Atwell, Graham J.; Milbank, Jared J. B.; Wilson, William R.; Hogg, Alison; Denny, William A. published the article 《5-Amino-1-(chloromethyl)-1,2-dihydro-3H-benz[e]indoles: Relationships between Structure and Cytotoxicity for Analogues Bearing Different DNA Minor Groove Binding Subunits》. Keywords: chloromethyl benzindole preparation cytotoxicity structure.They researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Name: 5-Methoxy-1H-indole-2-carbaldehyde. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:21778-81-4) here.
A series of 5-amino-seco-CBI compounds, designed for use as effectors for prodrugs, were prepared to study structure-activity relationships for the cytotoxicity of side chain analogs. Compounds were prepared by coupling 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benz[e]indole to appropriate carboxylic acids, followed by nitro group reduction, or by coupling suitable 5-amino-protected indolines to α,β-unsaturated acids, followed by deblocking. These AT-specific DNA alkylating agents were evaluated for cytotoxicity in a series of tumor cell lines (AA8, UV4, EMT6, SKOV3). For those analogs bearing an indolecarbonyl side chain, the 5′-methoxy derivative was the most cytotoxic (IC50 1.3 nM in AA8 cells, 4 h exposure), comparable to that of the parent CBI-TMI (5′,6′,7′-trimethoxyindole) derivative (IC50 0.46 nM in the above assay). A subset of solubilized derivatives bearing O(CH2)2NMe2 substituents were about 10-fold less potent. For compounds containing an acryloyl linker in the side chain, the 4′-methoxycinnamoyl derivative proved the most cytotoxic (IC50 0.09 nM in the above assay). A number of these 5-amino-seco-CBI-TMI analogs (including the solubilized compounds) are of interest both as cytotoxins and as components of amine-based prodrugs designed for tumor-specific activation.
There is still a lot of research devoted to this compound(SMILES：O=CC(N1)=CC2=C1C=CC(OC)=C2)Name: 5-Methoxy-1H-indole-2-carbaldehyde, and with the development of science, more effects of this compound(21778-81-4) can be discovered.
Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem