Synthesis, spectral, crystal structure and in vitro antimicrobial evaluation of imidazole/benzotriazole substituted piperidin-4-one derivatives

European Journal of Medicinal Chemistry

Volumn 46, Issue 5, 2011, Pages 1926-1934

  Ramachandran, R ^a,b   Rani, M ^a   Senthan, S ^a   Jeong, Yeon Tae ^b   Kabilan, S ^a  

^a ANNAMALAI UNIVERSITY   (India)

^b Pukyong National University   (South Korea)

Author keywords

2,6 Diarylpiperidin 4 ones; Antimicrobial activity; Benzotriazole; Imidazoles

Indexed keywords

1 [2 (1H BENZOTRIAZOL 1 YL)ACETYL] 3 ETHYL 2,6 BIS(P FLUOROPHENYL)PIPERIDIN 4 ONE; 1 [2 (1H BENZOTRIAZOL 1 YL)ACETYL] 3,5 DIMETHYL 2,6 BIS(M FLUOROPHENYL)PIPERIDIN 4 ONE; 1 [2 (1H BENZOTRIAZOL 1 YL)ACETYL] 3,5 DIMETHYL 2,6 BIS(P FLUOROPHENYL)PIPERIDIN 4 ONE; 1 [2 (1H BENZOTRIAZOL 1 YL)ACETYL] 3,5 DIMETHYL 2,6 BIS(P METHOXYPHENYL)PIPERIDIN 4 ONE; 1 [2 (1H IMIDAZOL 1 YL)ACETYL] 3 ETHYL 2,6 DIPHENYLPIPERIDIN 4 ONE; 1 [2 (1H IMIDAZOL 1 YL)ACETYL] 3 ISOPROPYL 2,6 DIPHENYLPIPERIDIN 4 ONE; 1 [2 (1H IMIDAZOL 1 YL)ACETYL] 3 METHYL 2,6 DIPHENYLPIPERIDIN 4 ONE; 1 [2 (1H IMIDAZOL 1 YL)ACETYL] 3,5 DIMETHYL 2,6 BIS(M FLUOROPHENYL)PIPERIDIN 4 ONE; 1 [2 (1H IMIDAZOL 1 YL)ACETYL] 3,5 DIMETHYL 2,6 BIS(P METHOXYPHENYL)PIPERIDIN 4 ONE; 1 [2 (1H IMIDAZOL 1 YL)ACETYL] 3,5 DIMETHYL 2,6 DIPHENYLPIPERIDIN 4 ONE; BENZOTRIAZOLE DERIVATIVE; BENZOTRIAZOLE PLUS IMIDAZOLE; IMIDAZOLE DERIVATIVE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BACTERIAL STRAIN; CRYSTAL STRUCTURE; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ESCHERICHIA COLI; IN VITRO STUDY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; X RAY DIFFRACTION;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; BACTERIA; CRYSTALLOGRAPHY, X-RAY; FUNGI; IMIDAZOLES; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PIPERIDINES; STEREOISOMERISM; TRIAZOLES;

EID: 79953187564     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.02.036     Document Type: Article

References (30)

