Tamibarotene

<h2 id="synthesis">Synthesis</h2>
Reaction of the
diol (1) with hydrogen chloride affords the corresponding dichloro derivative (2). Aluminum chloride mediated Friedel–Crafts alkylation of acetanilide with the dichloride affords the tetralin (3). Basic hydrolysis leads to the primary amine (4). Acylation of the primary amino group with the half acid chloride half ester from terephthalic acid (5) leads to
the amide (6). Basic hydrolysis of the ester grouping then affords (7).<a class="footnote-ref" id="fnref:8" href="#fn:8">8</a>

<h2 id="references">References</h2>

<ol>
<li id="fn:1">"Tamibarotene: AM 80, retinobenzoic acid, Tamibaro". Drugs in R&D. 5 (6): 359–62. 2004. doi:10.2165/00126839-200405060-00010. PMID 15563242. S2CID 34546131. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></li>
<li id="fn:2">Miwako, I; Kagechika, H (August 2007). "Tamibarotene". Drugs of Today. 43 (8): 563–568. doi:10.1358/dot.2007.43.8.1072615. PMID 17925887. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></li>
<li id="fn:3">"Syros Provides Update on SELECT-AML-1 Phase 2 Clinical Trial :: Syros Pharmaceuticals, Inc. (SYRS)". Syros Pharmaceuticals, Inc. 2024-08-12. Retrieved 2024-08-15. <a href="https://ir.syros.com/press-releases/detail/308/syros-provides-update-on-select-aml-1-phase-2-clinical-trial" target="_blank">https://ir.syros.com/press-releases/detail/308/syros-provides-update-on-select-aml-1-phase-2-clinical-trial</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></li>
<li id="fn:4">Arrieta, Oscar; Levitt, Daniel J.; Pendergrass, Kelly B.; Gladkov, Oleg; Bondarenko, Igor; Jain, Minish Mahendra; Wieland, Scott (2015-05-20). "Efficacy and safety of adding the retinoid tamibarotene or placebo to paclitaxel/carboplatin for advanced non-small cell lung cancer". Journal of Clinical Oncology. 33 (15_suppl): e19034. doi:10.1200/jco.2015.33.15_suppl.e19034. ISSN 0732-183X. <a href="https://ascopubs.org/doi/10.1200/jco.2015.33.15_suppl.e19034" target="_blank">https://ascopubs.org/doi/10.1200/jco.2015.33.15_suppl.e19034</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></li>
<li id="fn:5">Miwako, I; Kagechika, H (August 2007). "Tamibarotene". Drugs of Today. 43 (8): 563–568. doi:10.1358/dot.2007.43.8.1072615. PMID 17925887. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></li>
<li id="fn:6">Fukasawa, H; Nakagomi, M; Yamagata, N; Katsuki, H; Kawahara, K; Kitaoka, K; Miki, T; Shudo, K (2012). "Tamibarotene: a candidate retinoid drug for Alzheimer's disease" (PDF). Biological & Pharmaceutical Bulletin. 35 (8): 1206–1212. doi:10.1248/bpb.b12-00314. PMID 22863914. <a href="https://www.jstage.jst.go.jp/article/bpb/35/8/35_b12-00314/_pdf" target="_blank">https://www.jstage.jst.go.jp/article/bpb/35/8/35_b12-00314/_pdf</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></li>
<li id="fn:7">Arrieta, Oscar; Levitt, Daniel J.; Pendergrass, Kelly B.; Gladkov, Oleg; Bondarenko, Igor; Jain, Minish Mahendra; Wieland, Scott (2015-05-20). "Efficacy and safety of adding the retinoid tamibarotene or placebo to paclitaxel/carboplatin for advanced non-small cell lung cancer". Journal of Clinical Oncology. 33 (15_suppl): e19034. doi:10.1200/jco.2015.33.15_suppl.e19034. ISSN 0732-183X. <a href="https://ascopubs.org/doi/10.1200/jco.2015.33.15_suppl.e19034" target="_blank">https://ascopubs.org/doi/10.1200/jco.2015.33.15_suppl.e19034</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></li>
<li id="fn:8">Y. Hamada, I. Yamada, M. Uenaka, T. Sakata, U.S. patent 5,214,202 (1993). <a href="https://patents.google.com/patent/US5214202" target="_blank">https://patents.google.com/patent/US5214202</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></li>
</ol>

Tamibarotene open-in-new

Tamibarotene