69753-67-9Relevant academic research and scientific papers
Lipase-catalyzed amidation of carboxylic acid and amines
Manova, Daniela,Gallier, Florian,Tak-Tak, Lotfi,Yotava, Lyubov,Lubin-Germain, Nadège
supporting information, p. 2086 - 2090 (2018/05/04)
The amidation reaction is of a very particular interest, especially in the pharmaceutical industry and always requires the activation of the acid with a large excess of reactants. Therefore, a large amount of waste is generated. In order to reduce the environmental impact of such reaction, we have developed enzymatic amidation conditions which are compatible with a wide range of amines and acids, in particular with the biologically relevant lipoic acid. Water is the only by-product generated during this reaction thus a very high atom economy is obtained. In addition, we have shown that the lipase can be recovered and reused several times without a significant loss of activity.
A Photo-Triggered Traceless Staudinger–Bertozzi Ligation Reaction
Hu, Peng,Feng, Tianshi,Yeung, Chi-Chung,Koo, Chi-Kin,Lau, Kai-Chung,Lam, Michael H. W.
, p. 11537 - 11542 (2016/08/05)
The use of light to control the course of a chemical/biochemical reaction is an attractive idea because of its ease of administration with high precision and fine spatial resolution. Staudinger ligation is one of the commonly adopted conjugation processes that involve a spontaneous reaction between azides and arylphosphines to form iminophosphoranes, which further hydrolyze to give stable amides. We designed an anthracenylmethyl diphenylphosphinothioester (1) that showed promising Staudinger ligation reactivity upon photo-excitation. Broadband photolysis at 360–400 nm in aqueous organic solvents induced heterolytic cleavage of its anthracenylmethyl–phosphorus bond, releasing a diphenylphosphinothioester (2) as an efficient traceless Staudinger–Bertozzi ligation reagent. The quantum yield of such a photo-induced heterolytic bond-cleavage at the optimal wavelength of photolysis (376 nm) at room temperature is ≥0.07. This work demonstrated the feasibility of photocaging arylphosphines to realize the photo-triggering of the Staudinger ligation reaction.
A One-Pot, fast, and efficient amidation of carboxylic acids, α-amino acids and sulfonic acids using pph3/n-chlorobenzotriazole system
Rouhi-Saadabad, Hamed,Akhlaghinia, Batool
, p. 1703 - 1714 (2015/09/15)
Triphenylphosphine (PPh3)/N-chlorobenzotriazole (NCBT), and amine (primary and secondary aliphatic amines and also substituted anilines) in CH2Cl2 efficiently converted carboxylic acids, α-amino acids, and sulfonic acids to the corresponding amides and sulfonamides at room temperature. Good to excellent yields, inexpensive, and fast reaction conditions are the important features of this procedure.
B(OCH2CF3)3-mediated direct amidation of pharmaceutically relevant building blocks in cyclopentyl methyl ether
Karaluka, Valerija,Lanigan, Rachel M.,Murray, Paul M.,Badland, Matthew,Sheppard, Tom D.
supporting information, p. 10888 - 10894 (2015/11/17)
The use of B(OCH2CF3)3 for mediating direct amidation reactions of a wide range of pharmaceutically relevant carboxylic acids and amines is described, including numerous heterocycle-containing examples. An initial screen of solvents for the direct amidation reaction suggested that cyclopentyl methyl ether, a solvent with a very good safety profile suitable for use over a wide temperature range, was an excellent replacement for the previously used solvent acetonitrile. Under these conditions amides could be prepared from 18 of the 21 carboxylic acids and 18 of the 21 amines examined. Further optimisation of one of the low yielding amidation reactions (36% yield) via a design of experiments approach enabled an 84% yield of the amide to be obtained.
High-yielding staudinger ligation of a phosphinothioester and azide to form a peptide
Nilsson, Bradley L.,Kiessling, Laura L.,Raines, Ronald T.
, p. 9 - 12 (2007/10/03)
(eqution presented) The Staudinger ligation can be used to couple a peptide with a C-terminal phosphinothioester to another with an N-terminal α-azido group to form a single peptide that contains no residual atoms. Here, diphenylphosphinomethanethiol thio
Anticonvulsant drugs and pharmaceutical compositions thereof
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, (2008/06/13)
According to the present invention, anticonvulsant compounds N-acetyl,N'-benzylglycinamide and N-benzyloxycarbonylglycinamide-Z-glycinamide are disclosed. The present invention also discloses an anticonvulsant pharmaceutical composition comprising an effe
Amino acid derivative anticonvulsant
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, (2008/06/13)
The present invention relates to compounds of the formula STR1
Amino acid derivative anticonvulsant
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, (2008/06/13)
The present invention relates to compounds exhibiting central nervous system (CNS) activity which are useful in the treatment of epilepsy and other CNS disorders. The compounds of this invention have the following general formula: STR1 and pharmaceutically acceptable salts thereof.
Functionalized DL-Amino Acid Derivatives. Potent New Agents for the Treatment of Epilepsy
Conley, Judith D.,Kohn, Harold
, p. 567 - 574 (2007/10/02)
Structural analogues of the potent known anticonvulsant agent N-acetyl-DL-alanine N-benzylamide (1a) have been prepared (16 examples).The pharmacological activities of these products were evaluated in the maximal electroshock seizure (MES), the subcutaneous pentylenetetrazole seizure threshold (sc Met), and the rotorod (Tox) tests.The median effective doses (ED50) and the median toxic doses (TD50) for the most active compounds by both intraperitoneal and oral administration are reported.The most active compounds were N-acetyl-DL-phenylglycine N-benzylamide (1d) and N-acetyl-DL-alanine N-m-fluorobenzylamide (1m) along with the parent compound 1a.The ED50 values in the MES test for these three compounds compared well with phenobarbital, while their high TD50 values contributed to their large protective indexes, which approached that of phenytoin.When tested against four convulsant agents, compounds 1a and 1d displayed activity profiles significantly different from those reported for conventionally used antiepileptic drugs.
Heterocycles as Masked Diamide/Dipeptide Equivalents. Formation and Reactions of Substituted 5-(Acylamino)oxazoles as Intermediates en route to the Cyclopeptide Alkaloids
Lipshutz, Bruce H.,Hungate, Randall W.,NcCarthy, Keith E.
, p. 7703 - 7713 (2007/10/02)
A variety of novel 2,4-dialkyl-5-(acylamino)oxazoles have been prepared by using either amide nitriles or diamides/dipeptides as starting materials.Ring closure calls for the use of trifluoroacetic acid/trifluoroacetic acid anhydride or an acid halide in
