Design and synthesis of (2-(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)cyclopropyl)methanamine as a selective serotonin 2C agonist
Publication type: Journal Article
Publication date: 2015-06-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
PubMed ID:
26120215
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A conformationally restricted analog of a selective cyclopropane-bearing serotonin 2C agonist was designed and synthesized. A 2,2-dimethyl-2,3-dihydrobenzofuran scaffold was investigated as a constrained variant of a biologically active isopropyl phenyl ether. Construction of the required dimethyl-2,3-dihydrobenzofuran intermediate began using a procedure that relied on a microwave-assisted alkylation reaction. The synthesis of the designed compound as its HCl salt is reported in a total of 12 steps and 17% overall yield. Biological evaluation revealed the constrained analog to be a selective serotonin 2C agonist with modest potency.
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15
Total citations:
15
Citations from 2024:
1
(6.67%)
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GOST
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Cheng J. et al. Design and synthesis of (2-(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)cyclopropyl)methanamine as a selective serotonin 2C agonist // Tetrahedron Letters. 2015. Vol. 56. No. 23. pp. 3420-3422.
GOST all authors (up to 50)
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Cheng J., Lv W., Kozikowski A. P. Design and synthesis of (2-(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)cyclopropyl)methanamine as a selective serotonin 2C agonist // Tetrahedron Letters. 2015. Vol. 56. No. 23. pp. 3420-3422.
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RIS
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TY - JOUR
DO - 10.1016/j.tetlet.2015.01.060
UR - https://doi.org/10.1016/j.tetlet.2015.01.060
TI - Design and synthesis of (2-(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)cyclopropyl)methanamine as a selective serotonin 2C agonist
T2 - Tetrahedron Letters
AU - Cheng, Jianjun
AU - Lv, Wei
AU - Kozikowski, Alan P.
PY - 2015
DA - 2015/06/01
PB - Elsevier
SP - 3420-3422
IS - 23
VL - 56
PMID - 26120215
SN - 0040-4039
SN - 1873-3581
ER -
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BibTex (up to 50 authors)
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@article{2015_Cheng,
author = {Jianjun Cheng and Wei Lv and Alan P. Kozikowski},
title = {Design and synthesis of (2-(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)cyclopropyl)methanamine as a selective serotonin 2C agonist},
journal = {Tetrahedron Letters},
year = {2015},
volume = {56},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.tetlet.2015.01.060},
number = {23},
pages = {3420--3422},
doi = {10.1016/j.tetlet.2015.01.060}
}
Cite this
MLA
Copy
Cheng, Jianjun, et al. “Design and synthesis of (2-(5-chloro-2,2-dimethyl-2,3-dihydrobenzofuran-7-yl)cyclopropyl)methanamine as a selective serotonin 2C agonist.” Tetrahedron Letters, vol. 56, no. 23, Jun. 2015, pp. 3420-3422. https://doi.org/10.1016/j.tetlet.2015.01.060.