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Synthesis, characterisation and antimicrobial activities of novel 7,9-diphenyl-1,2,4-triaza-8-oxa-spiro[4.5]-decan-3-thiones

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Abstract

Some new 7,9-diaryl-1,2,4-triaza-8-oxa-spiro[4.5]-decan-3-thiones has been synthesised and their antibacterial activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi, and antifungal activity against Candida albicans, Rhizopus sp., Aspergillus flavus and Aspergillus niger were examined. Compounds 14 and 15 against E. coli and S. typhi showed marked antibacterial activity. Similarly, compounds 13 and 15 against Rhizopus sp. and 13 and 14 against A. flavus exerted significant antifungal activities.

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References

  • Aridoss G, Balasubramanian S, Parthiban P, Kabilan S (2007) Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6-diarylpiperidin-4-ones. Eur J Med Chem 42:851–860

    Article  PubMed  CAS  Google Scholar 

  • Aridoss G, Amirthaganesan S, Ashok kumar N, Kim JT, Kabilan S, Jeong YT (2008) A facile synthesis, antibacterial, and antitubercular studies of some piperidin-4-one and tetrahydropyridine derivatives. Bioorg Med Chem Lett 18(24):6542–6548

    Article  PubMed  CAS  Google Scholar 

  • Aridoss G, Parthiban P, Ramachandran R, Prakash M, Kabilan S, Jeong YT (2009) Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: antimicrobial, analgesic and antipyretic studies. Eur J Med Chem 44:577–592

    Article  PubMed  CAS  Google Scholar 

  • Balasubramanian S, Ramalingan C, Aridoss G, Parthiban P, Kabilan S (2004) Synthesis and microbiological evaluation of novel [N-acetyl-2,6-diarylpiperidin-4-YL]-5-spiro-4-acetyl-2-(acetylamino)-Δ2–1,3,4-thiadiazolines. Med Chem Res 13(5):297–311

    Article  CAS  Google Scholar 

  • Balasubramanian S, Ramalingan C, Aridoss G, Kabilan S (2005) Synthesis and study of antibacterial and antifungal activities of novel 8-methyl-7,9-diaryl-1,2,4,8-tetraazaspiro[4.5]decan-3-thiones. Eur J Med Chem 40:694–700

    Article  PubMed  CAS  Google Scholar 

  • Balasubramanian S, Aridoss G, Parthiban P, Kabilan S (2006) Synthesis and biological evaluation of novel benzimidazol/benzoxazolylethoxypiperidone oximes. Biol Pharm Bull 29(1):125–130

    Article  PubMed  CAS  Google Scholar 

  • Bradbury RH, Revett JE (1991) 1,2,4-Triazolo[4,3-a]pyrazine derivatives with human renin inhibitory activity. 3.1 Synthesis and biological properties of aminodeoxystatine and difluorostatone derivatives. J Med Chem 34:151–157

    Article  PubMed  CAS  Google Scholar 

  • Chai B, Qian X, Cao S, Liu H, Song G (2003) Synthesis and insecticidal activity of 1,2,4-triazole derivatives. Arkivoc ii:141–145

  • Demirbas N, Demirbas A, Alpay Karaoglu S, Celik E (2005) Synthesis and antimicrobial activities of some new [1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles and [1,2,4]triazolo[3,4-b] [1,3,4]thiadiazines. Arkivoc i:75–91

  • Dhar MH, Dhar MM, Dhawan BN, Mehrotra BN, Ray C (1968) Screening of Indian plants for biological activity: part I. Indian J Exp Biol 6:232–247

    PubMed  CAS  Google Scholar 

  • Foroumadi A, Kiani Z, Soltani F (2003) Synthesis and in vitro antimycobacterial activity of alkyl alpha-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2-ylthio]acetates. Il Farmaco 58:1073–1076

    Article  PubMed  CAS  Google Scholar 

  • Heindal ND, Reid JR (1980) 4-Amino-3-mercapto-4H–1,2,4-triazoles and propargyl aldehydes: a new route to 3-R-8-aryl-1,2,4-triazolo[3,4-b]-1,3,4-thiadiazepines. J Heterocycl Chem 17:1087–1088

    Article  Google Scholar 

  • Holla BS, Gonsalves R, Shenoy S (2000) Synthesis and antibacterial studies of a new series of 1,2-bis(1,3,4-oxadiazol-2-yl)ethanes and 1,2-bis(4-amino-1,2,4-triazol-3-yl)ethanes. Eur J Med Chem 35:267–271

    Article  PubMed  CAS  Google Scholar 

  • Jalilian AR, Sattari S, Bineshmarvasti M, Shafiee A, Daneshtalab M (2000) Synthesis and in vitro antifungal and cytotoxicity evaluation of thiazolo-4H-1,2,4-triazoles and 1,2,3-thiadiazolo-4H-1,2,4-triazoles. Arch Pharm Pharm Med Chem 333:347–354

