104224-62-6

Basic information

• Product Name: 3-(1-adamantyl)-4-methoxybenzoic acid
• Synonyms: 3-(1-adamantyl)-4-methoxybenzoic acid;benzoic acid, 4-methoxy-3-tricyclo[3.3.1.1~3,7~]dec-1-yl-
• CAS NO: 104224-62-6
• Molecular Formula: C₁₈H₂₂O₃
• Molecular Weight: 286.36548
• Mol File: 104224-62-6.mol

Chemical Properties

• Melting Point: 245-246 °C
• Boiling Point: 450.9±38.0 °C(Predicted)
• Appearance: /
• Density: 1.219±0.06 g/cm3(Predicted)
• PKA: 4.51±0.10(Predicted)
• CAS DataBase Reference: 3-(1-adamantyl)-4-methoxybenzoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(1-adamantyl)-4-methoxybenzoic acid(104224-62-6)
• EPA Substance Registry System: 3-(1-adamantyl)-4-methoxybenzoic acid(104224-62-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 104224-62-6(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 104224-63-7 2-(1-adamantyl)-4-bromoanisole 
• 22635-62-7 1-acetyloxyadamantane 
• 100-09-4 4-methoxybenzoic acid 
• 106-93-4 ethylene dibromide 
• 768-95-6 1-adamanthanol 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 104224-64-8 3-(1-adamantyl)-4-methoxybenzoic acid chloride 
• 142651-49-8 3-(1-Adamantyl)-4-methoxyphenylethanone 
• 1365531-25-4 3-adamantane-1-yl-N-(2,4-dihydroxybenzyl)-4-methoxybenzoic acid amide 
• 1422043-91-1 3-adamantan-1-yl-N-[2-(4-hydroxyphenyl)-ethyl]-4-methoxy-benzoic acid amide 
• 1422043-89-7 3-adamantan-1-yl-N-[2-(3,4-dihydroxyphenyl)-ethyl]-4-methoxy-benzoic acid amide 
• 1422043-87-5 3-adamantan-1-yl-N-(3,4-dihydroxybenzyl)-4-methoxy-benzoic acid amide 
• 1383106-23-7 (5-hydroxy-4-oxo-4H-pyran-2-yl)methyl 4-methoxy-3-(adamantan-1-yl)benzoate 

Relevant articles and documents

3D-QSAR study of adamantyl N-benzylbenzamides as melanogenesis inhibitors

Three-dimensional quantitative structure-activity relationship (3D-QSAR) modeling, comparative molecular field analysis (CoMFA), and comparative molecular similarity indices analysis (CoMSIA) of polyhydroxylated N-benzylbenzamide derivatives containing an

Adamantyl N-benzylbenzamide: New series of depigmentation agents with tyrosinase inhibitory activity

A new series of polyhydroxylated N-benzylbenzamide derivatives containing an adamantyl moiety has been synthesized, and the depigmenting and tyrosinase inhibitory activities of the molecules were evaluated. The lipophilic character of the adamantyl moiety

Depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities

We synthesized benzoate ester derivatives of kojic acid with and without adamantane moiety. Benzoate derivatives 2a-e that did not contain an adamantane moiety showed potent tyrosinase inhibitory activities. However, depigmenting activity was not noted in a cell-based assay. Contrasting results were obtained for benzoate derivatives (3a-e) containing an adamantane moiety. Compounds 3a-e showed potent depigmenting activities without tyrosinase inhibitory activities. To the best of our knowledge, this is the first study showing the depigmenting activities of kojic acid derivatives without tyrosinase inhibitory activities.

S1P RECEPTORS MODULATORS

The invention relates to novel compounds that have S1P receptor modulating activity and, preferably, apoptotic activity and/or anti proliferative activity against cancer cells and other cell types. Further, the invention relates to a pharmaceutical comprising at least one compound of the invention for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression, for example, cancer. A further aspect of the invention relates to the use of a pharmaceutical comprising at least one compound of the invention for the manufacture of a medicament for the treatment of diseases and/or conditions caused by or associated with inappropriate S1P receptor modulating activity or expression such as cancer.

