80384-27-6

Usage

Uses

Used in Pharmaceutical Industry:
Z-D-THR-OH is used as a synthetic intermediate for the production of chiral antibiotics, which are essential in the development of new drugs with improved efficacy and reduced side effects.
Used in Microbiology Research:
Z-D-THR-OH is used as a research tool to study the growth and cell wall synthesis of Mycobacterium smegmatis, a bacterium that can provide insights into the development of new antimicrobial agents and understanding the mechanisms of bacterial resistance.
Used in Chemical Synthesis:
Z-D-THR-OH is used as a building block in the synthesis of various chiral compounds, which have applications in various industries, including pharmaceuticals, agrochemicals, and materials science.

InChI:InChI=1/C12H15NO5/c1-8(14)10(11(15)16)13-12(17)18-7-9-5-3-2-4-6-9/h2-6,8,10,14H,7H2,1H3,(H,13,17)(H,15,16)/t8?,10-/m1/s1

Upstream product

• 72-19-5 D-threonine 
• 501-53-1 benzyl chloroformate 
• 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 
• 67646-42-8 4-Benzyloxycarbonylamino-2-cyano-5-hydroxy-3-oxo-hexanoic acid ethyl ester 
• 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 
• 112026-37-6 ethyl 2-(benzyloxycarbonylamino)acetoacetate 
• 78464-56-9 2-((E)-2-Benzyloxycarbonylamino-but-2-enoylamino)-3-methyl-but-2-enoic acid ethyl ester 
• 78464-38-7 (E)-2-(2-Benzyloxycarbonylamino-3-methanesulfonyloxy-butyrylamino)-but-2-enoic acid ethyl ester 
• 78464-40-1 2-(2-Benzyloxycarbonylamino-3-methanesulfonyloxy-butyrylamino)-3-methyl-but-2-enoic acid ethyl ester 
• 78464-39-8 (E)-2-(2-Benzyloxycarbonylamino-3-methanesulfonyloxy-butyrylamino)-pent-2-enoic acid ethyl ester 

Relevant academic research and scientific papers

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.

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

Synthesis and evaluation of lysophosphatidylserine analogues as inducers of mast cell degranulation. Potent activities of lysophosphatidylthreonine and its 2-deoxy derivative

In response to various exogenous stimuli, mast cells (MCs) release a wide variety of inflammatory mediators stored in their cytoplasmic granules and this release initiates subsequent allergic reactions. Lysophosphatidylserine (lysoPS) has been known as an exogenous inducer to potentiate histamine release from MCs, though even at submicromolar concentrations. In this study, through SAR studies on lysoPS against MC degranulation, we identified lysoPT, a threonine-containing lysophospholipid and its 2-deoxy derivative as novel strong agonists. LysoPT and its 2-deoxy derivative induced histamine release from MCs both in vitro and in vivo at a concentration less than one-tenth that of lysoPS. Notably, lysoPT did not activate a recently proposed lysoPS receptor on MCs, GPR34, demonstrating the presence of another undefined receptor reactive to both lysoPS and lysoPT that is involved in MC degranulation. Thus, the present strong agonists, lysoPT and its 2-deoxy derivative, will be useful tools to understand the mechanisms of lysoPS-induced activation of degranulation of MCs. 2009 American Chemical Society.

Enantioselective total synthesis of callipeltoside A: two approaches to the macrolactone fragment

The enantioselective total synthesis of callipeltoside A is described. Two syntheses of the macrolactone subunit are included: the first relies upon an Ireland-Claisen rearrangement to generate the trisubstituted olefin geometry and the second utilizes an enantioselective vinylogous aldol reaction for this purpose. Enantioselective syntheses of the sugar and chlorocyclopropane side chain fragments are also disclosed. The relative and absolute stereochemistry of this natural product was determined by fragment coupling with the two enantiomers of the side chain fragment.

Synthesis and biological activity of piperazine-Based dual MMP-13 and TNF-α converting enzyme inhibitors

A series of novel MMP-13 and TNF-α converting enzyme inhibitors based on piperazine 2-hydroxamic acid scaffolds are described. The TACE, MMP-1 and MMP-13 activity of these inhibitors as well as the effect of substitution of the piperazine nitrogen and the P-1′ benzyloxy tailpiece is discussed. Moderate in vivo activity is observed with several members of this group.

An aldol-based approach to the asymmetric synthesis of L-callipeltose, the deoxyamino sugar of L-callipeltoside A.

[reaction: see text] The L-callipeltose subunit of L-callipeltoside A has been synthesized in 10 steps and 13% overall yield from D-threonine. The key steps are a highly diastereoselective Felkin anti aldol addition to a methyl ketone and a selective methylation of a secondary alcohol in the presence of a secondary carbamate.

Selective inhibitors of aggrecanase in osteoarthritis treatment

This invention relates to a method of treatment for osteoarthritis involving inhibitors of aggrecanase that demonstrate IC50s of less than 20 nM and demonstrate differential potency against matrix metalloproteinases (MMPs) and a disintegrin and metalloproteinases (ADAMs or reprolysins). This invention also relates to compounds, methods of treatment and composition of Formula I: or a therapeutically acceptable salt thereof, whereinX is carbon or nitrogen;R1 and R2 are independently selected from the group consisting of hydrogen, hydroxy, and methyl, wherein at least one of R1 and R2 is methyl;R3 and R4 are independently selected from the group consisting of hydrogen, hydroxy, and methyl, or R3 and R4 may be taken together to form a carbonyl group; andR5 and R6 are independent substituents in the ortho, meta, or para positions and are independently selected from the group consisting of hydrogen, halogen, cyano, methyl, and ethyl;with the provisos:when X is carbon, then R7 and R8 are both hydrogen and at least one of R1, R2, R3, and R4 is hydroxy;when X is carbon and R5 is para-halo, then at least one of R6, R3, and R4 is not hydrogen;when X is nitrogen, then R8 is not present and R7 is hydrogen or a group of the formula:wherein, Y is -CH2-NH2 or -NH-CH3; andwhen X is nitrogen and R7 is H, then R3 and R4 are taken together to form a carbonyl group.

Synthesis of the Peptide Fragment of Pseudobactin

Synthesis of the peptide fragment, L-Lys-D-threo-β-OH-Asp-L-Ala-D-allo-Thr-L-Ala-N-OH-D-cOrn, of pseudobactin (2) is reported.By utilizing 2-ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline (EEDQ) as a coupling reagent, peptide bonds were constructed without requiring protection of hydroxyl groups.To access the D-allo-Thr residue in the peptide fragment of pseudobactin, the Thr residue in N-Cbz-L-Ala-D-Thr-L-Ala-O-t-Bu (4b) was converted to a peptidyl oxazoline using Burgess' reagent.Hydrolysis of the oxazoline with 1 N HCl followed by base-catalyzed acyl migration then provided the D-allo-Thr analog 4a.