Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization.

Literature DB >> 21113432

A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization.

Chul-Hee Cho¹, Dai-Il Jung, Richard C Larock.

Abstract

A formal total synthesis of the benzothiophene selective estrogen receptor modulator (SERM) desketoraloxifene and analogs has been accomplished from alkynes bearing electron-rich aromatic rings by electrophilic cyclization using I(2). This approach affords oxygen-bearing 3-iodobenzo[b]thiophenes in excellent yields, which are easily further elaborated using a two-step approach involving Suzuki-Miyaura and Mitsunobu coupling reactions.

Entities: CellLine Chemical Disease Gene

Year: 2010 PMID： 21113432 PMCID： PMC2989616 DOI： 10.1016/j.tetlet.2010.09.137

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

16 in total

1. A non-steroidal estrogen antiagonist 1-(p-2-diethylaminoethoxyphenyl)-1-phenyl-2-p-methoxyphenyl ethanol.

Authors: L J LERNER; F J HOLTHAUS; C R THOMPSON
Journal: Endocrinology Date: 1958-09 Impact factor: 4.736

Review 2. Quinoids formed from estrogens and antiestrogens.

Authors: Judy L Bolton; Linning Yu; Gregory R J Thatcher
Journal: Methods Enzymol Date: 2004 Impact factor: 1.600

3. Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4'-fluoro substitution prevents quinoid formation.

Authors: Hong Liu; Ju Liu; Richard B van Breemen; Gregory R J Thatcher; Judy L Bolton
Journal: Chem Res Toxicol Date: 2005-02 Impact factor: 3.739

4. Effects of anti-estrogens on bone in castrated and intact female rats.

Authors: V C Jordan; E Phelps; J U Lindgren
Journal: Breast Cancer Res Treat Date: 1987-10 Impact factor: 4.872

5. Endometrial adenocarcinoma in breast cancer patients receiving antiestrogens.

Authors: M A Killackey; T B Hakes; V K Pierce
Journal: Cancer Treat Rep Date: 1985-02

6. Molecular determinants of tissue selectivity in estrogen receptor modulators.

Authors: T A Grese; J P Sluka; H U Bryant; G J Cullinan; A L Glasebrook; C D Jones; K Matsumoto; A D Palkowitz; M Sato; J D Termine; M A Winter; N N Yang; J A Dodge
Journal: Proc Natl Acad Sci U S A Date: 1997-12-09 Impact factor: 11.205

7. Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes.

Authors: Dawei Yue; Richard C Larock
Journal: J Org Chem Date: 2002-03-22 Impact factor: 4.354

2. Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans.

Authors: Chul-Hee Cho; Richard C Larock
Journal: ACS Comb Sci Date: 2011-03-24 Impact factor: 3.784

2 in total

A new approach to desketoraloxifene analogs from oxygen-bearing 3-iodobenzo[b]thiophenes prepared via iodocyclization.

1. A non-steroidal estrogen antiagonist 1-(p-2-diethylaminoethoxyphenyl)-1-phenyl-2-p-methoxyphenyl ethanol.

Review 2. Quinoids formed from estrogens and antiestrogens.

3. Bioactivation of the selective estrogen receptor modulator desmethylated arzoxifene to quinoids: 4'-fluoro substitution prevents quinoid formation.

4. Effects of anti-estrogens on bone in castrated and intact female rats.

5. Endometrial adenocarcinoma in breast cancer patients receiving antiestrogens.

6. Molecular determinants of tissue selectivity in estrogen receptor modulators.

7. Synthesis of 2,3-disubstituted benzo[b]thiophenes via palladium-catalyzed coupling and electrophilic cyclization of terminal acetylenes.

Review 8. Tamoxifen: a most unlikely pioneering medicine.

9. Diverse methyl sulfone-containing benzo[b]thiophene library via iodocyclization and palladium-catalyzed coupling.

Review 10. Basic guide to the mechanisms of antiestrogen action.

1. Parallel synthesis of a desketoraloxifene analogue library via iodocyclization/palladium-catalyzed coupling.

2. Highly substituted lactone/ester-containing furan library by the palladium-catalyzed carbonylation of hydroxyl-substituted 3-iodofurans.