Synthesis, structure-affinity relationships, and biological activities of ligands binding to retinoic acid receptor subtypes

The retinoic acid receptors (RARs) transduce retinoid dependant gene regulation, and many biological effects of retinoids are mediated through binding and activation of three closely related receptor subtypes (RARα, RARβ, and RARγ). In order to investigate the role of receptor subtypes, we have carried out a chemical synthesis program to seek selective retinoids for these receptors. We measured receptor binding affinity using recombinant RARα, -β, and -γ proteins and assessed cellular differentiating activity in F9 murine teratocarcinoma cells (F9 cells). This research has identified the 4-substituted-3-(1-adamantyl)phenyl moiety as a new pharmacophore which can replace the β-cyclogeranylidene ring of the naturally ocurring all- trans-retinoic acid. Two chemical series derived from the general structures 6-(3-tertioalkyl-phenyl)-2-naphthoic acid (series I) and 4-[(E)-2-(3- tertioalkylphenyl)propenyl]benzoic acid (series II) were developed. In particular, we have obtained the RARγ selective derivatives 6-[3-(1- adamantyl)-4-hydroxyphenyl]-2-naphthoic acid (7) [K(i)(RARα) = 6500 nM, Ki(RARβ) = 2480 nM, K(i)(RARγ) = 77 nM] and 4-[(E)-2-[3-(1-adamantyl)-4- hydroxyphenyl]propenyl]benzoic acid (19) [K(i)(RARα) = 1 144 nM, K(i)(RARβ) = 1245 nM, K(i)(RARγ) = 53 nM]. In series I, the presence of a phenol group, irrespective of the nature of tertioalkyl group, imparted at least partial RARγ selectivity, whereas in series II, the presence of both adamantyl and phenol groups is needed to confer RARγ selectivity. The RARγ selective ligands induce differentiation in F9 cells (7, AC50 = 33 nM; 19, AC50 = 66 nM). From series I, a mixed RARβ-γ agonist with potent cellular differentiating activity was selected for development as a topical antiacne agent, 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthoic acid (5, CD 271) [K(i)(RARα) = 1100 nM, K(i)-(RARβ) = 34 nM, K(i)(RARγ) = 130 nM, AC50(F9) = 37 nM]. Finally, from series II, we have obtained a weak antagonist in the F9 cellular differentiation assay, 4-[(E)-2-(3-tert-butyl- 4-hydroxyphenyl)propenyl]benzoic acid (15, IC50 = 700 nM).

Process for the preparation of 1-adamantane derivatives

A process for the preparation of 1-adamantane derivatives characterized by the fact that a 1-acyloxyadamantane, in which the acyl group contains 1 to 4 carbon atoms, is reacted with a receptor compound in a linear aliphatic or cycloaliphatic type solvent in the presence of concentrated sulfuric acid and at ambient temperature.

Benzo (b) thiophene carboxylate derivatives and pharmaceutical compositions

Aromatic heterocyclic derivatives have the formula STR1 wherein R1 represents STR2 wherein R3 represents hydrogen, --OR4 wherein R4 represents hydrogen, alkyl having 1-20 carbon atoms or mono- or polyhydroxyalkyl or R3 represents STR3 wherein r' and r" represent hydrogen, lower alkyl or together form a heterocycle, R2 represents hydrogen or --CH3 and Ar represents STR4 wherein Z is O or S, STR5 wherein R5 is lower alkyl or STR6 wherein R6 is hydrogen or alkyl having 1-10 carbon atoms and R7 represents alkyl having 4-12 carbon atoms or cycloalkyl, Y is CH or a nitrogen atom and X represents oxygen, sulfur or --N--R8 when R8 represents hydrogen, lower alkyl or lower alkoxycarbonyl, with the proviso that (i) when Y is CH and X is oxygen or sulfur Ar is other than C and (ii) when Y is nitrogen and X is oxygen, Ar is other than (C) or (D) in which R6 is alkyl having 1-4 carbon atoms and R7 is branched alkyl having 4-12 atoms useful in veterinary or human therapy and in cosmetic formulations.