779357-85-6

Basic information

• Product Name: (R)-BoroLeu-(+)-Pinanediol-HCl
• Synonyms: (R)-BoroLeu-(+)-Pinanediol-HCl;(R)-BoroLeu-(+)-Pinanediol-hydrochloride;(R)-1-Amino-3-methylbutylboronic acid pinanediol ester hydrochloride;(αR)-(1S,2S,3R,5S)-Pinanediol-1-amino-3-methylbutane-1-boronate Hydrochloride;(αR,3aS,4S,6S,7aR)-Hexahydro-3a,5,5-triMethyl-α-(2-Methylpropyl)-4,6-Methano-1,3,2-benzodioxaborole-2-MethanaMine Hydrochloride
• CAS NO: 779357-85-6
• Molecular Formula: C15H28BNO2.ClH
• Molecular Weight: 301.663
• EINECS: 1806241-263-5
• Product Categories: Amines;Boron Derivatives;Chiral Reagents;Intermediates
• Mol File: 779357-85-6.mol
• Article Data: 22

Chemical Properties

• Melting Point: 176-178 °C
• Appearance: off-white solid
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Dimethylformamide, Ethanol, Methanol, Tetrahydrofuran,
• CAS DataBase Reference: (R)-BoroLeu-(+)-Pinanediol-HCl(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-BoroLeu-(+)-Pinanediol-HCl(779357-85-6)
• EPA Substance Registry System: (R)-BoroLeu-(+)-Pinanediol-HCl(779357-85-6)

Safety Data

• Hazardous Substances Data: 779357-85-6(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

InChI:InChI=1/C15H28BNO2.ClH/c1-9(2)6-13(17)16-18-12-8-10-7-11(14(10,3)4)15(12,5)19-16;/h9-13H,6-8,17H2,1-5H3;1H/t10-,11-,12+,13-,15-;/m0./s1

Upstream product

• 29333-10-6 (1S,2R,3R, 5S)-pinanediol 
• 7785-26-4 (-)-α-pinene 
• 1173167-09-3 2-methyl-4-chloro-butylboronic acid-(-)-α-pinanediol ester 
• 7785-70-8 (+)-α-pinene 
• 20536-51-0 (+)-α-pinanediol 
• 7647-01-0 hydrogenchloride 
• 514820-48-5 1,1,1-trimethyl-N-{(1R)-3-methyl-1-[(3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborol-2-yl]butyl}-N-(trimethylsilyl)silanamine 
• 179324-86-8 (1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,6]decan-4-yl]butan-1-amine 
• 84110-34-9 2-(2-methylpropyl)-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole 
• 18680-27-8 pinanediol 
• 87249-60-3 (3aS,4S,6S,7aR)-2-(dichloromethyl)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 
• 85167-14-2 (3aS,4S,6S,7aR)-2-[(1S)-1-chloro-3-methylbutyl]-3a,5,5-trimethylhexahydro-4,6-methano-1,3,2-benzodioxaborole 
• 87304-47-0 2-[(1S)-1-chloro-3-methylbutyl]-(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborole 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 

Downstream Products

• 1564251-59-7 C₃₁H₄₇BN₂O₇ 
• 1564251-60-0 C₃₂H₄₉BN₂O₇ 
• 1613134-42-1 N-[(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]butyl]-1-{2-[(2,3,4-trimethoxyphenyl)formamido]ethyl}-1H-1,2,3-triazole-4-carboxamide 

Relevant articles and documents

Structure-Based Optimization and Discovery of M3258, a Specific Inhibitor of the Immunoproteasome Subunit LMP7 (β5i)

Proteasomes are broadly expressed key components of the ubiquitin-dependent protein degradation pathway containing catalytically active subunits (β1, β2, and β5). LMP7 (β5i) is a subunit of the immunoproteasome, an inducible isoform that is predominantly expressed in hematopoietic cells. Clinically effective pan-proteasome inhibitors for the treatment of multiple myeloma (MM) nonselectively target LMP7 and other subunits of the constitutive proteasome and immunoproteasome with comparable potency, which can limit the therapeutic applicability of these drugs. Here, we describe the discovery and structure-based hit optimization of novel amido boronic acids, which selectively inhibit LMP7 while sparing all other subunits. The exploitation of structural differences between the proteasome subunits culminated in the identification of the highly potent, exquisitely selective, and orally available LMP7 inhibitor 50 (M3258). Based on the strong antitumor activity observed with M3258 in MM models and a favorable preclinical data package, a phase I clinical trial was initiated in relapsed/refractory MM patients.

Mercapto-amide boronic acid derivative and application thereof as MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase) inhibitor

The invention provides a compound of a formula (I) shown in the specification, or a conformational isomer, or an optical isomer or a pharmaceutically acceptable salt thereof. The compound of the formula (I) shown in the specification has excellent broad-spectrum inhibitory activity on MBL (metal beta-lactamase) and/or SBL (serine beta-lactamase), and can be used for preparing MBL and/or SBL inhibitors. Moreover, the compound disclosed by the invention has excellent antibacterial activity on multiple drug-resistant bacteria and is capable of reversing drug resistance of carbapenem drug-resistant bacteria, and the antibacterial effect of the compound is prior to those of positive control products such as L-captopril and tazobactam. The compound disclosed by the invention has very great potential in preparation of MBL/SBL dual inhibitors and medicines reversing drug resistance of carbapenem drug-resistance bacteria.

Discovery of novel 20S proteasome inhibitors by rational topology-based scaffold hopping of bortezomib

A series of structurally novel proteasome inhibitors 1–12 have been developed based rational topology-based scaffold hopping of bortezomib. Among these novel proteasome inhibitors, compound 10 represents an important advance due to the comparable proteasome-inhibitory activity (IC50 = 9.7 nM) to bortezomib (IC50 = 8.3 nM), the remarkably higher BEI and SEI values and the effectiveness in metabolic stability. Therefore, compound 10 provides an excellent lead suitable for further optimization.