24738-51-0Relevant articles and documents
ALKAMIDE COMPOUNDS AND USES THEREOF
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, (2019/04/27)
The present disclosure relates to alkamide compounds and compositions for treating allergic diseases, pain, or itch.
Synthesis and biological evaluation of a series of fatty acid amides from Echinacea
Moazami, Yasamin,Gulledge, Travis V.,Laster, Scott M.,Pierce, Joshua G.
, p. 3091 - 3094 (2015/07/08)
Abstract Alkylamides are lipophilic constituents of Echinacea and possess numerous biological activities. Although significant effort has been focused on the study of crude Echinacea extracts, very little is known regarding the activities of the individual constituents that make up these herbal treatments. Herein we explore the SAR of simple alkylamides found in Echinacea extracts with respect to their ability to decrease the production of the pro-inflammatory mediator TNF-α. Our results have revealed the key structural requirements for activity and provide lead compounds for further investigation of these poorly understood molecules.
DODECA-2E,4E-DIENE AMIDES AND THEIR USE AS MEDICAMENTS AND COSMETICS
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Paragraph 0082; 0091, (2015/11/16)
The present invention relates to a novel class of compounds, namely dodeca-2E, 4E-diem amides and their use a medicament, preferably as a dermatologic agent, and as a cosmetic:. These novel compounds are particularly useful in treating and/or preventing inflammation, irritation, itching, pruritus, pain, oedema and/or pro-allergic or allergic conditions in a patient. Usually they are topically applied to the skin or mucosa in the form of a pharmaceutical or cosmetic composition comprising the compound and a pharmaceutically and/or cosmetically acceptable carrier.
Polyunsaturated alkyl amides from echinacea: Synthesis of diynes, enynes, and dienes
Matovic, Nicholas J.,Hayes, Patricia Y.,Penman, Kerry,Lehmann, Reginald P.,De Voss, James J.
, p. 4467 - 4481 (2011/07/30)
The synthesis of 20 alkyl amides, including 15 naturally occurring polyunsaturated alkyl amides previously identified from Echinacea spp. (1-13 and 62) or from Achilla sp. (55) and five previously unknown geometric isomers (23, 28, 67, 73, and 80), is described. Importantly, these amides include all of the major alkyl amides present in commercially used Echinacea extracts. The syntheses demonstrate methodology used for constructing alkyl amides containing conjugated diyne and isomerically pure enyne and diene moieties and may be adapted easily for the preparation of other alkyl amides present in Echinacea spp. Terminal-conjugated diynes were prepared by a Cadiot-Chodkiewitz coupling/deprotection sequence utilizing a protected bromoacetylene, and methyl-substituted diynes were made via a base-catalyzed rearrangement of terminal-skipped diynes. Conjugated dienes were prepared conveniently and with high stereoselectivity by the reduction of enynes or diynes with Rieke zinc. With the exception of 1-2 and 11-12, the alkyl amides are synthesized here for the first time, and their NMR data are consistent with that of the reported isolated natural compounds.
Bioavailability of echinacea constituents: Caco-2 monolayers and pharmacokinetics of the alkylamides and caffeic acid conjugates
Matthias, Anita,Penman, Kerry G.,Matovic, Nick J.,Bone, Kerry M.,De Voss, James J.,Lehmann, Reg P.
, p. 1242 - 1251 (2007/10/03)
Many studies have been done over the years to assess the effectiveness of Echinacea as an immunomodulator. We have assessed the potential bioavailability of alkylamides and caffeic acid conjugates using Caco-2 monolayers and compared it to their actual bioavailability in a Phase I clinical trial. The caffeic acid conjugates permeated poorly through the Caco-2 monolayers. Alkylamides were found to diffuse rapidly through Caco-2 monolayers. Differences in diffusion rates for each alkylamide correlated to structural variations, with saturation and N-terminal methylation contributing to decreases in diffusion rates. Alkylamide diffusion is not affected by the presence of other constituents and the results for a synthetic alkylamide were in line with those for alkylamides found in an ethanolic Echinacea preparation. We examined plasma from healthy volunteers for 12 hours after ingestion of Echinacea tablets manufactured from an ethanolic liquid extract. Caffeic acid conjugates could not be identified in any plasma sample at any time after tablet ingestion. Alkylamides were detected in plasma 20 minutes after tablet ingestion and for each alkylamide, pharmacokinetic profiles were devised. The data are consistent with the dosing regimen of one tablet three times daily and supports their usage as the primary markers for quality Echinacea preparations.
Esters and amides from activated alcohols using manganese(IV) dioxide: Tandem oxidation processes
Foot, Jonathan S.,Kanno, Hisashi,Giblin, Gerard M. P.,Taylor, Richard J. K.
, p. 1055 - 1064 (2007/10/03)
Manganese(IV) dioxide can be used in conjunction with sodium cyanide in THF-methanol or in methanol alone for the direct conversion of activated alcohols into methyl esters. Ethyl and isopropyl esters can also be prepared. Similarly, use of manganese(IV) dioxide and sodium cyanide in THF containing ammonia or primary amines can be used to convert alcohols into the corresponding amides. Several activated alcohols and one non-activated alcohol example are reported.
A synthetic approach to natural dienamides of insecticidal interest
Abarbri, Mohamed,Parrain, Jean-Luc,Duchene, Alain
, p. 239 - 249 (2007/10/03)
An efficient synthesis of dienamides of insecticidal interest has been stereoselectively achieved featuring a Stille cross-coupling reaction as the key step.
Epoxy dodecadienamides
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, (2008/06/13)
Ethers, esters and amides of dodeca-2,4-dien 1-ols or 1-oic acids which have a methyl or ethyl side chain at the 11-position which are useful in killing and preventing proliferation of insects, by upsetting their hormone balance and a process for preparing these ethers, esters and amides including intermediates in this process.
