Synthesis and Biological Activities of 1‐Azaaurone Derivatives

Abstract

A series of 1-azaaurone derivatives were designed and synthesized from 3,5-dimethoxyaniline and 2-chloroacetonitrile. Their structures were characterized by melting point, 1 H NMR, IR, and elemental analysis, as well as 13 C NMR. The target compounds were evaluated for antitumor activities against human hepatocellular liver carcinoma cell line (HepG-2) and human cervix carcinoma cell line (Hela) using methyl thiazolyl tetrazolium method. The results revealed that several 1-azaaurones exhibited strong proliferation inhibition efficacy against HepG-2 and Hela with an IC 50 range of 5.6-8.8 μg/mL without damaging normal cell.

Advances in the Synthesis of Benzo‐Fused Spiro Nitrogen Heterocycles: New Approaches and Modification of Old Strategies

“…For this, 1-azaaurones, easily obtained from 3-indolones and aryl aldehydes, are very attractive. [197,198] With prolonged stirring of a solution of hydroxyaryl aldimine 133, azaaurone 134 and the organocatalyst 115 (10 mol-%) in the dry DCE products 135 are formed. When using methanol, enantioselectivity decreases dramatically, and in THF, in addition, a decrease in the productivity (16 %) of the reaction is also observed.…”

“…In a similar way, the spiro‐fused pyrrolidine ring can also be prepared from 2‐alkylidene‐3‐indolones. For this, 1‐azaaurones, easily obtained from 3‐indolones and aryl aldehydes, are very attractive [197,198] . With prolonged stirring of a solution of hydroxyaryl aldimine 133 , azaaurone 134 and the organocatalyst 115 (10 mol‐%) in the dry DCE products 135 are formed.…”

New azaaurone derivatives as potential multitarget agents in HIV‐TB coinfection

“…Azaaurones ( 2 ) are isosteric equivalents that are generated through an exchange of intracyclic oxygen atoms by nitrogen (Figure 1), which has shown significant biological activities [ 4–6 ] that are often better than those of aurones. [ 7 ]…”

“…[14] Our research group has extensive expertise in developing new compounds with antiretroviral activity. [15][16][17] An example is derivative 6, [16] a 1,2,3-triazolic hybrid between the nucleoside reverse transcriptase inhibitor zidovudine (AZT) and the gem-difluoride derivative of isatin (7) (Figure 3). The antiretroviral evaluations of Compound 6 showed an IC 50 of 0.6 µM in an enzymatic reverse transcriptase (RT) assay, and the compound was more active than the reference drug tenofovir (IC 50 of 1.2 µM) but less active than the standard AZT (IC 50 of 0.01 µM).…”

Novel base-initiated cascade reactions of hemiindigos to produce dipolar γ-carbolines and indole-fused pentacycles

“…Over the last decade, the hemiindigo scaffold has attracted considerable attention from synthetic chemists because of its unique reactivity and relevance to medicinal chemistry due to wide scope of bioactive properties. 29–31 Our research in the field of cascade reactions began with the discovery of a cationic domino reaction of hemiindigos that afford pentacyclic 3-hydroxyindolenines related to indolenine alkaloids in a diastereoselective fashion under the NMR experiment conditions. 32 This is the first example of the acid-catalyzed domino reaction that involved homocoupling of hemiindigos 1 followed by a reverse Wagner–Meerwein [1,2] type rearrangement of the intermediate 2-spiropseudoindoxyls.…”