15725-25-4

Usage

Appearance

Pale yellow color and mild odor

Classification

Ethyl ester derivative

Uses

Starting material in the synthesis of various pharmaceuticals and organic compounds, building block for the production of more complex molecules, potential applications in pharmaceutical development, agrochemical research, and material science studies.

Upstream product

• 141-97-9 ethyl acetoacetate 
• 591-31-1 3-methoxy-benzaldehyde 

Downstream Products

• 93181-53-4 4,7-dihydro-1,3,6-trimethyl-4-(3-methoxyphenyl)-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid ethyl ester, hydrochloride 
• 93181-59-0 4,7-dihydro-1,6-dimethyl-3-phenyl-4-(3-methoxyphenyl)-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid ethyl ester, hydrochloride 
• 86210-92-6 6-methoxy-2-methylquinoline-3-carboxylic acid ethyl ester 
• 114858-38-7 8-methoxy-2-methylquinoline-3-carboxylic acid ethyl ester 
• 69061-62-7 3-(3-methoxy-phenyl)-glutaric acid 
• 1263798-83-9 (R)-5-hydroxy-3-(3-methoxyphenyl)pentyl acetate 
• 1263798-65-7 (S)-5-hydroxy-3-(3-methoxyphenyl)pentyl acetate 
• 342821-10-7 C₁₆H₂₂O₅ 
• 1263798-50-0 (+/-)-5-hydroxy-3-(3-methoxyphenyl)pentyl acetate 
• 1263798-33-9 3-(3-methoxyphenyl)pentane-1,5-diyl diacetate 
• 1263798-19-1 3-(3-methoxyphenyl)pentane-1,5-diol 
• 103293-64-7 ethyl 4-(3-methoxyphenyl)-6-methyl-2-phenylpyrimidine-5-carboxylate 
• 1027905-11-8 6-[2-(2,4-diamino-5-methyl-pyrido[2,3-d]pyrimidin-6-ylmethyl)-4-methoxy-phenyl]-hex-5-ynoic acid benzyl ester 
• 1025971-40-7 5-[2-(2,4-diamino-5-methyl-pyrido[2,3-d]pyrimidin-6-ylmethyl)-4-methoxy-phenyl]-pent-4-ynoic acid benzyl ester 

Relevant academic research and scientific papers

Alkoxy base-mediated selective synthesis and new rearrangements of 1,2,4-triazolodipyrimidinones

A versatile approach for the synthesis of [1,2,4]triazolodipyrimidinones with various annulations of the triazole and pyrimidine rings was developed. The isomeric triazolodipyrimidinones were obtained by the stepwise condensation of partially hydrogenated

Visible-light-promoted iminyl-radical formation from Acyl oximes: A unified approach to pyridines, quinolines, and phenanthridines

A unified strategy involving visible-light-induced iminyl-radical formation has been established for the construction of pyridines, quinolines, and phenanthridines from acyl oximes. With fac-[Ir(ppy)3] as a photoredox catalyst, the acyl oximes were converted by 1 e- reduction into iminyl radical intermediates, which then underwent intramolecular homolytic aromatic substitution (HAS) to give the N-containing arenes. These reactions proceeded with a broad range of substrates at room temperature in high yield. This strategy of visible-light-induced iminyl-radical formation was successfully applied to a five-step concise synthesis of benzo[c]phenanthridine alkaloids.

Complementary lipase-mediated desymmetrization processes of 3-Aryl-1,5-disubstituted fragments. enantiopure synthetic valuable carboxylic acid derivatives

Desymmetrizaton enzymatic processes have been extensively studied searching for optimal methods of producing enantioenriched monoacetates from prochiral diols and diesters. AK lipase has been found as an excellent biocatalyst for the desymmetriaztion of a series of previously synthesized 3-arylpentane-1,5-diols derivatives. The access to (S)- or (R)-monoacetates in high optical purity (86-99% ee) has been possible by using acetylation or hydrolysis reactions, respectively, where the reaction parameters have been optimized in terms of source and amount of biocatalyst, temperature, solvent, and reaction time. The synthetic potential of enantiopure monoesters has been demonstrated by using these interesting chiral building blocks for the preparation of novel enantiopure carboxylic acid derivatives.

