ChemicalBook CAS DataBase List Bexarotene

Bexarotene synthesis

12synthesis methods

Product Name:Bexarotene
CAS Number:153559-49-0
Molecular formula:C24H28O2
Molecular Weight:348.48

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

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

ROUTE 8

ROUTE 9

ROUTE 10

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

110-03-2 Synthesis

110-03-2
354 suppliers
$6.00/25g

153559-49-0
293 suppliers
$25.00/5mg

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