90084-37-0

Usage

Uses

Used in Pharmaceutical Industry:
3-BROMOPROPANEBORONIC ACID (1S,2S,3R,5S)-(+)-2,3-PINANEDIOL ESTER is used as a precursor in the preparation of thrombin inhibitors for the treatment of various medical conditions, such as blood clotting disorders and cardiovascular diseases. Its unique structure allows for the development of selective and potent thrombin inhibitors, making it a valuable compound in drug discovery and development.

Upstream product

• 18680-27-8 pinanediol 
• 45770-13-6 2-hydroxy-1,3,2-benzodioxaborole 
• 106-95-6 allyl bromide 
• 90084-34-7 2-(3-Bromopropyl)-1,3,2-benzodioxaborole 
• 90084-43-8 (3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborole 
• 993-07-7 trimethylsilan 
• 10294-34-5 boron trichloride 
• 274-07-7 benzo[1,3,2]dioxaborole 
• 7785-70-8 (+)-α-pinene 

Relevant academic research and scientific papers

Peptide-Boronic Acid Inhibitors of Flaviviral Proteases: Medicinal Chemistry and Structural Biology

A thousand-fold affinity gain is achieved by introduction of a C-terminal boronic acid moiety into dipeptidic inhibitors of the Zika, West Nile, and dengue virus proteases. The resulting compounds have Ki values in the two-digit nanomolar range

BORONIC ACID DERIVATIVES AND USES THEREOF

This invention is directed to novel Boronic acid derivatives of Formula I, and pharmaceutically acceptable salts, solvate, solvate of the salt and prodrugs thereof, useful in the prevention (e.g., delaying the onset of or reducing the risk of developing) and treatment (e.g., controlling, alleviating, or slowing the progression of) of Age-related Macular Degeneration (AMD) and related diseases of the eye. These diseases include dry-AMD, Wet-AMD, geographic atrophy, diabetic retinopathy, retinopathy of prematurity, polypoidal choroidal vasculopathy, and degeneration of retinal or photoreceptor ceils. The invention disclosed herein is further directed to methods of prevention, slowing the progress of, and treatment of dry -AMD, Wet- AMD, and geographic atrophy, diabetic retinopathy, retinopathy of prematurity, polypoidal choroidal vasculopathy, and degeneration of retinal or photoreceptor cells, comprising: administration of a therapeutically effective amount of compound of the invention. The compounds of the invention are inhibitors of HTRA1. Thus, the compounds of the invention are useful in the prevention and treatment of a wide range diseases mediated (in whole or in part) by HTRA1. The compounds of the invention are also useful for inhibiting HTRA1 protease activity in an eye or locus of an arthritis or related condition.

Expanding the scope of PNA-encoded libraries: divergent synthesis of libraries targeting cysteine, serine and metallo-proteases as well as tyrosine phosphatases

Seven PNA-encoded combinatorial libraries targeting proteases and phosphatases with covalent reversible and irreversible mechanism-based inhibitors were prepared. The libraries were synthesized using modified PNA monomers, which dramatically increase the water solubility of the libraries in biologically relevant buffers. The libraries were shown to selectively inhibit targeted enzymes.

Hydroboration with haloborane/trialkylsilane mixtures

Trialkylsilanes or dialkylsilanes react rapidly with boron trichloride in the absence of ethereal solvents or other nucleophiles to form unsolvated dichloroborane. If no substrate is present, dichloroborane disproportionates to trichloroborane and two geo

Synthesis and properties of pinanediol α-amido boronic esters

The use of (+)-pinanediol as the chiral directing group for the synthesis of several α(R)-α-amido boronic esters and acids, which are boronic acid analogues of N-acyl-L-amino acids, has been explored. RBO2Pin (Pin = cis-pinane-2,3-diyl) was homologated to (S)-RCHClBO2Pin, which was converted to (R)-RCH-(NHAc)BO2Pin and, for R = isopropyl, to (R)-RCH(NHCOAc)B(OH)2 by previously reported methods. Where R = isobutyl, methyl, or (benzyloxy)methyl, zinc chloride catalysis was required for the homologation step. Two (S)-acetamido boronic esters (R = isopropyl, isobutyl) were made from (-)-pinanediol. Acylation of the unstable α-amino boronic ester intermediate with carbobenzyloxy chloride was accomplished in the synthesis of PhCH2CH(NHCOOCH2Ph)BO2Pin, but attempted boron trichloride cleavage of the pinanediol boronic ester to the acid also cleaved the benzyloxy group. Hydroboration of allyl halides or allyl benzyl ether with (1,2-phenyldioxy)borane has yielded γ-substituted boronic esters. These were converted to (+)-pinanediol esters and converted by the general route outlined above to α-acetamido δ-substituted boronic esters. (Pinanediyldioxy)borane has been prepared and found to be a sluggish hydroborating agent.