Abstract
Substituted 2-(benzothiazol-2-yl)-1-(alkyl-2,6-diarylpiperidin-4-ylidine)hydrazines 10–17 were synthesized by the condensation of different 2r,6c-diarylpiperidin-4-ones 1–8 with 2-hydrazinobenzothiazole 9. All the synthesized compounds were investigated in solution and in the solid state by IR, 1H, 13C and 2D NMR spectral techniques. The structure–activity relationships were studied by the screening of the antimicrobial activity over a representative panel of bacterial and fungal strains using two-fold serial dilution method.
Similar content being viewed by others
References
Aridoss G, Amirthaganesan S, Kim MS, Jeong MSYT (2009) Synthesis, spectral and biological evaluation of some new thiazolidinones. Eur J Med Chem 44:4199–4210
Barreca ML, Chimirri A, De Luca L, Monforte AM, Monforte P, Rao A, Zappala M, Balzarini J, De Clercq E, Pannecouque C, Witvrouw M (2001) Discovery of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV-1 agents. Bioorg Med Chem Lett 11:1793–1796
Bell FW, Cantrell AS, Hogberg M, Jaskunas SR, Johansson NG, Jordan CL, Kinnick MD, Lind P, Morin JM, Noreen R, Oberg B, Palkowitz JA, Parrish CA, Pranc P, Sahlberg C, Ternansky RJ, Vasileff RT, Vrang L, West SJ, Zhang H, Zhou XX (1995) Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors. 1. Synthesis and basic structure-activity relationship studies of PETT analogs. J Med Chem 38:4929–4936
Beraldo H (2004) Semicarbazones and thiosemicarbazones: their wide pharmacological profile and clinical applications. Quim Nova 27:461–471
Chande MS, Jathar KS, Pannikar KR, Pannikar B, Anto J (1995) Synthesis of new 1-(benzothiazol-2yl)triazole derivatives as potential anticancer agents. Indian J Chem 34:654–657
Dhar MH, Dhar MM, Dhawan BN, Mahrotra BN, Ray C (1968) Screening of Indian plants for biological activity: part I. Indian J Exp Biol 6:232–247
Dua R, Sonwane SK, Srivastava SK, Srivastava SD (2010) Greener and expeditious synthesis of 2-azetidinone derivative from 2-mercaptobenzothiazole and their pharmacological screening of the synthesized compounds using microwave irradiation. World J Chem 1:52–56
Geneste P, Kamenka JM, Hugon I, Graffin P (1976) Oximation of 3,5-dimethyl-4-piperidones configurations and conformations of the adducts. J Org Chem 22:3637–3640
Guru S, Yadav R, Srivastava S, Srivastava SK, Srivastava SD (2006) Synthesis of some new N-1-[(2-oxo-3-chloro-4-arylazitidin) (acetylamino)]indole derivatives and their pharmacological activity. J Indian Chem Soc 83:1236–1241
Krishnapillay M, Mohamed MIF (1997) Conformational studies of some 3-chloro-2,6-diarylpiperidin-4-ones by 1H NMR spectra. Indian J Chem B 36:50–53
Kucukguzel G, Kocatepe A, Clercq ED, Ahin FS, Gulluce M (2006) Synthesis and biological activity of thiazolidinones, thiosemicarbazides derived from diflunisisal hydrazide. Eur J Med Chem 41:353–359
Mistry KM, Desai KR (2006) Microwave assisted rapid and efficient synthesis of nitrogen and sulphur containing heterocylic compounds and their pharmacological evaluation. Indian J Chem B 45:1762–1766
Noller CR, Balliah V (1948) The preparation of some piperidine derivatives by the Mannich reaction. J Am Chem Soc 70:3853–3855
Pandiarajan K, Mohan RTS, Krishnakumar B (1987) PMR and 13C NMR spectral studies of some 2,6-diarylpiperidin-4-ones. Indian J Chem B 26:624–627
Pandiarajan K, Jegadish TN, Benny JCN (1991) Conformational studies of some 3-chloro-2r,6c-diarylpiperidin-4-ones by 1H NMR spectra. Indian J Chem B 36:662
Pattan SR, Reddy VVK, Manvi FV, Desai BG, Bhat AR (2006) Synthesis of N-3[4-(4-chlorophenyl)thiazole-2-yl]-2-(aminomethyl)quinazoline-4(3H)-one and their derivatives for antitubercular activity. Indian J Chem B 45:1778–1781
Rani BR, Bhalerao UT, Rahman MF (1990) Synthesis and biological activity of benzothiazolothiomethyloxadiazoles, thiadiazoles and triazoles. Indian J Chem 29:995–998
Ruiz P, Rodriguez-Cano F, Zerolo FJ, Casal M (2002) Investigation of the in vitro activity of streptomycin against Microbacterium tuberculosis. Microb Drug Resist 8:147–149
Sharma PK, Sawhney SN, Gupta A, Singh GB, Bani S (1998) Synthesis and anti-inflammatory activity of some 3-(2-thiozolyl)-1,2-benzothiazoles. Indian J Chem B 37:376–381
Sivasubramanian S, Sundharavadivelu M, Arumugam N (1981) Cis-2,6-diaryl-4-piperidinones and their derivatives: a PMR spectral study. Indian J Chem B 20:878–879
Srivastava SK, Srivastava S, Srivastava SD (2002) Synthesis of new 1,2,4-triazalo-thiadiazoles and 2-oxoazetidines as antimicrobial, anticonvulsant, and anti-inflammatory agents. Indian J Chem B 41:2357–2363
Valverde MG, Torroba T (2005) Synthesis of new multidentate sulphur heterocycles and metal, complexes structural studies. Molecules 10:318–320
Verma A, Saraf SK (2008) A biologically active scaffold. Eur J Med Chem 43:897–905
Acknowledgments
We are grateful to RMMCH, Annamalai University, Chidambaram, Tamil Nadu, India, for providing the facilities for antibacterial and antifungal activities. We also wish to thank, The Director, SAIF, Indian Institute of Technology, Chennai, India for recording NMR spectra. One of the authors John Francis Xavier is thankful to the University Grants Commission, New Delhi, India for the financial assistance.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Xavier, J.J.F., Venkateswaramoorthi, R., Kamaraj, A. et al. Synthesis, NMR spectral studies and antimicrobial evaluation of some 2-(benzothiazol-2-yl)-1-(alkyl-2r,6c-diarylpiperidin-4-ylidine)hydrazine derivatives. Med Chem Res 22, 5105–5111 (2013). https://doi.org/10.1007/s00044-013-0533-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-013-0533-4