1, 2, 4- Triazole Derivatives and its pharmacological activities

 

Vipul Singh*, Arvind Kumar Singh, Rohit Tripathi, Preeti Mishra, Roopes Kumar Maurya

Kamla Nehru Institute of Management and Technology (Faculty of Pharmacy), Sultanpur  UP-228001, India.

*Corresponding Author E-mail: adi_arv26@rediffmail.com

Triazole, a heterocyclic nucleus has attracted a wide attention of the medicinal chemist in search for the new therapeutic molecules. This review provides a brief summary of 1,2,4-triazole Derivatives and its Pharmacological activities and highlights some examples of 1,2,4-triazole-containing drug substances. Either as single heterocyclic derivatives or in fusion with the other cycles, these heterocycle is emerging as the most explored centre to obtain clinically significant compounds. The major activities exhibited by 1,2,4 derivatives include antibacterial, antifungal, antiviral, antidepressant, antimalarial, hypnotic, anticonvulsant and anti-inflammatory activities.

 

 

 

INTRODUCTION:

Triazole refers to either one of a pair of isomeric chemical compounds with molecular formula C₂H₃N₃, having a five-membered ring of two carbon atoms and three nitrogen atoms. The two isomers are:(1).1,2,3 Triazole (2) 1,2,4 Triazole 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. Out of the two triazoles, 1, 2, 4- triazole have drawn great attention to medicinal chemists from two decades due to its wide variety of activity, low toxicity and good Pharmacokinetic and Pharmacodynamic  profiles.

 

1,2,4-Triazole is a basic aromatic heterocycle. The derivatization of Triazole is considered to be based on the phenomenon of bioisosterism in which replacement of oxygen of oxadiazole nucleus with nitrogen atom yields triazole analogue. On substitution it have been found to have other interesting pharmacological responses such as Antibacterial, Antifungal, Antitumor, Anti-inflammatory, Anti-tubercular, Antidepressant, Anticonvulsant, Anticancer, Antimalarial, Antiviral, Analgesic and Hypoglycaemic activity. A sum of 1, 2, 4-triazole derivatives associated with large no. of biological responses is presented table.

 

 

