Citation: Hemalatha Gadegoni, Sarangapani Manda. Synthesis and screening of some novel substituted indoles contained 1,3,4-oxadiazole and 1,2,4-triazole moiety[J]. Chinese Chemical Letters, ;2013, 24(2): 127-130. shu

Synthesis and screening of some novel substituted indoles contained 1,3,4-oxadiazole and 1,2,4-triazole moiety

Hemalatha Gadegoni ^a,, ,
Sarangapani Manda ^b

1.
a Jayamukhi College of Pharmacy, Narsampet, Warangal 506332, India;
2.
b University College of Pharmaceutical Sciences, Kakatiya University, Warangal 506009, India

Corresponding author: Hemalatha Gadegoni,
Received Date: 21 August 2012
Available Online: 20 December 2012

A series of novel 3-[5-(1H-indol-3-yl-methyl)-2-oxo-[1,3,4]oxadiazol-3-yl]propionitrile (5), 3-[4-amino-3-(1H-indol-3-yl-methyl)-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl]propionitrile (6), 3-[5-(1H-indol-3-yl-methyl)-2-thioxo-[1,3,4]oxadiazol-3-yl]propionitrile (7) and 3-[4-amino-3-(1H-indol-3-ylmethyl)-5-thioxo-4,5-dihydro-[1,2,4]triazol-1-yl]propionitrile (8) were synthesized in good yields from the intermediate (1H-indol-3-yl)-acetic acid N'-(2-cyanoethyl)hydrazide (4). The chemical structures of the newly synthesized compounds were elucidated by their IR, ¹H NMR and MS. Further, all the compounds were screened for their antimicrobial activity against Gram-positive, Gram-negative bacteria and also tested their ability toward anti-inflammatory activity.
- 1,3,4-Oxadiazols,
- 1,2,4-Triazols,
- Antimicrobial activity,
- Anti-inflammatory
1. [1]
  [1] C.C. Paraschivescu, F. Dumitrascu, C. Draghici, et al., New non-symmetrical 2,5-disubstituted 1,3,4-oxadiazoles bearing a benzo[b]-thiophene moiety, Arkivoc (2008) 198-206.
2. [2]
  [2] M.P. Hutt, E.F. Elstager, L.M. Werbet, 2-Phenyl-5-(trichloromethyl)-1,3,4-oxadiazoles: a newclass of anti-malarial substances, J.Heterocycl. Chem. 7 (1970) 511-581.
3. [3]
  [3] F. Omar, N. Mahfouz, M. Rahman, Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives, Eur. J. Med. Chem. 31 (1996) 819-825.
4. [4]
  [4] M. Zareef, R. Iqbal, N.G. De Dominguez, et al., Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1,3,4-oxadiazole moieties, J. Enzyme Inhib. Med. Chem. 22 (2007) 301-308.
5. [5]
  [5] A. Omar, M.E. Mohsen, O.M. Aboulwafa, Synthesis and anticonvulsant properties of a novel series of 2-substituted amino-5-aryl-1,3,4-oxadiazole derivatives, J. Heterocycl. Chem. 21 (1984) 1415-1418.
6. [6]
  [6] A. Husain, M. Ajmal, Synthesis of novel 1,3,4-oxadiazole derivatives and their biological properties, Acta Pharm. 59 (2009) 223-233.
7. [7]
  [7] S.L. Gaonkar, K.M. Rai, Synthesis and antimicrobial studies of a new series of 2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phen-yl}-5-substituted-1,3,4-oxadiazoles, Eur. J. Med. Chem. 41 (2006) 841-846.
8. [8]
  [8] M.A. Ali, M.S. Yar, Oxadiazole mannich bases: synthesis and antimycobacterial activity, Bioorg. Med. Chem. Lett. 17 (2007) 3314-3316.
9. [9]
  [9] A. Zarghi, S.A. Tabatabai, M. Faizi, et al., Synthesis and anticonvulsant activity of new 2-substituted-5-(2-benzyloxyphenyl)-1,3,4-oxadiazoles, Bioorg. Med. Chem. Lett. 15 (2005) 1863-1865.
10. [10]
  [10] Z.H. Luo, S.Y. He, B.Q. Chen, et al., Synthesis and in vitro antitumor activity of 1,3,4-oxadiazole derivatives based on benzisoselenazolone, Chem. Pharm. Bull. 60 (2012) 887-891.
11. [11]
