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IJCRR - 2(3), March, 2010

Pages: 44-56

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TRIAZOLES: A VERSATILE THERAPEUTIC AGENT

Author: Khange S.G., Deshmukh V.K., Mohite P.B., Pandhare R.B.

Category: Healthcare

Abstract:The five membered heterocyclic rings containing at least one nitrogen atom are Azoles, important like Isoxazole, Thiazole, Pyrazole, Triazole, and Tetrazole. 1,2,4-Trizoles, which contains three nitrogen in five membered heterocyclic ring are of importance possessing high medicinal value and reported various pharmacological activities such as anticancer, hypoglycaemic activity, antifungal, antimicrobial, antiinflammatory, anticonvulsant, antitubercular and antidepressant activity. The present attempt is to review the importance of medicinal aspects of 1, 2, 4-Triazole ring.

Keywords: Heterocyclic ring, Azoles, 1, 2, 4-Triazole, Pharmacological activity, antifungal.

Full Text:

INTRODUCTION

Azoles are five membered Heterocyclic compounds with two or more heteroatoms in which at least one is nitrogen. Azoles are found widely in natural sources and there are several drugs available which contain azole ring discussed in Table 1.

Here we will focus on 1,2,4- Triazoles, which are by far the bestknown class of triazoles five membered heteroatoms with three nitrogen atoms in the ring and consist wide variety of medicinal activity. The action of azole on mycotic biochemistry and physiology has been studied extensively. At high concentrations (micromolar) the azoles are fugicidal and at low concentrations (nanomolar), they are fungistatic 1-3,6 . Synonyms - Triazole, Pyrrodiazoles, 1-H Triazole.

Constitution and chemistry of Triazoles:

Triazoles ring is basically of two types i.e. 1, 2, 3 and 1, 2, 4-Triazole.The derivatization of Triazole ring is based on the phenomenon of bioisosterism in which replacement of oxygen of oxadiazole nucleus with nitrogen atom yields triazole analogue. Out of the two triazoles 1,2,4- triazole have wide variety of activity4 .1,2,4-Triazole is one of a pair of isomeric chemical compounds with molecular formula C2H3N3 called triazoles, which have a five membered ring of two carbon atoms and three nitrogen atoms. 1,2,4-Triazole is a basic aromatic heterocycle. 1,2,4-Triazoles can be prepared using the Einhorn-Brunner reaction or the Pellizzari reaction5 .1, 2, 4- Triazoles are cyclic hydrazidines with hydrogen atom (or substituent) on either hydrazide nitrogen or on amide nitrogen. Parent 1, 2, 4-triazole (1-H form) is in tautomeric equilibrium with 1, 3, 4- triazole (4H form).The interconversion of two tautomeric forms occurs rapidly and their separation is difficult1 . 1, 2, 4-triazole tautomer is preferred over 1, 3, 4- triazole tautomer (less symmetrical 1H form is favoured over symmetrical 4H- form)

1, 2, 4-Triazole is considered to be derived form benzene by replacement of -CH=CH-by - NH- and the replacement of two -CH=by two - N= atoms. The replacement of -CH=CH- in benzene by - NH enhance the electron density and hence makes 1, 2, 4-triazole susceptible towards electrophilic attack as compared to benzene. But the replacement of two -CH=by two - N= atoms causes the resulting 1,2,4-triazole to be nearly unreactive towards electrophiles.Therefore 1,2,4-triazoles fails to undergo nitration, sulfonation, and N-oxidation. However, 1, 2, 4- triazole anion undergoes alkylation and acylation very readily 7 .1, 2, 4-Triazoles undergo nucleophilic substitution, if substituted with electron withdrawing substituents, the reactivity of 1,2,4- triazole ring towards nucleophile is enhanced in 1,2,4-triazolium cations and mesoionic 1,2,4-triazoles.

Need for the study

Various Triazole heterocyclic ring containing derivatives are known but its practical applications have been hitherto very little. The most of triazoles are easily prepared with good stability. But the starting materials are quite expensive or sensitive intermediates appear which depressed industrial synthesis and its wide applications. The Literature reviews suggests the synthesis of triazole derivatives and their remarkable antifungal, antibacterial, anticancer, antitubercular and antidepressant, hypoglycemic activities13-28 .

Medicinal utilities of Triazole derivatives promote to synthesize new potential triazole derivatives and evaluate its possible pharmacological activities like antifungal, antibacterial, anti-HIV, anticancer, antituberculine, antiviral etc.

Importance of Triazoles in Phytochemicals:

According to survey 1,2,4-Triazoles also show some activity like 1,2,4-Triazole shows fungicides activity against some fungus that are responsible for follicular disc are in ?Vinca minor Z?. Thus it shows activity in plants also.

Importance of Triazoles as Analytical Reagents:

Substituted 1,2,4, triazoles find many useful applications. Some of them are used as analytical reagents for determination of boron8 , antimony9 and cobalt10, other triazoles find many synthetic uses as halogenating agents11 or as activating polymeric reagents12. Now 1,2,4- triazoles derivatives are widely used as biocides and as antifungal agents13. Several 1,2,4-triazoles derivatives find applications as photographic reagents.

