Synthesis of phenoxyacetic acid derivatives as highly potent antagonists of gastrin/cholecystokinin-B receptors. III

DOI: 10.1248/cpb.47.755

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 755 - 771 (1999)

Update date:2022-07-29

Topics:

Authors:

Takeda, Yasuyuki

Kawagoe, Keiichi

Yokomizo, Aki

Yokomizo, Yoshihiro

Hosokami, Toru

Shimoto, Yoshimasa

Tabuchi, Yoshiaki

Ogihara, Yoshiyasu

Honda, Yuko

Kawarabayashi, Keiko

Iseri, Miki

Yokohama, Shuichi

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

Article abstract of DOI:10.1248/cpb.47.755

In order to improve the biological characteristics of DA-3934 (5), a novel gastrin/cholecystokinin (CCK)-B receptor antagonist, phenoxyacetic acid derivatives replacing the N-methyl-N-phenylcarbamoylmethyl moiety of 5 with various alkyl chains have been synthesized and their biological activity evaluated. The relationship between the structure of these compounds and their human gastrin receptor binding affinity showed that there should be the optimal size among the various N-alkyl chains. Also a significant increase in the receptor binding affinity was achieved by several compounds. Among those compounds, 2-[3-[3-[N-cyclohexylmethyl-N-[2-(N-methyl-N- phenylcarbamoylmethoxy)phenyl]carbamoylmethyl]ureido]phenyl]acetic acid (22c) and (±)-2-[3-[3[N-[2-(N-methyl-N-phenylcarbamoylmethoxy)phenyl]-N-(3- methylpentyl)carbamoylmethyl]ureido]phenyl]acetic acid (22h) exhibited high affinity for human gastrin receptors and were also more potent inhibitors in a pentagastrin-induced gastric acid secretion model than the parent compound, 5. The ED(50) values of these compounds when administered intraduodenally to rats were 0.12 and 0.63 mg/kg, respectively.

Full text of DOI:10.1248/cpb.47.755

NII-Electronic Library Service

Products guided by the article

Product name:N-(2-benzyloxyphenyl)-N-(3-methyl-2-butenyl)-2-(N-tert-butoxycarbonylamino)acetamide

Cas No:237747-77-2

R&D Labs maybe for 237747-77-2

NEWSTAR CHEM ENTERPRISE LTD.

Contact:0572-2722882

Address:1201,F3,xinghuibandao,
Shanghai Rainbow Chemistry Co., Ltd.

Contact:+86-21-64968086-5815/5812

Address:3rd floor, Building 7, 251 Faladi Road, Zhangjiang Hi-Tech Park, Pudong District, Shanghai, P.R. China
SuZhou Bichal Biological Technology CO.,LTD

Contact:+86-512-68051130

Address:NO.32 huoju road HI-TECH Industrial development zone SuZhou China
Lanling Hongchuang Flame Retardant Co., Ltd.

Contact:+86-531-68858132

Address:East Huafeichang Road, Cangshan County, Linyi, Shandong, China (Mainland)
JiangXi Hong Run Chemical Co., Ltd

Contact:+86-0791-88521351

Address:XingHuo industrial zone in YongXiu county

Relevant to this article

Transformation of isosteviol oxime to a lactone under Beckmann reaction conditions

Doi:10.1070/MC2005v015n01ABEH001946
(2005)
1,2-oxazines as building blocks for stereoselective synthesis: Preparation of oxygen-substituted 1,2-oxazines, either by alcohol addition or by epoxidation, and subsequent hydrogenation leading to 1,2-amino alcohols and pyrrolidines

Doi:10.1002/ejoc.201000425
(2010)
1,2-Dicyano-4,5-bis[2'-(2"-benzyloxyethoxy)ethoxy]benzene-precursor towards new functionalized phthalocyanines

Doi:10.1016/j.mencom.2010.06.019
(2010)
Syntheses of Novel Substituted Porphyrins by the Mercuration and Palladium/Olefin Methodology

Doi:10.1021/jo00291a024
(1990)
Photophysics of aromatic thiourea derivatives and their complexes with anions. Fast and ultrafast spectroscopic investigations

Doi:10.1039/b927442a
(2010)
Efficient synthesis of 2-fluoromethylated qninolines via copper catalyzed alkynylation and cyclization of fluorinated imidoyl iodides

Doi:10.1002/adsc.201000180
(2010)

Article Doi