5327-45-7Relevant academic research and scientific papers
Synthesis and biological screening of a library of macamides as TNF-α inhibitors
Apaza Ticona, Luis,Serban, Andreea Madalina,Acero Gómez, Javier,Rumbero Sánchez, ángel,Tena Pérez, Víctor
, p. 1196 - 1209 (2020/11/03)
Thirty-five macamide analogues were synthesised by modifying the initial molecular structure. The resulting structures were confirmed using NMR and MS. Cytotoxicity and the anti-inflammatory activity of these synthetic macamides were evaluated in the THP-1 cell line. Preliminary biological evaluation indicated that most of these synthetic macamides did not present cytotoxicity (MTT assay) in the tested cell line with respect to the control (actinomycin D). Regarding the anti-inflammatory activity, several analogues had a greater potential for inhibition of TNF-α than natural macamides. Synthetic macamide 4a was the most active (IC50 = 0.009 ± 0.001 μM) compared to the C87 (control). Through looking at the link between the chemical structure and the activity, our study proves that changes made to natural macamides at the level of the alkyl chain, the benzyl position, the amide bond, and the addition of two methyl groups to the aromatic ring (meta position) lead us to obtaining new macamides with greater anti-inflammatory activity. This journal is
N-Benzyl-linoleamide, a Constituent of Lepidium meyenii (Maca), Is an Orally Bioavailable Soluble Epoxide Hydrolase Inhibitor That Alleviates Inflammatory Pain
Singh, Nalin,Barnych, Bogdan,Morisseau, Christophe,Wagner, Karen M.,Wan, Debin,Takeshita, Ashley,Pham, Hoang,Xu, Ting,Dandekar, Abhaya,Liu, Jun-Yan,Hammock, Bruce D.
, p. 3689 - 3697 (2021/01/09)
Lepidium meyenii (maca), a plant indigenous to the Peruvian Andes, recently has been utilized globally for claimed health or recreational benefits. The search for natural products that inhibit soluble epoxide hydrolase (sEH), with therapeutically relevant potencies and concentrations, led to the present study on bioactive amide secondary metabolites found in L. meyenii, the macamides. Based on known and suspected macamides, 19 possible macamides were synthesized and characterized. The majority of these amides displayed excellent inhibitory potency (IC50 ≈ 20-300 nM) toward the recombinant mouse, rat, and human sEH. Quantitative analysis of commercial maca products revealed that certain products contain known macamides (1-5, 8-12) at therapeutically relevant total concentrations (≥3.29 mg/g of root), while the inhibitory potency of L. meyenii extracts directly correlates with the sum of concentration/IC50 ratios of macamides present. Considering both its in vitro efficacy and high abundance in commercial products, N-benzyl-linoleamide (4) was identified as a particularly relevant macamide that can be utilized for in vivo studies. Following oral administration in the rat, compound 4 not only displayed acceptable pharmacokinetic characteristics but effectively reduced lipopolysaccharide-induced inflammatory pain. Inhibition of sEH by macamides provides a plausible biological mechanism of action to account for several beneficial effects previously observed with L. meyenii treatments.
Amidation and esterification of carboxylic acids with amines and phenols by N,N′-diisopropylcarbodiimide: A new approach for amide and ester bond formation in water
Fattahi, Nadia,Ayubi, Morteza,Ramazani, Ali
, p. 4351 - 4356 (2018/07/13)
The present study reports the successful synthesis of two important and abundant functional groups “ester and amide” by N,N′-diisopropylcarbodiimide (DIC) in water as a green solvent. A wide range of substrates could be employed with high functional group tolerance. The products were obtained in high yields after short reaction times. This method provides an efficient, economic, simple and very mild protocol for ester and amide bond formation in aqueous media. In addition, this work not only may lead to environmentally benign systems but also will provide a new aspect of organic chemistry in water.
Nano-Magnetic Sulfonic Acid Catalyzed Facile Synthesis of Diverse Amide Derivatives
Kothandapani, Jagatheeswaran,Ganesan, Asaithampi,Ganesan, Subramaniapillai Selva
, p. 685 - 692 (2017/01/25)
The excellent surface catalytic potential of Fe3O4-OSO3H is utilized in the synthesis of symmetrically and unsymmetrically substituted urea derivatives via transamidation reactions. The scope of the surface catalysis is further extended in transamidation reactions of cyclic and acyclic amide derivatives, and in the amidation of fatty acids. In both transamidation and amidation reactions, the catalyst is reusable up to five times without significant loss in its activity.
