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

  • 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.
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    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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