Local Anaesthetic Activity of 1,2‐Disubstituted Imidazo[1,2‐a]benzimidazoles.

Abstract

Local Anaesthetic Activity of 1,2-Disubstituted Imidazo[1,2-a]benzimidazoles. -A series of new 1-dialkylaminoalkylimidazobenzimidazoles (VII) (11 examples) are synthesized, of which the majority displays marked local anaesthetic activity. Derivatives (VIIc) and (VIIe) appear to be the most active ones. -(ANISIMOVA, V. A.; OSIPOVA, M. M.; GALENKO-YAROSHEVSKII, A. P.; PONOMAREV, V. V.; POPKOV, V. L.; PRIKHOD'KO, A. K.; KADE, E. A.; SPASOV, A. A.; Khim.-Farm. Zh. 36 (2002) 8, 21-24; Nauchno-issled. inst. fiz. org. khim., Rostov. gos. univ., Rostov-na-Donu 344090, Russia; Russ.) -Koehler 03-103

Inhibition of Protein Kinase C-Driven Nuclear Factor-κB Activation: Synthesis, Structure−Activity Relationship, and Pharmacological Profiling of Pathway Specific Benzimidazole Probe Molecules

“…The low isolated yield was attributed to the formation of tricyclic side product 16 via an intramolecular Schiff-base formation. 19 Purified 16 was found to be inactive (IC 50 >25 μM) under the assay conditions. This competing intramolecular cyclization was completely eliminated by conducting the reaction at 23 °C in methanol using sodium bicarbonate as a mild base.…”

“…The final alkylation of intermediate 14a with α-bromo-3,5-di- tert -butyl-4-hydroxyacetophenone ( 15a ) was conducted in n -butanol at reflux to furnish 1a in moderate yield (Scheme , method A). The low isolated yield was attributed to the formation of tricyclic side product 16 via an intramolecular Schiff-base formation . Purified 16 was found to be inactive (IC 50 > 25 μM) under the assay conditions.…”

“…These have been utilized in the synthesis of biotinylated conjugates directed toward affinity-based target identification and future mode of action studies that will be reported separately. In addition, the equipotent 2-benzimidazolone analogues (19) provide a modified scaffold with an additional N 3 -site for future exploration. Compound 1a and its analogues represent new chemical tools that may be useful toward further development of therapeutically useful pathway selective modulators of NF-κB activity that may find application in disease models of inflammation, cancer and other autoimmune diseases.…”

Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity

“…Benzimidazole incorporating structures are of immense importance pharmacologically due to their significant bioactivities like anti-HIV (Burkholder et al, 2001), anticancer (El-Naem et al, 2003), local anesthetic (Anisimova et al, 2002), antituberculosis (Foks et al, 2006), antifungal (Enguehard et al, 2000), anti-bacterial (Ramanatham et al, 2008), etc. Moreover, the SAR study interestingly evokes that the minor change in the structure of substituent group flanked between two nitrogen atoms of benzimidazole commonly results in the change of its bioactivity (Ge et al, 2007;Kazimierczuk et al, 2005).…”

Синтез И Исследование Комплекса Включения 2-Фенил-1-[3-(Пирролидин-1-Ил)-Пропил]-1h- Имидазо[1,2-А]бензимидазола С Β-Циклодекстрином

“…2-Фенил-1-[3-(пирролидин-1-ил)-пропил]-1Н-имидазо[1,2-а]бензимидазол имеет высокую местноанестезирующую активность и может составить конкуренцию лидокаину и дикаину при переднекамерной анестезии глаза [1]. Комплекс включения β-циклодекстрина (β-ЦД) и производного имидазо[1,2-a]бензимидазолабыл получен взаимодействием эквимолярных количеств водных растворов соединений.…”