Synthesis, Characterization, Anticancer and Antimicrobial Activity Studies of Novel Isomeric 2,4‐Disubstituted Ureide Derivatives of Pyrimidinopiperidines

Abstract

A series of isomeric ureide derivatives of novel 2,4-disubstituted pyrimidinopiperidines were synthesized starting from 2,4dichloropyrimidine. All the final products were purified on silica and characterized by spectral analysis. Both the 2,4-disubstituted pyrimidinopiperidines were analyzed for their in vitro anticancer activity on the cell lines HCT116, MIA-PaCa2 and MDA-MB 231 by using MTT cell proliferation assay. Further, the antimicrobial studies were carried out against different bacterial and fungal strains by employing cup plate method. These compounds were showed significant anticancer activity on tested three cancer cell lines and exhibited potent antimicrobial activity in tested strains of bacteria and fungi. Results and Discussion Chemistry Synthesis of ureide derivatives of 2-aryl-4-(-4-amino piperidinyl) pyrimidines (5 a-l):The reaction of 2,4-dichloro-pyrimidine (1) with tert-butylpiperidin-4-ylcarbamate in presence of diisopropylethylamine in dichloromethane at room temperature afforded the 4-substituted 2-chloropyrimidine derivative 2 a with 62% yield (Scheme 1) after purifying by column Scheme 1. Reagents and conditions: i) tert-butyl-piperidin-4yl-carbamate, DIPEA, THF, rt, 4 h; ii) R = a-d, Pd 2 (dba) 3 , X-Phos, DIPEA, rt, 18 h; iii) TFA, DCM, rt, 10 min; iv) R 1 = e-g, DIPEA, reflux, 10 min. EntryAmino piperidine derivative (4 A-4D) Isocyanate (e-g) Urea derivative (5 A-5 L) Yield (%) 6 95 7 92 8 91 9 95 10 92

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An efficient approach for the synthesis of novel methyl sulfones in acetic acid medium and evaluation of antimicrobial activity

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