  [11] V.J. Ram, H.N. Pandey, Synthesis and anti-inflammatory activity of benzal-3-pentadecylaryloxyalkyl carboxylic acid hydrazides and 2-benzalamino-5-(3'-pentadecylaryloxyalkyl)-1,3,4-oxadiazo-les, Eur. J. Med. Chem. 25 (1990) 541-548.
12. [12]
  [12] P.J. Shirote, M.S. Bhatia, Synthesis, characterization and antiinflammatory activity of 5-{[((5-substituted-aryl)-1,3,4-thiadiazol-2-yl)thio]-n-alkyl}-1,3,4-oxadiazole-2-thiol, Chin. J. Chem. 28 (2010) 1429-1436.
13. [13]
  [13] V. Padmavathi, G.S. Reddy, A. Padmaja, P. Kondaiah, Ali-Shazia, Synthesis, antimicrobial and cytotoxic activities of 1,3,4-oxadiazoles, 1,3,4-thiadiazoles and 1,2,4-triazoles, Eur. J. Med. Chem. 44 (2009) 2106-2112.
14. [14]
  [14] B. Jayashankar, K.M.L. Rai, N. Baskaran, H.S.S. Shazia, Synthesis and pharmacological evaluation of 1,3,4-oxadiazole bearing bis(heterocycle) derivatives as antiinflammatory and analgesic agents, Eur. J. Med. Chem. 44 (2009) 3898-3902.
15. [15]
  [15] F.A. Omar, N.M. Mahfouz, M.A. Rahman, Design, synthesis and antiinflammatory activity of some 1,3,4-oxadiazole derivatives, Eur. J. Med. Chem. 31 (1996) 819-825.
16. [16]
  [16] N.D. Heindel, J.R. Reid, Synthesis and anticonvulsant properties of a novel series of 2-substituted amino-5-aryl-1,3,4-oxadiazole derivatives, J. Heterocycl. Chem. 17 (1980) 1087-1088.
17. [17]
  [17] J. Haber, Present status and perspectives on antimycoties with systematic effects, Cas. Lek. Cesk. 140 (2001) 596-604.
18. [18]
  [18] S.C. Benner, V.B. Jigajiani, V.V. Badiyer, Pyrimidines VI, synthesis of 2-methyl thio-5-bromo pyrimidine-4-carboxylic acid thiosemicarbazides, 3-pyrimidy-1,2,4(H)-triazole and 2-aryl amino-1,3,4-thiadiazole, Rev. Roum. Chim. 21 (1976) 757.
19. [19]
  [19] M. Nakanishi, T. Tahara, K. Araki, et al., Synthesis and structure-activity relations of 5-phenyl-1, 3-dihydro-2H-thieno[2,3][1,4]diazepin-2-ones, J. Med. Chem. 16 (1973) 214-219.
20. [20]
  [20] R.M. Shaker, The chemistry of mercapto and thione substituted 1,2,4-triazoles and their utility in heterocyclic synthesis, Arkivoc (2006) 59-112.
21. [21]
  [21] H.A. Burch, W.O. Smith, Nitrofuryl heterocycles. Ⅲ. 3-Alkyl-5-(5-nitro-2-furyl)-1,2,4-triazoles and intermediates, J. Med. Chem. 9 (1966) 405-408.
22. [22]
  [22] M.G. Mamolo, D. Zampieri, V. Falagiani, et al., Antifungal and antimycobacterial activity of new N1-[1-aryl-2-(1H-imidazol-1-yl and 1H-1,2,4-triazol-1-yl)-ethylidene]-pyridine-2-carboxami-drazone derivatives: a combined experimental and computational approach, Arkivoc (2004) 231-250.
23. [23]
  [23] I. Mir, M.T. Siddiqui, A. Comrie, Antituberculosis agents I: a-[5-(2-furyl)-1, 2,4-triazol-3-ylthio]acethydrazide and related compounds, Tetrahedron 26 (1970) 5235-5238.
24. [24]
  [24] B.S. Holla, B. Veerendra, M.K. Shivananda, B. Poojary, Synthesis characterization and anticancer activity studies on some mannich bases derived from 1,2,4-triazoles, Eur. J. Med. Chem. 38 (2003) 759-767.
25. [25]
  [25] H.L. Yale, J.J. Piala, Substituted s-triazoles and related compounds, J. Med. Chem. 9 (1966) 42-46.
26. [26]
  [26] M.Y. Mhasalkar, M.H. Shah, S.T. Nikam, K.G.A. Narayanan, C.V. Deliwala, 4-Alkyl-5-aryl-4H-1,2,4-triazole-3-thiols as hypoglycemic agents, J. Med. Chem. 13 (1970) 672-674.
27. [27]
  [27] C.A. Winter, E.A. Risley, G.N. Nus, Carrageenin-induced edema in hind paw of the rat as an assay for antiinflammatory drugs, Proc. Soc. Exp. Biol. Med. 111 (1962) 544-547.
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