成人免费xx,国产又黄又湿又刺激不卡网站,成人性视频app菠萝网站,色天天天天

Welcome to chemicalbook!
Chinese English Japanese Germany Korea
400-158-6606
Try our best to find the right business for you.
Do not miss inquiry messages Please log in to view all inquiry messages.

Welcome back!

ChemicalBook CAS DataBase List Bexarotene
153559-49-0

Bexarotene synthesis

12synthesis methods
Bexarotene, also known as LGD-1069, is a synthetic retinoic acid agent with potential antineoplastic, chemopreventive, teratogenic and embryotoxic properties. Bexarotene selectively binds to and activates retinoid X receptors (RXRs), thereby inducing changes in gene expression that lead to cell differentiation, decreased cell proliferation, apoptosis of some cancer cell types, and tumor regression.
Synthetic Routes
  • ROUTE 1
  • 202112071363265789.jpg

    Wagner, Carl E.; Jurutka, Peter W.; Marshall, Pamela A.; Groy, Thomas L.; van der Vaart, Arjan; Ziller, Joseph W.; Furmick, Julie K.; Graeber, Mark E.; Matro, Erik; Miguel, Belinda V.; Tran, Ivy T.; Kwon, Jungeun; Tedeschi, Jamie N.; Moosavi, Shahram; Danishyar, Amina; Philp, Joshua S.; Khamees, Reina O.; Jackson, Jevon N.; Grupe, Darci K.; Badshah, Syed L.; Hart, Justin W. Modeling, Synthesis and Biological Evaluation of Potential Retinoid X Receptor (RXR) Selective Agonists: Novel Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene). Journal of Medicinal Chemistry. Division of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences. Arizona State University. Glendale, USA 85306. Volume 52. Issue 19. Pages 5950-5966. 2009

  • ROUTE 2
  • 202112070944487540.jpg

    Yoshida, Hiroto; Takemoto, Yuki; Takaki, Ken. A masked diboron in Cu-catalyzed borylation reaction: highly regioselective formal hydroboration of alkynes for synthesis of branched alkenylborons. Chemical Communications (Cambridge, United Kingdom). Department of Applied Chemistry, Graduate School of Engineering. Hiroshima University. Higashi-Hiroshima, Japan 739-8527. Volume 50. Issue 61. Pages 8299-8302. 2014

  • ROUTE 3
  • 202112071404945156.jpg

    Zhang, Lin; Badea, Beth Ann; Enyeart, Debra; Berger, Elaine M.; Mais, Dale E.; Boehm, Marcus F. Synthesis of isotopically labeled 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid (LGD1069), a potent retinoid X receptor-selective Ligand. Journal of Labelled Compounds & Radiopharmaceuticals. Ligand Pharmaceutical Incorporated. Dep. Medicinal Chem. San Diego, USA 92121. Volume 36. Issue 7. Pages 701-12. 1995

  • ROUTE 4
  • 202112072273708755.jpg

    Zou, Yinjun; Qin, Liena; Ren, Xinfeng; Lu, Yunpeng; Li, Yongxin; Zhou, Jianrong. Selective arylation and vinylation at the α position of vinylarenes. Chemistry - A European Journal. Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences. Nanyang Technological University. Singapore 637371. Volume 19. Issue 10. Pages 3504-3511. 2013

  • ROUTE 5
  • 202112073888492286.jpg

    Bhunia, Samir Kumar; Das, Pritha; Nandi, Shantanu; Jana, Ranjan. Carboxylation of Aryl Triflates with CO2 Merging Palladium and Visible-Light-Photoredox Catalysts. Organic Letters. Organic and Medicinal Chemistry Division. CSIR-Indian Institute of Chemical Biology. West Bengal, India 700032. Volume 21. Issue 12. Pages 4632-4637. 2019

  • ROUTE 6
  • 202112076929338549.jpg

    Wei, Wei; Ma, Shuai; Han, Zeng-ying; Cao, Sheng-hua; Ding, Xiao-dong. Synthesis and optimization of bexarotene. Huaxue Yanjiu Yu Yingyong. Sichuan Industrial Institute of Antibiotics. China National Pharmaceutical Group Corporation. Chengdu, Peop. Rep. China 610052. Volume 25. Issue 3. Pages 388-390. 2013

  • ROUTE 7
  • 202112075232097117.jpg

    Bian, Haiyong; Xu, Wenfang; Yang, Penghui. Improved synthesis of bexarotene. Zhongguo Yaowu Huaxue Zazhi. School of Pharmacy. Shandong University. Jinan, Shandong Province, Peop. Rep. China 250012. Volume 20. Issue 3. Pages 187-189. 2010

  • ROUTE 8
  • 202112071880054704.jpg

    Pfahl, Magnus; Zhang, Xiao Kun; Lehmann, Jurgen M.; Dawson, Marcia I.; Camerion, James F.; Hobbs, Peter D.; Jong, Ling. RXR receptor homodimer formation and bridged bicyclic aromatic compounds and their use in modulating gene expression and screening modulating compounds. Assignee La Jolla Cancer Research Foundation, USA; SRI International. WO 9412880. 1994

  • ROUTE 9
  • 202112075464265212.jpg

    Bhirud, Shekhar Bhaskar; Sarin, Gurdeep Singh; Sharma, Bimal Kumar; Gera, Pardeep. Process for the preparation of highly pure bexarotene. Assignee Ind-Swift Laboratories Limited, India. WO 2011141928. 2011

  • ROUTE 10
  • 202112074498118400.jpg

    Boehm, Marcus F.; Heyman, Richard A. 1,1,4,4-Tetramethylcyclohexane derivatives as retinoid X receptors modulators and their preparation, pharmaceutical compositions and use in the treatment of cancers. Assignee Eisai Inc., USA. US 7655699.2010

202112071363265789.jpg

Wagner, Carl E.; Jurutka, Peter W.; Marshall, Pamela A.; Groy, Thomas L.; van der Vaart, Arjan; Ziller, Joseph W.; Furmick, Julie K.; Graeber, Mark E.; Matro, Erik; Miguel, Belinda V.; Tran, Ivy T.; Kwon, Jungeun; Tedeschi, Jamie N.; Moosavi, Shahram; Danishyar, Amina; Philp, Joshua S.; Khamees, Reina O.; Jackson, Jevon N.; Grupe, Darci K.; Badshah, Syed L.; Hart, Justin W. Modeling, Synthesis and Biological Evaluation of Potential Retinoid X Receptor (RXR) Selective Agonists: Novel Analogues of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene). Journal of Medicinal Chemistry. Division of Mathematical and Natural Sciences, New College of Interdisciplinary Arts and Sciences. Arizona State University. Glendale, USA 85306. Volume 52. Issue 19. Pages 5950-5966. 2009

-

Yield:-

Steps:

Multi-step reaction with 7 steps
1: HCl conc. / 3 h / 20 °C
2: 99 percent / AlCl3 / CH2Cl2 / 20 °C
3: 85 percent / Br2; AlCl3 / CH2Cl2
4: n-BuLi / tetrahydrofuran; hexane / 3 h / -78 - 20 °C
5: 2.38 g / aq. HCl / tetrahydrofuran / 2 h / 20 °C
6: 88 percent / Pd(OAc)2; P(o-Tol)3; Et3N / dimethylformamide / 2 h / 50 °C
7: H2O

References:

Faul;Ratz;Sullivan;Trankle;Winneroski [Journal of Organic Chemistry,2001,vol. 66,# 17,p. 5772 - 5782]

FullText

Bexarotene Related Search: