113250-72-9

Basic information

• Product Name: Benzaldehyde, 6-bromo-3-methoxy-2-(phenylmethoxy)-
• CAS NO: 113250-72-9
• Molecular Formula: C15H13BrO3
• Molecular Weight: 321.17
• Mol File: 113250-72-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 6-bromo-3-methoxy-2-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 6-bromo-3-methoxy-2-(phenylmethoxy)-(113250-72-9)
• EPA Substance Registry System: Benzaldehyde, 6-bromo-3-methoxy-2-(phenylmethoxy)-(113250-72-9)

Safety Data

• Hazardous Substances Data: 113250-72-9(Hazardous Substances Data)

Upstream product

• 20035-41-0 6-bromo-2-hydroxy-3-methoxybenzaldehyde 
• 100-39-0 benzyl bromide 
• 159263-87-3 2-acetyloxy-3-methoxy-6-bromobenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 100-44-7 benzyl chloride 

Downstream Products

• 208237-61-0 N-((2'-benzyloxy)-3'-methoxy-6'-bromobenzyl)-1-anthrylamine 
• 1385815-69-9 methyl 2-(2-benzyloxy-6-bromo-3-methoxyphenyl)ethanoate 
• 113250-75-2 N-(6-bromo-2-(benzyloxy)-3-methoxybenzylidene)-1-naphthylamine 

Relevant articles and documents

Prodrug Activation by Gold Artificial Metalloenzyme-Catalyzed Synthesis of Phenanthridinium Derivatives via Hydroamination

An emerging approach in the field of targeted drug delivery is the establishment of abiotic metal-triggered prodrug mechanisms that can control the release of bioactive drugs. Currently, the design of prodrugs that use abiotic metals as a trigger relies heavily on uncaging strategies. Here, we introduce a strategy based on the gold-catalyzed activation of a phenanthridinium-based prodrug via hydroamination under physiological conditions. To make the prodrug strategy biocompatible, a gold artificial metalloenzyme (ArM) based on human serum albumin, rather than the free gold metal complex, was used as a trigger for prodrug activation. The albumin-based gold ArM protected the catalytic activity of the bound gold metal even in the presence of up to 1 mM glutathione in vitro. The drug synthesized via the gold ArM exerted a therapeutic effect in cell-based assays, highlighting the potential usefulness of the gold ArM in anticancer applications.

Synthesis of NK109, an anticancer benzo[c]phenanthridine alkaloid

A total synthesis of NK109 (7-hydroxy-8-methoxy-5-methyl-2,3- methylenedioxybenzo[c]phenanthridinium hydrogensulfate dihydrate), an anticancer benzo[c]phenanthridine alkaloid, is reported. The primary structure of this compound was erroneously communicated in 1973 as fagaridine (from Fagara xanthoxyloides) which the 8-hydroxy regioisomer. NK109 has not yet been isolated from a natural source and therefore can only be obtained by synthesis. To study a wide variety of analogues, we decided to use a synthetic route via substituted benzylamine 5, which was obtained from the appropriate benzaldehyde ad naphthylamine units. The benzo[c]phenanthridine ring was conducted by radical cyclization with tri-n-octyltin hydride and 2,2'-azobis(2)-methylbutyronitrile], followed by oxidative aromatization with MnO2. The resulting benzo[c]phenanthridine 6 was successfully methylated with methyl 2-nitrobenzenesulfonate. After deprotection of the benzyl group and subsequent hydration, NK109 was obtained. All reactions were performed under normal conditions. Purification was achieved only by recrystallization to give an overall yield of 40%.