1132709-16-0

Basic information

• Product Name: Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-
• Synonyms: Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-;(1S,2R)-BortezoMib;(S)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butylboronic acid;N-(2-Pyrazinecarbonyl)-D-phenylalanine-D-leucine boronic anhydride;(1S,2R)-Bortezomib Impurity
• CAS NO: 1132709-16-0
• Molecular Formula: C19H25BN4O4
• Molecular Weight: 384.2372
• EINECS: -0
• Product Categories: Chiral Reagents, Boron Derivatives, Inhibitors, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 1132709-16-0.mol

Chemical Properties

• Appearance: /
• Density: 1.214±0.06 g/cm3(Predicted)
• PKA: 9.66±0.43(Predicted)
• CAS DataBase Reference: Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-(1132709-16-0)
• EPA Substance Registry System: Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-(1132709-16-0)

Safety Data

• Hazardous Substances Data: 1132709-16-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]is used as a pharmaceutical intermediate for the development of novel drugs targeting specific biological pathways. Its unique structure allows for the design of molecules with high specificity and affinity for their target proteins, making it a valuable tool in drug discovery and development.
Used in Chemical Synthesis:
In the field of chemical synthesis, Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]can be used as a building block or a reagent in the synthesis of complex organic molecules. Its ability to form stable bonds with a variety of other molecules makes it a versatile component in the creation of new chemical entities.
Used in Materials Science:
Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]may also find applications in materials science, where its unique structure and reactivity can be harnessed to create new materials with specific properties. These materials could have potential uses in various industries, such as electronics, energy, or biomedical applications.
Used in Research and Development:
Due to its unique structure and potential applications, Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]is also used in research and development settings. Scientists and researchers can explore its properties and reactivity to gain a better understanding of its potential uses and to develop new applications for Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-.

Upstream product

• 1422969-07-0 C₃₂H₄₃BN₂O₅ 
• 1161-13-3 N-Cbz-L-Phe 
• 789472-91-9 N-{(1S)-3-methyl-1-[(3aS,4S,6S,7aS)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}phenylalanine amide 
• 205393-22-2 N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide 
• 1029701-48-1 bortezomib pinacol ester 
• 1380504-20-0 3-methyl-1-(MIDA boryl)butyl isocyanate 
• 98-97-5 2-pyrazylcarboxylic acid 
• 1412807-88-5 tert-butyl ((S)-1-((3-methyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)butyl)amino)-1-oxo-3-phenylpropan-2-yl)carbamate 
• 114457-94-2 (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid 
• 16874-17-2 L-phenylalanine tert-butyl ester 
• 1446194-56-4 (S)-N-(1-(isopentylamino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide 
• 98-80-6 phenylboronic acid 
• 107-85-7 1-amino-3-methylbutane 

Downstream Products

• 73058-37-4 methyl (pyrazine-2-carbonyl)phenylalaninate 
• 289472-81-7 N-(1-(((R)-1-hydroxy-3-methylbutyl)amino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide 
• 289472-81-7 N-(1-(((S)-1-hydroxy-3-methylbutyl)amino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide 
• 150-30-1 Phenylalanine 
• 1608986-16-8 3-phenyl-2-(pyrazine-2-carboxamido)propanoic acid 
• 289472-80-6 N-(1-amino-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide 

Relevant articles and documents

α-boryl isocyanides enable facile preparation of bioactive boropeptides

Entry to bioactive boropeptides: MIDA-containing α-boryl isocyanides are isolable molecules which allow one-step access to boroalkyl-functionalized heterocycles as well as biologically active boropeptides through a multicomponent approach. Among these derivatives are 6-boromorpholinones, novel borocycles with nanomolar IC50 values for 20S proteasome inhibition. MIDA=N-methyliminodiacetyl. Copyright

Structure-Based Design of Selective LONP1 Inhibitors for Probing in Vitro Biology

LONP1 is an AAA+ protease that maintains mitochondrial homeostasis by removing damaged or misfolded proteins. Elevated activity and expression of LONP1 promotes cancer cell proliferation and resistance to apoptosis-inducing reagents. Despite the importance of LONP1 in human biology and disease, very few LONP1 inhibitors have been described in the literature. Herein, we report the development of selective boronic acid-based LONP1 inhibitors using structure-based drug design as well as the first structures of human LONP1 bound to various inhibitors. Our efforts led to several nanomolar LONP1 inhibitors with little to no activity against the 20S proteasome that serve as tool compounds to investigate LONP1 biology.

Discovery of Novel Peptidomimetic Boronate ClpP Inhibitors with Noncanonical Enzyme Mechanism as Potent Virulence Blockers in Vitro and in Vivo

Caseinolytic protease P (ClpP) is considered as a promising target for the treatment of Staphylococcus aureus infections. In an unbiased screen of 2632 molecules, a peptidomimetic boronate, MLN9708, was found to be a potent suppressor of SaClpP function. A time-saving and cost-efficient strategy integrating in silico position scanning, multistep miniaturized synthesis, and bioactivity testing was deployed for optimization of this hit compound and led to fast exploration of structure-activity relationships. Five of 150 compounds from the miniaturized synthesis exhibited improved inhibitory activity. Compound 43Hf was the most active inhibitor and showed reversible covalent binding to SaClpP while did not destabilize the tetradecameric structure of SaClpP. The crystal structure of 43Hf-SaClpP complex provided mechanistic insight into the covalent binding mode of peptidomimetic boronate and SaClpP. Furthermore, 43Hf could bind endogenous ClpP in S. aureus cells and exhibited significant efficacy in attenuating S. aureus virulence in vitro and in vivo.

