51759-60-5Relevant articles and documents
Synthesis of pyridinyl-benzo[d]imidazole/pyridinyl-benzo[d]thiazole derivatives and their yeast glucose uptake activity in vitro
Khan, Momin,Ahmad, Riaz,Rehman, Gauhar,Gul, Naeem,Shah, Sana,Salar, Uzma,Perveen, Shahnaz,Khan, Khalid Mohammed
, p. 984 - 993 (2019/10/28)
Background: Diabetes is the primary cause of fatality and disability all over the world, in recent past, we have reported various classes of compounds as anti-glycating agents and we have also reported benzimidazole and benzothiazole derivatives as a potential class of anti-glycating agents. This encouraged us to evaluate the pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 for yeast glucose uptake activity. Methods: In the present study, an equimolar mixture of pyridine carboxaldehyde derivatives (1 mmol) and sodium metabisulphite (1 mmol) in DMF (10 mL) was stirred for 10 to 15 min, followed by addition of o-phenylene diamine/2-aminothiophenol (1 mmol) into it and refluxed for 3 h. The progress of the reaction was monitored by TLC. After completion, the reaction mixture was poured into crushed ice. Precipitates were formed which were collected by filtration to produce compounds 1-27 in good yields. Recrystallization from methanol yielded pure crystals. Results: Our present study showed that all compounds showed a varying degree of yeast glucose uptake activity in the range IC50 = 36.43-272.20 μM, compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) showed an excellent yeast glucose uptake activity better than the standard. Conclusion: Pyridinyl benzimidazole/pyridinyl benzothiazole derivatives 1-27 were synthesized, structurally characterized, and evaluated for in vitro yeast glucose uptake activity. Compounds 5 (IC50 = 38.14 ± 0.17 μM), 6 (IC50 = 40.23 ± 0.20 μM), and 7 (IC50 = 36.43 ± 0.02 μM) demonstrated potent yeast glucose uptake activity as compared to standard metronidazole (IC50 = 41.86 ± 0.09 μM). This study identified a number of potential lead molecules which can be helpful in lowering the blood glucose level in hyperglycemia.
Metal-mediated inhibition of escherichia coli methionine aminopeptidase: Structure-activity relationships and development of a novel scoring function for metal-ligand interactions
Schiffmann, Rolf,Neugebauer, Alexander,Klein, Christian D.
, p. 511 - 522 (2007/10/03)
We report the discovery of thiabendazole as a potent inhibitor (K 1 = 0.4 μM) of Escherichia coli methionine aminopeptidase (ecMetAP) and the synthesis and pharmacological evaluation of thiabendazole congeners with activity in the upper nanomolar range, Elucidation of the X-ray structure of ecMetAP in complex with thiabendazole and an unrelated inhibitor that was independently described by another group showed that that both compounds bind to an additional CoII ion at the entrance of the active site. This unexpected finding explains the inactivity of the compounds under in vivo conditions. It also allows us to discuss the structure-activity relationships of this series of compounds in a meaningful way, based upon docking runs with an auxiliary metal ion, We describe a new scoring function for the evaluation of metal-mediated inhibitor binding that, unlike the previously used scoring function implemented in the docking program, allows us to distinguish between active and inactive compounds, Finally, conclusions for the structure-based design of in vivo-active inhibitors of ecMetAP are drawn.
Synthesis of benzoxazoles, benzothiazoles and benzimidazoles and evaluation of their antifungal, insecticidal and herbicidal activities
Hisano,Ichikawa,Tsumoto,Tasaki
, p. 2996 - 3004 (2007/10/02)
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