219752-67-7

Basic information

• Product Name: METHYL (R)-2-AMINO-4-BROMOBUTYRATE
• Synonyms: METHYL (R)-2-AMINO-4-BROMOBUTYRATE
• CAS NO: 219752-67-7
• Molecular Formula: C5H10BrNO2
• Molecular Weight: 196.04
• Mol File: 219752-67-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: METHYL (R)-2-AMINO-4-BROMOBUTYRATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (R)-2-AMINO-4-BROMOBUTYRATE(219752-67-7)
• EPA Substance Registry System: METHYL (R)-2-AMINO-4-BROMOBUTYRATE(219752-67-7)

Safety Data

• Hazardous Substances Data: 219752-67-7(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 10364-50-8 α-amino-γ-bromobutyric acid 
• 15159-65-6 (2S)-2-amino-4-bromobutanoic acid hydrobromide 

Downstream Products

• 76969-87-4 methyl (2S)-4-bromo-2-[(tert-butoxycarbonyl)amino]butanoate 
• 359781-97-8 methyl 4-azido-2S-{[(1,1-dimethylethoxy)carbonyl]amino}butyrate 
• 64896-37-3 methyl N-{[(1,1-dimethylethyl)oxy]carbonyl}-L-norvalinate 
• 87974-77-4 methyl (2S)-2-tert-butoxycarbonylaminohexanoate 
• 92136-57-7 (S)-2-tert-butoxycarbonylamino-hex-5-enoic acid methyl ester 

Relevant articles and documents

Optimal linker length for small molecule PROTACs that selectively target p38α and p38β for degradation

We report the design of hetero-bifunctional small molecules that selectively target p38α and p38β for degradation. These proteolysis targeted chimeras (PROTACs) are based on an ATP competitive inhibitor of p38α and p38β, which is linked to thalidomide analogues to recruit the Cereblon E3 ubiquitin ligase complex. Compound synthesis was facilitated by the use of a copper catalyzed “click” reaction. We show that optimization of the linker length and composition is crucial for the degradation-inducing activity of these PROTACs. We provide evidence that these chemical compounds can induce degradation of p38α and p38β but no other related kinases at nanomolar concentrations in several mammalian cell lines. Accordingly, the PROTACs inhibit stress and cytokine-induced p38α signaling. Our compounds contribute to understanding the development of PROTACs, and provide a useful tool to investigate functions of the p38 MAPK pathway and its involvement in diseases.

Exploration of the carmaphycins as payloads in antibody drug conjugate anticancer agents

Antibody–drug conjugates (ADCs) represent a new dimension of anticancer chemotherapeutics, with warheads to date generally involving either antitubulin or DNA-directed agents to achieve low-to sub-nanomolar potency. However, other potent cytotoxins working by different pharmacological mechanisms are under investigation, such as α,β-epoxyketone based proteasome inhibitors. These proteasome active agents are an emerging class of anticancer drug that possesses ultra-potent cytotoxicity to some cancer cell lines. The carmaphycins are representatives of this latter class that we isolated and characterized from a marine cyanobacterium, and these as well as several synthetic analogues exhibit this level of potency. In the current work, we investigated the use of these highly potent cytotoxic compounds as warheads in the design of novel ADCs. We designed and synthesized a library of carmaphycin B analogues that contain amine handles, enabling their attachment to an antibody linker. The basicity of these incorporated amine handles was shown to strongly affect their cytotoxic properties. Linear amines resulted in the greatest reduction in cytotoxicity whereas less basic aromatic amines retained potent activity as demonstrated by a 4-sulfonylaniline derivative. These investigations resulted in identifying the P2 residue in the carmaphycins as the most suitable site for linker attachment point, and hence, we synthesized a highly potent analogue of carmaphycin B that contained a 4-sulfonylaniline handle as an attachment point for the linker antibody.