Diversity-oriented synthesis of peptide-boronic acids by a versatile building-block approach

A new strategy for the synthesis of peptide-boronic acids (PBAs) is presented. 20 Fmoc-protected natural amino acids with orthogonal side-chain protection were straightforwardly converted into their corresponding boron analogues in three simple steps. Subsequent immobilisation on commercially available 1-glycerol polystyrene resin and on-resin transformations yielded a diversity of sequences in high purity. The strategy eliminates various synthetic obstacles such as multi-step routes, low yields, and inseparable impurities. The described method comprises great potential to be implemented in automated combinatorial approaches by markedly facilitating the access to a variety of PBAs. The coupling of amino acids or other building blocks with α-aminoboronates allows the creation of hybrid molecules with significant potential in various scientific disciplines, such as medicinal chemistry, structural biology, and materials science.

Asymmetric Synthesis of α-Aminoboronates via Rhodium-Catalyzed Enantioselective C(sp3)-H Borylation

α-Aminoboronic acids, isostructural boron analogues of α-amino acids, have received much attention because of the important biomedical applications implicated for compounds containing this structure. Additionally, the inherent versatility of α-aminoboronic acids as synthetic intermediates through diverse carbon-boron bond transformations makes the efficient synthesis of these compounds highly desirable. Here, we present a Rh-monophosphite chiral catalytic system that enables a highly efficient enantioselective borylation of N-adjacent C(sp3)-H bonds for a range of substrate classes including 2-(N-alkylamino)heteroaryls and N-alkanoyl- or aroyl-based secondary or tertiary amides, some of which are pharmaceutical agents or related compounds. Various stereospecific transformations of the enantioenriched α-aminoboronates, including Suzuki-Miyaura coupling with aryl halides and the Rh-catalyzed reaction with an isocyanate derivative of α-amino acid, affording a new peptide chain elongation method, have been demonstrated. As a highlight of this work, the borylation protocol was successfully applied to the catalyst-controlled site-selective and stereoselective C(sp3)-H borylation of an unprotected dipeptidic compound, allowing remarkably streamlined synthesis of the anti-cancer drug molecule bortezomib and offering a straightforward route for the synthesis of privileged molecular architectures.

PROCESS FOR PREPARING BORTEZOMIB, INTERMEDIATES, AND CRYSTALLINE FORMS THEREOF

The present disclosure provides a process for preparing Bortezomib, intermediates, and crystalline forms thereof.

Rhodium-catalyzed regiodivergent and enantioselective hydroboration of enamides

Chiral α- and β-aminoboronic acids exhibit unique biological activities. General methods for the synthesis of these bioisosteres of amino acids are highly desirable. We report a facile preparation of these compounds through rhodium-catalyzed regiodivergent and enantioselective hydroboration of enamides. Catalytic asymmetric synthesis of α- and β-aminoboronic esters with high regio-, diastereo-, and enantioselectivities were achieved through effective catalyst control and tuning substrate geometry. Starting from easily available materials this strategy provides a unified synthetic access to both enantioenriched α-boration and β-boration products. The synthetic utility of these methods was demonstrated by efficient synthesis of an anticancer drug molecule and diverse transformations of the boration products.

Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids

Boronic acids are an increasingly important compound class for many applications, including C-C bond formation reactions, medicinal chemistry, and diagnostics. The deprotection of boronic ester intermediates is frequently a problematic and inefficient step in boronic acid syntheses. We describe an approach that highly facilitates this transformation by leveraging the volatility of methylboronic acid and its diol esters. The method is performed under mild conditions, provides high yields, and eliminates cumbersome and problematic purification steps.

Preparation method of bortezomib synthesis intermediate

The present invention belongs to the technical field of pharmaceutical chemistry, and particularly relates to a preparation process of a bortezomib synthesis intermediate (R) 1-amino-3-methylbutyl boronic acid pinacol ester hydrochloride. The preparation

AN IMPROVED PROCESS FOR THE PREPARATION OF BORONIC ACID ESTERS

The present invention relates to an improved process for the preparation of a compound of formula (I), wherein PG1 may be independently selected from tert-butyloxycarbonyl (Boc), phthaloyl, 9-fluorenylmethyloxycarbonyl (Fmoc), triphenylmethyl (Trityl), carboxybenzyl (Cbz), trifluoroacetyl, benzyl (Bn), benzylidene, methanesulfonyl (Mesyl), toluene sulfonyl (Tosyl) or acyl; its isolation as solid and use for the preparation of the compound of formula (IV), in particular the compound of formula (IV) i.e. [(1R)-3-methyl-1[[(2S)-1-oxo-3-phenyl-2- [(pyrazinylcarbonyl) amino]propyl]amino]butyl] boronic acid with more than 99.95% chiral purity, as measured by HPLC.