NOVEL PYRIMIDINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF CANCER AND FURTHER DISEASES

The invention concerns compounds of Formula (I): wherein L1, R1, R2, R3, R4 and X are as defined in the description. The present invention also relates to processes for the preparation of such compoun

Design, synthesis, and antifolate activity of new analogues of piritrexim and other diaminopyrimidine dihydrofolate reductase inhibitors with ω-carboxyalkoxy or ω-carboxy-1-alkynyl substitution in the side chain

As part of a search for dihydrofolate reductase (DHFR) inhibitors combining the high potency of piritrexim (PTX) with the high antiparasitic vs mammalian selectivity of trimethoprim (TMP), the heretofore undescribed 2,4-diamino-6-(2′,5′-disubstituted benzyl)pyrido[2,3-d]pyrimidines 6-14 with O-(ω-carboxyalkyl) or ω-carboxy-1-alkynyl groups on the benzyl moiety were synthesized and tested against Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium DHFR vs rat DHFR. Three N-(2,4-diaminopteridin-6-yl)methyl)-2′-(ω-carboxy-1-alkynyl) -dibenz[b,f]azepines (19-21) were also synthesized and tested. The pyridopyrimidine with the best combination of potency and selectivity was 2,4-diamino-5-methyl-6-[2′-(5-carboxy-1-butynyl)-5′-methoxy]benzyl] pyrimidine (13), with an IC50 value of 0.65 nM against P. carinii DHFR, 0.57 nM against M. avium DHFR, and 55 nM against rat DHFR. The potency of 13 against P. carinii DHFR was 20-fold greater than that of PTX (IC50 = 13 nM), and its selectivity index (SI) relative to rat DHFR was 85, whereas PTX was nonselective. The activity of 13 against P. carinii DHFR was 20 000 times greater than that of TMP, with an SI of 96, whereas that of TMP was only 14. However 13 was no more potent than PTX against M. avium DHFR, and its SI was no better than that of TMP. Molecular modeling dynamics studies using compounds 10 and 13 indicated a slight binding preference for the latter, in qualitative agreement with the IC50 data. Among the pteridines, the most potent against P. carinii DHFR and M. avium DHFR was the 2′-(5-carboxy-1-butynyl) dibenz[b,f]azepinyl derivative 20 (IC50 = 2.9 nM), whereas the most selective was the 2′-(5-carboxy-1-pentynyl) analogue 21, with SI values of > 100 against both P. carinii and M. avium DHFR relative to rat DHFR. The final compound, 2,4-diamino-5-[3′-(4-carboxy-1-butynyl)-4′-bromo- 5′-methoxybenzyl]pyrimidine (22), was both potent and selective against M. avium DHFR (IC50 = 0.47 nM, SI = 1300) but was not potent or selective against either P. carinii or T. gondii DHFR.

Studies on cerebral protective agents. I. Novel 4-arylpyrimidine derivatives with anti-anoxic and anti-lipid peroxidation activities

Novel 4-arylpyrimidine derivatives were synthesized by the oxidation of 4-aryl-1,4-dihydropyrimidines, and their effects on anti-anoxic (AA) activity in mice and anti-lipid peroxidation (ALP) activity in rat brain mitochondria were investigated. Among these compounds, ethyl 6-methyl-2-phenyl-4-(4-pyridyl)-5-pyrimidinecarboxylate (4b) has AA activity (10mg/kg, i.p.) and ethyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (4f) has ALP activity (73% inhibition at 10-5 g/ml). The latter compound (100mg/kg, i.p.) was also effective on arachidonate-induced cerebral edema in rats with comparable potency to that of vitamin E.