85995-53-5

Upstream product

• 72-19-5 D-threonine 
• 501-53-1 benzyl chloroformate 
• 28954-12-3 (2S,3S)-2-amino-3-hydroxybutanoic acid 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 72-19-5 L-threonine 
• 80-68-2 DL-threonine 
• 72-19-5 rac-allo-threonine 
• 632-20-2 D-Threonine 

Downstream Products

• 34660-99-6 O-Trimethylsilyl-N-benzyloxycarbonyl-DL-threonin-trimethylsilylester 
• 78464-34-3 2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-but-2-enoic acid ethyl ester 
• 78464-32-1 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-but-2-enoic acid ethyl ester 
• 78464-33-2 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-pent-2-enoic acid ethyl ester 
• 78464-36-5 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-4-methyl-pent-2-enoic acid ethyl ester 
• 78464-35-4 (E)-2-(2-Benzyloxycarbonylamino-3-hydroxy-butyrylamino)-hex-2-enoic acid ethyl ester 
• 98132-34-4 Z-DL-Thr-DMPir 
• 23161-28-6 N-Carbobenzoxy-DL-threoninaethylester 
• 101890-79-3 2-benzyloxycarbonylamino-acetoacetic acid benzyl ester 
• 16597-50-5 2-benzyloxycarbonylamino-3-hydroxy-butyric acid benzyl ester 
• 57224-63-2 methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 
• 98777-34-5 (2S,3S)-methyl 2-(((benzyloxy)carbonyl)amino)-3-hydroxybutanoate 
• 109539-06-2 (2S,3S)-2-Benzyloxycarbonylamino-3-(diethoxy-phosphoryloxy)-butyric acid 
• 84500-41-4 benzyl N-(benzyloxycarbonyl)-L-allothreoninate 

Relevant academic research and scientific papers

Intramolecular Amidoalkylation of Chiral Imines and Iminium Ions: Stereoselective Synthesis of anti-1,2- and -1,3-Aminoalcohols

When treated with Lewis acids, 2- or 3-vinyl- or -phenylsiloxyaminoacetals generated the corresponding imines or iminium ions which in turn underwent smooth intramolecular amidoalkylation to afford anti-1,2- or -1,3-aminoalcohol derivatives in very high c

EP300/CREBBP INHIBITOR

The present invention provides a compound having excellent histone acetyltransferase inhibitory activity against EP300 and/or CREBBP, or a pharmacologically acceptable salt thereof. The compound is represented by the following formula (1) or a pharmacologically acceptable salt thereof: wherein ring Q1, ring Q2, R1, R2, R3 and R4 respectively have the same meanings as defined in the specification.

Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate

We discovered the orally active thyrotropin-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after intravenous (iv) administration is 100-fold higher than that of TRH. As 1 has four asymmetric carbons in its molecule, there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure?activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.

Total Synthesis of Pseudomonas aeruginosa 1244 Pilin Glycan via de Novo Synthesis of Pseudaminic Acid

Pseudaminic acid (Pse) is a nonulosonic acid unique to bacterial species, found as a component of important cell surface glycans and glycoproteins in various pathogenic species, such as the critical hospital threat Pseudomonas aeruginosa. Herein we present the development of a facile and scalable de novo synthesis of Pse and its functionalized derivatives from easily available Cbz-l-allo-threonine methyl ester (16 steps in 11% yield). The key reactions in our de novo synthesis involve the diastereoselective glycine thioester isonitrile-based aldol-type reaction to create the 1,3-anti-diamino skeleton, followed by the Fukuyama reduction and the indium-mediated Barbier-type allylation. Moreover, we have studied the glycosylation of the Pse glycosyl donors and identified the structural determinants for its glycosylation diastereoselectivity, which enabled us to complete the total synthesis of P. aeruginosa 1244 pilin trisaccharide α-5NβOHC47NFmPse-(2→4)-β-Xyl-(1→3)-FucNAc.

Potent α-amino-β-lactam carbamic acid ester as NAAA inhibitors. Synthesis and structure-activity relationship (SAR) studies

4-Cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate (3b) is a potent, selective and systemically active inhibitor of intracellular NAAA activity, which produces profound anti-inflammatory effects in animal models. In the present work, we describe structure-activity relationship (SAR) studies on 3-aminoazetidin-2-one derivatives, which have led to the identification of 3b, and expand these studies to elucidate the principal structural and stereochemical features needed to achieve effective NAAA inhibition. Investigations on the influence of the substitution at the β-position of the 2-oxo-3-azetidinyl ring as well as on the effect of size and shape of the carbamic acid ester side chain led to the discovery of 3ak, a novel inhibitor of human NAAA that shows an improved physicochemical and drug-like profile relative to 3b. This favourable profile, along with the structural diversity of the carbamic acid chain of 3b, identify this compound as a promising new tool to investigate the potential of NAAA inhibitors as therapeutic agents for the treatment of pain and inflammation.

BENZIMIDAZOLE DERIVATIVES AS BROMODOMAIN INHIBITORS

Compounds of formula (I) and salts thereof: wherein R1, R2, R3, R4 are defined herein. Compounds of formula (I) and salts thereof have been found to inhibit the binding of the BET family of bromodomain proteins to, for example, acetylated lysine residues and thus may have use in therapy, for example in the treatment of autoimmune and inflammatory diseases, such as rheumatoid arthritis; and cancers.

CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS

Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.

One enantiomeric fluorescent sensor pair to discriminate four stereoisomers of threonines

The BINOL-amino alcohol enantiomeric pair (S)-1 and (R)-1 are discovered to conduct both enantioselective and diastereoselective fluorescent discrimination of the four stereoisomers of threonine derivatives. This study utilizes different fluorescence resp

N -(2-Oxo-3-oxetanyl)carbamic acid esters as N-acylethanolamine acid amidase inhibitors: Synthesis and structure-activity and structure-property relationships

The β-lactone ring of N-(2-oxo-3-oxetanyl)amides, a class of N-acylethanolamine acid amidase (NAAA) inhibitors endowed with anti-inflammatory properties, is responsible for both NAAA inhibition and low compound stability. Here, we investigate the structure-activity and structure-property relationships for a set of known and new β-lactone derivatives, focusing on the new class of N-(2-oxo-3-oxetanyl)carbamates. Replacement of the amide group with a carbamate one led to different stereoselectivity for NAAA inhibition and higher intrinsic stability, because of the reduced level of intramolecular attack at the lactone ring. The introduction of a syn methyl at the β-position of the lactone further improved chemical stability. A tert-butyl substituent in the side chain reduced the reactivity with bovine serum albumin. (2S,3R)-2-Methyl-4-oxo-3-oxetanylcarbamic acid 5-phenylpentyl ester (27, URB913/ARN077) inhibited NAAA with good in vitro potency (IC50 = 127 nM) and showed improved stability. It is rapidly cleaved in plasma, which supports its use for topical applications.

Total synthesis of (-)-lemonomycin

When life gives you lemons: An efficient and convergent enantioselective total synthesis of (-)-lemonomycin, which shows potent activity against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VREF), is presented. The key reaction steps are a Hosomi-Sakurai-type cyclization, a thermodynamically controlled Pictet-Spengler reaction, and a glycosidation reaction with lemonose (see scheme). Copyright