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496868-77-0,MFCD05861282
Catalog No.:AA00DB1V

496868-77-0 | Adarotene

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Purity
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10mg
98+%
in stock  
$93.00   $65.00
- +
25mg
98+%
in stock  
$155.00   $109.00
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50mg
98+%
in stock  
$247.00   $173.00
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  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Upstream Synthesis Route
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00DB1V
Chemical Name:
Adarotene
CAS Number:
496868-77-0
Molecular Formula:
C25H26O3
Molecular Weight:
374.4721
MDL Number:
MFCD05861282
SMILES:
OC(=O)/C=C/c1ccc(cc1)c1ccc(c(c1)C12CC3CC(C2)CC(C1)C3)O
Properties
Computed Properties
 
Complexity:
574  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
4  
XLogP3:
6.5  

Upstream Synthesis Route

[1]JournalofMedicinalChemistry,2003,vol.46,#6,p.909-912

[2]JournalofMedicinalChemistry,2005,vol.48,#15,p.4931-4946

[3]EuropeanJournalofMedicinalChemistry,2014,vol.79,p.251-259

[1]BioorganicandMedicinalChemistry,2012,vol.20,#7,p.2405-2415

[1]BioorganicandMedicinalChemistry,2012,vol.20,#7,p.2405-2415

[1]BioorganicandMedicinalChemistry,2012,vol.20,#7,p.2405-2415

[1]BioorganicandMedicinalChemistry,2012,vol.20,#7,p.2405-2415

Downstream Synthesis Route

[1]JournalofMedicinalChemistry,2003,vol.46,p.909-912

[2]JournalofMedicinalChemistry,2005,vol.48,p.4931-4946

[3]EuropeanJournalofMedicinalChemistry,2014,vol.79,p.251-259

123-30-8    496868-77-0   
3-(3'-adamantan-1-yl-4'-hydroxy-biphenyl-4-yl)-<i>N</i>-(4-hydroxy-phenyl)-acrylamide 

[1]JournalofMedicinalChemistry,2005,vol.48,p.4931-4946

95-54-5    496868-77-0   
3-(3'-adamantan-1-yl-4'-hydroxy-biphenyl-4-yl)-<i>N</i>-(2-amino-phenyl)-acrylamide 

[1]JournalofMedicinalChemistry,2005,vol.48,p.4931-4946

[1]JournalofMedicinalChemistry,2005,vol.48,p.4931-4946

[2]JournalofMedicinalChemistry,2003,vol.46,p.909-912

[3]EuropeanJournalofMedicinalChemistry,2014,vol.79,p.251-259

[1]JournalofMedicinalChemistry,2005,vol.48,p.4931-4946

[2]JournalofMedicinalChemistry,2003,vol.46,p.909-912

[3]EuropeanJournalofMedicinalChemistry,2014,vol.79,p.251-259

Literature

Title: New retinoid derivatives as back-ups of Adarotene.

Journal: Bioorganic & medicinal chemistry 20120401

Title: Analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid. 2. Impact of 3-chloro group replacement on inhibition of proliferation and induction of apoptosis of leukemia and cancer cell lines.

Journal: Journal of medicinal chemistry 20120112

Title: Heteroatom-substituted analogues of orphan nuclear receptor small heterodimer partner ligand and apoptosis inducer (E)-4-[3-(1-Adamantyl)-4-hydroxyphenyl]-3-chlorocinnamic acid.

Journal: Journal of medicinal chemistry 20110609

Title: Adamantyl-substituted retinoid-derived molecules that interact with the orphan nuclear receptor small heterodimer partner: effects of replacing the 1-adamantyl or hydroxyl group on inhibition of cancer cell growth, induction of cancer cell apoptosis, and inhibition of SRC homology 2 domain-containing protein tyrosine phosphatase-2 activity.

Journal: Journal of medicinal chemistry 20080925

Title: Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.

Journal: Bioorganic & medicinal chemistry 20070715

Title: An adamantyl-substituted retinoid-derived molecule that inhibits cancer cell growth and angiogenesis by inducing apoptosis and binds to small heterodimer partner nuclear receptor: effects of modifying its carboxylate group on apoptosis, proliferation, and protein-tyrosine phosphatase activity.

Journal: Journal of medicinal chemistry 20070531

Title: Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways.

Journal: Molecular pharmacology 20060901

Title: Synthesis and structure-activity relationships of a new series of retinoid-related biphenyl-4-ylacrylic acids endowed with antiproliferative and proapoptotic activity.

Journal: Journal of medicinal chemistry 20050728

Title: Antagonist analogue of 6-[3'-(1-adamantyl)-4'-hydroxyphenyl]-2-naphthalenecarboxylic acid (AHPN) family of apoptosis inducers that effectively blocks AHPN-induced apoptosis but not cell-cycle arrest.

Journal: Journal of medicinal chemistry 20040701

Title: ST1926, a novel and orally active retinoid-related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis.

Journal: Blood 20040101

Title: A novel atypical retinoid endowed with proapoptotic and antitumor activity.

Journal: Journal of medicinal chemistry 20030313

Title: Cincinelli R, et al. A novel atypical retinoid endowed with proapoptotic and antitumor activity. J Med Chem. 2003 Mar 13;46(6):909-12.

Title: Garattini E, et al. ST1926, a novel and orally active retinoid-related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis. Blood. 2004 Jan 1;103(1):194-207.

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