550355-91-4

Upstream product

• 260391-49-9 (S)-(4-(benzyloxy)-5-methoxy-2-nitrophenyl)(2-(hydroxymethyl)pyrrolidin-1-yl)methanone 
• 60547-92-4 4-(benzyloxy)-5-methoxy-2-nitrobenzoic acid 
• 64154-78-5 4-benzyloxy-5-methoxy-2-nitrobenzoyl chloride 

Downstream Products

• 550355-92-5 allyl 5-hydroxy-2-{[(S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate 
• 550355-94-7 2,2,2-trichloroethyl (5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)acetate 
• 550355-95-8 2,2,2-trichloroethyl 4-(5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)butanoate 
• 550355-96-9 2,2,2-trichloroethyl 5-(5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)pentanoate 
• 550355-97-0 2,2,2-trichloroethyl 6-(5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)hexanoate 
• 550356-41-7 (2S)-1-(2-{[(allyloxy)carbonyl]amino}-5-methoxy-4-{[6-oxo-6-(2,2,2-trichloroethoxy)hexyl]oxy}benzoyl)-2-pyrrolidinecarboxylic acid 
• 550356-52-0 allyl 5-[3-(5-{[(allyloxy)carbonyl]amino}-4-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-2-methoxyphenoxy)propoxy]-2-{[(2S)-2-(hydroxymethyl)pyrrolidinyl]carbonyl}-4-methoxyphenylcarbamate 

Relevant academic research and scientific papers

In water alkylation of amines with alcohols through a borrowing hydrogen process catalysed by ruthenium nanoparticles

A simple and environmentally benign procedure for the synthesis of secondary amines in water has been developed. Combining Ru3(CO)12, tetraphenylcyclopentadienone and a small quantity of TGPS-750-M surfactant, primary and secondary alcohols were alkylated at N employing equimolar amounts of aromatic amines in water. The reaction occurs under microwave (MW) dielectric heating with high conversion and high yield. When required, the use of biomass-derived 2-MeTHF or GVL as a co-solvent is possible. Under the influence of MWs, a Ru nanoparticle-nanomicelle combination was formed acting as an effective and recyclable catalyst. This protocol was also employed for "in water" cyclisation to synthesise biologically relevant pyrrolobenzodiazepines (PBDs).

Unsymmetrical DNA cross-linking agents: Combination of the CBI and PBD pharmacophores

A set of 10 compounds, each combining the seco-1,2,9,9a-tetrahydrocyclopropa[c]benz[e]indol-4-one (seco-CBI) and pyrrolo [2,1-c] [1,4] benzodiazepine (PBD) pharmacophores, was designed and prepared. These compounds were anticipated to cross-link between N3 of adenine and N2 of guanine in the minor groove of DNA. The compounds, which differ in the chain length separating the two alkylation subunits, and the configuration of the CBI portion, showed great variation in cellular toxicity (over 4 orders of magnitude in a cell line panel) with the most potent example exhibiting IC50S in the pM range. Cytotoxicity correlated with the ability of the compounds to cross-link naked DNA. Cross-linking was also observed in living cells, at much lower concentrations than for a related symmetrical PBD dimer. A thermal cleavage assay was used to assess sequence selectivity, demonstrating that the CBI portion controlled the alkylation sites, while the PBD substituent increased the overall efficiency of alkylation. Several compounds were tested for in vivo activity using a tumor growth delay assay against WiDr human colon carcinoma xenografts, with one compound (the most cytotoxic and most efficient cross-linker) showing a statistically significant increase in survival time following a single iv dose.