Synthesis and evaluation of novel 2-butyl-4-chloro-1-methylimidazole embedded chalcones and pyrazoles as angiotensin converting enzyme (ACE) inhibitors

Chalcone scaffolds as anti-infective agents: Structural and molecular target perspectives

“…Kostanecki and Tambor were the first to synthesize a series of natural chromophoric products comprising of α, β unsaturated carbonyl bridge and termed them "chalcone" [11]. Chalcones have a very simple chemistry which enables multiplicity of substitutions with the ease of synthesis and possess multifarious pharmacological potentials such as anti-hypertensive [12], anti-arrhythmic [13], anti-platelet [14], anti-diabetic [15], antineoplastic [16], anti-angiogenic [17], anti-retroviral [18], anti-inflammatory [19], anti-gout [20], anti-histaminic [21], anti-oxidant [22], anti-obesity [23], hypolipidemic [24], anti-tubercular [25], anti-filarial [26], anti-invasive [27], anti-malarial [28], anti-protozoal [29], anti-bacterial M A N U S C R I P T A C C E P T E D ACCEPTED MANUSCRIPT 11 | P a g e Leishmania strains have been isolated and identified from patients co-infected with HIV, which can exhibit wider drug-resistance, and, interestingly, the majority of these cases where found on individuals in industrialized countries such France, Spain and Italy. There are 3 main forms of leishmaniasis -visceral (often known as kala-azar and the most serious form of the disease), cutaneous (the most common), and mucocutaneous.…”

Chalcones and Flavanones Bearing Hydroxyl and/or Methoxyl Groups: Synthesis and Biological Assessments

“…Compound 1 was synthesized by mixing 2′-hydroxy-4′,6′dimethoxyacetophenone (661.3 mg, 3.37 mmol) dissolved in a minimum (~15 mL) amount of tetrahydrofuran (THF) with sodium hydride (NaH) (2.5 equivalents), under nitrogen atmosphere at Besides their natural occurrence, both chalcones and flavanones can be obtained synthetically and are often used as the preferred starting material for the synthesis of other polycyclic aromatic compounds [4]. Furthermore, they present great pharmacological potential with a wide variety of biological activities, including antioxidant [5], anticancer [6][7][8], and antimicrobial activities [9][10][11][12], and also the ability to treat cardiovascular diseases and their risk factors [13][14][15][16], among others [17].…”

Current advances in the synthesis and biological potencies of tri- and tetra-substituted 1H-imidazoles

“…Among chalcones 237a-r, three products, namely, (E)-3-(2-butyl-4-chloro-1-methyl-1H -imidazol-5-yl)-1-(5-chlorothiophen-2-yl)prop-2-enone 237i, (E)-3-(2-butyl-4-chloro-1-methyl-1H -imidazol-5-yl)-1-(1H -pyrrol-2-yl)prop-2-enone 237l, and (E)-3-(2-butyl-4-chloro-1-methyl-1H -imidazol-5-yl)-1-(dibenzo[b, d] thiophen-2-yl) prop-2-enone 237q were found as the most active ACE inhibitors. The comparison of ACE-inhibitory activity (IC 50 ) of different chalcones and flavonoids, which were synthetic and naturally occurring, with imidazole chalcones 237i, 237l and 237q showed ∼100-fold more activity (Scheme 59) [193].…”

“…An efficient method was developed for the preparation of new 2-butyl-4-chloro-1-methylimidazole-embedded chalcones 237a-r and pyrazoles 239a-r as angiotensinconverting enzyme (ACE) inhibitors [193]. The synthesis of 2-butyl-4-chloroimidazole-5-carboxaldehyde 234, an important intermediate in the construction of an Angiotensin II antagonist Losartan, was reported starting from valeronitrile [194].…”