260418-09-5

Upstream product

• 5720-07-0 4-methoxyphenylboronic acid 
• 96042-30-7 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran 
• 53547-61-8 vinyl trifluoromethanesulfonate 
• 260418-04-0 (11aS)-1,2,3,11a-tetrahydro-10-(2-trimethylsilanylethoxymethyl)-7,8-dimethoxy-2-(tert-butyl-dimethylsilanyloxy)-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione 
• 260418-05-1 (11aS)-1,2,3,11a-tetrahydro-10-(2-trimethylsilanylethoxymethyl)-7,8-dimethoxy-2-hydroxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione 
• 260418-06-2 (11aS)-1,11a-dihydro-(2-trimethylsilanylethoxymethyl)-7,8-dimethoxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-2,5,11-trione 
• 260418-03-9 2-(tert-butyl-dimethyl-silanyloxy)-7,8-dimethoxy-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione 
• 54431-30-0 1-(4,5-dimethoxy-2-nitrobenzoyl)-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 
• 260418-02-8 (2R,11aS)-2-hydroxy-7,8-dimethoxy-1,2,3,10,11,11a-hexahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione 
• 4998-07-6 4,5-dimethoxy-2-nitro-benzoic acid 
• 260418-07-3 trifluoromethanesulphonic acid (11aS)-1,11a-dihydro-5,11-dioxo-10-(2-trimethylsilanylethoxymethyl)-7,8-dimethoxy-5H-pyrrolo[2,1-c][1,4]benzodiazepine-2-yl ester 

Relevant academic research and scientific papers

Pyrrolobenzodiazepines

Compounds of the formulae Ia and Ib: wherein: A is CH2, or a single bond; R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN; R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn; and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula —X—R′—X— linking the monomers, where R′ is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH═CH(CONH2) or CH═CH(CONMe2). Other related compounds are also disclosed.

Synthesis of a novel C2-aryl substituted 1,2-unsaturated pyrrolobenzodiazepine.

A novel C2-aryl 1,2-unsaturated PBD (14) has been prepared via an enol triflate intermediate (8). The regiochemistry of triflation is dependent upon the point at which the reaction is performed during the synthetic route.

Synthesis of novel C2-aryl pyrrolobenzodiazepines (PBDs) as potential antitumour agents

Three novel C2-aryl substituted pyrrolobenzodiazepines (PBDs) have been synthesised and evaluated in a number of cell lines revealing selective cytotoxicity at the sub-nanomolar level towards melanoma and ovarian cancer cell lines.

Pyrrolobenzodiazepines

Compounds of the formulae Ia and Ib: wherein:A is CH2, or a single bond;R2 is selected from: R, OH, OR, CO2H, CO2R, COH, COR, SO2R, CN;R6, R7 and R9 are independently selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn;and R8 is selected from H, R, OH, OR, halo, amino, NHR, nitro, Me3Sn, where R is as defined above, or the compound is a dimer with each monomer being the same or different and being of formula Ia or Ib, where the R8 groups of the monomers form together a bridge having the formula -X-R'-X- linking the monomers, where R' is an alkylene chain containing from 3 to 12 carbon atoms, which chain may be interrupted by one or more hetero-atoms and/or aromatic rings and may contain one or more carbon-carbon double or triple bonds, and each X is independently selected from O, S, or N; except that in a compound of formula Ia when A is a single bond, then R2 is not CH=CH(CONH2) or CH=CH(CONMe2). Other related compounds are also disclosed.