DESIGN, SYNTHESIS, AND BIO-EVALUATION OF NEW ISOINDOLINE-1,3-DIONE DERIVATIVES AS POSSIBLE ANTIMICROBIAL AND ANTIFUNGAL AGENT

Main Article Content

Avinash Mishra
Umesh Kumar
Satish Kumar Sharma

Keywords

Hydroxyl chalcone, Ampicillin, Clotrimazole, Phthalimide, Antimicrobial, Antifungal

Abstract

New series of 4-(2-(3-(substituted phenyl) acryloyl) phenoxy)-phenyl-2-(1,3-dio xoisoindolin-2-yl) acetamides, and N-(4-(substituted phenoxy) phenyl)-2-(1, 3-dioxoisoindolin -2-yl) acetamides were synthesized. Synthesis of these compound design in two scheme (A & B)The initial step of the reaction in scheme A, involve the reaction phthalic anhydride with and glycine yielded 2-(1, 3-dioxoisoindolin-2-yl) acetic acid, further chlorination of this product form yielded 2-(1, 3-dioxoisoindolin-2-yl) acetyl chloride. The second step involves the reaction para-bromoaniline and yield N-(4-bromophenyl)-2-(1, 3-dioxoisoindolin-2-yl) acetamide, the basic moiety was obtain by the reaction of hydroxyl chalcone i.e 4-(2-(3-(substituted phenyl) acryloyl) phenoxy)-phenyl-2-(1,3-dio xoisoindolin-2-yl) acetamides. Scheme B was design to substitute to bromide group on the 4th position in the respective compound with the phenol group and further change the R with H,4-CH3, 4-Cl, 2-Br, 3,4-Cl, 2-NO2, 4-Br, 4-NO2, 4-OCH3 and 2-Cl.  The confirmation of the newly synthsized compound by interpreting the essential analysis, spectral data, and alternative synthetic routes, Twenty of the synthesized compounds were screened for their antibacterial activity against S. aureus, and E. coli whereas AK1, BK1 and BK2 were  the potential compound in this study. They were showing the highest antibacterial activity against the two selected microorganisms. The antifungal activity of these compounds was also tested against C. albicans and A. niger . Compounds AK4, and BK5 exhibited the best antifungal activity against C. albicans and A. niger in all the synthesized compound in series A & B respectively.  The 4-(phenyl) acryloyl) phenoxy)-phenyl-2-(1,3-dio xoisoindolin-2-yl) acetamides synthesized compound could show the bacteriostatic property through binding to cell membrane, previous studies shows that phthalimide moiety have potential to interaction with cytochrome P450 enzyme’ of  the fungus due to the their aromatic character further impair ergosterol synthesis  of the fungal cell  membrane results abnormalities in the fungus cell. The comparative study few of the selected, newly synthesized compounds validated moderate to good antimicrobial and antifungal effect were also compared with the standard drug ampicillin and clotrimazole respectively.

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