Microwave-assisted synthesis of 4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-10-yl)phenoxy)thiophene-2-sulfonamide (B-355252): a new potentiator of nerve growth factor (NGF)-induced neurite outgrowth

TETRAHEDRON

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Article

Williams, Alfred L.^1,2  Dandepally, Srinivasa R.²  Gilyazova, Nailya²  Witherspoon, Sam M.²  Ibeanu, Gordon^1,2 

[1] N Carolina Cent Univ, Dept Pharmaceut Sci, Durham, NC 27707 USA

[2] N Carolina Cent Univ, Biomfg Res Inst & Technol Enterprise, Durham, NC 27707 USA

关键词: Microwave synthesis;    Nucleophilic aromatic substitution;    Nerve growth factor;    Neurite outgrowth;   

DOI  :  10.1016/j.tet.2010.09.028

来源: Elsevier

【 摘 要 】

The synthesis of 4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1 -y1)phenoxy)thiophene-2-sulfonamide (B-355252) using an MW-assisted nucleophilic aromatic substitution (SNAr) reaction will be discussed. Utilization of this method allowed for the rapid generation of B-355252 heteroaryl ether core structure in the presence of cesium carbonate in dimethylformamide or tripotassium phosphate in N-methyl-2-pyrrolidone in 94% yield. Evaluation of B-355252 enhancement of nerve growth factor's ability to stimulate neurite outgrowths was determined using NS-1 cells. (C) 2010 Elsevier Ltd. All rights reserved.

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