53527-04-1Relevant articles and documents
Vanilla amide synthesis method
-
Paragraph 0049-0052, (2021/06/13)
The invention discloses a vanilla amide synthesis method, which comprises the following step: by taking alcohol and vanilla amide as raw materials, or aldehyde and vanilla amide as raw materials, inorganic ferric salt and inorganic indium salt as a composite catalyst and oxygen as an oxidant, carrying out one-pot reaction in an organic solvent to generate vanilla amide. The synthesis raw materials adopted by the synthesis method are wide in source, a large amount of chemical reaction waste can be avoided in the whole reaction process, and the synthesis method is clean and environmentally friendly, has the advantages of mild and controllable reaction conditions, simple operation, convenience in product separation and purification, high product yield, wide universality of reaction substrates and the like, and is a method suitable for industrial production.
Biocatalytic N-Acylation of Amines in Water Using an Acyltransferase from Mycobacterium smegmatis
Contente, Martina Letizia,Pinto, Andrea,Molinari, Francesco,Paradisi, Francesca
, p. 4814 - 4819 (2018/11/10)
A straightforward one-step biocatalyzed synthesis of different N-acyl amides in water was accomplished using the versatile and chemoselective acyltransferase from Mycobacterium smegmatis (MsAcT). Acetylation of primary arylalkyl amines was achieved with a range of acetyl donors in biphasic systems within 1 hour and at room temperature. Vinyl acetate was the best donor which could be employed in the N-acetylation of a large range of primary amines in excellent yields (85–99%) after just 20 minutes. Other acyl donors (including formyl-, propionyl-, and butyryl-donors) were also efficiently employed in the biocatalytic N-acylation. Finally, the biocatalyst was tested in transamidation reactions using acetamide as acetyl donor in aqueous medium, reaching yields of 60–70%. This work expands the toolbox of preparative methods for the formation of N-acyl amides, describing a biocatalytic approach easy to accomplish under mild conditions in water. (Figure presented.).
Photoactivatable, biologically-relevant phenols with sensitivity toward 2-photon excitation
McLain, Duncan E.,Rea, Adam. C.,Widegren, Magnus B.,Dore, Timothy M.
, p. 2151 - 2158 (2015/12/04)
Spatio-temporal release of biologically relevant small molecules provides exquisite control over the activation of receptors and signaling pathways. This can be accomplished via a photochemical reaction that releases the desired small molecule in response to irradiation with light. A series of biologically-relevant signaling molecules (serotonin, octopamine, capsaicin, N-vanillyl-nonanoylamide, estradiol, and tyrosine) that contain a phenol moiety were conjugated to the 8-bromo-7-hydroxyquinolinyl (BHQ) or 8-cyano-7-hydroxyquinolinyl (CyHQ) photoremovable protecting groups (PPGs). The CyHQ caged compounds proved sensitive toward 1PE and 2PE processes with quantum efficiencies of 0.2-0.4 upon irradiation at 365 nm and two-photon action cross sections of 0.15-0.31 GM when irradiated at 740 nm. All but one BHQ caged compound, BHQ-estradiol, were found to be sensitive to photolysis through 1PE and 2PE with quantum efficiencies of 0.30-0.40 and two photon cross sections of 0.40-0.60 GM. Instead of releasing estradiol, BHQ-estradiol underwent debromination.
Application of hansch's model to capsaicinoids and capsinoids: A study using the quantitative structure-activity relationship. A novel method for the synthesis of capsinoids
Barbero, Gerardo F.,Molinillo, Jose M. G.,Varela, Rosa M.,Palma, Miguel,MacIas, Francisco A.,Barroso, Carmelo G.
experimental part, p. 3342 - 3349 (2011/07/30)
We describe a synthetic approach for two families of compounds, the capsaicinoids and capsinoids, as part of a study of the quantitative relationship between structure and activity. A total of 14 capsaicinoids of increasing lateral chain lengths, from 2 to 16 carbon atoms, were synthesized. In addition, 14 capsinoids with identical lateral chains, as well as capsiate and dihydrocapsiate, have been synthesized, and a new method for the synthesis of these compounds has been developed. The yields range from 48.35 to 98.98%. It has been found that the synthetic capsaicinoids and capsinoids present a lipophilia similar to those of the natural compounds and present similar biological activity. The bioactivity of the synthetic capsaicinoids and capsinoids decreases proportionally to the degree of difference in lipophilia (higher or lower) compared to the natural compounds. Biological activity was determined using the etiolated wheat (Triticum aestlvum L.) coleoptiles bioassay and by comparing results of the synthesis with those presented by their counterpart natural compounds. The bioactivities found correlated directly to the lipophilic properties of the synthesized compounds.
Model Compounds of Caged Capsaicin: Design, Synthesis, and Photoreactivity
Katritzky, Alan R.,Xu, Yong-Jiang,Vakulenko, Anatoliy V.,Wilcox, Allan L.,Bley, Keith R.
, p. 9100 - 9104 (2007/10/03)
Molecules were prepared with substituted nitrobenzyl groups covalently bonded to N-(4-hydroxy-3-methoxybenzyl)acetamide (2) by ether or carbonate linkages. These compounds decomposed under irradiation at 363 nm. Those with carbonate linkages decomposed at
