65527-54-0Relevant academic research and scientific papers
MACROCYCLIC FUSED PYRRAZOLES AS MCL-1 INHIBITORS
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Paragraph 0914, (2020/08/13)
Provided are compounds represented by Formula IA: (IA), and the pharmaceutically acceptable salts and solvates thereof, wherein R, R 1a, R 1b, L 1, L 2, L 3, X, A, B and C are as defined as set forth
Heterocyclic core analogs of a direct thrombin inhibitor
Blizzard, Timothy A.,Singh, Sanjay,Patil, Basanagoud,Chidurala, Naresh,Komanduri, Venukrishnan,Debnath, Samarpita,Belyakov, Sergei,Crespo, Alejandro,Struck, Alice,Kurtz, Marc,Wiltsie, Judyann,Shen, Xun,Sonatore, Lisa,Arocho, Marta,Lewis, Dale,Ogletree, Martin,Biftu, Tesfaye
, p. 1111 - 1115 (2014/03/21)
Thrombin is a serine protease that plays a key role in blood clotting. Pyrrolidine 1 is a potent thrombin inhibitor discovered at Merck several years ago. Seven analogs (2-8) of 1 in which the pyrrolidine core was replaced with various heterocycles were p
Enzymatic synthesis of cyclic amino acids by N-methyl-l-amino acid dehydrogenase from Pseudomonas putida
Yasuda, Mari,Ueda, Makoto,Muramatsu, Hisashi,Mihara, Hisaaki,Esaki, Nobuyoshi
, p. 1775 - 1779 (2007/10/03)
A new enzymatic system for the synthesis of enantiomerically pure cyclic amino acids (CAA) from the corresponding diamino acids or racemic CAA is described. α,ω-Diamino acids were oxidized to α-keto acids with amino acid oxidases (AAO). The α-keto acids were spontaneously transformed into cyclic imino acids in the reaction medium. The resulting imines were reduced to the l-form CAA with N-methyl-l-amino acid dehydrogenase (NMAADH) from Pseudomonas putida ATCC12633 using NADPH as a cofactor. l-Form CAA were also obtained from racemic CAA using d-amino-acid oxidase and NMAADH. Using this method, a new compound [1,4]-thiazepane-3-carboxylic acid (Fig. 1) was synthesized from aminopropylcystein.
Stereoselective preparation of cyclic l-amino acids
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Page/Page column 14, (2008/06/13)
The invention concerns a method for producing a cyclic L-amino acid of formula (I), characterised in that it consists in reacting a L-diamino acid of formula (II) or an enantiomeric mixture comprising such a L-diamino acid and a corresponding D-diamino acid in variable proportions, in the presence of an ornithine cyclodeaminase or a polypeptide homologous to the ornithine cyclodeaminase. 1
Synthesis of Optically Active 1,4-Thiazane-3-carboxylic Acid via Optical Resolution by Preferential Crystallization of (RS)2-Amino-3-[(2-chloroethyl)sulfanyl]propanoic Acid Hydrochloride
Shiraiwa, Tadashi,Tadokoro, Kohya,Tanaka, Haruyuki,Nanba, Keiichiro,Yokono, Noriyoshi,Shibazaki, Katsuyoshi,Kubo, Motoki,Kurokawa, Hidemoto
, p. 2382 - 2387 (2007/10/03)
Optically active 1,4-thiazane-3-carboxylic acid [TCA] was synthesized from cysteine via optical resolution by preferential crystallization. The intermediate (RS)-2-amino-3-[(2-chloroethyl)sulfanyl]propanoic acid hydrochloride [(RS)-ACS-HCl] was found to exist as a conglomerate based on its melting point, solubility and IR spectrum. (RS)-ACS·HCl was optically resolved by preferential crystallization to yield (R)- and (S)-ACS·HCl. (R)- and (S)-ACS·HCl thus obtained were recrystallized from a mixture of hydrochloric acid and 2-propanol, taking account of the solubility of (RS)-ACS·HCl, efficiently yielding both enantiomers in optically pure forms. (R)- and (S)-TCA were then respectively synthesized by the cyclization of (R)- and (S)-ACS·HCI in ethanol in the presence of triethylamine.
Synthesis of Amino Acids with Modified Principal Properties 3: Sulfur-Containing Amino Acids
Larsson, Ulf,Carlson, Rolf
, p. 517 - 525 (2007/10/02)
The synthesis and characterization of seven medium-sized, medium-polar, sulfur-containing amino acids are presented.The compounds were prepared with the objective of finding amino acids which possess physical and chemical properties such that their principal properties would be clearly different from those of previously known amino acids.The principal properties are determined as latent variables in principal component analysis of molecular property descriptors.The following amino acids were prepared in homochiral form from L-cysteine: (2R)-2-amino-3-(2-hydroxyethylsulfanyl)propanoic acid, (2R)-2-amino-3-(2-hydroxyethylsulfonyl)propanoic acid, (3R)-perhydro-1,4-thiazine-3-carboxylic acid and (3R)-1,1-dioxoperhydro-1,4-thiazine-3-carboxylic acid. (3R)-1-Oxoperhydro-1,4-thiazine-3-carboxylic acid was prepared in N,C protected form, but all attempts to obtain the free amino acid failed.The principal properties of this amino acid were determined on the racemic diastereomers obtained by oxidation of the racemic perhydro-1,4-thiazine-3-carboxylic acid prepared from 2-aminoethanethiol and ethyl 3-bromo-2-oxopropanoate.With the exception of (3R)-perhydro-1,4-thiazine-3-carboxylic acid for which the synthesis has been previously described, the amino acids described are new compounds.An improved synthesis of (3R)-perhydro-1,4-thiazine-3-carboxylic acid via the cyclization of (2R)-benzyl-2-amino-3-(2-hydroxyethylsulfanyl)propanoate under Mitsunobu conditions is presented.Full experimental details for the syntheses are given.The principal property scores of the synthesized sulfur-containing amino acids and of the structurally related 3-(2-aminoethyl)cysteine which was commercially available are given.
