9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites
Publication type: Journal Article
Publication date: 2010-02-01
scimago Q2
wos Q2
SJR: 0.472
CiteScore: 5.1
Impact factor: 2.2
ISSN: 0960894X, 14643405
PubMed ID:
20045641
Organic Chemistry
Drug Discovery
Biochemistry
Molecular Biology
Pharmaceutical Science
Clinical Biochemistry
Molecular Medicine
Abstract
Synthesis, radioligand binding and molecular modeling studies of several 9-aminomethyl-9,10-dihydroanthracene (AMDA) analogs were carried out to determine the extent of the steric tolerance associated with expansion of the tricyclic ring system and amine substitution at 5-HT(2A) and H(1) receptors. A mixture of (7,12-dihydrotetraphene-12-yl)methanamine and (6,11-dihydrotetracene-11-yl)methanamine in a 75-25% ratio was found to have an apparent K(i) of 10nM at the 5-HT(2A) receptor. A substantial binding affinity for (7,12-dihydrotetraphene-3-methoxy-12-yl)methanamine at the 5-HT(2A) receptor (K(i)=21 nM) was also observed. Interestingly, this compound was found to have 100-fold selectivity for 5-HT(2A) over the H(1) receptor (K(i)=2500 nM). N-Phenylalkyl-AMDA derivatives, in which the length of the alkyl chain varied from methylene to n-butylene, were found to have only weak affinity for both 5-HT(2A) and H(1) receptors (K(i)=223 to 964 nM). Our results show that large rigid annulated AMDA analogs can be sterically accommodated within the proposed 5-HT(2A) binding site.
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Shah J. R. et al. 9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites // Bioorganic and Medicinal Chemistry Letters. 2010. Vol. 20. No. 3. pp. 935-938.
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Shah J. R., Mosier P. D., Peddi S., Roth B. L., Westkaemper R. B. 9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites // Bioorganic and Medicinal Chemistry Letters. 2010. Vol. 20. No. 3. pp. 935-938.
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TY - JOUR
DO - 10.1016/j.bmcl.2009.12.064
UR - https://doi.org/10.1016/j.bmcl.2009.12.064
TI - 9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites
T2 - Bioorganic and Medicinal Chemistry Letters
AU - Shah, Jitesh R
AU - Mosier, Philip D
AU - Peddi, Srinivas
AU - Roth, Bryan L.
AU - Westkaemper, Richard B
PY - 2010
DA - 2010/02/01
PB - Elsevier
SP - 935-938
IS - 3
VL - 20
PMID - 20045641
SN - 0960-894X
SN - 1464-3405
ER -
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BibTex (up to 50 authors)
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@article{2010_Shah,
author = {Jitesh R Shah and Philip D Mosier and Srinivas Peddi and Bryan L. Roth and Richard B Westkaemper},
title = {9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites},
journal = {Bioorganic and Medicinal Chemistry Letters},
year = {2010},
volume = {20},
publisher = {Elsevier},
month = {feb},
url = {https://doi.org/10.1016/j.bmcl.2009.12.064},
number = {3},
pages = {935--938},
doi = {10.1016/j.bmcl.2009.12.064}
}
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MLA
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Shah, Jitesh R., et al. “9-Aminomethyl-9,10-dihydroanthracene (AMDA) analogs as structural probes for steric tolerance in 5-HT2A and H1 receptor binding sites.” Bioorganic and Medicinal Chemistry Letters, vol. 20, no. 3, Feb. 2010, pp. 935-938. https://doi.org/10.1016/j.bmcl.2009.12.064.