Literature DB >> 16078826

Synthesis and structure-activity relationship of novel 6-aryl-1,4-dihydrobenzo[d][1,3]oxazine-2-thiones as progesterone receptor modulators leading to the potent and selective nonsteroidal progesterone receptor agonist tanaproget.

Andrew Fensome1, Reinhold Bender, Rajiv Chopra, Jeff Cohen, Mark A Collins, Valerie Hudak, Karl Malakian, Susan Lockhead, Andrea Olland, Kristine Svenson, Eugene A Terefenko, Ray J Unwalla, James M Wilhelm, Scott Wolfrom, Yuan Zhu, Zhiming Zhang, Puwen Zhang, Richard C Winneker, Jay Wrobel.   

Abstract

Tanaproget represents a potential first-in-class nonsteroidal PR agonist for contraception with improved safety and side effect profiles versus currently available steroidal oral contraceptives. Additional SAR, biological activity, and structural information from a tanaproget/hPR-LBD (hPR-LBD = human progesterone receptor ligand binding domain) cocrystal structure will also be presented.

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Year:  2005        PMID： 16078826     DOI： 10.1021/jm050358b

Source DB:  PubMed          Journal:  J Med Chem        ISSN： 0022-2623            Impact factor:   7.446


  11 in total

Review 1.  Nitrile-containing pharmaceuticals: efficacious roles of the nitrile pharmacophore.

Authors:  Fraser F Fleming; Lihua Yao; P C Ravikumar; Lee Funk; Brian C Shook
Journal:  J Med Chem       Date:  2010-08-30       Impact factor: 7.446

Review 2.  Progestin therapy to prevent preterm birth: History and effectiveness of current strategies and development of novel approaches.

Authors:  Sam A Mesiano; Gregory A Peters; Peyvand Amini; Rachel A Wilson; Gregory P Tochtrop; Focco van Den Akker
Journal:  Placenta       Date:  2019-01-28       Impact factor: 3.481

3.  Imaging progesterone receptor in breast tumors: synthesis and receptor binding affinity of fluoroalkyl-substituted analogues of tanaproget.

Authors:  Hai-Bing Zhou; Jae Hak Lee; Christopher G Mayne; Kathryn E Carlson; John A Katzenellenbogen
Journal:  J Med Chem       Date:  2010-04-22       Impact factor: 7.446

4.  Development of N-(4-Phenoxyphenyl)benzenesulfonamide Derivatives as Novel Nonsteroidal Progesterone Receptor Antagonists.

Authors:  Ayumi Yamada; Yuko Kazui; Hiromasa Yoshioka; Aya Tanatani; Shuichi Mori; Hiroyuki Kagechika; Shinya Fujii
Journal:  ACS Med Chem Lett       Date:  2016-09-15       Impact factor: 4.345

5.  Novel Nonsteroidal Progesterone Receptor (PR) Antagonists with a Phenanthridinone Skeleton.

Authors:  Yuko Nishiyama; Shuichi Mori; Makoto Makishima; Shinya Fujii; Hiroyuki Kagechika; Yuichi Hashimoto; Minoru Ishikawa
Journal:  ACS Med Chem Lett       Date:  2018-06-23       Impact factor: 4.345

6.  Synthesis of 1,4-dihydro-benzo[d][1,3]oxazin-2-ones from phthalides via an aminolysis-Hofmann rearrangement protocol.

Authors:  Eliud Hernández; Jessica M Vélez; Cornelis P Vlaar
Journal:  Tetrahedron Lett       Date:  2007-12-17       Impact factor: 2.415

7.  Synthesis of a benzoxazinthione derivative of tanaproget and pharmacological evaluation for PET imaging of PR expression.

Authors:  Louis Allott; Cecilia Miranda; Angela Hayes; Florence Raynaud; Christopher Cawthorne; Graham Smith
Journal:  EJNMMI Radiopharm Chem       Date:  2019-01-10

8.  DeepSnap-Deep Learning Approach Predicts Progesterone Receptor Antagonist Activity With High Performance.

Authors:  Yasunari Matsuzaka; Yoshihiro Uesawa
Journal:  Front Bioeng Biotechnol       Date:  2020-01-22

Review 9.  PET Imaging Agents (FES, FFNP, and FDHT) for Estrogen, Androgen, and Progesterone Receptors to Improve Management of Breast and Prostate Cancers by Functional Imaging.

Authors:  John A Katzenellenbogen
Journal:  Cancers (Basel)       Date:  2020-07-23       Impact factor: 6.639

10.  Facile cleavage of C-C bond: conversion of pyrane derivative to 1,3-oxazin derivative.

Authors:  Zhilan Lin; Xueli Zhang; Xinkui You; Yuan Gao
Journal:  Tetrahedron       Date:  2012-05-30       Impact factor: 2.457
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