Convenient and Scalable Synthesis of 2,3-Dihydroquinazolin-4(1<i>H</i>)-one Derivatives and Their Anticancer Activities

<div><p></p><p>An efficient and mild InBr₃-catalyzed approach to synthesize 2,3-dihydroquinazolin-4(1<i>H</i>)-one derivatives (<b>3a–3aa</b>) has been developed. Notably, all the products were isolated by recrystallization and the reaction is accessible on a gram scale. Moreover, the reactions only require 10–60 min. All the synthesized compounds were evaluated for their in vitro anticancer activity against four human cancer cell lines.</p></div

Organogelation and cytotoxic evolution of phosphonate ester functionalised hydrophobic alkanediamide motifs

<div><p>Here we report various rigid alkanediamide derivatives, with three different substitution patterns of phosphonate ester for investigation of organogelation properties. The gelation properties of these compounds can be tuned by altering the number and position of the phosphonate esters. It was found that supramolecular self-assembly of the bisphosphonate esters (<b>1a, 1d, 1h</b> and <b>2a</b>–<b>b</b>) resulted gel formation, whereas that of the tetraphosphonate esters (<b>3a, 3d, 3h</b>) resulted in construction of nanospheres and microspheres. The diverse morphology of the gel formation appears to depend predominantly on the substituted phenyl ring of the phosphonate ester functionality. Subsequent <i>in vitro</i> cytotoxic screening against four human tumour cell lines (A549, MDA-MB-231, MCF-7 and HeLa) using MTT assays revealed that derivatives <b>1f</b>–<b>h</b> and <b>3a</b> show cytotoxic potencies at concentrations less than 5 μM (IC₅₀ values). Compounds <b>1f</b>–<b>h</b> exhibited promising activity against A549 cell line, <b>1g</b>–<b>h</b> were highly effective against MDA-MB-231, <b>1f</b> and <b>3a</b> show potential against MCF-7 and <b>1f</b>–<b>g</b> were active against the HeLa cell line.</p></div