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Alitretinoin

CAT#: H100020

CAS#: 5300-03-8

Description: Alitretinoin, or 9-cis-retinoic acid, is a form of vitamin A. Alitretinoin is an orally- and topically-active naturally-occurring retinoic acid with antineoplastic, chemopreventive, teratogenic, and embryotoxic activities. Alitretinoin binds to and activates nuclear retinoic acid receptors (RAR) and retinoid X receptors (RXR); these activated receptors act as transcription factors, regulating gene expression that results in the inhibition of cell proliferation, induction of cell differentiation, and apoptosis of both normal cells and tumor cells.

Synthetic Routes

Alitretinoin - Synthetic Route 1

Synthetic reference

Suzuki, Masaaki; Takashima-Hirano, Misato; Ishii, Hideki; Watanabe, Chika; Sumi, Kengo; Koyama, Hiroko; Doi, Hisashi. Synthesis of 11C-labeled retinoic acid, [11C]ATRA, via an alkenylboron precursor by Pd(0)-mediated rapid C-[11C]methylation. Bioorganic & Medicinal Chemistry Letters. Volume 24. Issue 15. Pages 3622-3625. 2014.

Alitretinoin - Synthetic Route 2

Synthetic reference

Wada, Akimori; Fukunaga, Kouki; Ito, Masayoshi; Mizuguchi, Yukari; Nakagawa, Kimie; Okano, Toshio. Preparation and biological activity of 13-substituted retinoic acids. Bioorganic & Medicinal Chemistry. Volume 12. Issue 14. Pages 3931-3942. 2004.

Alitretinoin - Synthetic Route 3

Synthetic reference

Pazos, Yolanda; Iglesias, Beatriz; de Lera, Angel R. The Suzuki Coupling Reaction in the Stereocontrolled Synthesis of 9-cis-Retinoic Acid and Its Ring-Demethylated Analogues. Journal of Organic Chemistry. Volume 66. Issue 25. Pages 8483-8489. 2001.

Alitretinoin - Synthetic Route 4

Synthetic reference

Okitsu, Takashi; Iwatsuka, Kinya; Wada, Akimori. Caesium fluoride-promoted Stille coupling reaction: an efficient synthesis of 9Z-retinoic acid and its analogues using a practical building block. Chemical Communications (Cambridge, United Kingdom). Issue 47. Pages 6330-6332. 2008.

Alitretinoin - Synthetic Route 5

Synthetic reference

Savoca, Ann C.; Urgaonkar, Sameer. 1,5-Diazabicyclo[4.3.0]non-5-ene. e-EROS Encyclopedia of Reagents for Organic Synthesis. Pages 1-5. 2006.

Alitretinoin - Synthetic Route 6

Synthetic reference

Kahremany, Shirin; Sander, Christopher Lane; Tochtrop, Gregory P.; Kubas, Adam; Palczewski, Krzysztof. Z-Isomerization of retinoids through combination of monochromatic photoisomerization and metal catalysis. Organic & Biomolecular Chemistry. Volume 17. Issue 35. Pages 8125-8139.2019.

Alitretinoin - Synthetic Route 7

Synthetic reference

DeLuca, Hector F.; Tadikonda, Praveen K. Method of synthesis of retinoic acid. Assignee Wisconsin Alumni Research Foundation. 1998.

Alitretinoin - Synthetic Route 8

Synthetic reference

White, Steven K.; Hwang, Chan K.; Winn, David T. Methods for stereospecific synthesis of polyene aldehydes. Assignee Ligand Pharmaceuticals Inc. 1996.

Alitretinoin - Synthetic Route 9

Synthetic reference

Bennani, Youssef L. Methods for the synthesis of 9-cis retinoids and their novel intermediates. Assignee Ligand Pharmaceuticals Incorp. 1995.

Alitretinoin - Synthetic Route 10

Synthetic reference

John, Michael; Paust, Joachim. Preparation of 9-(Z)-retinoic acid from mother liquor from preparation of C15 triarylphosphonium salts. Assignee BASF A.-G. 1995.