Importance of Triazoles containing compounds:

Literature survey of 1,2,4-Triazoles reveals different biological activity. Important activity of them is discussed here.

A) Antimicrobial agents

Schiff bases of Triazole(s) show antibacterial as well as antifungal activity13 like-5-phenyl, 4-(substituted)amino, 3- mercapto 1,2,4-triazoles show antimicrobial activity14.4-Amino-5-Aryl-1, 2,4- triazole-3- thione and their derivatives show antimicrobial activity15 .

B) Anti-inflammatory activity

Anti-inflammatory activity has been shown by [(4-Amino 5-Disubstituted-4- H-1, 2,4-triazole-3yl) thio] alkanoic acids16 .

4-Amino-3-Aryloxy alkyl, 5-Mercapto-1, 2,4-Triazoles also show this activity17

Here

R1 = H, R2 = H, CH3, Cl

R3 = H, CH3 R4 = H, Cl

Some new 3-substituted-4-Amino-5- mercapto- (4H)-1,2,4-Triazoles18 .

1-acyl triazoles also act as antiinflammatory agents19 .

Some 5- Aryl,-2-H-tetrazole, 2-aryl-2Htetrazole-2 acetic acids and [(4-phenyl-5- aryl-4H-1,2,4triazole-3yl) thio] acetic acid as possible super oxide scavengers and anti-inflammatory agents20,21 .

C) Hypoglycaemic agents:

Substituted-1, 2,4-Triazoles also show hypoglycemic activity like 5-(substituted aryl), 4-(alkyl, 3-mercapto) 1,2,4- Triazole show hypoglycemic agents22 .

R= CH3,C2H5,Cl,F, NO2, NH2

R'= CH3,C2H5, C3H7,C4H3

R=pp-H2NSO2C6H4

or R = p - ClC6H4

Like this 5-(substituted aryl), 4-ethyl, 3- Mercapto-1, 2,4-Triazole show Hypoglycaemic activity22 .

D) Antidepressant agents

Some substituted triazoles also acts as antidepressant like 2,4-Dihydro-3H-1, 2,4-triazole-3-thiones potential antidepressant agents23 .

E) Antifungal activity

Substituted 1,2,4-Triazoles also show good antifungal activity like.Some 5-substituted, 4-(substituted aryl), 3-mercapto 1,2,4-triazole show antifungal activity24. Similarly 5(p-Sec- .amyl benzene) methoxy-, 3-mercapto 1,2,4-Triazole show good antifungal activity25 .

Several 3-(4'-nitrophenyl)-4-(4''-chloro benzamido)-5-substituted phenyl)-4H- 1,2,4-triazole and 3-(4'-nitrophenyl)-4- (4''-methyl benzenesulphonamido)-5- substituted phenyl)-4H-1,2,4-triazole.

have been synthesized and shown significant antifungal activity against C.albicans and C.krusei26 .

Various novel Mannich bases derived from 3-(4,6-disubstituted -2- thiomethyl)3-amino-5-mercapto-1,2,4- triazoles showed good antifungal activity27 .

F) Anti Tubercular agents

Substituted 1,2,4-triazoles also show anti tubercular activities like-α-[5-(2-furyl)-1,2,4-triazoles-3yl thio] acehydrazide and related compounds show anti-tubercular activities28 .

G) Anti Convulsant agents

Some substituted triazoles also found as possible anticonvulsants like, newsubstituted Mercapto-triazoles and thiazolidiones and their MAO Inhibitory. and anticonvulsants27. Also some 2,4- Dihydro-3H- 1,2,4-triazoles-3-ones as anticonvulsant agents29 .

H) Anti tumor agents

Some 1,2,4-triazole derivatives as potential anti-tumor agents29 .

Some new unsymmetrical 3, 5-Diaryl- 4H-1, 2, 4-triazole derivatives and were tested for anticancer activity, compound chosen for its higher anticancer activity in the preliminary tests with the cancer.

Marketed Formulations Which Contain1,2,4-Triazole Ring

i.Terconozole, U.S.P.

It is a triazole derivative that is used exclusively for the control of valvo-vaginal moniliasis caused by candida albicans and other candida species.

ii. Itraconazole, U.S.P.

Itraconazole is an orally active, broad-spectrum antifungal agent that has become an important alternative to ketoconazole. The primary indications for itraconazole are for the treatment of systemic fungal infection including blastomycosis, histoplasmosis (including patients infected with HIV virus) and sporotrichosis2 .

iii. Fluconazole, USP

It is a water-soluble bis-triazole with broad-spectrum antifungal properties that is suitable for both oral and intravenous administration as the free base30, 2 .

iv. Trazodone

It is a triazolopyridine antidepressant, which selectively inhibits central serotonin uptake2 .

v. Triazolam

It is used as sedative and hypnotic31,2 .

vi. Bittertanol

It is used as broad-spectrum fungicide32, 2 .

