34079-31-7Relevant articles and documents
Fast Cyclization of a Proline-Derived Self-Immolative Spacer Improves the Efficacy of Carbamate Prodrugs
Belvisi, Laura,Borlandelli, Valentina,Corno, Cristina,Dal Corso, Alberto,Gennari, Cesare,Perego, Paola,Pignataro, Luca
supporting information, p. 4176 - 4181 (2020/02/05)
Self-immolative (SI) spacers are sophisticated chemical constructs designed for molecular delivery or material degradation. We describe herein a (S)-2-(aminomethyl)pyrrolidine SI spacer that is able to release different types of anticancer drugs (possessing either a phenolic or secondary and tertiary hydroxyl groups) through a fast cyclization mechanism involving carbamate cleavage. The high efficiency of drug release obtained with this spacer was found to be beneficial for the in vitro cytotoxic activity of protease-sensitive prodrugs, compared with a commonly used spacer of the same class. These findings expand the repertoire of degradation machineries and are instrumental for the future development of highly efficient delivery platforms.
INHIBITORS OF HEPATITIS C VIRUS REPLICATION
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Paragraph 0734-0735, (2019/05/15)
The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.
Mechanistic Insight Facilitates Discovery of a Mild and Efficient Copper-Catalyzed Dehydration of Primary Amides to Nitriles Using Hydrosilanes
Liu, Richard Y.,Bae, Minwoo,Buchwald, Stephen L.
supporting information, p. 1627 - 1631 (2018/02/17)
Metal-catalyzed silylative dehydration of primary amides is an economical approach to the synthesis of nitriles. We report a copper-hydride(CuH)-catalyzed process that avoids a typically challenging 1,2-siloxane elimination step, thereby dramatically increasing the rate of the overall transformation relative to alternative metal-catalyzed systems. This new reaction proceeds at ambient temperature, tolerates a variety of metal-, acid-, or base-sensitive functional groups, and can be performed using a simple ligand, inexpensive siloxanes, and low catalyst loading.
Total syntheses of smenothiazoles A and B
Ma, Xiao,Chen, Yajie,Chen, Sigui,Xu, Zhengshuang,Ye, Tao
, p. 7196 - 7203 (2017/09/07)
Concise total syntheses of smenothiazoles A (1) and B (2), two distinguished vinyl chloride containing natural products isolated from the marine sponge S. aurea, have been developed. Silastannation, Stille reaction and a carefully controlled desilylchlorination were employed as key steps to construct unique polyketide acid fragments, and the optimized reaction conditions avoided migration of 2,5-diene to a 2,4-conjugated system. This report unambiguously confirmed the structures of both natural products.
A N-benzyloxycarbonyl-L-prolinamide method for the preparation of
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Paragraph 0026, (2018/02/04)
The invention relates to a preparation method of N-carbobenzoxy-L-prolinamide. The preparation method is characterized by comprising following steps of (1) putting L-proline and alkali into a solvent and dropwise adding benzyl chloroformate; at the end of reaction, heating up till backflow, separating out water, cooling down to obtain liquid N-carbobenzoxy-L-proline; (2) dropwise adding sulfoxide chloride into the liquid N-carbobenzoxy-L-proline, heating up till backflow, distilling at reduced pressure to obtain N-carbobenzoxy-L-prolyl chloride solution; and (3) introducing ammonia gas into the N-carbobenzoxy-L-prolyl chloride solution, and at the end of reaction, concentrating at reduced pressure till drying the solvent, adding dichloromethane, cooling down, regulating pH value of the system to be 12-13, standing to separate liquid to obtain a water layer, decoloring, filtering to obtain distilled residue, crystallizing, filtering, washing by petroleum ether, drying to obtain the N-carbobenzoxy-L-prolinamide. The preparation method is simple, has high yield, can prepare the product with high purity and optical purity and no inorganic salt, and can be used for industrial production of N-carbobenzoxy-L-prolinamide in large scale.
FUSED TRICYCLIC SILYL COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES
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Paragraph 0313; 0314, (2015/12/08)
no abstract published
One-pot synthesis of orthogonally protected dipeptide selenazoles employing Nα-amino selenocarboxamides and α-bromomethyl ketones
Madhu, Chilakapati,Panguluri, Nageswara Rao,Narendra,Panduranga,Sureshbabu, Vommina V.
supporting information, p. 6831 - 6835 (2015/01/09)
A simple and efficient protocol for the synthesis of selenazole containing dipeptidomimetics using Nα-amino selenocarboxamides and α-bromomethyl ketones is described. All the compounds made were isolated in good yields and fully characterized.
Glycosylation mediated - BAIL in aqueous solution
Delacroix, Sébastien,Bonnet, Jean-Pierre,Courty, Matthieu,Postel, Denis,Van Nhien, Albert Nguyen
, p. 12 - 18 (2013/10/08)
The use of Br?nsted acid ionic liquid (BAIL) as a catalyst for the activation of unreactive and unprotected glycosyl donors has been demonstrated for the first time in aqueous solution.
A convenient method for the one-step synthesis of phosphonic peptides
Skoreński, Marcin,Oleksyszyn, Józef,Sieńczyk, Marcin
supporting information, p. 4975 - 4977 (2013/09/02)
A novel and efficient method for the synthesis of peptidyl derivatives of 1-aminoalkylphosphonate diaryl esters is presented. Phosphonic peptides were obtained in one step via an amidoalkylation reaction using amides of N-protected amino acids or peptides, triphenyl phosphite, and an appropriate aldehyde.
Enzymatic C-terminal amidation of amino acids and peptides
Nuijens, Timo,Piva, Elena,Kruijtzer, John A.W.,Rijkers, Dirk T.S.,Liskamp, Rob M.J.,Quaedflieg, Peter J.L.M.
experimental part, p. 3777 - 3779 (2012/09/22)
Herein, we describe two versatile and high yielding enzymatic approaches for the conversion of semi-protected amino acid and peptidyl C-terminal α-carboxylic acids into their corresponding amides. In the first approach, the lipase Candida antarctica lipase-B (Cal-B), and in the second approach, the protease Subtilisin A, are used, respectively. We found that by using the ammonium salt of the α-carboxylic acid instead of separate ammonia sources, the enzymatic amidation reactions proceeded much faster without side reactions and gave near to quantitative yields of products.
