Development of potent serotonin-3 (5-HT3) receptor antagonists. I. Structure-activity relationships of 2-alkoxy-4-amino-5-chlorobenzamide derivatives

DOI: 10.1248/cpb.43.1364

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1364 - 1378 (1995)

Update date:2022-07-31

Topics:

Authors:

Harada Harada

Morie Morie

Hirokawa

Yoshida Yoshida

Kato Kato

Read Full Text PDF DownLoad Join now for total 90,000,000 free articles

Article abstract of DOI:10.1248/cpb.43.1364

A new series of 2-alkoxy-4-amino-5-chlorobenzamide derivatives hearing five- to seven-membered heteroalicyclic rings in the amine moiety was synthesized and evaluated for serotonin-3 (5-HT₃) receptor antagonistic activity by assaying the ability to antagonize the yon Bezold-Jarisch reflex in rats. The five- to seven-membered heteroalicycles comprise pyrrolidine, morpholine, 1,4-thiazine, piperidine, piperazine, 1,4-oxazepine, 1,4- thiazepine, azepine, and 1,4-diazepine rings. Among them, some benzamide derivatives having a 1,4-diazepine ring showed a potent 5-HT₃ receptor antagonistic activity. In particular, 4-amino-5-chloro-N-(1,4- dimethylhexahydro-1H-1,4-diazepin-6-yl)-2-ethoxyhenzamide (96) and the 1- benzyl-4-methylhexahydro-1H-1,4-diazepine analogue 103 showed potent 5-HT₃ receptor antagonistic activity without 5-HT₄ receptor binding affinity.

Full text of DOI:10.1248/cpb.43.1364

NII-Electronic Library Service

Products guided by the article

Product name:6-(acetylamino)-1,4-dibenzylhexahydro-1H-1,4-diazepine

Cas No:124257-73-4

R&D Labs maybe for 124257-73-4

Shanghai Run-Biotech Co., Ltd.

website:http://www.run-biotech.com

Contact:+86-21-31576854/57171705 / 57171706

Address:second floor, building 3, No.999, jiangyue Road, minghang District, Shanghai, China
Shanghai Hanshare Industry Co.,Ltd.

Contact:86 21 20960688

Address:RM902-903,Building E, Wanda Plaza,No.26,Zhoukang Road, Pudong District, Shanghai, China
Oceachem Group Limited

website:http://www.oceanchem-group.com

Contact:86-536-8596048

Address:9th floor,Building B future Plaza, No.88.Fenghuang Street,Weifang,Shandong,China
Shijiazhuang Haotian Chemical Co., Ltd.

Contact:86-311-85044374

Address:293 Donggang Road
Henan violettech chemical industries co.,ltd

website:http://www.violettech.net/index.html

Contact:+86-371-55361188

Address:Yuhong World Port, Zhengzhou Airport, Zhengzhou City, Henan Province

Relevant to this article

Synthesis of 2-(4-substituted benzyl-1,4-diazepan-1-yl)-N-(3,4-dihydro-3- oxo-2H-benzo[b][1,4]oxazin-7-yl)acetamides and their positive inotropic evaluation

Doi:10.1016/j.bmcl.2010.06.046
(2010)
Ru-X-C (X=F or H) interactions in complex compounds. Preparation and crystal structures of <<*>Ru)>(SC6F5)2(PMe2Ph)2> and <<*>Ru(SC6F5)2-2)(C6H5)2>2>

Doi:10.1016/0022-328X(89)85432-4
(1989)
CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates

Doi:10.1039/c6cc08601b
(2016)
Iron and copper salts in the synthesis of benzo[b]furans

Doi:10.1002/adsc.201000269
(2010)
Organocatalytic asymmetric Mannich-type reaction of N-sulfonylimines with isocyanoacetate leading to optically active 2-imidazoline-4-carboxylates

Doi:10.1016/j.tetasy.2010.04.029
(2010)
Photoinduced C(sp²)-H/C(sp²)-H Cross-Coupling of Alkenes: Direct Synthesis of 1,3-Dienes

Doi:10.1021/acs.orglett.9b04201
(2020)

Article Doi