COMPOSITIONS AND METHODS FOR TREATING ATHEROSCLEROTIC CARDIOVASCULAR DISEASE

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SUBSTITUTED 2-PHENYL-PYRIDINE DERIVATIVES

The present invention relates to compounds of formula I wherein R1, R2, R4, R5, Ra, Rb, n, W and Z are as defined in the application, their preparation and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals.

SUBSTITUTED 2-PHENYL-PYRIDINE DERIVATIVES

The present invention relates to compounds of formula (I) wherein R1, R2, R4, R5, Ra, Rb, n, W and Z are as defined in the application, their preparation and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals.

Prodrug forms of N-[(4-deoxy-4-amino-10-methyl)pteroyl]glutamate-γ- [ψP(O)(OH)]-glutarate, a potent inhibitor of folylpoly-γ-glutamate synthetase: Synthesis and hydrolytic stability

Ester prodrugs of the phosphinate pseudopeptide N-[(4-deoxy-4-amino-10- methyl)pteroyl]glutamate-γ-[ψP-(O)(OH)]-glutarate (1a) were synthesized. H-phosphinic acids derived from N-Cbz vinyl glycine esters were converted to the desired pseudopeptides by Michael addition to α-methyleneglutarate esters. Pivaloyloxymethyl (POM) ester moieties were incorporated in both the N-terminal and C-terminal fragments prior to formation of either C-P bond, N-Alkylation of the corresponding amides derived from N-(N-methyl)aminobenzoic acid with 2,4-diamino-6-(bromomethyl)pteridine gave the target compounds. POM esters of methotrexate and the corresponding γ-glutamyl conjugate were also synthesized using the same strategy. All prodrugs were evaluated in Chinese hamster ovary cells. Although the pseudopeptide prodrugs were ineffective, prodrugs of methotrexate and the corresponding γ-glutamyl conjugate were equipotent with the parent compounds. Stability of the prodrugs was investigated in both phosphate buffer and cell line medium to provide a rationale for the observed biological data.

AGENTS FOR IMAGING AND DIAGNOSTIC METHODS USING THEM

The present invention provides novel compounds that bind selectively to cells undergoing perturbations and alterations of the normal organization of their plasma membrane, while binding to a lesser degree to cells having membranes of normal organization,

An efficient procedure for the preparation of 4-substituted 5-aminoimidazoles

The preparation of O-methylimidates from α-aminonitriles and their subsequent co-cyclization with primary amines to afford 4-substituted 5-aminoimidazoles was studied. It was found that the mildly acidic pyridinium p-toluenesulfonate efficiently catalyzed each stage of the reaction sequence: (a) the formation of the O-methylimidates, (b) their co-cyclization with a variety of primary amines, and (c) certain derivatizations of the resultant heterocycles. The developed reaction conditions tolerate a wide variety of α-aminonitriles and primary amine co-reactants. Thus, it is possible to easily prepare a diverse array of substituted heterocyclic compounds in good yield. The requisite α-aminonitriles were synthesized either from amino acids or by phase-transfer alkylation of a glycine anion equivalent. The unstable free 5-aminoimidazoles were normally protected in situ to provide derivatives (methyl imidates or N,N-dimethylamidines) that were amenable to characterization.

Synthesis of the γ-sulfinic acid and γ-nitro analogues of 5- deazatetrahydrofolic acid

Analogues of 5-deaza-5,6,7,8-tetrahydrofolic acid with a γ-sulfinic acid group or γ-nitro group in place of the γ-carboxyl group of the glutamate side chain were synthesized as diastereomeric mixtures, and were tested for their ability to inhibit the grow

LES ORGANOCUPRATES DANS UNE NOUVELLE SYNTHESE D'AMINOACIDES ENANTIOMERIQUEMENT PURS

A new general method of synthesis of optically pure α- amino esters was elaborated during studies on the reaction of organocuprates with tosyl and halogeno derivatives of L-serine and L-homoserine.