Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity
Jennifer M. Frost
1
,
Michael J. Dart
1
,
Karin R Tietje
1
,
Tiffany R Garrison
1
,
George K. Grayson
1
,
Anthony V Daza
1
,
Odile F El-Kouhen
1
,
Betty B. Yao
1
,
Gin C. Hsieh
1
,
Madhavi Pai
1
,
Chang Z Zhu
1
,
Prasant Chandran
1
,
Michael Meyer
1
1
Neurological Diseases Research, Global Pharmaceutical Research and Development, Abbott Laboratories, R47W, AP9A, 100 Abbott Park Road, Abbott Park, Illinois 60064
|
Publication type: Journal Article
Publication date: 2009-11-18
scimago Q1
wos Q1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
19921781
Drug Discovery
Molecular Medicine
Abstract
Several 3-acylindoles with high affinity for the CB(2) cannabinoid receptor and selectivity over the CB(1) receptor have been prepared. A variety of 3-acyl substituents were investigated, and the tetramethylcyclopropyl group was found to lead to high affinity CB(2) agonists (5, 16). Substitution at the N1-indole position was then examined. A series of aminoalkylindoles was prepared and several substituted aminoethyl derivatives were active (23-27, 5) at the CB(2) receptor. A study of N1 nonaromatic side chain variants provided potent agonists at the CB(2) receptor (16, 35-41, 44-47, 49-54, and 57-58). Several polar side chains (alcohols, oxazolidinone) were well-tolerated for CB(2) receptor activity (41, 50), while others (amide, acid) led to weaker or inactive compounds (55 and 56). N1 aromatic side chains also afforded several high affinity CB(2) receptor agonists (61, 63, 65, and 69) but were generally less potent in an in vitro CB(2) functional assay than were nonaromatic side chain analogues.
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Total citations:
130
Citations from 2025:
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GOST
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Frost J. M. et al. Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity // Journal of Medicinal Chemistry. 2009. Vol. 53. No. 1. pp. 295-315.
GOST all authors (up to 50)
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Frost J. M., Dart M. J., Tietje K. R., Garrison T. R., Grayson G. K., Daza A. V., El-Kouhen O. F., Yao B. B., Hsieh G. C., Pai M., Zhu C. Z., Chandran P., Meyer M. Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity // Journal of Medicinal Chemistry. 2009. Vol. 53. No. 1. pp. 295-315.
Cite this
RIS
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TY - JOUR
DO - 10.1021/jm901214q
UR - https://doi.org/10.1021/jm901214q
TI - Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity
T2 - Journal of Medicinal Chemistry
AU - Frost, Jennifer M.
AU - Dart, Michael J.
AU - Tietje, Karin R
AU - Garrison, Tiffany R
AU - Grayson, George K.
AU - Daza, Anthony V
AU - El-Kouhen, Odile F
AU - Yao, Betty B.
AU - Hsieh, Gin C.
AU - Pai, Madhavi
AU - Zhu, Chang Z
AU - Chandran, Prasant
AU - Meyer, Michael
PY - 2009
DA - 2009/11/18
PB - American Chemical Society (ACS)
SP - 295-315
IS - 1
VL - 53
PMID - 19921781
SN - 0022-2623
SN - 1520-4804
ER -
Cite this
BibTex (up to 50 authors)
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@article{2009_Frost,
author = {Jennifer M. Frost and Michael J. Dart and Karin R Tietje and Tiffany R Garrison and George K. Grayson and Anthony V Daza and Odile F El-Kouhen and Betty B. Yao and Gin C. Hsieh and Madhavi Pai and Chang Z Zhu and Prasant Chandran and Michael Meyer},
title = {Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity},
journal = {Journal of Medicinal Chemistry},
year = {2009},
volume = {53},
publisher = {American Chemical Society (ACS)},
month = {nov},
url = {https://doi.org/10.1021/jm901214q},
number = {1},
pages = {295--315},
doi = {10.1021/jm901214q}
}
Cite this
MLA
Copy
Frost, Jennifer M., et al. “Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity.” Journal of Medicinal Chemistry, vol. 53, no. 1, Nov. 2009, pp. 295-315. https://doi.org/10.1021/jm901214q.