Synthesis, anti‐bacterial, anti‐asthmatic and anti‐diabetic activities of novel N‐substituted‐2‐(benzo[d]isoxazol‐3‐ylmethyl)‐1H‐benzimidazoles

Abstract

-92 % )Synthesis of a series of novel class of N-substituted-2-(benzo[d]isoxazol-3-ylmethyl)-1H-benzimidazoles (4) by the condensation of o-phenylenediamine (1) with benzo[d]isoxazol-3-yl-acetic acid (2) and subsequent reactions with different types of electrophiles have been reported. Some compounds exhibited promising anti-bacterial activity against Salmonella typhimurium, however poor activity against Staphylococcus aureus. The compound 4t was found to have high activity even at 1 μg/ml compared to Cephalexin against S. aureus. The biological activity against PDE-IV for potential anti-asthmatic effect and against DP-IV and PTP-1B for potential anti-diabetic effects was disappointing.

New Pyrazole‐ and Benzimidazole‐derived Ligand Systems

“…Ligands that incorporate pyridyl, benzimidazolyl, quinolyl, and indazole groups in their framework have had frequent applications due to their relative ease of synthesis and the ready incorporation of steric constraints . Pyrazole derivatives, especially pyrazoles substituted with N ‐containing heterocycles, have been reported to exhibit antitumor and antifungal properties , while benzimidazole and pyrazole moieties are among the most frequently used ring systems for small molecule drugs listed by the US FDA .…”

Synthesis of Novel Benzazole Derivatives and Evaluation of Their Antidepressant-Like Activities with Possible Underlying Mechanisms

“…The benzazole type compounds such as benzimidazoles and benzothiazoles are frequently preferred rings in drug development studies because of their widespread pharmacological activity potential. For example, various benzimidazole-based compounds have been reported for their antibacterial [ 5 ], anticancer [ 6 ], anti-HIV [ 7 ], anti-ulcer [ 8 ], anti-asthmatic [ 9 ], antidiabetic [ 10 , 11 ], anti-inflammatory [ 11 ], antihypertensive [ 12 ], cholinesterase inhibitory, and anti-oxidant [ 13 ] effects. Numerous benzothiazole derivatives have also been shown to induce antibacterial, antifungal, anticancer [ 14 ], anti-oxidant [ 15 ], antiviral [ 16 ], antituberculosis [ 17 ], antidiabetic [ 18 ], and anti-inflammatory [ 19 ] activities, so far.…”

Solution-Phase Synthesis of a Diverse Library of Benzisoxazoles Utilizing the [3 + 2] Cycloaddition of in Situ-Generated Nitrile Oxides and Arynes

“…1 Among them, the benzisoxazole scaffold has evolved as a convenient bioisosteric replacement for the benzoyl functionality of some biologically active molecules. 2 Benzisoxazoles, particularly their 3-alkyl and 3-aryl substituted derivatives, have displayed a broad range of biological activities, such as antipsychotic, 2a,3 antitumor, 4 anticonvulsant, 5 antimicrobial, 6 antibacterial, 7 diuretic, 8 antithrombotic, 2c and acetylcholinesterase-inhibition 2b,9 (Alzheimer’s disease treatment) activities (Figure 1). …”