Adverts

Open Access Articles- Top Results for Tamibarotene

Tamibarotene

Tamibarotene
200px
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Names

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

IUPAC name
4-[(1,1,4,4-tetramethyltetralin-6-yl)carbamoyl]benzoic acid
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Identifiers#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-


3564473
94497-51-5
ChEMBL ChEMBL25202
ChemSpider 97231
DrugBank DB04942
Jmol-3D images Image
PubChem Template:Chembox PubChem/format
colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Properties

#REDIRECTmw:Help:Magic words#Other
This page is a soft redirect.-

C22H25NO3
Molar mass Lua error in Module:Math at line 495: attempt to index field 'ParserFunctions' (a nil value). g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Tamibarotene (brand name: Amnolake), also called retinobenzoic acid, is orally active, synthetic retinoid, developed to overcome all-trans retinoic acid (ATRA) resistance, with potential antineoplastic activity against acute promyelocytic leukaemia (APL) .[1] It is currently marketed only in Japan and early trials have demonstrated that it tends to be better tolerated than ATRA.[2] It has also been investigated as a possible treatment for Alzheimer's disease, multiple myeloma and Crohn's disease.[2][3]

Synthesis

The tetralin-based compound tamibarotene (7) has been tested as an agent for treating leukaemias.

700px

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).[4]

References

  1. ^ "Tamibarotene: AM 80, retinobenzoic acid, Tamibaro". Drugs in R&D 5 (6): 359–62. 2004. PMID 15563242. doi:10.2165/00126839-200405060-00010. 
  2. ^ a b Miwako, I; Kagechika, H (August 2007). "Tamibarotene". Drugs Today (Barc) 43 (8): 563–568. PMID 17925887. doi:10.1358/dot.2007.43.8.1072615. 
  3. ^ 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. PMID 22863914. doi:10.1248/bpb.b12-00314. 
  4. ^ Y. Hamada, I. Yamada, M. Uenaka, T. Sakata, U.S. Patent 5,214,202 (1993).

Lua error in package.lua at line 80: module 'Module:Buffer' not found.