Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes

Synthesis, antimicrobial and antiviral evaluation of substituted imidazole derivatives

“…The appearance of medium bands at 3696.2 cm À1 in the IR spectra of compound 17 indicated the presence of a free OH in the carboxylic acid group of 2-substituted benzene. Further, the appearance of strong C]O stretching bands at 1695-1670 cm À1 in the IR spectra of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26) demonstrated the presence of tertiary amide linkage between substituted benzoic acid and imidazole nucleus. Compounds 23 and 25 showed C-Br stretching at 522.8 cm À1 and 533.8 cm À1 , which confirms the presence of 2-bromo substituted benzene ring.…”

“…Therefore, coupling was carried out using sodium acetate along with stirring in cold conditions for the initial 3 h followed by 48 h stirring at room temperature which resulted in a solid product. For the synthesis of (substituted phenyl)-[2-(substituted phenyl)-imidazol-1-yl]-methanones (13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26), the key intermediates (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) were reacted with substituted benzoyl chloride which was prepared by the reaction of substituted benzoic acid with thionyl chloride. The physicochemical characteristics of the synthesized compounds are presented in Table 1.…”

“…Imidazole drugs have broadened scope in remedying various dispositions in clinical medicines. Medicinal properties include anticancer [11], b-lactamase inhibitors [12], 20-HETE synthase inhibitors [13], carboxypeptidase inhibitors [14], hemeoxygenase inhibitors [15], antiaging agents [16], anticoagulants [17], anti-inflammatory [18], antibacterial [19], antifungal [20], antiviral [21], antitubercular [22], antidiabetic [23] and antimalarial [24], all are unique characteristics known for imidazole derivatives.…”

Antiglycation and antioxidant potential of novel imidazo[4,5-b]pyridine benzohydrazones

“…Compounds having fused imidazole ring, had been reported for various activities such as urease inhibition (Saify et al, 2014), antibacterial (Vijesh et al, 2011), anticancer (Yang et al, 2012), antitubecular (Lee et al, 2011) and analgesics (Uc¸ucu et al, 2001) activities. Imidazole had also been reported to show in vivo antihyperglycemic activity for the treatment of type 2 diabetes mellitus by stimulating insulin secretion and decreasing insulin resistance of peripheral tissues via reduction of hyperglycemia (Plant and Henquin, 1990;Crane et al, 2006). Interestingly, imidazole moiety is also considered significant for antiglycation activity as it was found that, free amino group of imidazole ring will competes with amine side groups of proteins in the presence of reactive dicarbonyl compounds (Brownson and Hipkiss, 2000).…”

Biological importance of imidazole nucleus in the new millennium

“…Imidazoline derivatives have been reported to show antihyperglycemic activity in vivo. In view of above, Crane et al (2006) designed and synthesized novel imidazoline derivatives and screened them for their potent anti-hyperglycemic activity in type-2 diabetes rat model. Among the synthesized compounds, 2-(a-cyclohexyl-benzyl)-4,5-dihydro-1H-imidazole 68 exhibited potent anti-hyperglycemic property having pK i values of 7.23 and 7.38 against imidazoline preferring binding sites I 1 and I 2 , respectively.…”