S.No	Compound	Derivatives	Biological Activities
1.	4-(substituted ethanoyl) amino-3-mercapto-5-(4-nitro) phenyl-1,2,4-triazoles 1	1(a-d)	Antimicrobial  activity
2.	4-[Substituted]-3-phenyl-5-(4-tolyl)-4H-1,2,4-triazole2	2(a-d)	Antimicrobial  activity
3.	5-asromatic substituted-4H-  1,2,4-triazole-3-thiol3	3(a-c)	Antimicrobial  activity
4.	1-(2-Hydroxy-2-phenyl-ethyl)-3-   thiophen-2-ylmethyl-4 Substituted  4,5-dihydro-1H-[1,2,4] triazole-5-one4	4(a-d)	Antimicrobial  activity
5.	3,4-diaryl-1,2,4-triazol 5ylpropenoic acid5	5(a-i)	Antimicrobial  activity
6.	[3-(cyanomethyl)-5-alkyl-4H-1,2,4- triazol-4-yl] carbamates6	6(a-d)	Antimicrobial  activity
7.	2,4 dihydro-[1,2,4]triazol-3-one derivatives7	7(a-e)	Antimicrobial  activity
8.	Thiazolidine-4-one substituted 1, 2, 4- triazole benzofuran 8	R=Phenyl               R=2-Nitro Phenyl               R=3-Chloro Phenyl               R=2-Chloro Phenyl                           8(a-d)	Antimicrobial  activity
9.	5-Substituted-4-(1-phenylpropyl)-2H-1,2,4- triazole-3(4H)-thiones 9	9(a-i)	Antimicrobial  activity
10.	5-substituted-3-pyridine-1,2,4-triazol10	10(a-c)	Antimicrobial  activity
11.	2-aryl-5-(6’-chloro-1’,3’- benzothiazol-2-yl-amino)-1,3,4-thiadiazoles11	a: Ar = -C6H4NO2(p-)               b: Ar = -C6H4Br(p-)               c: Ar = -C6H4Cl(p-)                       11(a-c)	Antimicrobial  activity
12.	1-[5-(substituted aryl)-1,2-oxazol-3-yl]- 3,5-diphenyl-1H-1,2,4-triazoles12	R=R’=Phenyl ring                          12(a-d)	Antimicrobial  activity
13.	4-allyl-5-aryl-1,2,4-triazoles13	Ar =2-OH-C6H4- Ar =4-OH-C6H4- Ar =2-OH-5-Cl-C6H4- Ar =4-C2H5O-C6H4-CH2-            13(a-d)	Antibacterial and Antifungal
14.	3-[4-(4- Substituted phenyl-5-thioxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl-methoxy)-phenyl]- 2-phenyl- 3H-quinazolin-4-one14	14(a-d)	Antibacterial and Antifungal
15.	2,6-diphenyl-3-(4-(3-phenyl- [1,2,4]triazolo[3,4-b][1,3,4]thiadiazol6yl)phenyl)-2H-1,3,5-oxadiazine4(3H)thione15	Ar - a )- phenyl           b) - 4 - methoxy phenyl           c) - 4 - Hydroxy phenyl           d )- 2 - hydroxy phenyl           e )- 4 - methyl phenyl           f )- 3,4 - methylenedioxy phenyl           g) - 4 - hydroxy - 3 - methoxy phenyl             h )- 3,4 -diethoxy phenyl                                            15(a-h)	Antibacterial and Antifungal
16.	3-(3-pyridyl)-5-(4-nitrophenyl)-4(N-substituted-1,3-benzothiazol-2-amino)-4H-1,2,4-triazole16	R = a. 6-F, d. 6-CH3, g. 4-CH3, j. 4-Cl b. 6-Br, e. 6-OCH3, h. 4-NO2, c. 6-NO2, f. 6-Cl, i. 5-Cl                              16(a-j)	Antibacterial and Antifungal
17.	3-pyridyl-6-aryl-1, 2, 4 -triazolo (3, 4-b) (1, 3, 4) –Thiadiazoles17	17(a-d)	Antibacterial and Antifungal
18.		R = -C2H5       R= -4-CH3C6H4       R= -4-CH3OC6H4                  18(a-c)	Antifungal activity
19.	1H-1,2,4-triazol-3-ylbenzenesulfonamide derivatives19	19(a-e)	Anti-malarial  activity
20.	5-methyl-2-[(5-substituted aryl-4H-1, 2, 4-triazol-3-yl)methyl]-2,4-dihydro-3H-pyrazol-3-one20	20(a-d)	Analgesic activity
21.	substituted 1,2,4-triazol-3-yl)benzene-1,2,3-triol21	21(a-e)	Anti- tubercular Activity
22.	3-Substituted-4-(3-diSubstituted-1-triazenyl)-4H-1,2,4-triazol-5-thiol22	22(a-d)	Anti inflammatory activity
23.	Ethyl [4-amino-3-(1,3-diphenyl-1H-pyrazol-4-yl)-4H-[1,2,4]triazol-5-ylthio]-acetate23	23(a-b)	Antiviral activity
24.	3,6-disubstituted-[1,2,4]-triazolo-[3,4b]-1,3,4-thiadiazoles24	24(a-c)	Anti-convulsant activity
25.	3-Substituted-4-Amino-5-Mercapto-4(H)-1, 2, 4-Triazole25	25(a-d)	Anti- convulsant activity
26.	2-[(substitutedphenyl)imino]-5-(Z)-1-arylmethylidene-3-(2-[5-(1- phenoxyethyl)-4H-1,2,4-triazol-3-yl]sulfanylacetyl)-1,3-thiazolan-4-one26	26(a-d)	Anti -convulsant activity
27.	4-arylmethylenamino-4H-1,2,4-triazoles27	27(a-d)	Antitumor activity
28.	3-substituted-6-(3- substituted -1H-pyrazol-4-yl)[1,2,4] triazolo[3,4-b] [1,3,4] Thiadiazole28	28(a-d)	Anticancer activity
29.	(2R)-4-Oxo-4-[3-(Trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin- 7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine29		Hypoglycemic activity
30.	5-Benzyl-4-substituted-4H-1,2,4-triazole-3-thiol30	a) C6H5 b) p-C6H4OCH3 c) p-C6H4Cl d) p-C6H4NO2 e) p-C6H4CH3                                                       30(a-e)	Antidepressant activity

 

 

CONCLUSION:

The brief information available on the triazole derivatives clearly indicates their therapeutic importance. The literature review reveals that 1,2,4-triazole has diverse biological activity. It has shown good antimicrobial activity.

 

ACKNOWLEDGEMENT:

The authors would like to express gratitude and thanks to Faculty of Pharmacy, KNIMT, Sultanpur for providing necessary facilities to carry out this research work.

 

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Received on 04.04.2013       Modified on 19.04.2013

Accepted on 30.04.2013      © AJRC All right reserved