Synthesis of Bioorganometallic Nanomolar-Potent CB2 Agonists Containing a Ferrocene Unit

被引：10

作者：

Sansook, Supojjanee ^{[1
]}

Tuo, Wei ^{[3
]}

Lemaire, Lucas ^{[3
]}

Tourteau, Aurelien ^{[3
]}

Barczyk, Amelie ^{[3
]}

Dezitter, Xavier ^{[3
]}

Klupsch, Frederique ^{[3
]}

Leleu-Chavain, Natascha ^{[3
]}

Tizzard, Graham J. ^{[2
]}

Coles, Simon J. ^{[2
]}

Millet, Regis ^{[3
]}

Spencer, John ^{[1
]}

机构：

[1] Univ Sussex, Sch Life Sci, Dept Chem, Brighton BN1 9QT, E Sussex, England

[2] Univ Southampton, Sch Chem, UK Natl Crystallog Serv, Southampton SO17 1BJ, Hants, England

[3] Univ Lille, ICPAL, LIRIC Lille Inflammat Res Int Ctr, INSERM,U995, 3 Rue Prof Laguesse,BP83, F-59006 Lille, France

来源：

ORGANOMETALLICS | 2016年 / 35卷 / 19期

关键词：

CANNABINOID RECEPTOR LIGANDS; HISTONE DEACETYLASE INHIBITORS; INVERSE AGONIST; SR; 144528; BIOLOGICAL EVALUATION; EXPERIMENTAL COLITIS; TRANSFECTED CELLS; NEUROPATHIC PAIN; CANCER CELLS; DERIVATIVES;

D O I：

10.1021/acs.organomet.6b00575

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A small library of ferrocene-containing amides has been synthesized using standard amide coupling chemistry with ferrocenylamine. Ferrocene analogues of known bioactive adamantylamides were shown to be effective cannabinoid receptor (CB1 and CB2) agonists, displaying, in many cases, single-digit nanomolar potency. Three final ferrocene-containing derivatives have been characterized in the solid state by Xray crystallography and display intramolecular hydrogen bonding of the type NH---C=O. N-Methylation of the amide, confirmed by X-ray crystallography, leads to both loss of hydrogen bonding and biological activity.

引用

页码：3361 / 3368

页数：8

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