61312-35-4

Usage

InChI:InChI=1/C12H14O4/c1-9(13)7-12(14)16-8-10-3-5-11(15-2)6-4-10/h3-6H,7-8H2,1-2H3

Upstream product

• 674-82-8 4-methyleneoxetan-2-one 
• 105-13-5 4-Methoxybenzyl alcohol 
• 141-97-9 ethyl acetoacetate 
• 5394-63-8 2,2,6-trimethyl-4H-1,3-dioxin-4-one 
• 105-45-3 acetoacetic acid methyl ester 
• 1694-31-1 tert-butyl acetoacetate 

Downstream Products

• 299918-66-4 C₃₃H₃₃NO₄ 
• 1442442-94-5 C₂₀H₂₀N₂O₄ 
• 1430815-67-0 4-methoxybenzyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1442442-09-2 C₂₀H₁₉BrN₂O₄ 
• 303204-56-0 4-methoxybenzyl 4-(3-bromophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 306749-42-8 C₂₀H₁₉BrN₂O₄ 
• 347353-60-0 4-methoxybenzyl 4-(3-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 306751-45-1 4-methoxybenzyl 4-(2-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 330674-54-9 4-methoxybenzyl 4-(4-fluorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 
• 1442442-11-6 C₂₀H₁₉IN₂O₄ 
• 1442442-12-7 C₂₀H₁₈ClFN₂O₄ 
• 402503-21-3 C₂₁H₁₉F₃N₂O₄ 
• 347351-72-8 C₂₀H₁₉N₃O₆ 
• 1442442-13-8 C₂₁H₁₉N₃O₄ 

Relevant academic research and scientific papers

NEW ANALOGS AS ANDROGEN RECEPTOR AND GLUCOCORTICOID RECEPTOR MODULATORS

The present invention relates to novel dihydropyridine derivatives of formula (I): as modulators of nuclear receptors selected from androgen receptor and glucocorticoid receptor, to processes for their preparation, to pharmaceutical compositions comprising said compounds and to the use of said for manufacturing a medicament for the treatment of pathological conditions or diseases that can improve by modulation of androgen receptor and/or glucocorticoid receptor, selected from cancer, metastasizing cancers, benign prostate hyperplasia, polycystic ovary syndrome (PCOS), hair loss, hirsutism, acne, hypogonadism, muscle wasting diseases, cachexia, Cushing's syndrome, anti-psychotic drug induced weight gain, obesity, post-traumatic stress disorder and alcoholism.

Enzymatic Synergism in the Synthesis of β-Keto Esters

Reaction of alcohols with ethyl and tert-butyl acetoacetate catalyzed by a combination of commercially available enzymes is shown to be a convenient method for the preparation of a range of acetoacetic acid derivatives. Systematic studies proved that the combination of two or more enzymes enhances the yield of the reaction. Application of the selected enzyme mixture for enzymatic transesterification of various β-keto esters provided the respective products in excellent yields up to 96% and quantitative within 24 and 48 hours, respectively. The presented methodology is simple and mild, and can be used to prepare acetoacetates from primary and secondary alcohols. Application of a selected enzyme mixture for enzyme-catalyzed esterification of various carboxylic acids provided the respective β-hydroxy esters in excellent yields up to 96% and quantitative within 24 and 48 hours, respectively.

Nano CuFe2O4: An efficient, magnetically separable catalyst for transesterification of β-ketoesters

The preparation of a variety of β-ketoesters was achieved in high yields from methyl acetoacetate under neutral conditions through the utilization of magnetic CuFe2O4 nanoparticles as catalyst. Recycling of the catalyst was performed up to eight times without significant loss in activity. The catalyst was characterized using XRD, XPS, SEM and TEM techniques.

Straightforward access to the [3.2.2]nonatriene structural framework via intramolecular cyclopropenation/buchner reaction/cope rearrangement cascade

A one-pot cascade process of benzyl enoldiazoacatates, initiated by dirhodium(II)-catalyzed intramolecular cyclopropene formation, occurs via a subsequent Buchner reaction and Cope rearrangement to provide straightforward access to bicyclo[3.2.2]nonatriene derivatives in high yields and selectivities.

