An efficient one pot I₂/DMSO mediated synthesis and molecular modeling of novel fused pyrimidine‐chromone hybrids bearing potential antibacterial and antifungal pharmacophores sites

Abstract

A series of novel ethyl‐l, 1, 2, 3, 6‐tetrahydro‐4‐methyl‐1‐(6‐methyl‐4‐oxo‐4H‐chromene‐2‐yl)‐2‐oxo/thioxo‐6‐phenyl pyrimidine‐5‐carboxylate compounds (2a–2k) were synthesized using I2/DMSO as a competent and cost‐effective catalyst in one pot green solvent system from corresponding chalcones (1a–1k) in better yields. IR, 1H‐NMR, 13C‐NMR, Mass, and X‐ray diffraction spectroscopic techniques were used for the characterization of newly synthesized compounds. All the compounds were tested for in‐vitro antibacterial activities against gram‐positive and gram‐negative bacteria like Staphylococcus aureus, Salmonella abony, Staphylococcus epidermidis, and Escherichia coli. Antifungal activities were also performed against Candida albicans and Aspergilus niger. It was found that the presence of electron withdrawing group on the aromatic ring attached to chromone ring increases the antibacterial activities (2g, 2h, and 2k); while the presence of electron releasing groups decreases activities. The presence of electron donating groups (─OCH3, ─Cl), on the phenyl ring attached to pyrimidine skeleton influenced negatively for the antibacterial activities.

I2/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

“…Pathan, Ali, et al 57 devised a very efficient one-pot synthesis approach using an I 2 /DMSO green solvent. This methodology allows the rapid synthesis of 2-substituted 4- H -1-benzopyran-4-one derivatives 8, which are considered significant pharmacophores.…”

“…The aforementioned process, which serves as a viable synthetic method, provides simple and efficient access to oheteropolycyclic scaffolds under mild conditions (Scheme 4). Pathan, Ali, et al 57 devised a very efficient one-pot synthesis approach using an I 2 /DMSO green solvent. This methodology allows the rapid synthesis of 2-substituted 4-H-1-benzopyran-4one derivatives 8, which are considered signicant pharmacophores.…”

Chromone Containing Hybrid Analogs: Synthesis and Applications in Medicinal Chemistry

“…I 2 /DMSO catalyzed simple and economical method was developed by Pathan et al for the synthesis of chromone-pyrimidine hybrids (Scheme 11), having antibacterial and antifungal pharmacophoric features (Figure 6). [47] For the anti-bacterial screening of the synthesized analogs, classical paper disk method was utilized against S. aureus, S. abony, S. epidermidis and E. coli. After analysing the activities, preliminary SAR was generated.…”

Recent advances in the synthesis of 4H-chromen-4-ones (2012 − 2021)

“…92 Moreover, a series of ethyl l,1,2,3,6-tetrahydro-4-methyl-1-(6-methyl-4-oxo-4H-chromen-2yl)-2-oxo/thioxo-6-phenyl pyrimidine-5-carboxylates were synthesized using molecular iodine in DMSO as catalytic system starting from the corresponding chalcone derivatives. 93 Polysubstituted 2-(9-ethyl-9H-carbazol-3-yl)-4H-chromen-4-ones were prepared through oxidative cyclization of (E)-3-(9-ethyl-9H-carbazol-3-yl)-1-(2-hydroxyaryl)prop-2-en-1-ones in the presence of a catalytic amount of iodine in DMSO in conventional refluxing conditions for 4-6h under microwave irradiation (320 W, 2-4 min). In these examples, microwave-assisted procedure proved to give better yields in shorter reaction times (Scheme 7).…”