    Article  CAS  Google Scholar 

  • Japp FR, Maitland W (1904) Reduction products of αβ-dimethylanhydracetonebenzil, and condensation products of benzaldehyde with ketones. J Chem Soc 85:1473–1489

    CAS  Google Scholar 

  • Komurcu SG, Rollas S, Yilmaz Z, Ceuikbas A (1995) Synthesis of 3-methyl-4-[(2, 4-dihydro-4-substituted-3H–1, 2, 4-triazole-3-thione-5-yl)phenylhydrazono]-5-isoxazolone and evaluation of their antimicrobial activities. Drug Metab Drug Intract 12:161–169

    CAS  Google Scholar 

  • Modzelewska-Banachiewicz B, Banachiewicz J, Chodkowska A, Jagiello-Wo jtowicz E, Mazur L (2004) Synthesis and biological activity of new derivatives of 3-(3, 4-diaryl-1,2,4-triazole-5-yl)propenoic acid. Eur J Med Chem 39:873–877

    Article  PubMed  CAS  Google Scholar 

  • Nezhad AK, Rad MNS, Mohabatkar H, Asrari Z, Hemmateenejad B (2005) Design, synthesis, antibacterial and QSAR studies of benzimidazole and imidazole chloroaryloxyalkyl derivatives. Bioorg Med Chem Lett 13:1931–1938

    Article  Google Scholar 

  • Ramalingan C, Balasubramanian S, Kabilan S (2003) Synthesis of 6-substituted/unsubstituted-7,9-diaryl-1,2,4,8-tetraazaspiro[4.5]-decan-3-thiones. Synth Commun 33(9):1443–1448

    Article  CAS  Google Scholar 

  • Sharma S, Gangal S, Rauf A, Zahin M (2008) Synthesis, antibacterial and antifungal activity of some novel 3,5-disubstituted-1H–1,2,4-triazoles. Arch Pharm Chem Life Sci 341:714–720

    Article  CAS  Google Scholar 

  • Stevens CL, Blumbergs P, Daniher FA (1963) Stereochemistry and synthesis of amosamine: 4,6-dideoxy-4-dimethylamino-d-glucose. J Am Chem Soc 85:1552–1553

    Article  CAS  Google Scholar 

  • Stevens CL, Blumbergs P, Otterbach DH, Stronming JL, Matsuhashi M, Dietzler DN (1964) Synthesis of 4-amino-4,6-dideoxy-d-galactose and Identification with the 4-amino-4,6-dideoxyhexose from Escherichia coli strain Y-10. J Am Chem Soc 86:2937–2938

    Article  CAS  Google Scholar 

  • Tozkoparan B, Kupeli E, Yesilada E, Ertan M (2007) Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatory-analgesic activity. Bioorg Med Chem 15:1808–1814

    Google Scholar 

  • Turan-Zitouni G, Sıvacı M, Kılıc FS, Erol K (2001) Synthesis of some triazolyl-antipyrine derivatives and investigation of analgesic activity. Eur J Med Chem 36:685–689

    Article  PubMed  CAS  Google Scholar 

  • Turan-Zitouni G, Kaplancıklı ZA, Yıldız MT, Chevallet P, Kaya D (2005) Synthesis and antimicrobial activity of 4-phenyl/cyclohexyl-5-(1-phenoxyethyl)-3-[N-(2-thiazolyl)acetamido]thio-4H–1,2,4-triazole derivatives. Eur J Med Chem 40:607–613

    Article  PubMed  CAS  Google Scholar 

  • Varvaresou A, Siatra-Papastaikoudi T, Tsotinis A, Tsantili-Kakoulidou A, Vamvakides A (1998) Synthesis, lipophilicity and biological evaluation of indole-containing derivatives of 1,3,4-thiadiazole and 1,2,4-triazole. Il Farmaco 53:320–326

    Article  PubMed  CAS  Google Scholar 

  • Zanatta N, Alves SH, Coelho HS, Borchhardt DM, Santurio JM, Bonacorso HG, Martin MAP (2007) Synthesis, antimicrobial activity, and QSAR studies of furan-3-carboxamides. Bioorg Med Chem Lett 15:1947–1958

    Article  CAS  Google Scholar 

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Acknowledgements

We are thankful to Prof. K. Pandiarajan, Head, Department of Chemistry, Annamalai University for the facilities provided. One of the authors SK is grateful to Council of Scientific and Industrial Research, New Delhi, India for financial support in the form of Research Project. We also thank NMR Research Centre, IISc, Bangalore for providing all the NMR facilities to record NMR spectra.

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Correspondence to Senthamaraikannan Kabilan.

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Kabilan, S., Umamatheswari, S. Synthesis, characterisation and antimicrobial activities of novel 7,9-diphenyl-1,2,4-triaza-8-oxa-spiro[4.5]-decan-3-thiones. Med Chem Res 20, 542–548 (2011). https://doi.org/10.1007/s00044-010-9348-8

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