Home
Resources
Publications
New Synthesis of 6[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic Acid and Evaluation of the Influence of Adamantyl Group on the DNA Binding of a Naphthoic Retinoid

New Synthesis of 6[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic Acid and Evaluation of the Influence of Adamantyl Group on the DNA Binding of a Naphthoic Retinoid

Alberto Milanese, Elena Gorincioi, Mehdi Rajabi, Giulio Vistoli, Enzo Santaniello

Bioorg Chem. 2011 Aug;39(4):151-8.

PMID: 21864882

Abstract:

6[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid (Adapalene®), a synthetic aromatic retinoid specific for RARβ and RARγ receptors, has been prepared utilizing a Pd/C-mediated Suzuki coupling between 6-bromo-2-naphthoic acid and 4-methoxyphenyl boronic acid, followed by introduction of an adamantyl group in the position 3 of the formed 6-(4-methoxyphenyl)-2-naphthoic acid. The interaction of 6-(4-methoxyphenyl)-2-naphthoic acid/ethyl ester and the 3-adamantyl analogs with DNA was studied in aqueous solution at physiological conditions by UV-vis spectroscopy. The calculated binding constants K(ligand-DNA) ranged between 1.1×10(4) M(-1) and 1.1×10(5) M(-1), the higher values corresponding to those of the adamantylated compounds. Molecular modeling studies have emphasized that the intercalative binding of adapalene and its derivatives to DNA is mainly stabilized by hydrophobic interactions related to the presence of the adamantyl group.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP43109779	Adapalene Related Compound C		43109-77-9	Price

As a specialist in analytical chemical Products, Alfa Chemistry offers consumers a wealth of raw materials and a full range of technologies and services.

QUICK LINKS

HEADQUARTERS

Tel:

Fax:

Email: