Tamibarotene

Base Information

• Chemical Name: Tamibarotene
• CAS No.: 94497-51-5
• Molecular Formula: C22H25NO3
• Molecular Weight: 351.445
• Hs Code.: 2924299090
• NSC Number: 608000
• UNII: 08V52GZ3H9
• DSSTox Substance ID: DTXSID5046853
• Nikkaji Number: J227.635F
• Wikipedia: Tamibarotene
• Wikidata: Q7681221
• NCI Thesaurus Code: C71025
• Pharos Ligand ID: 7CLT73A6ZVBQ
• Metabolomics Workbench ID: 43645
• ChEMBL ID: CHEMBL25202
• Mol file: 94497-51-5.mol

Synonyms:4-((5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl)benzoic acid;Am 80;AM-80;Am80;tamibarotene

Chemical Property of Tamibarotene

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 7.2E-09mmHg at 25°C
• Melting Point: 231-232 °C
• Refractive Index: 1.593
• Boiling Point: 449.6 °C at 760 mmHg
• PKA: 3.83±0.10(Predicted)
• Flash Point: 225.7 °C
• PSA: 66.40000
• Density: 1.154 g/cm³
• LogP: 5.05910
• Storage Temp.: Store at RT
• Solubility.: Soluble to 50 mM in DMSO
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 351.18344366
• Heavy Atom Count: 26
• Complexity: 546

Purity/Quality:

99% ^*data from raw suppliers

Tamibarotene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CCC(C2=C1C=CC(=C2)NC(=O)C3=CC=C(C=C3)C(=O)O)(C)C)C
• Recent ClinicalTrials: Tamibarotene Plus Azacitidine in Participants With Newly Diagnosed RARA-positive Higher-Risk Myelodysplastic Syndrome
• Recent EU Clinical Trials: A Randomized, Double-blind, Placebo-controlled Phase 3 Study of SY-1425 Plus Azacitidine Versus Placebo Plus Azacitidine in Newly Diagnosed, RARA-positive Adult Patients with Higher-risk Myelodysplastic Syndrome
• Recent NIPH Clinical Trials: Efficacy and safety study of a therapeutic regimen using Tamibarotene (Am80) and arsenic trioxide (ATO) in combination with Gemtuzumab Ozogamicin (GO) as a post-remission therapy for relapsed acute promyelocytic leukemia (APL)
• General Description: Tamibarotene (Am80) is a synthetic retinoid that selectively activates retinoic acid receptors (RARs) without stimulating retinoic acid X receptors (RXRs), making it a promising therapeutic agent for conditions requiring targeted retinoid activity, such as cancer and dermatological disorders. Its design focuses on improved selectivity and potency compared to natural retinoids like all-trans-retinoic acid (ATRA).

Technology Process of Tamibarotene

There total 11 articles about Tamibarotene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 90.0%

ethyl 4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylcarbamoyl)benzenecarboxylate (1446134-13-9) → Am80 (94497-51-5)

Guidance literature:

With sodium hydroxide; In methanol; water; at 80 ℃; for 3h; Schlenk technique;

DOI:10.1021/ol401550h

Reference yield:

methyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-carbamoyl]benzoate (94497-53-7) → Am80 (94497-51-5)

Guidance literature:

With sodium hydroxide; In ethanol; Ambient temperature;

DOI:10.1021/jm00119a021

Reference yield:

2,5-dimethyl-2,5-hexanediol (110-03-2) → Am80 (94497-51-5)

Guidance literature:

Multi-step reaction with 6 steps

1: conc. HCl, HCl gas / 0.25 h / 0 °C

2: 81.9 percent / AlCl₃ / 24 h / Heating

3: 49.9 percent / HNO₃, H₂SO₄ / 1 h / -10 °C

4: 48 percent / hydrogen / Pd/C / ethanol

5: 86.7 percent / pyridine / benzene / Ambient temperature

6: aq. NaOH / ethanol / Ambient temperature

With pyridine; hydrogenchloride; sodium hydroxide; aluminium trichloride; sulfuric acid; hydrogen; nitric acid; palladium on activated charcoal; In ethanol; benzene;

DOI:10.1021/jm00119a021

upstream raw materials:

methyl 4-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-carbamoyl]benzoate

2,5-dimethyl-2,5-hexanediol

2,5-dichloro-2,5-dimethyl hexane

1,1,4,4-Tetramethyl-1,2,3,4-tetrahydro-naphthalene

Downstream raw materials:

4-<(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-nitro-2-naphthalenyl)carbamoyl>benzoic acid

methyl 4-benzoate

4-<(3-amino-5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl>benzoic acid

C₃₃H₃₄N₄O₆

Refernces

Design, synthesis and evaluation of retinoids with novel bulky hydrophobic partial structures

10.1016/j.bmc.2013.04.053

Retinoic acid, specifically all-trans-retinoic acid (ATRA), is an active metabolite of vitamin A. It plays a crucial role in regulating various critical biological functions, including cell proliferation, morphogenesis, and the differentiation of embryonic stem cells and committed cells such as blood, dermal, immunological, and neuronal cells. ATRA achieves these functions by activating retinoic acid receptors (RARs). The study highlights that ATRA and related compounds, collectively known as retinoids, have been extensively investigated for their chemistry and biology. The research aims to develop new retinoids that selectively bind to RARs without activating retinoic acid X receptors (RXRs), which is important for therapeutic applications. The study evaluates the agonistic activities of newly synthesized retinoids towards RARs and RXRs, with the goal of finding compounds that are more selective and effective than existing retinoids like ATRA and tamibarotene (Am80).