Abstract
A series of novel pyrimidine (2, 3), pyrazole (4, 5), and pyridine (6) derivatives were synthesized using a chalcone-bearing thiophene nucleus (1). The target compounds were synthesized by reaction of compound (1) with urea, thiourea, malononitrile, hydrazine hydrate, and 2,4-dinitrophenyl hydrazine, respectively. Molecular electronic structures have been modeled within density functional theory framework (DFT). Reactivity indices and electrostatic surface potential maps (ESP maps) allow us to establish trends that enable making predictions about chemical characteristics of the newly synthesized molecules and their proton transfer tautomers. Proton transfer is generally more favored in solution than in the gas phase. In acetonitrile, keto-form tautomers and thione-form tautomers become more energetically stable than the corresponding enol or thiol tautomers due to solvent-induced enhancement in the molecular polarity identified by computed dipole moment.
Highlights
Chalcone derivatives from natural sources or synthetic origin exhibit diverse pharmacological activities, such as antimicrobial [1], anticancer [2], antioxidant [3], antitumor [4], anti-inflammatory [5], and antitubercular [6].Heterocyclic compounds five- or sixmembered ring compounds have occupied the first place among various classes of organic compounds for their diverse biological activities. ese compounds possess diverse chemotherapeutic and pharmacological activities
Proton transfer is generally more favored in solution than in the gas phase
We synthesized five new products of pyrimidine, pyrazole, and pyridine derivatives using a chalcone substituted with a thiophene nucleus
Summary
Chalcone derivatives from natural sources or synthetic origin exhibit diverse pharmacological activities, such as antimicrobial [1], anticancer [2], antioxidant [3], antitumor [4], anti-inflammatory [5], and antitubercular [6].Heterocyclic compounds five- or sixmembered ring compounds have occupied the first place among various classes of organic compounds for their diverse biological activities. ese compounds possess diverse chemotherapeutic and pharmacological activities. Chalcone derivatives from natural sources or synthetic origin exhibit diverse pharmacological activities, such as antimicrobial [1], anticancer [2], antioxidant [3], antitumor [4], anti-inflammatory [5], and antitubercular [6]. Ese compounds possess diverse chemotherapeutic and pharmacological activities Pyrimidine and their derivatives have been found to possess a broad spectrum of biological activities such as antimicrobial, anti-inflammatory, analgesic, antiviral, and anticancer activities [7]. It is worthy to mention that pyrazoline derivatives have been known to possess widespread pharmacological activities, such as anti-inflammatory [8], anticonvulsant [9, 10], antimicrobial [11, 12], anticancer [13], antiviral [14], and hypotensive [15] activities. ESP maps of the energetically optimized new molecules will be reported
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