Design, synthesis, and characterization of novel pyrimidines bearing indole as antimicrobial agents

Abstract

Pyrimidines and pyrimidine bearing indole derivatives are very important species in organic chemistry due to their wide use as bioactive compounds with a broad range of good biological activities. Due to the wide spread of different species of bacteria and fungi nowadays, in the present work, a novel series of indolyl‐pyrimidines (2–13) were synthesized starting from 3‐chloro‐1H‐indole‐2‐carbaldehyde (1). Elemental analysis, IR, 1H‐NMR, 13C‐NMR, and mass spectral data elucidated the structure of newly synthesized compounds. All compounds were screened for their in vitro antibacterial and antifungal activity, and they demonstrated promising results; all the new compounds synthesized from compound (1), which allowed reactions with thiourea and ethyl cyanoacetate, gave the target compound (2), which was used as a precursor for the synthesis of indolylthiazolopyrimidine derivatives (3–8) by reactions with halocarbonyl compounds such as chloroacetone, phancyl bromide, and chloroacetic acid through alkylation of the mercapto group followed by cyclization through a nucleophilic attack. When compound (2) subjected to react with hydrazine hydrate gave 4‐indolyl‐2‐hydrazinopyrimidine (5), the latter compound, when allowed to react with ethyl chloroacetate or diethyloxalate, gave indolylpyrimidotriazine derivatives (10,11); in contrast, when the compound reacted with acetic anhydride or formic acid, it gave triazolopyrimidine derivatives (12, 13).

Solid-State Luminescent Materials Containing Both Indole and Pyrimidine Moieties: Design, Synthesis, and Density Functional Theory Calculations

“…Compounds 4−8 were previously synthesized according to reported procedures. 17,28 2-((6-(3-Chloro-1H-indol-2-yl)-5-cyano-2-(p-tolylamino)pyrimidin-4-yl)thio)acetamide (9). A mixture of compound 8 (3.9 g, 10 mmol), fused sodium acetate (1.64 gm, 20 mmol), and chloroacetamide (0.94 gm, 12 mmol) in 50 mL of ethanol was refluxed for 3 h. The solid precipitate formed during reflux was filtrated off, washed with water and ethanol, and dried in air to afford the opened structure compound 9 as off-white crystals in 95% yield.…”

“…As a response to the challenges outlined above in addition to what we have already accomplished, − we present here a synthetic strategy for several novel indole–pyrimidine hybrids. Some substances’ photophysical characteristics in solid and solution forms were investigated.…”

The Effect of 3-(Glycidoloxy Propyl) Trimethoxy Silane Concentration on Surface Modification of SiO2 Nanoparticles

“…NPs; symmetric Si-O-Si, C-CH2, C-CH3 and N-H stretching (amide bonds) occurred at 1110 cm -1 , 2877 cm -1 , 2935 cm -1 and 3426 cm -1 , respectively [30,[32][33][34].…”

Anti-biofilm Formation Activities of 4-hydroxyindole Azo Compounds against Pseudomonas aeruginosa and Staphylococcus aureus

“…Furthermore, there are review studies that indicate that in the field of pharmaceutical chemistry. Moreover, synthesis and full characterisation by spectral and thermal techniques have been reported in the literature for various derivatives bearing the indole nucleus [18]. The synthetic scheme of the azo dyes involves the diazotisation of primary aromatic amines and an electron rich moiety (coupling reagents) which mimics the principle of pharmacophore hybridisation [19,20].…”