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

Alfred L Williams; Srinivasa R Dandepally; Nailya Gilyazova; Sam M Witherspoon; Gordon Ibeanu

doi:10.1016/j.tet.2010.09.028

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

Tetrahedron. 2010 Dec 11;66(50):9577-9581. doi: 10.1016/j.tet.2010.09.028.

Authors

Alfred L Williams¹, Srinivasa R Dandepally, Nailya Gilyazova, Sam M Witherspoon, Gordon Ibeanu

Affiliation

¹ Department of Pharmaceutical Sciences, North Carolina Central University, Durham, NC, 27707 USA 2.

Abstract

The synthesis of 4-chloro-N-(naphthalen-1-ylmethyl)-5-(3-(piperazin-1-yl)phenoxy)thiophene-2-sulfonamide (B-355252) using a MW-assisted nucleophilic aromatic substitution (S(N)Ar) 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.

Abstract

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