International Journal of Medicine and Pharmaceutical Research. Library 1H-1, 2, 4,-Triazole Having Significant Pharmacological Activities
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1 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) Available online at Pharma esearch Library International Journal of Medicine and Pharmaceutical esearch 2013, Vol.1 (2): I Pharma esearch Library 1-1, 2, 4,-Triazole aving ignificant Pharmacological Activities akshi Gupta*, Dharmendra Kumar Department of Pharmaceutical Technology, Meerut Institute of Engineering and Technology, Meerut, U. P., India. * sakshi.mpharm2011@gmail.com Abstract In the last few years, heterocyclic compounds have attracted strong interest and a lot of work has been done on triazole ring. Many different derivatives have been prepared from it which possesses useful pharmacological activities. In the present review, we have compiled the different pharmacological activities of triazole ring and its derivatives. It has been observed that triazole derivatives possess a wide range of pharmacological activities such as anticancer, anticonvulsant, antimicrobial, anti-inflammatory, antioxidant, antitubercular, antimalarial, antinociceptive etc. In triazole ring, substitution at 1, 4 and 1, 3 positions of a more electronegative group will possess more active analogues. This review contains various pharmacological activities of triazole in one place and it is also the milestone for the new research towards this moiety. Key words: Triazole, anticancer, anticonvulsant, Antimicrobial, Anti-inflammatory. Introduction Medicinal chemistry is an aspect of biological, medical and pharmaceutical sciences. It is concerned with the invention, discovery, design and identification of biologically active compounds. It also involves study of metabolism, interpretation of mode of action at the molecular level and the development of structure activity relationship (A) of the active nuclei [1]. It is devoted to the discovery and development of new agents for treating diseases. Inorganic compound continue to be important in therapy, for example, antacids, mineral supplements and radiopharmaceuticals, but organic molecules with increasingly specific pharmacological activities are clearly dominant[2]. eterocyclic compounds are cyclic compounds with at least two different elements as ring member atoms [3]. They are the counterparts of homocyclic compounds, which have only ring atoms from the same element. Although heterocyclic compounds may be inorganic, most contain at least one carbon atom, and one or more atoms Pharma esearch Library 250
2 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) of elements other than carbon within the ring structure, such as sulfur, oxygen or nitrogen. In organic chemistry noncarbons which replace carbon atoms are called heteroatoms [4]. Triazole and its derivatives possess a great significance in medicinal chemistry and numerous heterocyclic compounds containing triazole with different biological activities can be synthesized from them. Triazole has a basic, five membered, heterocyclic ring containing two carbon and three nitrogen atoms having molecular formula C It forms a pair of isomeric chemical compounds. These are: 1, 2, 4 triazole and 1, 2, 3 triazole (Fig.1) [5]. 1-1,2,4-triazole 1-1,2,3-triazole Figure.1 ut of these two, 1, 2, 4-triazole possess significant and wide variety of activity in comparison to 1, 2, 3-triazole [6]. 1, 2, 3-triazole is considered to be the most stable organic compound in comparison to all other organic compounds possessing three adjacent nitrogen atoms. Aziridine was formed by flash vacuum pyrolysis from 1, 2, 3-triazole at 500 C which leads to loss of molecular nitrogen ( 2 ). Certain triazoles undergo cleavage very easily due to socalled ring-chain tautomerism such as in the Dimroth rearrangement. 1, 2, 3-triazole is considered to be the most useful component, widely used in research purpose as a building block for complex chemical compounds such as pharmaceutical drugs like tazobactam[7]. 