Synthesis and biological evaluation of ferrocene-based cannabinoid receptor 2 ligands

被引：8

作者：

Sansook, Supojjanee ^{[1
]}

Tuo, Wei ^{[2
]}

Bollier, Melanie ^{[2
]}

Barczyk, Amelie ^{[2
]}

Dezitter, Xavier ^{[2
]}

Klupsch, Frederique ^{[2
]}

Leleu-Chavain, Natascha ^{[2
]}

Farce, Amaury ^{[2
]}

Tizzard, Graham J. ^{[3
]}

Coles, Simon J. ^{[3
]}

Spencer, John ^{[1
]}

Millet, Regis ^{[2
]}

机构：

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

[2] Univ Lille, INSERM, CHU Lille, U995,LIRIC, F-59000 Lille, France

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

来源：

FUTURE MEDICINAL CHEMISTRY | 2018年 / 10卷 / 06期

关键词：

cannabinoids; FAAH; ferrocene; isoxazole; ACID AMIDE HYDROLASE; TRANSFECTED CELLS; FAAH INHIBITORS; CB2; AGONISTS; ANANDAMIDE; AM630; TRANSPORT; MOIETY; BRAIN;

D O I：

10.4155/fmc-2017-0200

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Ferrocene analogs of known fatty acid amide hydrolase inhibitors and CB2 ligands have been synthesized and characterized spectroscopically and crystallographically. The resulting bio-organometallic isoxazoles were assayed for their effects on CB1 and CB2 receptors as well as on fatty acid amide hydrolase. None had any fatty acid amide hydrolase activity but compound 3, 5-(2-(pentyloxy)phenyl)-N-ferrocenylisoxazole-3carboxamide, was found to be a potent CB2 ligand (K-i = 32.5 nM).

引用

页码：631 / 638

页数：8

共 50 条

[1] Ferrocene-Based with Thiadiazole Antibacterial Agents: Synthesis, Characterization, and Biological Evaluation
Yin, Dawei
Sun, Xiaoming
Liu, Yuting
FRONTIER IN INFORMATION ENGINEERING FOR MECHANICS AND MATERIALS, 2012, 189 : 181 - 184
[2] Synthesis and Biological Evaluation of JAHAs: Ferrocene-Based Histone Deacetylase Inhibitors
Spencer, John
Amin, Jahangir
Wang, Minghua
Packham, Graham
Alwi, Sharifah S. Syed
Tizzard, Graham J.
Coles, Simon J.
Paranal, Ronald M.
Bradner, James E.
Heightman, Tom D.
ACS MEDICINAL CHEMISTRY LETTERS, 2011, 2 (05): : 358 - 362
[3] Rapid convenient synthesis of ferrocene-based triphos analogue) ligands
Butler, IR
Davies, RL
SYNTHESIS-STUTTGART, 1996, (11): : 1350 - &
[4] Synthesis and Biological Evaluation of Thiophene-Based Cannabinoid Receptor Type 2 Radiotracers for PET Imaging
Haider, Ahmed
Herde, Adrienne Mueller
Slavik, Roger
Weber, Markus
Mugnaini, Claudia
Ligresti, Alessia
Schibli, Roger
Mu, Linjing
Ametamey, Simon Mensah
FRONTIERS IN NEUROSCIENCE, 2016, 10
[5] Synthesis of ferrocene-based polysubstituted pyrrolidines
Zhang, Wensheng
Xu, Wenjing
Ma, Chunyu
Li, Yan
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2019, 55 (10) : 939 - 942
[6] Synthesis of ferrocene-based polysubstituted pyrrolidines
Wensheng Zhang
Wenjing Xu
Chunyu Ma
Yan Li
Chemistry of Heterocyclic Compounds, 2019, 55 : 939 - 942
[7] Synthesis and Preliminary Biological Evaluation of Indol-3-yl-oxoacetamides as Potent Cannabinoid Receptor Type 2 Ligands
Moldovan, Rares-Petru
Deuther-Conrad, Winnie
Horti, Andrew G.
Brust, Peter
MOLECULES, 2017, 22 (01):
[8] Synthesis of Soluble Ferrocene-Based Polythiophenes and Their Properties
Khalid, Hamad
Wang, Li
Yu, Haojie
Akram, Muhammad
Abbasi, Nasir M.
Sun, Ruoli
Saleem, Muhammad
Zain-ul-Abdin
Chen, Yongsheng
JOURNAL OF INORGANIC AND ORGANOMETALLIC POLYMERS AND MATERIALS, 2015, 25 (06) : 1511 - 1520
[9] Synthesis of Soluble Ferrocene-Based Polythiophenes and Their Properties
Hamad Khalid
Li Wang
Haojie Yu
Muhammad Akram
Nasir M. Abbasi
Ruoli Sun
Muhammad Saleem
Yongsheng Zain-ul-Abdin
Journal of Inorganic and Organometallic Polymers and Materials, 2015, 25 : 1511 - 1520
[10] Synthesis and biological evaluation of bivalent cannabinoid receptor ligands based on hCCB2R selective benzimidazoles reveal unexpected intrinsic properties
Nimczick, Martin
Pemp, Daniela
Darras, Fouad H.
Chen, Xinyu
Heilmann, Joerg
Decker, Michael
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (15) : 3938 - 3946

← 1 2 3 4 5 →