71189-13-4

Usage

InChI:InChI=1/C8H6BrNO/c1-6-2-3-8(10-5-11)7(9)4-6/h2-4H,1H3

Upstream product

• 32315-10-9 bis(trichloromethyl) carbonate 
• 583-68-6 2-bromo-p-toluidine 
• 13194-71-3 2-bromo-4-methyl-aniline; hydrochloride 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 26792-85-8 (2-Bromo-4-methyl-phenyl)-carbamic acid 4-[(2,4-dinitro-phenoxyimino)-methyl]-2,6-diiodo-phenyl ester 
• 26724-43-6 (2-Bromo-4-methyl-phenyl)-carbamic acid 2,6-dichloro-4-[(2,4-dinitro-phenoxyimino)-methyl]-phenyl ester 
• 56462-08-9 1-amidino-3-(2-bromo-4-methylphenyl)urea 
• 247075-35-0 N-(4-methyl-2-bromophenyl) O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 247075-38-3 N-[4-(daunorubicin-N-carbonyloxymethyl)-2-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 247075-44-1 N-[4-(daunorubicin-N-carbonyloxymethyl)-3-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 247075-37-2 N-[4-(hydroxymethyl)-2-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 
• 247075-36-1 N-[4-(bromomethyl)-2-bromophenyl] O-(methyl 2,3,4-tri-O-acetyl-β-D-glucopyranuronosyl) carbamate 

Relevant academic research and scientific papers

N - (4 - (3 - amino - 1 H - indazole - 4 - yl) phenyl) - N' - (2 - fluoro - 5 - methylphenyl) urea intermediate preparation method

The invention provides a preparation method of N-(4-(3-amino-1H-indazol-4-yl) phenyl)-N'-(2-fluoro-5-methylphenyl) urea and an intermediate thereof. Specifically, the invention provides a preparation method of a borate ester compound as shown in a formula I, and the preparation method comprises the following steps: enabling a compound as shown in a formula III to react with a compound as shown in a formula IV to generate a compound as shown in a formula V, and enabling the compound as shown in the formula V to react with a boron reagent to generate the compound as shown in the formula I. The method has the characteristics of convenience in reaction, easiness in obtainment of the intermediate, high yield, high product purity of above 98.5%, low cost of raw materials and the like, and is suitable for industrial application.

Carbonylation of doubly lithiated N′-aryl-N,N-dimethylureas: A novel approach to isatins via intramolecular trapping of acyllithiums

Lithiation of N′-(2-bromoaryl)-N,N-dimethylureas with methyllithium and tert-butyllithium under nitrogen in anhydrous THF at 0°C gave doubly lithiated arylurea derivatives, which react with carbon monoxide at 0°C to give isatins in good yields. The scope of the reaction has been demonstrated by application to the synthesis of isatin itself and four substituted isatins beating alkyl, chloro or fluoro groups.

Novel anthracycline-spacer-β-glucuronide, -β-glucoside, and -β-galactoside prodrugs for application in selective chemotherapy

A series of anthracycline prodrugs containing an immolative spacer was synthesized for application in selective chemotherapy. The prodrugs having the general structure anthracycline-spacer-β-glycoside were designed to be activated by β-glucuronidase or β-galactosidase. Prodrugs with -chloro, -bromo or -n-hexyl substituents on the spacer were synthesized as well as prodrugs containing a -β-glucuronyl, -β-glucosyl or -β-galactosyl carbamate specifier. The key step in the synthesis of all prodrugs is the highly β-diastereoselective addition reaction of the anomeric hydroxyl of a glycosyl donor to a spacer isocyanate resulting in the respective β-glycosyl carbamate pro-moieties. The resulting protected pro-moieties were coupled to an anthracycline. Prodrugs were evaluated with respect to activation rate by the appropriate enzyme and additionally, their IC50 values were determined. Optimal prodrugs in this study were at least 100- to 200-fold less toxic than their corresponding drug in vitro and were activated to the parent drug in a half-life time of approximately 2h. Copyright (C) 1999 Elsevier Science Ltd.

A new class of inhibitors of secretory phospholipase A2: enolized 1,3-dioxane-4,6-dione-5-carboxamides

Enolized 1,3-dioxane-4,6-dione-5-carboxamides a were identified as a new class of inhibitors of secretory phospholipase A2 from human polymorphonuclear leucocytes (h-PMN PLA2).Among the more than 30 compounds synthesized, the most potent inhibitors (IC50 0.6-10 μM) were found in the series of 2,4-disubstituted phenyl analogues of a.Compound 1a was selected for evaluation of its biological profile.This substance potently inhibited secretory PLA2s from several sources other than human PMNs, with a clear preference for group II over group I PLA2, whereas humancytosolic PLA2 and phospholipase C were not significantly affected.Inhibition of h-PMN PLA2 was calcium-dependent.In intact mammalian cells stimulated in vitro, the release of arachidonic acid and the generation of prostaglandins and leukotrienes were inhibited at concentrations compatible with inhibition of PLA2 as an underlying mechanism.In animal models in vivo (carragheenan oedema, adjuvant arthritis, pertussis pleurisy) 1a showed antiinflammatory activity, although the effect was rather weak compared with standard reference compounds. secretory human PMN phospholipase A2 / enolized 1,3-dioxane-4,6-dione-5-carboxamide inhibitors / cellular eicosanoid synthesis / in vivo antiinflammatory activity / molecular modelling / structure-activity relationship