880384-30-5Relevant academic research and scientific papers
Exploration of SAR for novel 2-benzylbenzimidazole analogs as inhibitor of transcription factor NF-κB
Boggu, Pulla Reddy,Venkateswararao, Eeda,Manickam, Manoj,Kim, Youngsoo,Jung, Sang-Hun
, p. 469 - 479 (2017)
A novel series of 2-benzylbenzimidazole analogs was designed, synthesized and investigated for their in vitro activities against LPS induced NF-κB inhibition in RAW 264.7 cells using the SEAP assay. Among them, 4-((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)phenol (6e, >100% inhibition at 30?μM, IC50?=?3.0?μM), 4-((5-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)phenol (6j, 96% inhibition at 30?μM, IC50?=?4.0?μM) and 2-((4-(cyclohexylmethoxy)-1H-benzo[d]imidazol-2-yl)methyl)phenol (6k, 95% inhibition at 30?μM, IC50?=?5.0?μM) showed strong inhibitory activity. The structure activity relationship confirmed that the substitution on benzimidazole ring A with hydrophobic cyclohexylmethoxy group at position 4 or 5 markedly enhances the activity. In addition, the hydrophilic hydrogen bonding donor group (OH) at position 2 or 4 on phenyl ring B connected with one methylene spacer to the benzimidazole ring is favorable for the inhibitory activity. However, hydrophobic (–OCH3 and –Cl) groups on phenyl ring B decrease the activity.
Facile preparation of substituted benzimidazole-2-carboxylates
Zhu, Yongbao,Skupinska, Krystyna A.,McEachern, Ernest J.
, p. 769 - 775 (2007/10/03)
Mild conditions for the preparation of benzimidazole-2-carboxylates have been developed. Condensation of a substituted 1,2-phenylenediamine with methyl trichloroacetamidate in the presence of TFA rapidly affords the 2-trichloromethylbenzimidazole; hydroly
