62023-65-8

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is used as a key intermediate in the synthesis of bestatin and its analogs for the pharmaceutical industry. Bestatin is a natural product with immunomodulatory, antitumor, and protease inhibitory properties. Its analogs have been developed to enhance these properties and explore their potential in treating various diseases.
Used in Biochemical Research:
N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is used as a protected amino acid in biochemical research for the development of novel peptides, peptidomimetics, and other bioactive molecules. The Boc protection group allows for selective deprotection and coupling reactions, enabling the synthesis of complex molecular structures with specific biological activities.
Used in Drug Discovery:
N-BOC-(2S,3R)-2-HYDROXY-3-AMINO-4-PHENYLBUTANOIC ACID is used as a building block in drug discovery for the design and synthesis of new pharmaceutical agents. Its unique structure and functional groups can be exploited to create molecules with improved pharmacokinetic and pharmacodynamic properties, leading to the development of more effective and safer drugs.

Upstream product

• 116565-03-8 N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 24424-99-5 di-tert-butyl dicarbonate 
• 209173-80-8 2(RS)-hydroxy-3(S)-amino-4-phenylbutanoic acid 
• 290836-37-2 (3S)-3-tert-butoxycarbonylamino-1,1-dichloro-4-phenyl-2-butanone 
• 290836-34-9 (3S)-1,1-dibromo-3-tert-butoxycarbonylamino-4-phenyl-2-butanone 
• 149451-80-9 (2S,3S)-3-(t-butoxycarbonylamino)-4-phenylbutane-1,2-diol 
• 123054-12-6 (2S)-N,N-dibenzylphenylalaninal 
• 147915-02-4 (2S,3S)-3-amino-4-phenylbutane-1,2-diol 
• 66605-57-0 (S)-N-tert-butoxycarbonyl-2-amino-3-phenylpropanol 
• 191849-93-1 3(S)-(N-tert-butoxycarbonylamino)-2(R,S)-hydroxy-4-phenylbutyric acid 
• 3236-56-4 dipercarbonate de O,O-t-butyle 
• 98760-08-8 (2R,3S)-3-[N-(tert-butyloxycarbonyl)amino]-1,2-epoxy-4-phenylbutane 
• 81926-51-4 N-(tert-butyloxycarbonyl)-(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester 
• 223763-55-1 (4R,5S)-4-Benzyl-2-oxo-oxazolidine-5-carboxylic acid benzyl ester 

Downstream Products

• 145986-90-9 N-Boc-(2S,3S)-AHPA-L-Leu-tert-butyl ester 
• 1054684-42-2 ((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyrylamino)-acetic acid tert-butyl ester 
• 159000-71-2 Boc-Apns-Dmt-NHtBu 
• 478699-59-1 Boc-Apns-Dmt-NH(o-methylbenzyl) 
• 478699-11-5 {(1S,2S)-1-Benzyl-3-[(R)-4-(2-chloro-benzylcarbamoyl)-5,5-dimethyl-thiazolidin-3-yl]-2-hydroxy-3-oxo-propyl}-carbamic acid tert-butyl ester 
• 177355-09-8 [(1S,2S)-1-Benzyl-3-((2S,4S)-2-tert-butylcarbamoyl-4-chloro-pyrrolidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 144069-71-6 [1-benzyl-3-(2-tert-butylcarbamoyl-piperidin-1-yl)-2-hydroxy-3-oxo-propyl]-carbamic acid tert-butyl ester 
• 359691-66-0 (S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester 
• 359691-63-7 (S)-2-{[(R)-3-((2S,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butyryl)-5,5-dimethyl-thiazolidine-4-carbonyl]-amino}-3-methyl-butyric acid methyl ester 
• 521275-21-8 carbonic acid 1-{N-benzyl-N'-[(2,6-dimethyl-phenoxy)-acetyl]-hydrazinocarbonyl}-2-tert-butoxycarbonylamino-3-phenyl-propyl ester isobutyl ester 
• 521275-20-7 acetic acid 3-[N'-benzyl-N'-(3-tert-butoxycarbonylamino-2-isobutoxycarbonyloxy-4-phenyl-butyryl)-hydrazinocarbonyl]-2-methyl-phenyl ester 
• 602319-20-0 Benzoic acid (1S,2S)-2-tert-butoxycarbonylamino-1-carboxy-3-phenyl-propyl ester 
• 858780-97-9 ((1S,2S)-1-Benzyl-3-{(R)-5,5-dimethyl-4-[(pyridin-4-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-2-hydroxy-3-oxo-propyl)-carbamic acid tert-butyl ester 
• 858780-96-8 ((1S,2S)-1-Benzyl-3-{(R)-5,5-dimethyl-4-[(pyridin-3-ylmethyl)-carbamoyl]-thiazolidin-3-yl}-2-hydroxy-3-oxo-propyl)-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Design, synthesis and biological evaluation of hybrid of ubenimex-fluorouracil for hepatocellular carcinoma therapy

In our previous study, we discovered a ubenimex-fluorouracil (5FU) conjugates BC-02, which displays significant in vivo anti-tumor activity, however, the instability of BC-02 in plasma limits its further development as a drug candidate. Herein, we designe

Chemically synthesized LYRM03 could inhibit the metastasis of human breast cancer MDA-MB-231 cells in vitro and in vivo

Aminopeptidase N (APN) belongs to the aminopeptidase family, which is widely distributed throughout the animal and plant kingdoms. APN is thought to be a very important target for cancer therapy as it is linked to cancer progression and metastasis. Howeve

(2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative as well as preparation method and application thereof

The invention discloses a (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative shown as a formula (I) or an optical isomer, a diastereomer and racemate mixture and pharmaceutically acceptable salt thereof as well as a preparation method and application of the (2S, 3R)-3-amino-2-hydroxy-4-phenylbutyrylamide derivative. It is shown by comparison of results of a positive control group and a model group on lymphedema prevention experiments that the compound disclosed in the invention shows obvious anti-edema activity.

