Synthesis and Biological Evaluation of New 3-Phenyl-1-[(4-arylpiperazin-1-yl)alkyl]-piperidine-2,6-diones

A set of 13 alkyl derivatives of 3-phenylpiperidine-2,6-dione were synthesized. Newly obtained compounds were investigated in vitro against HIV-1 and other selected viruses. The benzyl 3f and fluorophenyl 3g derivatives showed moderate protection against CVB-2 and the compound 3g also against HSV-1. Derivatives were tested also for their antibacterial and antifungal activity. The molecular structures of 3a and 3d were determined by an X-ray analysis.

[1]  S. Kabilan,et al.  Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents , 2012, Medicinal Chemistry Research.

[2]  R. Loddo,et al.  Biological evaluation of novel 1,4-dithiine derivatives as potential antimicrobial agents , 2011, Medicinal Chemistry Research.

[3]  P. Manisankar,et al.  Synthesis and in vitro antimicrobial evaluation of novel fluoroquinolone derivatives. , 2010, European journal of medicinal chemistry.

[4]  C. Pannecouque,et al.  A 1,8-naphthyridone derivative targets the HIV-1 Tat-mediated transcription and potently inhibits the HIV-1 replication. , 2010, Journal of medicinal chemistry.

[5]  R. Loddo,et al.  Synthesis and Evaluation of in Vitro Biological Activity of 4-Substituted Arylpiperazine Derivatives of 1,7,8,9-Tetrachloro-10,10-dimethoxy-4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione , 2009, Molecules.

[6]  R. Loddo,et al.  Biological evaluation of 10-(diphenylmethylene)- 4-azatricyclo[5.2.1.02,6]dec-8-ene-3,5-dione derivatives , 2009, Central European Journal of Biology.

[7]  R. Araya-Maturana,et al.  Synthesis of 2‐Benzothienyl Carbonyl 4‐Arylpiperazines as Novel Delavirdine Analogs , 2007 .

[8]  S. Nimesh,et al.  Synthesis, characterization and in vitro biological studies of novel cyano derivatives of N-alkyl and N-aryl piperazine. , 2007, European journal of medicinal chemistry.

[9]  P. Yogeeswari,et al.  Synthesis and in vitro anti-HIV activities of didanosine prodrugs , 2007, Journal of enzyme inhibition and medicinal chemistry.

[10]  K. Kuhen,et al.  Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors. , 2006, Bioorganic & medicinal chemistry letters.

[11]  Ramesh Chandra,et al.  Synthesis and antimicrobial activity of N-alkyl and N-aryl piperazine derivatives. , 2006, Bioorganic & medicinal chemistry.

[12]  A. Shafiee,et al.  Synthesis and antibacterial activity of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol-2-yl)piperazinyl quinolone derivatives. , 2005, Bioorganic & medicinal chemistry letters.

[13]  A. Bojarski,et al.  New imide 5-HT1A receptor ligands - modification of terminal fragment geometry. , 2004, Molecules.

[14]  Silvio Massa,et al.  Computer-aided design, synthesis, and anti-HIV-1 activity in vitro of 2-alkylamino-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones as novel potent non-nucleoside reverse transcriptase inhibitors, also active against the Y181C variant. , 2004, Journal of medicinal chemistry.

[15]  G. Marshall,et al.  Design, synthesis and QSAR studies on N-aryl heteroarylisopropanolamines, a new class of non-peptidic HIV-1 protease inhibitors. , 2002, Bioorganic & medicinal chemistry.

[16]  P. la Colla,et al.  Synthesis and anti-HIV-1 activity of new delavirdine analogues carrying arylpyrrole moieties. , 2001, Chemical & pharmaceutical bulletin.

[17]  G. Boiteau,et al.  J. Virol. Methods , 1996, Journal of Virological Methods.

[18]  J. Maguire,et al.  Colorimetric hydroxylamine-iron (III) methods for studies of the enzymatic hydrolyses of cyclic imides and of amic acids. , 1977, Analytical chemistry.

[19]  V. Jain,et al.  SYNTHESIS, CHARACTERIZATION AND ANTIMICROBIAL SCREENING OF SOME 4- SUBSTITUTED ­1­(4­SUBSTITUTED PHENYL) PIPERAZINE DERIVATIVES , 2011 .

[20]  H. Pessoa‐Mahana,et al.  Synthesis of a novel series of 4-arylpiperazinyl derivatives linked to a 2-(pyridin-3-yl)-1H-benzimidazole as new Delavirdine analogues , 2010 .

[21]  L. Di,et al.  Chapter 4 – Rules for Rapid Property Profiling from Structure , 2008 .

[22]  G. Sheldrick A short history of SHELX. , 2008, Acta crystallographica. Section A, Foundations of crystallography.

[23]  F. Hadizadeh,et al.  Synthesis of Some New 1-(2-(alkylthio-1-benzyl-5- imidazolyl) carbonyl)-4-(3-(isopropylamino)-2-pyridyl) piperazines as Anti-HIV , 2004 .