Dihydropyrimidin-2(1H)-ones and dihydropyrimidin-2(1H)-thiones as inhibitors of sodium iodide symporter

The invention relates to novel dihydropyrimidin-2(1H)-ones and dihydropyrimidin-2(1H)-thiones of formula (I): for use as medicaments, and in particular as inhibitors of sodium iodide symporter (NIS) and reducers of iodine transport and/or accumulation into NIS-expressing cells. The invention also relates to a pharmaceutical composition comprising at least one compound of formula (I) as active principle. Finally, the present invention relates to specific dihydropyrimidin-2(1H)-ones and dihydropyrimidin-2(1H)-thiones of formula (I) as such.

DIHYDROPYRIMIDIN-2(1H)-ONES AND DIHYDROPYRIMIDIN-2(1H)-THIONES AS INHIBITORS OF SODIUM IODIDE SYMPORTER

The invention relates to novel dihydropyrimidin-2(lH)-ones and dihydropyrimidin- 2(lH)-thiones of formula (la). The invention also relates to the use of such compounds as medicaments, and in particular as inhibitors of sodium iodide symporter (NIS) and reducers of iodine transport and/or accumulation into NIS expressing cells. The invention also concerns a pharmaceutical composition comprising at least one compound of formula (la) as active principle.

An efficient synthesis of β-ketoesters via transesterification and its application in Biginelli reaction under solvent-free, catalyst-free conditions

A simple and efficient transesterification process for the synthesis of β-ketoester derivatives has been achieved by the reaction of methyl β-ketoester with higher alcohols at 110 C under solvent-free, catalyst-free conditions and its application in synthesis of 3,4-dihydropyrimidin-2(1H)-ones C-5 ester derivatives via Biginelli reaction has been described.

Synthesis and Evaluation of 3,4-Dihydropyrimidin-2(1H)-ones as Sodium Iodide Symporter Inhibitors

The sodium iodide symporter (NIS) is responsible for the accumulation of iodide in the thyroid gland. This transport process is involved in numerous thyroid dysfunctions and is the basis for human contamination in the case of exposure to radioactive iodine species. 4-Aryl-3,4-dihydropyrimidin-2(1H)-ones were recently discovered by high-throughput screening as the first NIS inhibitors. Described herein are the synthesis and evaluation of 115 derivatives with structural modifications at five key positions on the pyrimidone core. This study provides extensive structure-activity relationships for this new class of inhibitors that will serve as a basis for further development of compounds with invivo efficacy and adequate pharmacokinetic properties. In addition, the SAR investigation provided a more potent compound, which exhibits an IC50 value of 3.2nM in a rat thyroid cell line (FRTL5).

Synthesis, evaluation and absolute configuration assignment of novel dihydropyrimidin-2-ones as picomolar sodium iodide symporter inhibitors

A small library of dihydropyrimidin-2-ones (DHPMs) was synthesized and evaluated for their potency to block iodide entrapment in rat thyroid cells. Synthesis was achieved using the multicomponent Biginelli reaction. Twelve compounds were tested for the inhibition of sodium iodide symporter (NIS) in a cell-based assay. One newly synthesized derivative exhibited a remarkably strong activity, with a half-maximum inhibitory concentration value (IC50) of 65 pM. Three DHPMs were further resolved from racemates using chiral HPLC and absolute configurations were assigned using circular dichroism spectroscopy. Biological evaluation showed that most of the activity against NIS resides in one enantiomer. This study provides new insights for the development of anti-thyroid drugs, as well as for the synthesis of novel pharmacological tools designed to investigate iodide transport mechanisms at cellular and molecular levels.

AgOTf-catalyzed transesterification of β-keto esters

AgOTf proved to be an effective catalyst for the transesterification of β-keto esters with primary, secondary and tertiary alcohols. The products were obtained in high yield within a reasonable reaction time period. The kinetics of the transesterification reaction were also studied and the reaction was found to follow second-order kinetics. Copyright