Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline-Reference-Cited by-同舟云学术

Synthesis of 2,2-difluoro-2-arylethylamines as fluorinated analogs of octopamine and noradrenaline

Published:2022-01-01 Issue:1 Volume:28 Page:26-34
ISSN:2191-0197
Container-title:Heterocyclic Communications
language:en
Short-container-title:

Author:

Tarui Atsushi¹,Kamata Erika¹,Ebisu Koji¹,Kawai Yui¹,Araki Ryota¹,Yabe Takeshi¹,Karuo Yukiko¹,Sato Kazuyuki¹,Kawai Kentaro¹,Omote Masaaki¹

Affiliation:

1. Faculty of Pharmaceutical Sciences, Setsunan University , 45-1, Nagaotoge-cho , Hirakata , Osaka 573-0101 , Japan

Abstract

Abstrtact A series of 2,2-difluoro-2-arylethylamines was synthesized as fluorinated analogs of octopamine and noradrenaline with the expectation of bioisosteric OH/F exchanges. The syntheses of these compounds were performed by a Suzuki–Miyaura cross-coupling reaction of 4-(bromodifluoroacetyl)morpholine with aryl boronic acids to produce the intermediate 2,2-difluoro-2-arylacetamides, followed by transformation of difluoroacetamide to difluoroethylamine.

Publisher

Walter de Gruyter GmbH

Subject

Organic Chemistry

Link

https://www.degruyter.com/document/doi/10.1515/hc-2022-0005/pdf

Reference26 articles.

1. Iversen SD, Iversen LL. Dopamine: 50 years in perspective. Trends Neurosci. 2007;30(5):188–93.

2. Arancibia S, Marambio M, Campusano JM, Fierro A. Modeling of the binding of octopamine and dopamine in insect monoamine transporters reveals structural and electrostatic differences. ACS Chem Neurosci. 2019;10(5):2310–7.

3. Huang J, Hamasaki T, Ozoe F, Ohta H, Enomoto K, Kataoka H, et al. Identification of critical structural determinants responsible for octopamine binding to the α-adrenergic-like bombyx mori octopamine receptor. Biochemistry. 2007;46(20):5896–903.

4. Ehrlich K, Gotz A, Bollinger S, Tschammer N, Bettinetti L, Harterich S, et al. Dopamine D2, D3, and D4 selective phenylpiperazines as molecular probes to explore the origins of subtype specific receptor binding. J Med Chem. 2009;52(15):4923–35.

5. Bautista DL, Morris DH, Stein L, Asher W, Hammitt TA. Two model receptor system of the alpha1D adrenergic receptor to describe interactions with epinephrine and BMY7378. J Chem Inf Model. 2006;46(1):334–44.

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