13471-69-7

Usage

Chemical Properties

yellow crystals

InChI:InChI=1/C8H6N2O3/c1-6-2-3-7(9-5-11)4-8(6)10(12)13/h2-4H,1H3

Upstream product

• 119-32-4 4-Methyl-3-nitroanilin 
• 201230-82-2 carbon monoxide 
• 121-14-2 2,4-dinitrotoluene 
• 51085-53-1 4-methyl-3-nitroaniline hydrochloride 
• 503-38-8 trichloromethyl chloroformate 

Downstream Products

• 16648-53-6 ethyl 3-nitro-4-methylphenylcarbamate 
• 1226972-60-6 1-((2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)methyl)-3-(4-methyl-3-nitrophenyl)urea 
• 390824-59-6 N-[(3-amino-4-methylphenyl)carbamoyl]valine 

Relevant academic research and scientific papers

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.

Catalysis by palladium salts XIII. The reductive carbonylation of nitroaromatic compounds to isocyanates with PdII and Pd0 complexes as homogeneous catalysts

A study has been made of the reductive carbonylation of 2,4-dinitrotoluene (2,4-DNT) to 2,4-diisocyanotoluene (2,4-TDI) with catalysis either by , in the presence of FeO3 and MoO3 or of Fe(MoO4)3 as cocatalysts, or by Pd0 complexes without cocatalysts.In the case of catalytic systems based upon the reaction can be carried out at about 200 deg C and under 200 atm of CO to produce 2,4-TDI with high conversions and acceptable selectivities.With Pd0 complexes as catalysts good conversions can be achieved at much lower temperatures (100-120 deg C) but with a low selectivity when a higher pressure of CO is used (300 atm or more).An investigation of the reductive cabonylation of nitrobenzene to phenylisocyanate as a model system, together with a study of the thermal stability of in the presence of CO, has provided evidence that the actual active catalyst could be a reduced (probably zerovalent) form of palladium stabilised by the nitroaromatic substrate or by some of the products formed from it as ligands.

Process for producing isocyanate from nitro compounds and carbon monoxide using rhodium oxide catalysts

In the process for preparing isocyanate, particularly aromatic isocyanate, by the reaction of an organic nitro compound, particularly an aromatic dinitro compound with carbon monoxide in the presence of a catalyst, the improvement which comprises employing as said catalyst rhodium oxide, particularly substantially amorphous rhodium oxide, and conducting the reaction in the presence of a promoter quantity of a nitrilic solvent, such as acetonitrile.