So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Jaffar, Mohammed; Naylor, Matthew A.; Robertson, Naomi; Lockyer, Stacey D.; Phillips, Roger M.; Everett, Steven A.; Adams, Gerald E.; Stratford, Ian J. researched the compound: 5-Methoxy-1H-indole-2-carbaldehyde( cas:21778-81-4 ).Formula: C10H9NO2.They published the article 《5-Substituted analogs of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) and their regioisomers as hypoxia-selective agents: structure-cytotoxicity in vitro》 about this compound( cas:21778-81-4 ) in Anti-Cancer Drug Design. Keywords: hydroxymethylaziridinylindoledionepropenol preparation hypoxia selective agent; indoledionepropenol hydroxymethylaziridinyl preparation hypoxia selective agent; aziridinylindoledionepropenol hydroxymethyl preparation hypoxia selective agent. We’ll tell you more about this compound (cas:21778-81-4).
A series of regioisomeric analogs of 3-hydroxymethyl-5-aziridinyl-1-methyl-2-[1H-indole-4,7-dione]prop-2-en-1-ol (EO9, NSC 382459) with the hydroxymethyl and hydroxypropenyl substituents situated at either the 2- or the 3-position of the indole ring were synthesized. The compound lacking the 2-hydroxypropenyl substituent had similar properties to EO9 under both aerobic and hypoxic conditions against V79 cells and was more potent against a human tumor cell line (A549) than EO9. It was reduced by human DT-diaphorase (DTD) at more than double the rate of EO9, thus implicating the importance of the enzyme activation step. The compound lacking the 3-hydroxymethyl substituent was a better substrate for human DTD than EO9, yet exhibited lesser toxicity under both aerobic and hypoxic conditions. The toxicity of EO9 was attributed to a combination of the aziridinyl group and the leaving group properties of the 3-hydroxymethyl substituent. In general, compounds with a 5-methylaziridinyl moiety, such as EO8, exhibited substantially better hypoxia-selectivity due to much slower reduction by DTD (20-fold), thus reducing aerobic potency. All compounds had similar electron affinities, as indicated by their one-electron reduction potentials.
There is still a lot of research devoted to this compound(SMILES：O=CC(N1)=CC2=C1C=CC(OC)=C2)Formula: C10H9NO2, and with the development of science, more effects of this compound(21778-81-4) can be discovered.
Reference:
Pyridazine – Wikipedia,
Pyridazine | C4H4N2 – PubChem