- A Convenient Protocol for the Synthesis of Fatty Acid Amides
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Several classes of biologically occurring fatty acid amides have been reported from mammalian and plant sources. Many amides conjugated with fatty acids of mammalian origin exhibit specific activation of individual receptors. Their potential as pharmacological tools or as lead compounds towards the development of novel therapeutics is of great interest. Hence, access to such amides by a practical, high-yielding and scalable protocol without affecting the geometry or position of sensitive functionalities is needed. A protocol that meets all these requirements involves activation of the corresponding acid with carbonyl diimidazole (CDI) followed by reaction with the desired amine or its hydrochloride. More than fifty compounds have been prepared in generally high yields.
- Johansson, Silje J. R.,Johannessen, Tonje,Ellefsen, Christiane F.,Ristun, Mali S.,Antonsen, Simen,Hansen, Trond V.,Stenstrom, Yngve,Nolsoe, Jens M. J.
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supporting information
p. 213 - 217
(2019/01/14)
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- Acyl-CoA: Cholesterol acyltransferase inhibitory activities of fatty acid amides isolated from Mylabris phalerate Pallas
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Unsaturated fatty acid amides, 9(Z)-octadecenamide (2) and 9(Z),12(Z)-octadecadienamide (4) as inhibitors of acyl-CoA: cholesterol acyltransferase (ACAT) were isolated from the ethyl acetate extracts of the insect, Mylabris phalerate Pallas, and elucidated by their spectroscopic data analysis. Compounds 2 and 4 inhibited rat liver microsomal ACAT, hACAT-1, and hACAT-2 with IC50 values of 170, 85, and 63μM for 2 and of 151, 53, and 45μM for 4, respectively.
- Xu, Ming-Zhe,Lee, Woo Song,Kim, Mi Jeong,Park, Doo-Sang,Yu, Hana,Tian, Guan-Rong,Jeong, Tae-Sook,Park, Ho-Yong
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p. 4277 - 4280
(2007/10/03)
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- The invention of radical reactions. Part XXIII new reactions: Nitrile and thiocyanate transfer to carbon radicals from sulfonyl cyanides and sulfonyl isothiocyanates
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Reaction of p-toluenesulphonyl cyanide or methanesulfonyl cyanide with carbon radicals, generated from the corresponding O-acyl-N-hydroxy-2-thiopyridone derivatives by visible light photolysis gives nitriles in good yield. The homolysis products of these sulfonyl nitriles can also be trapped by electron rich olefins. We have also found that carbon radicals react easily with mesyl or tosyl isothiocyanate producing thiocyanates.
- Barton,Jaszberenyi,Theodorakis
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p. 2613 - 2626
(2007/10/02)
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