Design and synthesis of orally efficacious benzimidazoles as melanin-concentrating hormone receptor 1 antagonists

Wu, Wen‐Lian; Burnett, Duane A.; Caplen, Mary Ann; Domalski, Martin S.; Bennett, Chad E.; Greenlee, William J.; Hawes, Brian E.; O’Neill, Kim; Weig, Blair; Weston, Daniel J.; Spar, Brian D.; Kowalski, Timothy J.

doi:10.1016/j.bmcl.2006.04.062

Cited by 16 publications

(2 citation statements)

References 26 publications

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“…Trisubstituted aryl cyclopropylnitriles have found utility in organic synthesis as precursors to a wide variety of natural products, , biologically active compounds, , and important materials. , Current methodology to rapidly assemble these compounds primarily relies on addition/cyclization reactions between aryl acetonitriles and epihalohydrins , or 1,4-additions of aryl acetonitriles in anionic − or ylide − forms to Michael acceptors followed by a cyclization step. Additional approaches to access trisubstituted aryl cyclopropylnitriles include carbenoid chemistry − or the treatment of acrylonitriles with sulfur/sulfoxonium ylides , or photochemical conditions . A rapid method for the introduction of a wider variety of groups on the cyclopropyl ring directly from aryl acetonitriles in one step is, however, lacking.…”

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Diastereoselective One-Pot Knoevenagel Condensation/Corey–Chaykovsky Cyclopropanation

et al. 2012

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Efforts to substitute the cyclopropane ring in a series of aryl cyclopropylnitriles led to the discovery of an operationally simple one-pot method for Knoevenagel condensation and subsequent Corey-Chaykovsky cyclopropanation giving diastereomerically pure products as a racemic mixture of enantiomers. Method development and results for variably substituted aryl acetonitriles and aldehydes in the reaction are reported. A concise synthesis of (±)-bicifadine in two steps is provided to demonstrate the utility of the method.

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Diastereoselective One-Pot Knoevenagel Condensation/Corey–Chaykovsky Cyclopropanation

et al. 2012

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“…Han et al synthesized some imidazo[1,2-a] benzimidazoles as CRF1R antagonists and found that compound 38, cyclopropylmethyl-propyl-[2-trifluoromethyl-4-(2,4,5-trimethyl-benzyl)-4H-benzo[d]pyrrolo[1,2-a]imidazol-1-yl methyl]-amine, has the potential to be used as anxiolytic agent (Han et al, 2005). (Wu et al, 2006).…”

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Benzimidazole: a medicinally important heterocyclic moiety

2010

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Benzimidazole nucleus is a constituent of many bioactive heterocyclic compounds that are of wide interest because of their diverse biological and clinical applications. Moreover, benzimidazole derivatives are structural isosters of naturally occurring nucleotides, which allows them to interact easily with the biopolymers of the living system. This created interest in researchers who have synthesized variety of benzimidazole derivatives and screened them for their various biological activities, viz.

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