Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 6-Bromo-3-methyl-1H-indole, is researched, Molecular C9H8BrN, CAS is 1219741-50-0, about Investigation of the molecular characteristics of bisindole inhibitors as HIV-1 glycoprotein-41 fusion inhibitors.Computed Properties of C9H8BrN.
In previous work, we described 6-6′-bisindole compounds targeting a hydrophobic pocket on the N-heptad repeat region of viral glycoprotein-41 as effective inhibitors of HIV-1 fusion. Two promising compounds with sub-micromolar IC50’s contained a benzoic acid group and a benzoic acid ester attached at the two indole nitrogens. Here we have conducted a thorough structure-activity relationship (SAR) study evaluating the contribution of each of the ring systems and various substituents to compound potency. Hydrophobicity, polarity and charge were varied to produce 35 new compounds that were evaluated in binding, cell-cell fusion and viral infectivity assays. We found that (a) activity based solely on increasing hydrophobic content plateaued at ∼ 200 nM; (b) the bisindole scaffold surpassed other heterocyclic ring systems in efficacy; (c) a polar interaction possibly involving Gln575 in the pocket could supplant less specific hydrophobic interactions; and (d) the benzoic acid ester moiety did not appear to form specific contacts with the pocket. The importance of this hydrophobic group to compound potency suggests a mechanism whereby it might interact with a tertiary component during fusion, such as membrane. A promising small mol. 10b with sub-μM activity was discovered with mol. weight <500 da and reduced logP compared to earlier compounds The work provides insight into requirements for small mol. inhibition of HIV-1 fusion. Although many compounds look similar to this compound(1219741-50-0)Computed Properties of C9H8BrN, numerous studies have shown that this compound(SMILES:CC1=CNC2=C1C=CC(Br)=C2), has unique advantages. If you want to know more about similar compounds, you can read my other articles.
Reference:
Bromide – Wikipedia,
bromide – Wiktionary