(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid Chemical Properties

Melting point:

>240 °C

Boiling point:

574.1±50.0 °C(Predicted)

Density 

1.257

storage temp. 

Store at -20°C

solubility 

≥37.4 mg/mL in DMSO; insoluble in H2O; ≥10.97 mg/mL in EtOH with gentle warming and ultrasonic

form 

solid

pka

-95.54±0.10(Predicted)

color 

White to green

(2E)-3-(4'-Hydroxy-3'-tricyclo[3.3.1.13,7]dec-1-yl[1,1'-biphenyl]-4-yl)-2-propenoic acid Usage And Synthesis

Uses

Adarotene has been found to have antitumor activity against different types of cancer, including acute myeloid leukemia, primary effusion lymphoma, prostate cancer and glioma. It may also be useful in treating acute lung injury through inflammation and ROS suppression via inactivating TLR4?/NF-?κB and p38?/ERK1?/2 signaling pathways.

Biological Activity

ST1926 is an atypical retinoid th at is able to overcome resistance to ATRA. ST1926 appears to induce apoptosis by production of DNA double-strand breaks (DSB) and chromosomal lesions during the S phase of the cell cycle.', 'ST1926 is considered to be more apoptotic than CD437. It is much effective in mobilizing calcium than CD437. ST1926 repress toll-like receptor 4 (TLR4)/myeloid differentiation factor 88 (MyD88) signal pathway to disable the actions of nuclear factor-KB (NF-KB). It has the ability to repress inflammation response and ROS synthesis in lung epithelial cells in vitro.

Synthesis

General procedure for the synthesis of (E)-3-(3'-(adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid from methyl (E)-3-(3'-(adamantan-1-yl)-4'-hydroxy-[1,1'-biphenylyl]-4-yl)propenoate: the (E )-3-(3'-adamantan-1-yl-4'-hydroxybiphenyl-4-yl)acrylic acid methyl ester (3.28 g, 8.45 mmol) was added to a solution of LiOH-H2O (1.77 g, 42.25 mmol) in 340 mL of THF/H2O (1:1) and the mixture was stirred at room temperature overnight. After evaporation of THF, the mixture was extracted with hexane, acidified with 2N HCl and filtered to give 2.82 g (94%) of (E)-3-(3'-(adamantan-1-yl)-4'-hydroxy-[1,1'-biphenylyl]-4-yl)propenoic acid with a melting point of > 240 °C. 1H NMR (DMSO-d6): δ 1.74 (6H, s, 6Ad), 2.04 (3H, s, 3Ad), 2.12 (6H, s, 6Ad), 6.51 (1H, d, -CH, J=16.1Hz), 6.85 (1H, d, 1Ar, J=8.8Hz), 7.30-7.40 (2H, m, 2Ar). 7.55-7.63 (3H, m, 2Ar + CH), 7.70 (2H, d, 2Ar, J=8.0Hz), 9.54 (1H, s, -OH), 12.34 (1H, brs, -COOH).MS (m/z): 374 (M+, 100).

in vivo

target

RAR β

References

[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 6, p. 909 - 912
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 15, p. 4931 - 4946
[3] European Journal of Medicinal Chemistry, 2014, vol. 79, p. 251 - 259

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