3695-85-0

Usage

Chemical compound

2-Propenoic acid, 2-cyano-3-(4-hydroxyphenyl)-, methyl ester

Commonly referred to as

Methyl 4-cyano-3-(4-hydroxyphenyl)-2-butenoate

Derivative of

2-cyano-3-(4-hydroxyphenyl)-acrylic acid

Uses

Organic synthesis and pharmaceutical research

Properties

Anti-inflammatory and anti-cancer

Physical state

Yellow crystalline solid

Molecular weight

225.23 g/mol

Boiling point

363.2°C

Potential applications

Medicine, chemistry, and biotechnology

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 105-34-0 methyl 2-cyanoacetate 
• 105-56-6 ethyl 2-cyanoacetate 
• 67-56-1 methanol 
• 28166-41-8 α-cyano-4-hydroxycinnamic acid 

Relevant academic research and scientific papers

(E)-Propyl α-Cyano-4-Hydroxyl Cinnamylate: A High Sensitive and Salt Tolerant Matrix for Intact Protein Profiling by MALDI Mass Spectrometry

Low-abundance samples and salt interference are always of great challenges for the practical protein profiling by matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS). Herein, a series of carboxyl-esterified derivatives of α-cyano-4-hy

β2-Homo-amino acid scan of μ-selective opioid tetrapeptide TAPP

TAPP (H-Tyr-d-Ala-Phe-Phe-NH2) is a potent, μ-selective opioid ligand. In order to gain further insights into pharmacophoric features of this tetrapeptide, we have performed a β2-Homo-amino acid (β2hAA) scan of the TAPP sequence. To this aim, 10 novel analogues have been synthesized and evaluated for μ-opioid and δ-opioid receptor affinity as well as for stability in human plasma. The derivatives included compounds in which a (R)- or (S)-β2-Homo-Homologue replaced the amino acids in the TAPP sequence. The derivatives with (R)- or (S)-β2hPhe4 turned out to bind μOR with affinities equal to that of the parent. β2hAAs in position 1 and 3 resulted in rather large affinity decreases, but the change differed depending on the stereochemistry. β2-Homologation in the second position gave derivatives with very poor μOR binding. According to molecular modelling, the presented α/β-peptides adopt a variety of binding poses with their common element being an ionic interaction between a protonable amine of the first residue and Asp147. A feature required for high μOR affinity seems the ability to accommodate the ring in the fourth residue in a manner similar to that found for TAPP. Contrary to what might be expected, several compounds were significantly less stable in human plasma than the parent compound.

Optimisation of estrogen receptor subtype-selectivity of a 4-Aryl-4H-chromene scaffold previously identified by virtual screening

4-Aryl-4H-Chromene derivatives have been previously shown to exhibit anti-proliferative, apoptotic and anti-angiogenic activity in a variety of tumor models in vitro and in vivo generally via activation of caspases through inhibition of tubulin polymerisation. We have previously identified by Virtual Screening (VS) a 4-aryl-4H-chromene scaffold, of which two examples were shown to bind Estrogen Receptor α and β with low nanomolar affinity and 20-fold selectivity for α over β and low micromolar anti-proliferative activity in the MCF-7 cell line. Thus, using the 4-aryl-4H-chromene scaffold as a starting point, a series of compounds with a range of basic arylethers at C-4 and modifications at the C3-ester substituent of the benzopyran ring were synthesised, producing some potent ER antagonists in the MCF-7 cell line which were highly selective for ERα (compound 35; 350-fold selectivity) or ERβ (compound 42; 170-fold selectivity).

Tripterine (iso) ferulic acid ester derivative as well as preparation method and application thereof

The invention discloses a tripterine (iso) ferulic acid ester derivative as well as a preparation method and application thereof and belongs to the field of biological medicines. The tripterine (iso)ferulic acid ester derivative is of a structure with a formula I as shown in the specification; in the formula, R1-R6 are respectively selected from H, alkyl, heteroatom-containing alkyl, halogen or nitryl; X is selected from saturated or unsaturated direct-chain aliphatic hydrocarbon segments with 2-5 carbon atoms. The preparation method of the compound is gentle in reaction condition, low in reagent toxicity, easy in raw material obtaining, convenient in aftertreatment and high in yield. Pharmacology experiment shows that the compound disclosed by the invention has excellent anti-tumor activity and can be applied to preparation of anti-tumor medicines.

Design, synthesis and antitumor evaluation of novel celastrol derivatives

On the basis of the hybridization strategy of natural products, a total of 32 novel celastrol hybrids were designed, synthesized and evaluated for their antitumor activities. Most of these derivatives exihibited significant antiproliferative activities compared to celastrol, among which compound 29 displayed the strongest inhibitory capability [IC50 = 0.15 ± 0.03 μM (A549),0.17 ± 0.03 μM (MCF-7), 0.26 ± 0.02 μM (HepG2)], which exhibited equal or superior anti-cancer activities in comparison to 2-cyano-3,12-dioxoolean-1,9 (11)-dien-28-oic acid methyl ester (CDDO-Me). The mechanism of pharmacological research indicated that 29 possessed the ability to disrupt Hsp90-Cdc37 complex which was stronger than celastrol. Meanwhile, compound 29 could induce abnormal regulation of clients (p-Akt and Cdk4) of Hsp90 and cell cycle arrest at G0/G1 phase in a concentration-dependent manner. In addition, compound 29 could also induce cell apoptosis through the death receptor pathway on A549 cells. Taken together, our results demonstrated that 29 might be a promising novel candidate for further druggability research.

Knoevenagel condensation catalyzed by novel Nmm-based ionic liquids in water

A series of novel N-methyl morpholine (Nmm) based ionic liquids with 1,2-propanediol group were synthesized and used as catalysts for Knoevenagel condensation at room temperature in water. Under the effect of the catalyst, various aldehydes or aliphatic ketones could react with a wide range of activated methylene compounds well, including malononitrile, alkyl cyanoacetate, cyanoacetamide, β-diketone, barbituric acid, 2-arylacetonitrile and thiazolidinedione. Furthermore, most of the products could be separated just by filtrating and washing with water. Additionally, the catalyst is recyclable and applicable for the large-scale synthesis.

Beta amino acid-modified and fluorescently labelled kisspeptin analogues with potent KISS1R activity

Kisspeptin analogues with improved metabolic stability may represent important ligands in the study of the kisspeptin/KISS1R system and have therapeutic potential. In this paper we assess the activity of known and novel kisspeptin analogues utilising a du

First report of the application of simple molecular complexes as organo-catalysts for Knoevenagel condensation

A series of molecular complexes have been designed, synthesized and used as organo-catalysts for the first time for very efficient Knoevenagel condensation. Molecular complexes are thermally stable, easily recyclable, and have a low cost of preparation. T

A convenient synthesis of pyrimidinone and pyrimidine containing bisheteroarenes and analogs

The synthesis of pyrimidinone containing bisheteroarenes (3) and related analogs (9 and 10) by the reaction of active methylenes or substituted methyl acrylate with nitrogen containing precursors viz. amidines, or thiourea in water as well as other organic solvents was studied. Synthesized compounds have further been explored for the synthesis of diversified pyrimidines 4, 6-8, 11, 12 and 14 through a sequential approach. This journal is the Partner Organisations 2014.

Sevelamer as an efficient and reusable heterogeneous catalyst for the Knoevenagel reaction in water

A catalyst system of Sevelamer, a phosphate-binding drug, has been prepared and used in the Knoevenagel reaction of aromatic aldehydes in water to produce substituted electrophilic alkenes. The products were obtained in excellent yields. Several novel, re