232931-63-4

Basic information

• Product Name: 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-hydroxymethyl-4-methylidene-2,3-dihydropyrrole]
• Synonyms: 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-hydroxymethyl-4-methylidene-2,3-dihydropyrrole]
• CAS NO: 232931-63-4
• Molecular Weight: 764.83
• Mol File: 232931-63-4.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-hydroxymethyl-4-methylidene-2,3-dihydropyrrole](CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-hydroxymethyl-4-methylidene-2,3-dihydropyrrole](232931-63-4)
• EPA Substance Registry System: 1,1'-[[(propane-1,3-diyl)dioxy]-bis[(2-amino-N-allyloxycarbonyl-5-methoxy-1,4-phenylene)carbonyl]]-bis[(2S)-2-hydroxymethyl-4-methylidene-2,3-dihydropyrrole](232931-63-4)

Safety Data

• Hazardous Substances Data: 232931-63-4(Hazardous Substances Data)

Upstream product

• 95687-41-5 (2S,4R)-N1-(benzyloxycarbonyl)-4-hydroxy-2-(hydroxymethyl)-pyrrolidine 
• 130107-96-9 1',3'-bis<2-methoxy-(4-methoxycarbonyl)phenoxy>propane 
• 140658-45-3 1',3'-bis(4-carboxy-2-methoxy-5-nitrophenoxy)propane 
• 140658-44-2 1,1'-[(propane-1,3-diyl)dioxy]bis[(5-methoxy-2-nitro-1,4-phenylene)carbonyl]bis[(2S,4R)-methyl-4-hydroxypyrrolidine-2-carboxylate] 
• 232931-60-1 [4-[3-[4-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylenepyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitrophenyl]-[(2S)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-methylene-pyrrolidin-1-yl]methanone 
• 232931-61-2 [4-[3-[4-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidine-1-carbonyl]-2-methoxy-5-nitrophenoxy]propoxy]-5-methoxy-2-nitro-phenyl]-[(2S)-2-(hydroxymethyl)-4-methylene-pyrrolidin-1-yl]methanone 
• 126408-59-1 (S)-N-(allyloxycarbonyl)-2-(tert-butyldimethylsilyloxymethyl)-4-methylidenepyrrolidine 
• 126408-57-9 (2S,4R)-N-(allyloxycarbonyl)-2-(tert-butyldimethylsilyloxymethyl)-4-hydroxypyrrolidine 
• 126408-58-0 (2S)-N-(allyloxycarbonyl)-2-(tert-butyldimethylsilyloxymethyl)-4-oxopyrrolidine 
• 232931-59-8 (2S)-2-(tert-butyldimethylsilyloxymethyl)-4-methylidenepyrrolidine 
• 126408-56-8 (2S,4R)-N-(allyloxycarbonyl)-4-hydroxy-2-(hydroxymethyl)pyrrolidine 
• 126408-14-8 methyl (2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate 
• 51-35-4 4R-4-hydroxyproline 
• 126407-76-9 (2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 

Downstream Products

• 232931-57-6 1,1'-[[(propane-1,3-diyl)dioxy]bis[(11aS)-7-methoxy-2-methylidene-1,2,3,11a-tetrahydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-5-one]] 

Relevant articles and documents

Linker Length Modulates DNA Cross-Linking Reactivity and Cytotoxic Potency of C8/C8′ Ether-Linked C2-exo-Unsaturated Pyrrolo[2,1-c][1,4]benzodiazepine (PBD) Dimers

A C2/C2′-exo-unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimer 4b (DRG-16) with a C8-O(CH2)nO-C8′ diether linkage (n = 5) has been synthesized that shows markedly superior in vitro cytotoxic potency (e.g., > 3400-fold in IGRO

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 the first example of a C2-C3/C2'-C3'-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine dimer.

We report the first example of a C2-C3/C2'-C3'-endo unsaturated pyrrolo[2,1-c][1,4]benzodiazepine (PBD) dimer 16 synthesised through a new and efficient route, thus establishing that C2-C3-endo unsaturation enhances both cytotoxicity and DNA-binding affin