ChemicalBook CAS DataBase List 94497-51-5

94497-51-5

Name	Tamibarotene
CAS	94497-51-5
EINECS(EC#)	1806241-263-5
Molecular Formula	C22H25NO3
MDL Number	MFCD00866188
Molecular Weight	351.44
MOL File	94497-51-5.mol

Synonyms

AM80 C12864 Amnoid Amnolake NSC 608000 Tamibarotene UNII-08V52GZ Retinoid AM 80 Tamibarotene, >=99% Am 80 (pharmaceutical) N-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)terephthalamic acid N-(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl)-2-naphthyl)terephthalamic acid 4-[(5,5,8,8-Tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid 4-[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]benzoicacid -((5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acid 4-[(5,5,8,8-tetraMethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbaMoyl]benzoic acid 4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-ylaminocarbonyl)benzoic acid 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphthalen)-2-yl]aminocarbonyl]benzoic acid 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethylnaphthalen-2-yl)amino]carbonyl]benzoic acid 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino]carbonyl]benzoic Acid 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetraMethyl-2-naphthalenyl)carbaMoyl]benzoic acid, 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetraMethyl-2-naphthyl)carbaMoyl] benzoic acid

Chemical Properties

Appearance	Crystalline Solid
Melting point	231-232°C
Boiling point	449.6±45.0 °C(Predicted)
density	1.154±0.06 g/cm3(Predicted)
RTECS	DH6940000
storage temp.	Store at RT
solubility	Soluble to 50 mM in DMSO
form	powder
pka	3.83±0.10(Predicted)
color	white to off-white
InChI	InChI=1S/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26)
InChIKey	MUTNCGKQJGXKEM-UHFFFAOYSA-N
SMILES	C(O)(=O)C1=CC=C(C(NC2=CC=C3C(=C2)C(C)(C)CCC3(C)C)=O)C=C1

Safety Data

WGK Germany	3
Storage Class	11 - Combustible Solids

Hazard Information

Chemical Properties

Crystalline Solid

Uses

A RARα agonist that induces differentiation and apoptosis

Uses

Synthetic retinoic acid receptor-a/?selective retinoid. Antineoplastic

Uses

Synthetic retinoic acid receptor-α/β-selective retinoid. Antineoplastic.

Biological Activity

Retinoic acid receptor α (RAR α ) agonist that induces differentiation (ED 50 = 0.79 nM) and apoptosis of HL-60 cells in vitro . Exhibits antiproliferative effects against a variety of human tumor cells lines (mean values of 35, 40 and 60% growth inhibition at 0.1, 1 and 10 μ M respectively) and displays anticancer activity against acute promyelocytic leukemia in vivo .

Originator

Toko Yakuhin Kogyo (Japan)

Definition

ChEBI: A dicarboxylic acid monoamide resulting from the condensation of one of the carboxy groups of terephthalic acid with the amino group of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine.

Brand name

Amnolake

Biochem/physiol Actions

Tamibarotene (Am80) is a RAR α agonist. Tamibarotene was developed to overcome resistance to ATRA and is currently approved in Japan for treatment of recurrent acute promyelocytic leukemia (APL). The compound induces HL-60 cells differentiation and apoptosis. Similarly to TTNPB, the compound neither binds to nor transactivates the RXRs. In contrast to TTNPB (pan RAR agonist), Tamibarotene is rather specific toward RAR α. The compound is approximate 10 times more potent than ATRA.

Synthesis

Several synthesis of tamibarotene have been disclosed in the literature including the process scale synthesis as shown in the scheme. The synthesis started with preparation of dichloride 134 in 82% yield from diol 133 by treating with concentrated HCL in DCM. Friedal Crafts reaction of dichloride 134 with acetanilide in the presence of aluminum chloride at -15??C for 2h provided acetanilide derivative 136 in 78% yield. In a single pot, the acetanilide was reacted with PCl5 and dimethylaniline at -25??C for 1.5h followed by quenching the reaction with methanol for 2h after addition at -25??C. Addition of dimethylaniline and terepthalic chloride mono-methylester at -30 - - 20??C for 1 hr provided the tamibarotene methyl easter 137 in 81% yield. Hydrolysis of the ester by heating with sodium hydroxide in MeOH:water mixture for 1h followed isolation and crystallization gave tamibarotene (XIX) in 92% yield.

Synthesis_94497-51-5

storage

Store at RT

Questions And Answer

Spectrum Detail

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