61844-62-0

Upstream product

• 7400-08-0 para-coumaric acid 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 7400-08-0 p-Coumaric Acid 
• 100-51-6 benzyl alcohol 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 27724-89-6 4-(Benzyloxycarbonylamino-methyl)-cyclohexanecarboxylic acid 4-((E)-2-benzyloxycarbonyl-vinyl)-phenyl ester 
• 1070774-65-0 benzyl O-TIPS-para-cumarate 
• 1016892-02-6 benzyl (E)-3-(4-tert-butyldimethylsilyloxyphenyl)prop-2-enoate 

Relevant academic research and scientific papers

BIVALENT LECA INHIBITORS TARGETING BIOFILM FORMATION OF PSEUDOMONAS AERUGINOSA

The present invention relates to divalent compounds binding to LecA. The compounds are useful to block biofilm formation of Pseudomonas aeruginosa. The invention further relates to pharmaceutical compositions comprising these compounds and to therapeutic methods and uses of these compounds, in particular to therapeutic methods and uses for the treatment of Pseudomonas aeruginosa infections in a subject. The invention also relates to imaging of infections, such as biofilms produced by Pseudomonas aeruginosa, by using these divalent compounds.

Synthesis and Mesomorphic Properties of a Novel Ester Homologous Series: 4-(4'- n -Alkoxy Benzoyloxy) Benzyl Cinnamates

A novel homologous series 4-(4'-n-alkoxy benzoyloxy) benzyl cinnamates was synthesized and studied with a view to understanding and establishing the relationships between mesomorphism and molecular structure. The novel series consists of eleven members with the commencement of mesomorphism from the pentyloxy homologue onwards to the hexadecyl homologue. The remaining homologues are nonmesomorphic. All the mesomorphic homologues exhibit smectogenic mesomorphism in addition to nematogenic mesomorphism for a definite temperature range in an enantiotropic manner, except for the pentyloxy homologue, which exhibits only a nematogenic mesophase in an enantiotropic manner without the formation of a smectic phase. The texture of the nematic mesophase is of the threaded or Schlieren type and the smectic mesophase is of the type A or C texture, as determined by a miscibility method. Transition temperatures were observed through an optical polarizing microscope equipped with a heating stage. The transition curves of a phase diagram predominantly behave in a normal manner, but partly deviated from normal behavior with the exhibition of an odd-even effect. Analytical and spectral data confirms the molecular structures of all homologues. The mesomorphic behavior of the present series is compared with other structurally similar known series. The mesomorphic temperatures vary between 106°C and 180°C. The mesophase length varies between 33°C to 53°C. Thus, the novel series is predominantly nematogenic and partly smectogenic with relatively high transition temperatures and is of a high melting type. The average thermal stabilities for smectic and nematic phases are 144.1°C and 171.4°C, respectively.

Inhibition of mammalian carbonic anhydrase isoforms I-XIV with a series of phenolic acid esters

A series of phenolic acid esters incorporating caffeic, ferulic, and p-coumaric acid, and benzyl, m/p-hydroxyphenethyl- as well as p-hydroxy-phenethoxy-phenethyl moieties were investigated for their inhibitory effects against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). Many of the mammalian isozymes of human (h) or murine (m) origin, hCA I-hCA XII, mCA XIII and hCA XIV, were inhibited in the submicromolar range by these derivatives (with KIs of 0.31-1.03 μM against hCA VA, VB, VI, VII, IX and XIV). The off-target, highly abundant isoforms hCA I and II, as well as hCA III, IV and XII were poorly inhibited by many of these esters, although the original phenolic acids were micromolar inhibitors. These phenols, like others investigated earlier, possess a CA inhibition mechanism distinct of the sulfonamides/sulfamates, clinically used drugs for the treatment of a multitude of pathologies, but with severe side effects due to hCA I/II inhibition. Unlike the sulfonamides, which bind to the catalytic zinc ion, phenols are anchored at the Zn(II)-coordinated water molecule, binding more externally within the active site cavity, and making contacts with amino acid residues at the entrance of the active site. As this is the region with the highest variability between the many CA isozymes found in mammals, this class of compounds shows isoform-selective inhibitory profiles, which may be exploited for obtaining pharmacological agents with less side effects compared to other classes of inhibitors.