1, 2, 4-Triazole is a basic aromatic heterocycle and its derivatives posses a wide variety of pharmacological activity such as antifungal [8], anticancer [9], anticonvulsant [10], antimicrobial [11], anti-inflammatory [12], antioxidant [13], anti-tubercular [14], anti-malarial [15], anti-nociceptive [16]. ome of the marketed preparation which contains triazole ring is fluconazole (Fig 2) and itraconazole (Fig. 3). F F Fluconazole; Figure.2 Itraconazole; Figure.3 The attachment of quinoline ring to triazole ring is responsible for producing anti-bacterial effect and further modifications can be made on it to enhance its pharmacological effect [11]. ubstitution at 3 rd position may also increase the pharmacological activity of a compound for e.g.:- 3-Amino-1, 2, 4 triazole (Fig.4) is a competitive inhibitor of the production of I 3 gene, imidazoleglycerolphosphate dehydratase. It is an enzyme catalyzing the sixth step of the histidine production and is also a non selective systemic triazole herbicide used on non food crop land to control annual grasses and broad leaf and aquatic weeds [13]. Pharma esearch Library 251
3 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) tereochemistry A group of interesting target molecules can be made from 4 - Amino - 1, 2, 4 - triazoles with substitutions at 3, 5 positions (Fig.4a). These target compounds can be used for studying their stereochemistry and biological properties. 2 2 C 1 a b c Figure 4 The nitrogen of 4 amino group is attached with other ring system (Fig.4b) from which we can study the restricted rotation about sp 2 -sp 2 single bond. Whereas, (Fig.4c) the 4 amino group is condensed with carbonyl compounds to give derivatives which involve restricted rotation about the sp 2 - sp 2 single bond and sp 2 - Csp 2 double bond together in one system, therefore they represent a group of interesting molecules from the point of studying their stereochemistry [17] C 3 5a 5b Figure 5 5a 1 : 1 = C 6 5, 2 =C 3 ; 5a 2 : 1 = C 2 C 6 5, 2 =C 3 ; 5a 3 : 1 = C 2 C 6 5, 2 =C 6 5 ; 5a 4 : 1 = C 6 4 C 3, 2 =C 3 5b 1 : 1, 3, 4 =C 6 5, 2 = C 3 ; 5b 2 : 1, 3 = C 6 5, 2 = C 3, 4 = ; 5b 3 : 1 = C 2 C 6 5, 2 = 3 = 4 = C 6 5 ; 5b 4 : 1 =C 2 C 6 5, 2 =, 3 = C 6 5, 4 = ; 5b 5 : 1 = C 3, 2 = C 6 4 C 3, 3 = 4 =C 6 5. Pharmacological Activities Anticancer activity K. ubrahmanya Bhat et al. synthesized a series of compound 3-(2,4-dichloro-5-fluorophenyl)-6-(substituted phenyl)-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazines (Fig.6) by the cyclization of 3-(2,4-dichloro-5-fluorophenyl)-1,2,4- triazol-5-thiol with substituted phenacyl bromides. All the synthesized compounds were tested for their antitumor activity. Among the synthesized compounds, compound 6a, 6b and 6c exhibited most potent activity against sixty cancer cell lines of leukemia, non-small cell lung cancer, melanoma, ovarian cancer, prostate and breast cancer [18]. F = 6a ; 4-, 6b ; 2,4-6c ; 2,4-5-F Figure 6 Pharma esearch Library 252
4 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) C. Kurumurthy et al. synthesized a series of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives (Fig.7). These derivatives were then screened for their in-vitro anticancer activity against three cancer cell lines such as U937, TP-1 and Colo205. Compounds 7a and 7b showed potent anti-cancer activity against the respective cell lines [19]. 1 CF 3 7a: =, 1 = C 3 -(C 2 ) 8 -C 2 ; 7b: = C 3, 1 = C 3 - (C 2 ) 8 -C 2 Ph Figure 7 Anticonvulsant activity Li-Ping Guan et al. synthesized a series of 6-alkoxy-[1, 2, 4] triazolo [4, 3-b] pyridazine derivatives (Fig.8) and screened them for anticonvulsant activity. In all synthesized derivative, compound 8 was found to be most active and exhibiting the lowest toxicity [10] 6-(2, 4-dichlorophenoxy)-[1, 2, 4] triazolo [4, 3-b] pyridazine Figure 8 M. halini et al synthesized a series of 4, 5-diphenyl-2-1, 2, 4-triazol-3(4)-one (Fig.9) compounds and screened them for their anticonvulsant activity. Compounds 9d, 9i, 9n-r exhibited potent anticonvulsant activity in all the four animal models of seizure which are maximal electroshock seizure (ME), subcutaneous pentylenetetrazole, subcutaneous strychnine, and subcutaneous picrotoxin -induced seizure threshold tests [20]., 1, 2 9d:, 2-C 3, 4-C 3 ; 9i:, 2-C 3, 5-C 3 ; 9n: 2,, 4-F; 9o: 2,, 4-F;9p: C 3,, 4-F; 9q:,, 4-F; 9r:,, 4-F 2 1 Figure 9 Antimicrobial activity umesh Eswaran et al. synthesized a series 5-(4-amino substituted-8-(trifluoromethyl) quinolin-3-yl)-4-(un) substituted phenyl -4-1,2,4-triazole-3-thiols (Fig.10) from derivatives of 4-hydroxy-8-(trifluoromethyl) quinoline- 3-carbohydrazide and screened for their antimicrobial activity against Escherichia coli (ATTC-25922), taphylococcus aureus(attc-25923), Pseudomonas aeruginosa(atcc-27853), Klebsiella pneumonia. The activity of these compounds was compared with ciprofloxacin as standard drug. The compounds10a, 10b and 10c showed comparatively very good activity against all the bacterial strains [11]. Pharma esearch Library 253