A synthesis method of ubenimex

The invention discloses a method for synthesizing ubenimex. The method comprises the following steps: by taking D-Boc-phenyl alaninal as a raw material, sequentially preparing hydroxynitrile, carrying out a nitrile hydrolysis reaction, performing amino protection, performing chiral resolution on (2RS,3R)-3-tert-butoxyacylamino-2-hydroxy-4-phenylbutyric acid, and synthesizing (S)-phenyl-2-((2S,3R)-3-(tert-butoxyacylamino)-2-hydroxy-4-phenylbutyramide)-4-mevalonate, thereby synthesizing the ubenimex. According to the synthetic method disclosed by the invention, the defect that the resolving agent used in the conventional synthetic method is high in toxicity (such as strychnine) or high in price (such as alpha-phenylethylamine) is overcome, the synthetic method is simple in steps and low in cost, and use of reagents such as strychnine is avoided; and moreover, a dextro-amino compound is taken as the chiral resolution agent, the price is low, the operation is simple, the stirring and recrystallization time is shortened, and the synthetic efficiency is greatly improved.

TUBULIN BINDING AGENTS

The invention provides combretastatin A-4 like compounds that are modified to have enhanced tubulin binding activity and in some embodiments the ability to promote accumulation in the vasculature undergoing angiogenesis (homing activity). The compounds are based on the combretastatin A-4 skeletal structure having a tubulin-binding pharmacophore comprising two fused rings (A and B rings) in which the B ring is substituted with (a) an aromatic ring structure (C ring) and (b) a second substituent/functional group that comes off the B ring. The aromatic ring structure is typically a six membered ring phenolic or aniline structure, or may also be a fused ring structure such as a substituted or unsubstituted naphthalene. The second substituent on the B ring may for example be a substituent which has been found to provide enhanced tubulin binding activity (for example a carbonyl group), or may be a substituent that facilitates functionalisation of the B ring (for example an hydroxyl or amine group), or it may be a binding agent for a target that is preferentially expressed on vasculature undergoing angiogenesis, and not expressed on quiescent vasculature.

Synthesis of new (-)-bestatin-based inhibitor libraries reveals a novel binding mode in the S1 pocket of the essential malaria M1 metalloaminopeptidase

The malarial PfA-M1 metallo-aminopeptidase is considered a putative drug target. The natural product dipeptide mimetic, bestatin, is a potent inhibitor of PfA-M1. Herein we present a new, efficient, and high-yielding protocol for the synthesis of bestatin derivatives from natural and unnatural N-Boc-d-amino acids. A diverse library of bestatin derivatives was synthesized with variants at the side chain of either the α-hydroxyβ-amino acid (P1) or the adjacent naturalα-amino acid (P1′). Surprisingly, we found that extended aromatic side chains at the P1 position resulted in potent inhibition against PfA-M1. To understand these data, we determined the X-ray cocrystal structures of PfA-M1 with two derivatives having either a Tyr(OMe) 15 or Tyr(OBzl) 16 at the P1 position and observed substantial inhibitor-induced rearrangement of the primary loop within the PfA-M1 pocket that interacts with the P1 side chain. Our data provide important insights for the rational design of more potent and selective inhibitors of this enzyme that may eventually lead to new therapies for malaria.

Design and synthesis of several small-size HTLV-I protease inhibitors with different hydrophilicity profiles

The human T cell leukemia/lymphotropic virus type 1 (HTLV-I) is clinically associated with adult T cell leukemia/lymphoma, HTLV-I associated myelopathy/tropical spastic paraparesis, and a number of other chronic inflammatory diseases. To stop the replication of the virus, we developed highly potent tetrapeptidic HTLV-I protease inhibitors. In a recent X-ray crystallography study, several of our inhibitors could not form co-crystal complexes with the protease due to their high hydrophobicity. In the current study, we designed, synthesized and evaluated the HTLV-I protease inhibition potency of compounds with hydrophilic end-capping moieties with the aim of improving pharmaceutic and pharmacokinetic properties.

A practical and convenient synthesis of the protease inhibitor epibestatin

A convenient synthesis of the protease inhibitor epibestatin, a useful component in protease inhibition cocktails for use in proteomics research, is described. The synthesis sequence consists of seven steps, starting from phenylacetaldehyde, yielding enantiopure epibestatin in 8% overall yield. A regioselective Mitsunobu transformation of a diol is the key step in the sequence. Georg Thieme Verlag Stuttgart.

PROCESSES FOR PRODUCING OXAZOLIDINONE DERIVATIVE OF BETA-HYDROXYETHYLAMINE COMPOUND AND FOR PRODUCING BETA-HYDROXYETHYLAMINE COMPOUND

The present invention provides a process of starting from N-alkoxycarbonyl-ethylamine compounds having a leaving group at the β-position to prepare oxazolidinone derivatives of β-hydroxyethylamine compounds having an inverted steric configuration at the β

New stereoselective synthesis of the peptidic aminopeptidase inhibitors bestatin, phebestin and probestin

Peptidic aminopeptidase inhibitors, bestatin, phebestin and probestin have been prepared by stereo- and regiocontrolled reactions from a common α,β-epoxy ester precursor.