Synthesis of caffeic acid phenethyl ester derivatives, and their cytoprotective and neuritogenic activities in PC12 cells

Twenty-one caffeic acid phenethyl ester (CAPE) derivatives were synthesized, and characterized by IR, HR-MS, 1H and 13C NMR analyses. All compounds were evaluated for their cytoprotective effects against H2O2-induced cytotoxicity and neuritogenic activities in the neurite outgrowth in PC12 cells. Compounds 1 and 20 exhibited stronger cytoprotective activities than their parent compound CAPE at 4 nM. Compounds 1, 4, 12 and 13 showed potential neuritogenic activities at 0.5 nM, while compounds 19 and 20 induced neurite outgrowth at 10 nM. The results from this study suggested that CAPE and its derivatives may be potential functional food ingredients for the prevention of neurodegenerative diseases.

Novel Cinnamate Esters - Synthesis and Mesomorphic Properties in Relation to Molecular Structure

A novel homologous series 4-[4′-n-alkoxy cinnamoyloxy] benzyl cinnamates consisting of 11 homologs was synthesized and studied with a view to understanding and establishing the relation between molecular structure and mesomorphic behavior of a substance. Mesomorphic behavior of the series commences from the third homolog and then continues until the last hexadecyloxy homolog. The first and second members of a series are non-mesomorphic. Nematogenic mesophase formation is observed from the propoxy homolog to the hexadecyloxy homolog, but the smectogenic mesophase formation is observed from the hexyloxy homolog to the tetradecyloxy homolog. All mesomorphic transitions are enantiotropic in nature. Transition temperatures were determined by an optical polarizing microscopy equipped with a heating stage. The textures of the nematic mesophase are threaded or Schlieren in type and that of the smectic mesophases are focal conic fan shaped of the smectic A or smectic C type. A phase diagram of the series shows a normal behavior of the transition curves with a minor abnormality of the last three homologs for the nematic-isotropic transition curve. The average thermal stability for smectic and nematic mesophases is 176.0°C and 219.3°C, respectively. Analytical and spectral data agree with the molecular structures of homologs. Mesomorphic phase length varies between 22°C and 76°C. Smectic phase length varies from 6°C to 33°C and nematic phase length varies from 22°C to 54°C. Thus, the novel present series is predominantly nematogenic and partly smectogenic. Mesomorphic properties of the novel series are compared with structurally similar other known homologous series.

Synthesis and structure-activity correlation of natural-product inspired cyclodepsipeptides stabilizing F-actin

The fundamental role played by actin In the regulation of eukaryotic cell maintenance and motility renders it a primary target for small-molecule intervention. in this arena, a class of potent cytotoxic cyclodepsipeptide natural products has emerged over the last quarter-century to stimulate the fields of biology and chemistry with their unique actin-stabilizing properties and complex peptide-polyketide hybrid structures. Despite considerable research effort, a structural basis for the activity of these secondary metabolites remains elusive, not least for the lack of high-resolution structural data and a reliable synthetic route to diverse compound libraries. in response to this, an efficient solid-phase approach has been developed and successfully applied to the total synthesis of Jasplakinolide and chondramide C and diverse analogues. The key macrocylization step was realized using ruthenium-catalyzed ring-closing metathesis (RCM) that in the course of a library synthesis produced discernible trends in metathesis reactivity and E/Z-selectivity, After optimization, the RCM step could be operated under mild conditions, a result that promises to facilitate the synthesis of more extensive analogue libraries for structure-function studies. The growth inhibitory effects of the synthesized compounds were quantified and structure-activity correlations established which appear to be in good alignment with relevant biological data from natural products. in this way a number of potent unnatural and simplified analogues have been found. Furthermore, potentially important stereochemical and structural components of a common pharmacophore have been identified and rationalized using molecular modeling. These data will guide in-depth mode-of-action studies, especially into the relationship between the cytotoxicity of these compounds and their actin-perturbing properties, and should inform the future design of simplified and functionalized actln stabilizers as well.

Chemoselective esterification of phenolic acids in the presence of sodium bicarbonate in ionic liquids

Chemoselective esterification of phenolic acids with dialkyl sulphates or alkyl halides in the presence of sodium bicarbonate in 1,3-dialkylimidazolium ionic liquids is reported in excellent yields and less reaction time as compared to organic solvents. Copyright Taylor & Francis Group, LLC.

A simple and effective method for chemoselective esterification of phenolic acids

A new method for efficient and chemoselective esterification of phenolic acids in KHCO3/alkyl halide/DMF reaction system is described, by which a series of phenoic acid esters were obtained in excellent yields.