193225-57-9

Basic information

• Product Name: Propanedioic acid, [2-[[(4-methoxyphenyl)methoxy]carbonyl]-4-nitro-1-naphthalenyl]-, dimethyl ester
• CAS NO: 193225-57-9
• Molecular Formula: C24H21NO9
• Molecular Weight: 467.432
• Mol File: 193225-57-9.mol

Chemical Properties

• CAS DataBase Reference: Propanedioic acid, [2-[[(4-methoxyphenyl)methoxy]carbonyl]-4-nitro-1-naphthalenyl]-, dimethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Propanedioic acid, [2-[[(4-methoxyphenyl)methoxy]carbonyl]-4-nitro-1-naphthalenyl]-, dimethyl ester(193225-57-9)
• EPA Substance Registry System: Propanedioic acid, [2-[[(4-methoxyphenyl)methoxy]carbonyl]-4-nitro-1-naphthalenyl]-, dimethyl ester(193225-57-9)

Safety Data

• Hazardous Substances Data: 193225-57-9(Hazardous Substances Data)

Upstream product

• 584-08-7 potassium carbonate 
• 108-59-8 malonic acid dimethyl ester 
• 193225-56-8 4-methoxybenzyl 4-nitro-1-(trifluoromethanesulfonyloxy)naphthalene-2-carboxylate 
• 193225-55-7 4-methoxybenzyl 1-hydroxy-4-nitronaphthalene-2-carboxylate 
• 193225-54-6 4-methoxybenzyl 1-hydroxynaphthalene-2-carboxylate 
• 824-94-2 p-methoxybenzyl chloride 
• 18396-51-5 1-hydroxynaphthalene-2-carboxylic acid sodium salt 

Relevant articles and documents

Condensed N-aclyindoles as antitumor agents

The invention provides compounds of general formula (I), wherein: X is halogen or OSO2R, where R represents H or is unsubstituted or hydroxy-or amino-substituted lower alkyl; Y is a nitro or amine group or a substituted derivative thereof; W is selected from the structures of formulae (Ia, Ib or Ic), where E is -N= or -CH=, G is O, S, or NH, and Q is either up to three of R, OR, NRR, NO2, CONHR, NHCOR or NHCONHR, or is an additional group of formulae (Ia, Ib or Ic) and HET represents a 5- or 6-membered carbocycle or heterocycle; and A and B collectively represent a fused benzene or 2-CO2R pyrrole ring. In one embodiment, the group Y is an amine derivative substituted by a group which is a substrate for a nitroreductase or carboxypeptidase enzyme such that one of said enzymes is able to bring about removal of that group.

Synthesis and cytotoxicity of 5-amino-1-(chloromethyl)-3-[(5,6,7- trimethoxyindol-2-yl)carbonyl], 1,2 dihydro-3H-benz[e]indole (Amino-seco- CBI-TMI) and related 5-alkylamino analogues: New DNA minor groove alkylating agents

The first synthesis of seco-CBI-TMI alkylating agents with 5-nitrogen substituents is reported. The parent 5-amino compound was prepared in a 15- step synthesis from 1-hydroxynaphthalene-2-carboxylic acid. Reductive alkylation of the 5-amino compound gave the corresponding 5-methylamino and 5-dimethylamino analogues, while resolution of an intermediate by chiral HPLC allowed preparation of the R and S enantiomers of the 5-amino analogue. Absolute configuration was assigned by X-ray crystallography. The S enantiomer was about 65-fold more cytotoxic than the R enantiomer in cell line assays. The 5-amino and 5-methylamino compounds had in vitro cytotoxicities comparable to that of the known 5-hydroxy analogue (0.2-0.5 nM), while the 5-dimethylamino derivative was about 10-fold less potent. The high potencies of the 5-amino and 5-methylamino analogues make them of interest for the formation of relatively stable amine-based prodrugs.

Synthesis and cytotoxicity of amino analogues of the potent DNA alkylating agent seco-CBI-TMI

The synthesis of racemic seco-CBI-TMI analogues containing nitrogen-based groups in place of the 5-OH is reported, employing a synthetic strategy where the incipient C-5 amino substituent is generated in the last step from a nitro precursor. The resulting