304431-56-9

Upstream product

• 89793-12-4 ethyl 2-chloropyrimidine-5-carboxylate 
• 763-69-9 ethyl 3-ethoxypropionate 
• 2974-30-3 (Z)-ethyl-2-(ethoxymethyl)-3-methoxyacrylate 
• 2380-36-1 3,5-di-tert-butylaniline 
• 33458-27-4 ethyl 2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 95928-49-7 ethyl 2-oxo-1,2-dihydropyrimidine-5-carboxylate 
• 304431-55-8 ethyl 2-[N-(3,5-di-tert-butylphenyl)amino] pyrimidine-5-carboxylate 
• 74-88-4 methyl iodide 

Relevant academic research and scientific papers

HETEROCYCLIC CARBOXYLIC ACID DERIVATIVES

Compounds or salts thereof represented by the formula (I) wherein R1 represents hydrogen atom, a C1-6 alkyl group, a C1-6 alkenyl group, or an acyl group, R2 and R3 represent hydrogen atom or a C1-6 alkyl group, or adjacent R2 and R3 may combine to form 5- to 7-membered ring, R4 represents hydrogen atom, hydroxyl group, a C1-6 alkoxyl group, a C1-6 alkyl group, HAr represents a heteroaryl-diyl group consisting of a 5-membered or 6-membered ring containing 1 to 3 hetero atoms, R5 represents hydrogen atom or a C1-6 alkyl group. The compounds or the salts thereof have retinoid-like physiological activities or controlling activity on physiological activities of retinoid.

Retinoidal pyrimidinecarboxylic acids. Unexpected diaza-substituent effects in retinobenzoic acids

Several pyridine- and pyrimidine-carboxylic acids were synthesized as ligand candidates for retinoid nuclear receptors, retinoic acid receptors (RARs) and retinoic X receptors (RXRs). Although the pyridine derivatives, 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carbamoyl]pyridine- 3-carboxylic acid (2b) and 6-[(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)carboxamido]pyridin e-3-carboxylic acid (5b) are more potent than the corresponding benzoic acid-type retinoids, Am80 (2a) and Am580 (5a), the replacement of the benzene ring of Am580 (5a), Am555 (6a), or Am55 (7a) with a pyrimidine ring caused loss of the retinoidal activity both in HL-60 cell differentiation assay and in RAR transactivation assay using COS-1 cells. On the other hand, pyrimidine analogs (PA series, 10 and 11) of potent RXR agonists (retinoid synergists) with a diphenylamine skeleton (DA series, 8 and 9) exhibited potent retinoid synergistic activity in HL-60 cell differentiation assay and activated RXRs. Among the synthesized compounds, 2-[N-n-propyl-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino] pyrimidine-5-carboxylic acid (PA013, 10e) is most active retinoid synergist in HL-60 assay.