138175-49-2

Usage

InChI:InChI=1/C11H10N2O3/c1-16-10-5-7(2-3-9(10)14)4-8(6-12)11(13)15/h2-5,14H,1H3,(H2,13,15)/b8-4+

Upstream product

• 121-33-5 vanillin 
• 3696-12-6 2-(4-hydroxy-3-methoxybenzylidene)malononitrile 
• 107-91-5 cyanoacetic acid amide 

Relevant academic research and scientific papers

LQFM184: A Novel Wide Ultraviolet Radiation Range Absorber Compound

The use of sunscreen has become an indispensable daily routine since UV radiation is a critical environmental stress factors for human skin. This study focused on the design, synthesis, thermal/chemical stability and efficacy/safety evaluations of a new h

Synthesis of 2-cyanoacrylamides through Pd-catalyzed monohydration of methylenemalononitriles

A straightforward and efficient method has been developed for the synthesis of 2-cyanoacrylamide from 2-methylenemalononitriles through monohydration. A series of methylenemalononitriles underwent the reaction under mild and simple reaction conditions wit

Use of a water solution of surfactant in Knoevenagel reaction

In reaction of vanillin with active methylene compounds in the presence of detergent Oksipav AP the corresponding substituted alkenes were formed in high yields.

(E)-2-Cyano-3-(substituted phenyl)acrylamide analogs as potent inhibitors of tyrosinase: A linear β-phenyl-α,β-unsaturated carbonyl scaffold

In this study, we synthesized (E)-2-cyano-3-(substituted phenyl)acrylamide (CPA) derivatives which possess a linear β-phenyl-α,β-unsaturated carbonyl scaffold and examined their inhibitory activities against tyrosinase. CPA analogs exerted inhibitory acti

Arylcyanoacrylamides as inhibitors of the Dengue and West Nile virus proteases

The 3-aryl-2-cyanoacrylamide scaffold was designed as core pharmacophore for inhibitors of the Dengue and West Nile virus serine proteases (NS2B-NS3). A total of 86 analogs was prepared to study the structure-activity relationships in detail. Thereby, it turned out that the electron density of the aryl moiety and the central double bond have a crucial influence on the activity of the compounds, whereas the influence of substituents of the amide residue is less relevant. The para-hydroxy substituted analog was found to be the most potent inhibitor in this series with a Ki-value of 35.7 μM at the Dengue and 44.6 μM at the West Nile virus protease. The aprotinin competition assay demonstrates a direct interaction of the inhibitor molecule with active centre of the Dengue virus protease. The target selectivity was studied in a counterscreen with thrombin and found to be 2.8:1 in favor of DEN protease and 2.3:1 in favor of WNV protease, respectively.

An efficient benzyltriethylammonium chloride catalysed preparation of electrophilic alkenes: a practical synthesis of trimethoprim

The Knoevenagel condensation of carbonyl compounds with active methylene compounds was readily carried out with benzyltriethylammonium chloride as a catalytic agent, under solvent-free conditions to produce olefinic products in high yeilds: the scope of this protocol is utilised for the synthesis of the antibacterial agent trimethoprim.

Structural studies on bioactive compounds. 32. Oxidation of tyrphostin protein tyrosine kinase inhibitors with hypervalent iodine reagents

Hydroxylated styrenes (tyrphostins) undergo oxidation by hypervalent iodine oxidants such as [(diacetoxy)iodo]benzene (DAIB) to give a range of products depending on the structure of the phenolic substrate, the solvent, the oxidant stoichiometry, and the purification strategy. Conditions have been developed to modify the phenolic component of the tyrphostin without affecting the appended substituted-vinyl moiety. Novel products include: unstable 2-acyloxy-2-methoxy-4-(substituted-vinyl)cyclohexadienones and their rearrangement products 2-acyloxy-4-hydroxy-3-methoxy-1-(substituted- vinyl)benzenes; phenyliodoniophenolates and their rearrangement products iodophenoxytyrphostins; and 3,3'-dialkoxy-2,2'-dihydroxy-5,5'-di(substituted- vinyl)biphenyls. None of these oxidation products displayed enhanced activity in vitro in the NCI 60-cell line panel or in a panel of human breast cancer cell lines, compared to their tyrphostin precursors. The inhibitory activity of three representative tyrphostins (3e,n, 28) was not modulated by aerobic/anaerobic conditions in MCF-7 and MDA 468 cells and was independent of EGFR status in clones of ZR75B cells transfected with this receptor. Basal growth of MCF-7 cells was unaffected by co-administration of the growth factors EGF, TGF-α, IGF-I, and IGF-II, and the new agents did not inhibit EGFR and c-erbB2 autophosphorylation in cell lysates from MDA 468 or SkBr3 cells, respectively, suggesting that receptor tyrosine kinases are not targets for these compounds. Growth stimulation by the tyrphostin 3n in the ER+ breast cell lines MCF-7, T47D, and ZR75-1 was abolished by 1 μM tamoxifen, suggesting that this compound has estrogen agonist activity.

Tellurium(IV) tetrachloride catalysed facile Knoevenagel reaction

Non-enolisable aldehydes (I) and active methylene compounds (II) react in the presence of tellurium(IV) tetrachloride (catalytic) to give the corresponding α,β-unsaturated carbonyl compounds (III) in excellent yields and high purity.

Zinc chloride as a new catalyst for Knoevenagel condensation

The Knoevenagel condensation of carbonyl substrates with acidic methylene reagents proceeds smoothly in presence of zinc chloride, without the need for solvent, to produce products of good purity in high yield.