5 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) CF = Ph, -C 2 Ph, -C 2 C 2 Me 2 = substituted amines 2 : 10a: cyclopropyl amine, 10b: cyclohexyl amine, 10c: 3,3 Dimethyl butylamine. 10d: Piperidine-4-propanol, 10e:Morpholine, 10f: 4-Piperidine morpholine Figure 10 Xian-Long Wang et al. synthesized a series of novel sulfanilamide-derived 1, 2, 3-triazole compounds (Fig.11 and 12) via 1, 3-dipolar cycloaddition and screened them in vitro for their antibacterial and antifungal activities against. aureus(atcc25923), E. typhosa, P. aeruginosa(atcc-27853),. dysenteriae, B. subtilis(atcc6633), E. coli(attc-25922), as well as C. albicans (ATCC76615) and C. mycoderma. The activity of the synthesized compounds was compared with the reference drug chloramphenicol. (C 2 ) 11 C 3 2 Figure a 1 =, 2 =, 3 = ; 12b 1 = F, 2 =, 3 = F Figure 12 The compounds 11, 12a and 12b bearing dodecyl, 2,4-dichlorobenzyl and 2,4-difurobenzyl group, respectively, showed the most potent antibacterial activities against all tested bacterial strains with the minimum inhibitory concentration (MIC) values ranging from 32 to 128 µg/ml[21]. Anti-inflammatory activity Xian-Yu un et al. synthesized a series of several new 6-alkoxy (phenoxy)-[1, 2, 4] triazole [3, 4-a] phthalazine-3- amine derivatives (Fig.13). All synthesized derivative further screened for their anti-inflammatory activity. The compounds 13a and 13b possess highest anti-inflammatory activity in comparison to the reference drug Ibuprofen. 13a: = -C 6 4 (o-);13b: = -C 6 4 (p- 2 ) 2 Figure 13 Pharma esearch Library 254
6 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) Anti-oxidant activity:- Yasemin unver et al. synthesized a series of 4-(3, 4-dihydroxyphenethyl)-5-methyl-2-1,2,4-triazol 3(4)-one derivatives (Fig.14 and 15) which were then screened for anti-oxidant activity. It was found that compounds 14a-d and compound 15 possess highest degree of antioxidant activity [13]. (Ar) Figure 14 Figure 15 4-(2, 3-dihydroxyphenethyl)-5-(3, 4-dihydroxybenzyl)-2-1, 2, 4-triazol-3(4)-one Compound: 14a 14b 14c 14d Ar: C 3 C 2 C 2 C 3 Yuksek et al. synthesized a series of 3-alkyl (aryl)-4-(3, 4-dihydroxybenzylidenamino)-4, 5-dihydro-1-1, 2, 4- triazol-5-one (Fig.16) and were evaluated for their antioxidant activity by DPP free radical scavenging method. Among the synthesized compounds 16a, 16b shows more potent antioxidant activity [22]. C 16a:=C 3 ; 16b:=C 2 C 6 5 Figure 16 Anti-malarial activity Eric M. Guantai et al. synthesized a series of chalcone and dienone hybrid compounds (Fig.17) containing aminoquinoline and nucleoside templates which were then screened for in-vitro antimalarial activity. Amongst the synthesized compounds, three compounds were found to be most active that is compounds 17a, 17b and 17c, compound 17a was the most active and potent against D10, Dd2 and W2 strains of P. falciparum compared with the standard drug chloroquine [14]. Me Me 17a and b 17c Figure 17; 17a: 2, 4-diMe; 17b: 2, 3, 4-triMe; 17c: 2, 3, 4-triMe Pharma esearch Library 255
7 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) Anti-tubercular activity udeep K. Mandal et al. synthesized various derivatives of substituted 1, 2, 4-triazol-(3-yl) benzene-1, 2, 3-triol derivative (Fig.18) and screened them for anti-tubercular activity. It was found that compounds 18a and b possess comparable activity with that of standard drug ifampicin against Mycobacterium tuberculosis. The remaining compounds are found to be less active than standard [15]. C a: 2 ; 18b: Figure 18 Anti-nociceptive activity Aiyalu ajasekaran et al. synthesized a series of 1-[2-(1-tetrazol-5-yl) ethyl]-1-benzo-1,2,3 triazole derivative (Fig.19) and the synthesized compounds were screened for anti-nociceptive and anti-inflammatory activity. It was found that compounds 19a and 19b possess significant anti-nociceptive activity while compounds 19c and 19d possess significant anti-inflammatory activity [16]. Figure 19 = 19a 2 19b 3 C 19c 2 19d Conclusion Triazole is a unique moiety that is responsible for various biological activities. This article