles, 4-(1-aryl)ethylidenamino-4H-1,2,4-triazoles, 4-arylmethyl amino-4H-1,2,4-triazoles, 4-(1-aryl)ethylamino-4H-1,2,4-triazoles and investigated as weak anticancer agents 41.
Zhi Zhang Li et al, were prepared various 4-(arylmethyl benzylidene amino)-5-phenyl-2H-1,2,4-triazole-3-(3H)-thiones and N-2,3,4,6-tetra-O-acetyl-acetyl-σ-D-glucopyranosyl-4-(arylmethylideneamino)-5-phenyl-2H-1,2,4-triazole-3(4H)-thione and investigated for their antiproliferative agents 42.
Elzbieto Pomarnacka et al, synthesized 2-arylamino-8-chloro-5,5-dioxo[1,2,4]-triazolo[2,3-b][1,4,2]benzodithi -azines and investigated for their anticancer and antibacterial activities 43.
Wageesh S.El Hamouly et al, reported the synthesis of N-substituted sulphonyl, 1,2,4-triazole, N-substituted benzylidene and pyrazole analogues bearing 4-(benzo(d)thiazol-2-yl)benzohydrazide and evaluated for antibreast cancer activity 44.
Hend A. A. Abd El-Wahab et al, synthesized substituted 1,2,4- triazole-3-acetic acid derivatives and evaluated for antitumor and anti-inflammatory activities 45.
Ibrahim F. Nasser et al, were synthesized 2- alkylthio-7-tosyl-7H-pyrazolo (4,3-e)[1,2,4-]-triazolo[1,5-c] pyrimidines and other pyrazole derivatives and evaluated for their antitumour activity 46.
As antitubercular agents: Shashikant Patten et al, reported the synthesis of 5-mercapto 1,2,4-triazole derivatives and evaluated for antimicrobial, anti-inflammatory, antitubercular activities 47.
Mahendra Ramesh Shiradkar et al, reported the synthesis of various derivatives of N-{4-[(4-amino-5-sulphanyl-4H-1,2,4-triazol-3-yl)methyl]-1,3-thiazol-2-yl}-2-substituted amides and tested for antibacterial and antitubercular potency 48.
Mahendra Shiradkar et al, synthesized analogues of thiazolyl triazoles and tested for their antimycobacterial and antimicrobial activities 49.
As anticonvulsant agents: Hong Guang Jin et al., reported the synthesis of 7-alkoxy-4,5-dihydro[1,2,4]triazolo[4,3-a]quinoline1(2H)-ones and investigated for anticonvulsant activity and neurotoxicity 50.
- Moreau et al., reported the synthesis of 3-amino-7-(2,6-dichlorobenzyl)-6-methyltriazolo[4,3-b]pyridine derivatives of amide and carboxylic acid and investigated for their anticonvulsant potency51.
Zhi-Feng Xie et al, prepared various 7-alkoxy-4,5-dihydro-[1,2,4]triazolo[4,3-a]quinoline analogues and were investigated for their anticonvulsant activity and neurotoxicity. Compound(4l) is found to be very active 52.
Dayanand Kadadevar et al., reported the synthesis and evaluation of N-(substitutedphenyl)-2-[5-phenyl-2H-1,2,4-triazol-3-yl-amino]acetamide for their anticonvulsant activity 53.
As Anxiolytic agents: Anil M. Manikaro et al, synthesized carboxamidoethylthio-(4H)-1,2,4-triazoles and evaluated for anxiolytic, anti-inflammatory, analgesic activity 54.
As Antioxidant agents: M. Suresh et al, reported the synthesis of 8-chloro-1,4-substituted (1,2,4[4,3-a]quinoxalines and evaluated for antioxidant and antimicrobial activity 55.
As Human V1A receptor antagonists: Akio Kakefuda et al, synthesized 5-(4-biphenyl)-3-methyl-4-phenyl-1,2,4-triazole derivatives and investigated as selective antagonists for the human vasopression V1A receptor 56.
As PPARα agonists: Yan Ping Xu et al., reported the design and synthesis of various 2, 4-dihydro-3H-1, 2, 4-triazol-3-one, and investigated as most potent and selective PPARα agonist 57.
As Analgesic agents: P. K. Goyal et al., were synthesized s-substituted -4-(3-disubtituted-1-triazenyl)-4H-1,2,4-triazol-5-thiol and tested for analgesic activity 58.
CONCLUSION: The present study revealed that 1,2,4-triazole derivatives are the significant class of heterocyclic compounds and showed promising pharmacological activities like antibacterial, antifungal, antitubercular, antioxidant, anticancer, anti-inflammatory, analgesic, anticonvulsant, anxiolytic, activities. These observations have been useful for the development of 1, 2, 4-triazole nucleus which can be taken as a lead for future development to get safer and effective compounds.
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How to cite this article:
Kumudha D, Reddy RR and Kalavathi T: 1, 2, 4-Triazoles: As Biologically important Agents. Int J Pharm Sci Res. 3(12); 4562-4572.
Article Information
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4562-4572
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English
Ijpsr
D. Kumudha*, R. R. Reddy and T. Kalavathi
Assistant Professor, Arya College of Pharmacy, Kandi, Sangareddy, Medak- 85, Andra Pradesh, India
kumudhachem@gmail.com
02 August, 2012
20 September, 2012
10 November, 2012
http://dx.doi.org/10.13040/IJPSR.0975-8232.3(12).4562-72
01 December, 2012