223595-20-8

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Dihydro-(1R)-methyl-5-(tetrahydro-4H-1,3,6,2-dioxazaborocin-2-yl)-2-(triphenylmethyl)-1H-isoindole is used as a potential pharmaceutical agent for its unique structure that may offer novel therapeutic applications. The chiral nature and the presence of the boron-containing heterocycle could provide new avenues for drug development, targeting specific biological pathways or receptors.
Used in Materials Science:
In the field of materials science, 2,3-Dihydro-(1R)-methyl-5-(tetrahydro-4H-1,3,6,2-dioxazaborocin-2-yl)-2-(triphenylmethyl)-1H-isoindole may serve as a component in the development of new materials with specialized properties. Its structural features could contribute to the creation of materials with enhanced mechanical, electronic, or optical characteristics.
Used in Organometallic Chemistry:
2,3-Dihydro-(1R)-methyl-5-(tetrahydro-4H-1,3,6,2-dioxazaborocin-2-yl)-2-(triphenylmethyl)-1H-isoindole is utilized in organometallic chemistry for its potential to form complexes with metal ions. These complexes could have applications in catalysis, providing new catalysts for various chemical reactions, or in the development of metal-based pharmaceuticals.
Further research and studies are necessary to explore the specific uses and potential benefits of 2,3-Dihydro-(1R)-methyl-5-(tetrahydro-4H-1,3,6,2-dioxazaborocin-2-yl)-2-(triphenylmethyl)-1H-isoindole in the mentioned industries, as its unique structure and properties may lead to innovative applications and advancements.

InChI:InChI=1/C32H33BN2O2/c1-25-31-18-17-30(33-36-21-19-34-20-22-37-33)23-26(31)24-35(25)32(27-11-5-2-6-12-27,28-13-7-3-8-14-28)29-15-9-4-10-16-29/h2-18,23,25,34H,19-22,24H2,1H3/t25-/m1/s1

Upstream product

• 111-42-2 2,2'-iminobis[ethanol] 
• 194805-14-6 (+)-(R)-5-bromo-1-methyl-2-(triphenylmethyl)isoindoline 

Downstream Products

• 194804-45-0 ethyl 1-cyclopropyl-8-methoxy-7-[(1R)-1-methyl-2-trityl-2,3-dihydro-1H-5-isoindolyl]-4-oxo-1,4-dihydro-3-quinolinecarboxylate 
• 479091-04-8 1-Cyclopropyl-8-difluoromethoxy-7-((R)-1-methyl-2-trityl-2,3-dihydro-1H-isoindol-5-yl)-1H-quinazolinedione 
• 194804-75-6 garenoxacin 

Relevant academic research and scientific papers

Processes for producing 7-isoindolinequinolonecarboxylic derivatives and intermediates therefor, salts of 7-isoindolinequinolonecarboxylic acids, hydrates thereof, and composition containing the same as active ingredient

This invention relates to processes for producing a 7-isoindoline-quinolonecarboxylic acid derivative represented by the general formula [1] which is useful as an antibacterial agent, and an intermediate thereof: wherein R1represents a hydrogen atom or a carboxyl-protecting group; R2represents a substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl or heterocyclic group; R3represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aryl, alkoxy or alkylthio groups, nitro group, cyano group, acyl groups, protected or unprotected hydroxyl groups and protected or unprotected or substituted or unsubstituted amino groups; R4represents at least one group selected from hydrogen atom, halogen atoms, substituted or unsubstituted alkyl, alkenyl, cycloalkyl, aralkyl, aryl, alkoxy or alkylthio groups, protected or unprotected hydroxyl or imino groups, protected or unprotected or substituted or unsubstituted amino groups, alkylidene groups, oxo group and groups each forming a cycloalkane group together with the carbon atom to which R4bonds; R5represents a hydrogen atom, an amino-protecting group, a substituted or unsubstituted alkyl, cycloalkyl, alkylsulfonyl, arylsulfonyl, acyl or aryl group; R6represents a hydrogen atom, a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group, a protected or unprotected hydroxyl or amino group or a nitro group; and A represents CH or C—R7in which R7represents a halogen atom, a substituted or unsubstituted alkyl, alkoxy or alkylthio group or a protected or unprotected hydroxyl group, and to a salt of a 7-isoindoline-quinolonecarboxylic acid represented by the general formula [1], a hydrate thereof and a composition comprising them as an active ingredient.

Synthesis, antibacterial activity, and toxicity of 7-(isoindolin-5-yl)-4-oxoquinoline-3-carboxylic acids: Discovery of the novel Des-F(6)-quinolone antibacterial agent garenoxacin (T-3811 or BMS-284756)

The palladium-catalyzed cross-coupling reaction of 5-(tributylstannyl)isoindoline and its 1- and 3-methyl derivatives with 6-fluoro or 6-unsubstituted 7-bromo-1-cyclopropyl-8-methoxy (or difluoromethoxy)-4-oxoquinoline-3-carboxylate afforded the corresponding 1-cyclopropyl-7-(5-isoindolinyl)-4-oxoquinoline-3-carboxylic acids: 6-fluoro, 1a-7a and 6-nonfluoro, 1b-7b. The in vitro antibacterial spectra of the newly synthesized quinolones were mostly characterized by excellent Gram-positive activity against Staphylococcus aureus and Streptococcus pneumoniae including quinolone-resistant strains, and also by significant Gram-negative activity comparable to 7-(1-piperazinyl)fluoroquinolones. Comparative examinations of the in vitro antibacterial profiles and the in vivo toxicity in terms of intravenous lethality, micronuclei-inducing potential and convulsive activity provided 6-nonfluorinated 1-cyclopropyl-8-(difluoromethoxy)-7-(1-methylisoindolin-5-yl)-4- oxoquinoline-3-carboxylic acid [(±)-5b] as the candidate for evaluation of the stereoisomers. The enantiomers (R)-5b and (S)-5b were synthesized via the Suzuki coupling reaction of (R)- and (S)-1-methyl derivatives of 2-(triphenylmethyl)isoindolin-5-boronic acid with the corresponding 7-bromo-8-(difluoromethoxy)-4-oxoquinoline-3-carboxylate. The (R)-5b stereoisomer proved to be 2- to 4-fold more active than the (S)-5b stereoisomer against the organisms tested, with the exception of an equal potency observed with S. pneumoniae IID553 and Haemophilus influenzae ATCC49247. A noticeable in vitro antibacterial profile of (R)-5b was that it is 16- and 64-fold more active than levofloxacin (CAS 100986-85-4) and ciprofloxacin (CAS 86393-32-0), respectively, against Mycoplasma pneumoniae IID813 (MIC of 0.0313 μg/ml), and 4-fold more active than ciprofloxacin and levofloxacin against Mycobacterium tuberculosis M-4 (MIC of 0.0313 μg/ml). Additional studies indicate that (R)-5b (T-3811, CAS 194804-75-6) exhibits excellent antibacterial activity against a wide range of organisms including anaerobes and common respiratory pathogens, while demonstrating a high selectivity against the mammalian homolog topoisomerases. The methane-sulfonate of (R)-5b (T-3811ME, CAS 223652-90-2) is now undergoing clinical testings.