52535-61-2

Basic information

• Product Name: Ethyl 5-methoxy-1,2-dimethyl-4-nitroindole-3-carboxylate
• Synonyms: Ethyl 5-methoxy-1,2-dimethyl-4-nitroindole-3-carboxylate;ethyl 5-methoxy-1,2-dimethyl-4-nitro-1H-indole-3-carboxylate
• CAS NO: 52535-61-2
• Molecular Formula: C14H16N2O5
• Molecular Weight: 292.28724
• Mol File: 52535-61-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Ethyl 5-methoxy-1,2-dimethyl-4-nitroindole-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 5-methoxy-1,2-dimethyl-4-nitroindole-3-carboxylate(52535-61-2)
• EPA Substance Registry System: Ethyl 5-methoxy-1,2-dimethyl-4-nitroindole-3-carboxylate(52535-61-2)

Safety Data

• Hazardous Substances Data: 52535-61-2(Hazardous Substances Data)

Usage

General Description

Ethyl 5-methoxy-1,2-dimethyl-4-nitroindole-3-carboxylate is a chemical compound with the molecular formula C14H16N2O5. It belongs to the class of nitroindole derivatives and is commonly used in organic synthesis and pharmaceutical research. Ethyl 5-methoxy-1,2-dimethyl-4-nitroindole-3-carboxylate displays a yellow crystalline appearance and is soluble in organic solvents such as ethanol and acetone. It is often employed as an intermediate in the production of various pharmaceutical drugs and can also be used as a reference standard in analytical chemistry. Additionally, its unique structural properties make it a valuable tool for studying the structure-activity relationships of related compounds.

Upstream product

• 40963-98-2 ethyl 5-methoxy-1,2-dimethyl-1H-indole-3-carboxylate 
• 65578-36-1 ethyl N-methyl β-aminocrotonate 
• 141-97-9 ethyl acetoacetate 
• 15574-49-9 mecarbinate 

Downstream Products

• 930285-79-3 carbonic acid 5-methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indol-3-ylmethyl ester 4-nitro-phenyl ester 
• 52535-65-6 ethyl 4-amino-1,2-dimethyl-5-methoxyindole-3-carboxylate 

Relevant articles and documents

PYRROLOBENZODIAZEPINE PRODRUGS AND ANTIBODY CONJUGATES THEREOF

The invention relates generally to pyrrolobenzodiazepine monomer and dimer prodrugs having a glutathione-activated disulfide prodrug moiety, a DT-diaphorase-activated quinone prodrug moiety or a reactive oxygen species-activated aryl boronic acid or aryl boronic ester prodrug moiety. The invention further relates to pyrrolobenzodiazepine prodrug dimer-antibody conjugates.

Indolequinone antitumor agents: Reductive activation and elimination from (5-methoxy-1-methyl-4,7-dioxoindol-3-yl)methyl derivatives and hypoxia- selective cytotoxicity in vitro

A series of indolequinones bearing a variety of leaving groups at the (indol-3-yl)methyl position was synthesized by functionalization of the corresponding 3-(hydroxymethyl)indolequinone, and the resulting compounds were evaluated in vitro as bioreductively activated cytotoxins. The elimination of a range of functional groups-carboxylate, phenol, and thiol- was demonstrated upon reductive activation under both chemical and quantitative radiolytic conditions. Only those compounds which eliminated such groups under both sets of conditions exhibited significant hypoxia selectivity, with anoxic:oxic toxicity ratios in the range 10-200. With the exception of the 3-hydroxymethyl derivative, radiolytic generation of semiquinone radicals and HPLC analysis indicated that efficient elimination of the leaving group occurred following one-electron reduction of the parent compound. The active species in leaving group elimination was predominantly the hydroquinone rather than the semiquinone radical. The resulting iminium derivative acted as an alkylating agent and was efficiently trapped by added thiol following chemical reduction and by either water or 2-propanol following radiolytic reduction. A chain reaction in the radical-initiated reduction of these indolequinones (not seen in a simpler benzoquinone) in the presence of a hydrogen donor (2-propanol) was observed. Compounds that were unsubstituted at C-2 were found to be up to 300 times more potent as cytotoxins than their 2-alkyl-substituted analogues in V79-379A cells, but with lower hypoxic cytotoxicity ratios.