403699-41-2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 89980-92-7 (2-bromo-1,4-phenylene) dimethyl carbinol 
• 586-35-6 2-bromo-1,4-benzenedicarboxylic acid 
• 13815-89-9 2-bromobenzene-1,4-dicarbonyl dichloride 
• 154239-21-1 diethyl 2-Bromoterephthalate 
• 553-94-6 4-bromo-m-xylene 
• 18643-86-2 dimethyl 2-bromoterephthalate 

Downstream Products

• 452978-20-0 2,5-bis[(tetrahydropyran-2-yl)oxymethyl]benzoic acid 
• 1222009-53-1 1-hydroxy-N-phenyl-1,3-dihydrobenzo[c][1,2]oxaborole-6-carboxamide 

Relevant academic research and scientific papers

QUINAZOLINE DERIVATIVES AS ECTONUCLEOTIDE PYROPHOSPHATASE PHOSPHODIESTERASE 1 INHIBITORS

The present disclosure provides certain quinazoline compounds that inhibit ectonucleotide pyrophosphatase/phosphodiesterase 1 (ENPP1) enzymatic activity and are therefore useful for the treatment of diseases and conditions modulated at least in part by ENPP1. Also provided are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

PROTECTIVE GROUPS AND METHODS FOR PROTECTING BENZOXABOROLES OR OXABOROLES

The present invention relates in part protective groups that can be used to reversibly protect benzoxaboroles and/or oxaboroles and yield the corresponding protected complexes. The invention further relates to the use of these protective groups to protect benzoxaboroles and/or oxaboroles.

Protection of the Benzoxaborole Moiety: Synthesis and Functionalization of Zwitterionic Benzoxaborole Complexes

The synthesis and utility of three benzoxaborole protecting groups are reported. These protecting groups improve organic solubility and allow otherwise incompatible reactions (oxidations, substitutions, and mild reductions) to be achieved in the presence of the benzoxaborole moiety. 3-(N,N-Dimethylamino)-1-propanol was determined to be useful in one-step sequences and is readily cleaved upon workup. Two other groups, N-methylsalicylidenimine and 2-[1-(methylimino)ethyl]phenol, are suitable for multistep syntheses. Deprotection with mild aqueous acid allows for chromatography-free isolation of the benzoxaborole in high yields.

THERAPEUTIC INHIBITORY COMPOUNDS

Provided herein are heterocyclic derivative compounds and pharmaceutical compositions comprising said compounds that are useful for inhibiting plasma kallikrein. Furthermore, the subject compounds and compositions are useful for the treatment of diseases wherein the inhibition of plasma kallikrein inhibition has been implicated, such as angioedema and the like.

Chalcone–benzoxaborole hybrids as novel anticancer agents

In this study, we report the synthesis of a series of chalcone–benzoxaborole hybrid molecules and the evaluation of their anticancer activity. Their anticancer potency and toxicity were tested on three human cancer cell lines and two normal cell lines. The 4-fluoro compound 15 was found to be the most potent compound with an IC50value of 1.4 μM on SKOV3 cells. The 4-iodo compound 18 and 3-methyloxy-4-amino compound 47 showed good potency on SKOV3 cells while exhibiting low toxicity on normal cells. This work extended the application of benzoxaboroles to the field of anticancer research.

Chalcone-benzoxaborole hybrid molecules as potent antitrypanosomal agents

We report the novel chalcone-benzoxaborole hybrids and their structure-activity relationship againstTrypanosoma brucei parasites. The 4-NH2 derivative 29 and 3-OMe derivative 43 were found to have excellent potency. The synergistic 4-NH2-3-OMe compound 49 showed an IC50 of 0.010 μ/mL and resulted in 100% survival and zero parasitemia in a murine infection model, which represents one of the most potent compounds discovered to date from the benzoxaborole class that inhibit T. brucei growth.

Convenient and versatile synthesis of formyl-substituted benzoxaboroles

Despite of the medicinal significance of benzoxaboroles, with the newly discovered clinical compound AN2690 as an example, the synthetic method for rapid diversification of this novel scaffold is lacking. To this end, a versatile and scalable synthesis of formyl-substituted benzoxaboroles is described here. A key step is the mono-oxidation of the two hydroxyls in compound 4 by taking advantage of the stable oxaborole ring in non-coordinating solvents, which was devised based on the study of the intramolecular coordination and exchange properties.

WATER-SOLUBLE TRIAZOLE FUNGICIDE

A triazole compound of the general formula (I) or a pharmacologically acceptable salt thereof: [wherein,X represents a group of formula X-OH which has antifungal activity,L represents a -(adjacently substituted C6-C10 aryl)-CH2-group and the like, andR represents a -P(=O) (OH)2 group and the like.

Sterically hindered fluorenyl-substituted poly(p-phenylenevinylenes) for light-emitting diodes

A new series of processable dihexylfluorenyl-substituted poly(p-phenylenevinylene) derivatives (DHF-PPVs) were synthesized by dehydrohalogenation-condensation polymerization (GILCH polymerization). The polymers were characterized by NMR, FT-IR, and elemen