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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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
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
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
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
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
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
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
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
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
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
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
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
Japp FR, Maitland W (1904) Reduction products of αβ-dimethylanhydracetonebenzil, and condensation products of benzaldehyde with ketones. J Chem Soc 85:1473–1489
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
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
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
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
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
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
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
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
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
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
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
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
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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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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DOI: https://doi.org/10.1007/s00044-010-9348-8