Design and synthesis of novel piperazine unit condensed 2,6-diarylpiperidin-4-one derivatives as antituberculosis and antimicrobial agents

Abstract

A new series of 1-[2-(4-ethoxycarbonylpiperazine-1-yl)acetyl]-2,6-diarylpiperidin-4-ones (3a-3j) has been synthesized by conventional method and were characterized by IR, elemental analysis, mass spectral, 1 H NMR, 13 C NMR, and single crystal X-ray diffraction analysis. The synthesized compounds were evaluated for their antituberculosis activity against Mycobacterium tuberculosis H37Rv (ATCC-27294) and also its antimicrobial activity were examined against five familiar bacterial and fungal strains. Among the synthesized compounds, compounds 3e-3j exhibit higher inhibition potency (16 lg/ml) against M. tuberculosis H37Rv. Furthermore, compounds containing fluoro substituent in the phenyl ring at C-2 and C-6 positions of the piperidin-4-one motif (compounds 3c, 3d, and 3i) exerted better antibacterial and antifungal activity than the other phenyl-substituted compounds.

Piperazine scaffold: A remarkable tool in generation of diverse pharmacological agents

“…Rani et al synthesized several piperazine derivatives and evaluated them for antifungal activity. Compounds 120a-120c displayed significant antifungal activity [206]. Kulandaivelu et al synthesized a series of thiosemicarbazones of piperazine and screened them for antifungal potential.…”

“…Compounds 164a, 164b and 164c were reported as most active with MIC of 0.2 µg/mL against MTB[268]. Amongst the derivatives synthesized by Rani et al, compounds 165a-165d exerted significant antitubercular activity with MIC of 16 µg/mL against H37Rv strain of M. tuberculosis[269]. In a series of compounds developed by Kanagarajan and Gopalakrishnan, compounds 166a-166e exerted significant antimycobacterial activity against H 37 Rv strain.…”

New structural classes of antituberculosis agents

“…139 Rani et al synthesized a series of 2,6-diaryl piperidinones compounds and noted that compounds 154-158 were more potent (MIC = 16 g/mL) than standard drug rifampin (MIC = 32 g/mL). 140…”

Synthesis of 1-(4-((E)-3-arylacryloyl) phenyl)-3,4-dibromo-1H-pyrrole-2,5-diones and screening for anti-Candida and antituberculosis activity

“…Solvents employed were purified by standard procedure before to use. Maleic anhydride and p-aminoacetophenone was purchased from Aldrich, and bromine was purchased from Merck (Perrin and Armarego, 1988). The melting points were determined in open capillary on Veego (Model: VMP-D) electronic apparatus and are uncorrected.…”