Maca amide synthesis method and use thereof
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Paragraph 0043-0045, (2017/09/12)
The invention relates to a synthetic method of MACAmide. The method includes following steps: with a fatty acid and benzylamine or m-methoxybenzylamine as reaction raw materials, mixing the raw materials in a dichloromethane solution in which HOAt, EDC.HCl and DIPEA are dissolved; performing a reaction with stirring; washing a reaction product with water; and drying a substance being undissolved in water to obtain the MACAmide. The method is simple in processes and the raw materials are easy to obtain. Operation conditions of the method are easy to control. The reaction product can reach a purity of 95% without purification. The invention provides basis for industrialized synthesis of the MACAmide. In addition, the MACAmide has effects of enhancing male reproductive ability and treating male sexual dysfunction. The invention provides market prospects to application of the MACAmide.
Synthesis and biological evaluation of macamides derivatives as potent inhibitors of breast cancer cell MCF-7
Liang, Xiao Xia,Xiong, Cheng,He, Min,He, Changliang,Yin, Zhongqiong
, p. 489 - 494 (2016/07/19)
A series of macamides (1-4) and their synthetic analogs (5-14) were synthesized and evaluated for in vitro inhibitory activities against breast cancer cell MCF-7. The results of bioactive assay showed that two of the macamides (compound 1 and 4) and one synthetic analog (compound 5) displayed comparable inhibitory activities against MCF-7 cell line, with IC50 values of 29.6, 36.2 and 27.2 μM, respectively.
Carboxyl activation via silylthioesterification: One-pot, two-step amidation of carboxylic acids catalyzed by non-metal ammonium salts
Lamar, Angus A.,Liebeskind, Lanny S.
, p. 6034 - 6037 (2015/10/28)
The first organo-catalyzed silylthioesterification of a carboxylic acid and a commercially available mercaptoorganosilane results in the in situ production of an O-silylthionoester. Subsequent amine addition forms amides in an operationally simple one-pot procedure without removal of water. The scope and efficiency of these reactions with respect to the catalyst, carboxylic acid, amine, [Si-S] moiety, and solvent are investigated. A number of functionalities are tolerated in the two-step amidation including alkene, alkyne, alkyl and aryl halides, benzylic ethers, and heterocycles with free coordinating sites.
Processes for forming amide bonds and compositions related thereto
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Page/Page column 32, (2015/01/07)
The disclosure relates to methods for producing amide bonds and reagents related thereto. In some embodiments, the disclosure relates to methods of producing an amide comprising mixing an O-silylated thionoester and an amine under conditions such that an amide is formed. In another embodiment, the disclosure relates to mixing a thiolacid, a silylating agent, and an amine under conditions such that an amide is formed.
Facile preparation of amides from carboxylic acids and amines with ion-supported Ph3P
Kawagoe, Yuhsuke,Moriyama, Katsuhiko,Togo, Hideo
, p. 3971 - 3977 (2013/06/27)
Ion-supported Ph3P, 4-(diphenylphosphino)benzyltrimethylammonium bromide (IS-Ph3P), could be used for the facile amidation of a wide range of carboxylic acids with amines in the presence of bromotrichloromethane to provide the corresponding amides in good yields. In the present reaction, the desired amides were obtained in good yields with high purity by simple extraction of the reaction mixture with diethyl ether or chloroform and subsequent removal of the solvent from the extract. Moreover, ion-supported Ph3PO (IS-Ph3PO), which was a co-product derived from IS-Ph3P in the present reductive condensation, was recovered in high yield and could be reduced to IS-Ph3P for reuse in the same amidation of carboxylic acid.
Macamides and their synthetic analogs: Evaluation of in vitro FAAH inhibition
Wu, Hui,Kelley, Charles J.,Pino-Figueroa, Alejandro,Vu, Huyen D.,Maher, Timothy J.
, p. 5188 - 5197 (2013/09/02)
Maca (Lepidium meyenii), a traditional food crop of the Peruvian Andes is now widely touted as a dietary supplement. Among the various chemical constituents isolated from the plant are a unique series of non-polar, long-chain fatty acid N-benzylamides known as macamides. We have synthesized 11 of the 19 reported macamides and have tested each as potential inhibitors of the human enzyme, fatty acid amide hydrolase (FAAH). The five most potent macamides were FAAH inhibitors (IC50 = 10-17 μM). These amides were derivatives of oleic, linoleic and linolenic acids and benzylamine or 3-methoxybenzylamine. Of the three compounds evaluated in a pre-incubation time study, two macamides were not irreversible inhibitors of FAAH. The third, a carbamate structurally related to macamides, was shown to be an irreversible inhibitor of FAAH (IC50 = 0.153 μM).