highlighted research work of many researchers reported in literature for different pharmacological activities on synthesized triazole compounds. This review has presented comprehensive details of triazole analogues, potent compounds reported for particular pharmacological activity and the method or technique involved in evaluation process. More investigations must be carried out to evaluate more activities of triazole for many diseases whose treatment are difficult in the medical sciences. This has been noticed so far, that modifications on triazole moiety results in the formation of compounds with valuable biological activities. It will be interesting to observe that these modifications can be utilized as potent therapeutic agents in future. Thus many more modifications on triazole moiety can be possible and needs to be continued for the use of mankind.. Pharma esearch Library 256
8 akshi Gupta and Dharmendra Kumar Int. J. Med. Pharm. es., 2013,Vol.1(2) eferences 1. D.A. Williams, L.L. Thomas, Foye s principles of medicinal chemistry, Lippincott Williams and Wilkins publishers, 2002, 5, Wilson, Gisvold, Text book of organic medicinal and pharmaceutical chemistry, Lippincott-aven publishers, 2003, 11, T. Eicher,. auptmann, The chemistry of heterocycles: structure, reaction, synthesis, and Applications, Wiley-VC, 2003, 2, T.L. Gilchrist, rganic synthesis of heterocyclic chemistry, wedish press publication,1963, iddiquia, W.Ahsana, M..Alama,.Alia,.Jainb, B.Azada, J.Akhtara, Triazoles: as potential bioactive agents. I J Pharm cie ev ese., 2011, 8, K.T.Potts, The Chemistry of 1, 2, 4-Triazoles, Chemical eviews. 1961, 61, ussain, J.harma, M.Amir, ynthesis and Antimicrobial Activities of 1, 2, 4-Triazole and 1,3,4- Thiadiazole Derivatives of 5-Amino-2-ydroxybenzoic Acid, E J Chem., 2008, 5, ztanke, K.Tuzimski, T.J.zymowska, K.Pasternak, M.K.zerszen, ynthesis, determination of the lipophilicity, anticancer and antimicrobial properties of some fused 1,2,4-triazole derivatives, E J Med Chem., 2008, 43, K..Bhat, B.Poojary, D.J.Prasad, P.aik, B..olla, ynthesis and antitumor activity studies of some new fused 1,2,4-triazole derivatives carrying 2,4-dichloro-5-fluorophenyl moiety, E J Med Chem., 2009, 44, K.Wahi, A.ingh, Triazole: ecent Development and Biological Activities, Asian J Biochem Pharm ese. 2011, 2, C.Kurumurthy, P..ao, B.V.wamy, G..Kumar, P..ao, B.arsaiah, L..Velatooru,.Pamanji, J.V.ao, ynthesis of novel alkyltriazole tagged pyrido[2,3-d]pyrimidine derivatives and their anticancer activity, European J Med Chem 2011, 46, L.P.Guan, X.ui, X.Q.Deng, Y.C. Quan, Z.. Quan, ynthesis and anticonvulsant activityof a new 6- alkoxy-[1,2,4]triazolopyridazine, European J Med Chem 2010,45, Eswaran, A.V.Adhikari, hetty.. ynthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety European J Med Chem,2009,44, X.L Wang, K.Wan,C..Zhou, ynthesis of novel sulfanilamide-derived 1,2,3-triazoles and their evaluation for antibacterial and antifungal activities, European J Med Chem 2010, 45, X.Y.un, C.ua, X.Q.Deng, C.X.Wei, Z.G.un, Z..Quan, ynthesis and antiinflammatory activity evaluation of some novel 6-alkoxy(phenoxy)-[1,2,4]triazolo[3,4- a]phthalazine-3-amine derivatives, European J Med Chem,2010, 45, Y.Unver,.Meydanal, K.ancak, D.Unluer,.Ustabas, E.Dugdu, ynthesis, crystal structure, and antioxidant properties of novel 1,2,4-triazol-5-ones containing 3,4- dimethoxyphenyl and 3,4- dihydroxyphenyl moiety, Turk J Chem,2011,35, E.M.Guantai, K.cokazi, T.J.Egan, J.Gut, P.J.osenthal, P.J.mith, K.Chibale, Design, synthesis and in vitro antimalarial evaluation of triazole-linked chalcone and dienone hybrid compounds, Bio & Med Chem, 2010, 18, K.Mandal,D.aha,V.K.Jain, B.Jain, ynthesis and Antitubercular activity of some Triazole derivatives of Propyl gallate, International J Pharma ci and ese (IJP), 2010, 1, A.ajasekaran, K.A.ajagopal, ynthesis of some novel triazole derivatives as antinociceptive and antiinflammatory agents, Acta Pharm., 2009, 59, L..Devi,.Devi, B.ingh, M.D.ingh, ynthesis and tereochemistry of 4 Amino-1,2,4 -Triazoles with Unsymmetrical ubstituents at 3,5-Positions, J. Chem. Pharm. es.,2011,3, Yuksek,.Kolayli,M.Kucuk, M.Yuksek, ynthesis and antioxidant activities of some 4-benzylidenamino -4, 5-dihydro-1-1,2,4-triazole-5-one derivatives, Ind. J. Chem., 2006, 45, Pharma esearch Library 257
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