CONCLUSION

So, from above study it is predictable that 1,2,4-triazoles is an important pharmacophore and have a wide range of therapeutic properties. It plays vital role as medicinal agents due to different biological activities. At present several-marketed preparation of triazoles are available like Flutrox, Zocon, Fluzone, Trazadone, Trazonil, Trazalon etc.Thus we can conclude that 1,2,4- triazole is an important emerging moiety in pharmaceutical study and a lot of work can be carried out by integrating 1, 2, 4- triazole moiety with other heterocyclic ring systems like oxdiazole, imidazole, azatidinone, thiazolidone etc. to obtain better pharmacological activity.

ACKNOWLEDGEMENT

The authors are thankful to Principal, Prof. V.K.Deshmukh, M.E.S. College of Pharmacy and Mula Education Society, Sonai, for encouragement and availing of the necessary facilities during the course of investigation.

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A Study by Sudha Ramachandra & Vinay Chavan entitled "Enhanced-Hybrid-Age Layered Population Structure (E-Hybrid-ALPS): A Genetic Algorithm with Adaptive Crossover for Molecular Docking Studies of Drug Discovery Process" is awarded Best article for Vol 12 issue 15
A Study by Varsha M. Shindhe et al. entitled "A Study on Effect of Smokeless Tobacco on Pulmonary Function Tests in Class IV Workers of USM-KLE (Universiti Sains Malaysia-Karnataka Lingayat Education Society) International Medical Programme, Belagavi" is awarded Best article of Vol 12 issue 14, July 2020
A study by Amruta Choudhary et al. entitled "Family Planning Knowledge, Attitude and Practice Among Women of Reproductive Age from Rural Area of Central India" is awarded Best Article for special issue "Modern Therapeutics Applications"
A study by Raunak Das entitled "Study of Cardiovascular Dysfunctions in Interstitial Lung Diseas epatients by Correlating the Levels of Serum NT PRO BNP and Microalbuminuria (Biomarkers of Cardiovascular Dysfunction) with Echocardiographic, Bronchoscopic and HighResolution Computed Tomography Findings of These ILD Patients" is awarded Best Article of Vol 12 issue 13 
A Study by Kannamani Ramasamy et al. entitled "COVID-19 Situation at Chennai City – Forecasting for the Better Pandemic Management" is awarded best article for  Vol 12 issue 12
A Study by Muhammet Lutfi SELCUK and Fatma entitled "Distinction of Gray and White Matter for Some Histological Staining Methods in New Zealand Rabbit's Brain" is awarded best article for  Vol 12 issue 11
A Study by Anamul Haq et al. entitled "Etiology of Abnormal Uterine Bleeding in Adolescents – Emphasis Upon Polycystic Ovarian Syndrome" is awarded best article for  Vol 12 issue 10
A Study by entitled "Estimation of Reference Interval of Serum Progesterone During Three Trimesters of Normal Pregnancy in a Tertiary Care Hospital of Kolkata" is awarded best article for  Vol 12 issue 09
A Study by Ilona Gracie De Souza & Pavan Kumar G. entitled "Effect of Releasing Myofascial Chain in Patients with Patellofemoral Pain Syndrome - A Randomized Clinical Trial" is awarded best article for  Vol 12 issue 08
A Study by Virendra Atam et. al. entitled "Clinical Profile and Short - Term Mortality Predictors in Acute Stroke with Emphasis on Stress Hyperglycemia and THRIVE Score : An Observational Study" is awarded best article for  Vol 12 issue 07
A Study by K. Krupashree et. al. entitled "Protective Effects of Picrorhizakurroa Against Fumonisin B1 Induced Hepatotoxicity in Mice" is awarded best article for issue Vol 10 issue 20
A study by Mithun K.P. et al "Larvicidal Activity of Crude Solanum Nigrum Leaf and Berries Extract Against Dengue Vector-Aedesaegypti" is awarded Best Article for Vol 10 issue 14 of IJCRR
A study by Asha Menon "Women in Child Care and Early Education: Truly Nontraditional Work" is awarded Best Article for Vol 10 issue 13
A study by Deep J. M. "Prevalence of Molar-Incisor Hypomineralization in 7-13 Years Old Children of Biratnagar, Nepal: A Cross Sectional Study" is awarded Best Article for Vol 10 issue 11 of IJCRR
A review by Chitra et al to analyse relation between Obesity and Type 2 diabetes is awarded 'Best Article' for Vol 10 issue 10 by IJCRR. 
A study by Karanpreet et al "Pregnancy Induced Hypertension: A Study on Its Multisystem Involvement" is given Best Paper Award for Vol 10 issue 09

List of Awardees

A Study by Ese Anibor et al. "Evaluation of Temporomandibular Joint Disorders Among Delta State University Students in Abraka, Nigeria" from Vol 13 issue 16 received Emerging Researcher Award


A Study by Alkhansa Mahmoud et al. entitled "mRNA Expression of Somatostatin Receptors (1-5) in MCF7 and MDA-MB231 Breast Cancer Cells" from Vol 13 issue 06 received Emerging Researcher Award


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International Journal of Current Research and Review (IJCRR) provides platform for researchers to publish and discuss their original research and review work. IJCRR can not be held responsible for views, opinions and written statements of researchers published in this journal

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