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Chemical synthesis of tetracyclic terpenes and evaluation of antagonistic activity on endothelin-A receptors and voltage-gated calcium channels.

Abstract：

:A class of tetracyclic terpenes was synthesized and evaluated for antagonistic activity of endothelin-1 (ET-1) induced vasoconstriction and inhibitory activity of voltage-activated Ca(2+) channels. Three repeated Robinson annulation reactions were utilized to construct the tetracyclic molecules. A stereoselective reductive Robinson annulation was discovered for the formation of optically pure tricyclic terpenes. Stereoselective addition of cyanide to the hindered α-face of tetracyclic enone (-)-18 was found and subsequent transformation into the aldehyde function was affected by the formation of bicyclic hemiiminal (-)-4. Six selected synthetic tetracyclic terpenes show inhibitory activities in ET-1 induced vasoconstriction in the gerbil spiral modiolar artery with putative affinity constants ranging between 93 and 319 nM. Moreover, one compound, (-)-3, was evaluated further and found to inhibit voltage-activated Ca(2+) currents but not to affect Na(+) or K(+) currents in dorsal root ganglion cells under similar concentrations. These observations imply a dual mechanism of action. In conclusion, tetracyclic terpenes represent a new class of hit molecules for the discovery of new drugs for the treatment of pulmonary hypertension and vascular related diseases.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Lu J,Aguilar A,Zou B,Bao W,Koldas S,Shi A,Desper J,Wangemann P,Xie XS,Hua DH

doi

10.1016/j.bmc.2015.06.055

subject

Has Abstract

pub_date

2015-09-01 00:00:00

pages

5985-98

issue

17

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(15)00549-0

journal_volume

23

pub_type

杂志文章

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