1. A.R. Katritzky, A.K. Verma, H. He, and R. Chandra Novel synthesis of 1,2,3,4-tetrahydropyrazino[1,2-a]indoles J. Org. Chem. 68 2003 4938 4940 (Pubitemid 36682724)
2. R.K. Tiwari, J. Singh, D. Singh, A.K. Verma, and R. Chandra Highly efficient one-pot synthesis of 1-substituted-1,2,3,4-tetrahydropyrazino[1,2-a] indoles Tetrahedron 61 2005 9513 9518 (Pubitemid 41583469)
3. A.R. Katritzky, X. Lan, J.Z. Yang, and O.V. Denisko Properties and synthetic utility of N-substituted benzotriazoles Chem. Rev. 98 1998 409 548 (Pubitemid 128631433)
4. R.K. Tiwari, D. Singh, J. Singh, V. Yadav, A.K. Phatak, R. Dabur, A. Chhillar, R. Singh, G.L. Sharma, R. Chandra, and A.K. Verma Synthesis and antibacterial activity of substituted 1,2,3,4-tetrahydropyrazino [1,2-a] indoles Bioorg. Med. Chem. Lett. 16 2006 413 416 (Pubitemid 41680637)
5. K.Z. Katarzyna, N. Andzelika, Z. Justyna, C. Lidia, P. Janusz, M. Przemysław, and B. Maria Synthesis and activity of 1H-benzimidazole and 1H-benzotriazole derivatives as inhibitors of Acanthamoeba castellanii Bioorg. Med. Chem. 12 2004 2617 2624
6. M.D. Kamal, A.G. Hassan, E. Mohey, A.M. Hanan, and H. Bahira Synthesis, anticonvulsant, and anti-inflammatory evaluation of some new benzotriazole and benzofuran-based heterocycles Bioorg. Med. Chem. 14 2006 3672 3680
7. Y.A. Al-Soud, N.A. Al-Masoudi, and A.S. Ferwanah Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents Bioorg. Med. Chem. 11 2003 1701 1708 (Pubitemid 36349151)
8. C.Y. Wu, K.Y. King, C.J. Kuo, J.M. Fang, Y.T. Wu, M.Y. Ho, C. L Liao, J.J. Shie, P.H. Liang, and C.H. Wong Stable benzotriazole esters as mechanism-based inactivators of the severe acute respiratory syndrome 3CL protease Chem. Biol. 13 2006 261 268
9. Shinohara, and Ken-Ichi Anticancer activities of alkylating pyrrole-imidazole polyamides with specific sequence recognition Anti-Cancer Drugs 21 2010 228 242
10. Yaseen A. Al-Soud, Najim A. Al-Masoudi, and Abd El-Rahman S. Ferwanah Synthesis and properties of new substituted 1,2,4-triazoles: potential antitumor agents Bioorg. Med. Chem. 11 2003 1701 1708 (Pubitemid 36349151)
11. J. Fatimi, J.F. Lagorce, J.L. Duroux, M.L. Chabernaud, J. Buxeraud, and C. Raby 1,4,5-Trialkyl imidazole system anti-inflammatory properties of new substituted derivatives Chem. Pharm. Bull. 42 1994 698 701 (Pubitemid 24156298)
12. 1A adrenoceptor partial agonists Bioorg. Med. Chem. Lett. 18 2008 6437
13. S. Emami, M. Falahati, A. Banifatemi, and A. Shafiee Stereoselective synthesis and antifungal activity of (Z)-trans-3-azolyl-2-methylchromanone oxime ethers Bioorg. Med. Chem. 12 2004 5881 5889 (Pubitemid 39388187)
14. G. Biagi, I. Giorgi, O. Livi, V. Scartoni, P.L. Barili, and V. Calderone Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)-benzotriazol-1(2)- yl]acrylonitriles variously substituted: part 4 Il Farmaco 56 2001 827 834
15. G. Scapin, S.B. Patel, J.W. Becker, Q. Wang, C. Desponts, D. Waddleton, K. Skorey, W. Cromlish, C. Bayly, M. Therien, J.Y. Gauthier, C.S. Li, C.K. Lau, C. Ramachandran, and B.P. Kennedy Asante-Appiah E 42 2003 11,451 11,459
16. C. Antonio, P. Michele, B. Gianpiero, B. Bernardetta, M. Marta, and L. Roberta Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)- benzotriazol-1(2)-yl]acrylonitriles variously substituted: part 4 Il Farmaco 59 2004 637 644
17. R. Ramachandran, M. Rani, and S. Kabilan Design, synthesis and biological evaluation of novel 2-[(2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ylidene) hydrazono]-1,3-thiazolidin-4-ones as a new class of antimicrobial agents Bioorg. Med. Chem. Lett. 19 2009 2819 2823
18. M. Rani, R. Ramachandran, and S. Kabilan Efficient synthesis, spectral analysis and antimicrobial studies of nitrogen and sulfur containing spiro heterocycles from 2,4-diaryl-3-azabicyclo[3.3.1]nonan-9-ones Bioorg. Med. Chem. Lett. 20 2010 6637 6643
19. P. Parthiban, G. Aridoss, P. Rathika, V. Ramkumar, and S. Kabilan Synthesis, spectral, crystal and antimicrobial studies of biologically potent oxime ethers of nitrogen, oxygen and sulfur heterocycles Bioorg. Med. Chem. Lett. 19 2009 2981 2985
20. P. Parthiban, G. Aridoss, P. Rathika, V. Ramkumar, and S. Kabilan Synthesis, stereochemistry and antimicrobial studies of novel oxime ethers of aza/diazabicycles Bioorg. Med. Chem. Lett. 19 2009 6981 6985
21. C.R. Noller, and V. Baliah The preparation of some piperidine derivatives by the mannich reaction J. Am. Chem. Soc. 970 1948 3853 3855
22. G. Aridoss, S. Balasubramanian, P. Parthiban, and S. Kabilan Synthesis, stereochemistry and antimicrobial evaluation of some N-morpholinoacetyl-2,6- diarylpiperidin-4-ones Eur. J. Med. Chem. 41 2007 851 860 (Pubitemid 46810068)
23. G. Aridoss, P. Parthiban, R. Ramachandran, M. Prakash, S. Kabilan, and Y.T. Jeong 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 2009 577 592
24. R. Krishnakumar, M. Krishnapillai, A. Nagarajan, and G. Jeyaraman Conformational analysis of some heterocyclic systems: part II - conformational analysis of substituted N-benzoylpiperidin-4-ones Ind. J. Chem. 39B 2000 419 425
25. R. Krishnakumar, and M. Krishnapillai Conformational analysis of some heterocyclic systems: part 1 - conformational analysis of substituted N-phenyl carbamoylpiperidin-4-ones Ind. J. Chem. 35B 1996 418 425
26. A. Greenberg, T.D. Thomas, C.R. Berilacqua, M. Coville, D. Ji, J.C. Tsai, and G.J. Wu Determination of the nitrogen N1s and oxygen O1s core energies in planar and distorted lactams and amides: relationships with the concept of resonance J. Org. Chem. 57 1992 7093 7099
27. Bruker APEXII and SAINT-Plus, Area Detector Control and Integration Software 2004 Bruker AXS Inc. Madison, WI, USA
28. G.M. Sheldrick SHELXS97 and SHELXL97, Program for the refinement of crystal structures, University of Gottingen: Germany, 2003; G.M. Sheldrick Acta Cryst A64 2008 112 122
29. L.J. Farrugia ORTEP-3 for Windows J. Appl. Cryst 30 1997 565
30. National Committee for Clinical Laboratory Standards Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically fifth ed. 2000 National Committee for Clinical Laboratory Standards Villanova, PA Approved Standard. NCCLS Document M7-A5