64741-15-7

Upstream product

• 621-82-9 Cinnamic acid 
• 108-42-9 3-chloro-aniline 
• 102-92-1 Cinnamoyl chloride 
• 66680-87-3 (E)-1-phenyl-(2-tributylstannyl)ethene 
• 2909-38-8 m-chlorophenyl isocyanate 
• 140-10-3 (E)-3-phenylacrylic acid 
• 15386-81-9 N-(3-chlorophenyl)malonamic acid 
• 100-52-7 benzaldehyde 
• 102-92-1 cinnamoyl chloride 

Relevant academic research and scientific papers

Synthesis, structure, and biological assay of cinnamic amides as potential EGFR kinase inhibitors

A series of derivatives of cinnamic amide (compounds 2a-2v) were synthesized and evaluated for antiproliferative activities against the human breast cancer cell line MCF-7- and EGFR-inhibitory activities. The structures of compounds 2b and 2i were determined by single-crystal X-ray diffraction analysis. Compounds 2f and 2j showed moderate EGFR inhibitory activity with IC50 values of 5.16 and 7.37 μM, respectively. Docking simulation of compound 2f was carried out to illustrate the binding mode of the molecule into the EGFR active site. Structure-activity relationship analysis found that the N-phenyl rings are required for enhancing the activities.

Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors

Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.

Esters, amides and substituted derivatives of cinnamic acid: Synthesis, antimicrobial activity and QSAR investigations

A series of esters (Ia-k), substituted derivatives (II a-d) and amides (IIIa-q) of cinnamic acid were synthesized and evaluated as antibacterial and antifungal agents. All the derivatives belonging to the series I, II and III showed antimicrobial activity comparable to the standard. Compounds If and IIc proved to be the most effective compounds. Quantitative structure-activity relationship (QSAR) investigation with multiple linear regression analysis was applied to find a correlation between different calculated physicochemical parameters of the compounds and biological activity. The quantitative models relating the structural features of cinnamic acid derivatives Ia-k, II a-d and IIIa-q and their antimicrobial activity showed that Gram negative Escherichia coli and Candida albicans (fungus) were the most sensitive microorganisms.

Nucleophilic substitution reactions of cinnamoyl chlorides with anilines in acetonitrile and acetonitrile-methanol mixtures

Kinetic studies on the solvolysis (in MeOH-MeCN mixtures) and aminolysis (with anilines in MeCN) of cinnamoyl chlorides have been carried out at 25.0 deg C.The relatively large negative values of ρY+ = -0.9 ca. -1.5 for the methanolysis are consistent with a dissociative SN2-like mechanism.For the aminolysis, the ρy values are positive (ρY = 0.52 ca. 1.64) and ρX values range from -1.68 to -2.51 in acetonitrile.The positive values of βX = 0.6-0.9 and ρXY = 0.88 in acetonitrile, and isotope effect data suggest that the aminolysis proceeds by a stepwise mechanism with rate-limiting breakdown of the tetrahedral intermediate, T+/-.It is noted that in the acyl-transfer reactions proceeding by rate-limiting departure of the leaving group from the tetrahedral intermediate the signs of both ρY and ρXY are positive and the reactivity-selectivity principle (RSP) is valid in general.

Tin for Organic Synthesis, 11. A Mild and Effective Synthesis of α,β-unsaturated Carboxamides and Sulfonamides by Electrophilic Substitution of Alkenylstannanes with Isocyanates

A new and effective method for the preparation of a variety of olefinic carboxamides 6a-k and N-(4-methylphenylsulfonyl)carboxamides 7a-d is described.The reaction of aryl and alkyl isocyanates 4a-c or 4-methylphenylsulfonyl isocyanate 5 with 1-alkenyltrialkylstannanes 1a-e and di-1-alkenyldibutylstannanes 2a-c in the presence of aluminium trichloride provides the corresponding N-aryl-substituted olefinic carboxamides 6a-k or the N-(4-methylphenylsulfonyl)-substituted olefinic carboxamides 7a-d in good yields.The stannyl moiety is superior to hydrogen as a leaving group and enables electrophilic ipso substitution at the vinylic system.In the case of di-1-alkenyldibutylstannanes the substitutions are also stereospecific, whereas the reactions of 1-alkenyltrialkylstannanes with isocyanates proceed with partial isomerisation. - Key Words: Electrophilic vinylic substitution / Isocyanates / α,β-Unsaturated amides, synthesis of / Carbodestannylation / Alkenylstannanes, applications of