An operationally simple, one-pot, two-step cascade method has been developed to afford biologically important fused 1,2,3-triazolo-heterocyclic scaffolds from 2-alkynyl aryl(heteroaryl) aldehydes and phenacyl azides. This unique atom economical transformation engages four reactive centers (aldehyde, alkyne, active methylene, and azide) under metal-free catalysis.
Phenacyl azides were reacted with pyridinium ylides in the presence of Cu(OAc)2 (2 mol%) and Et3N utilizing molecular oxygen as a green oxidant to yield imidazo[1,2-a]pyridines in exclusive regioselectivity. Following the optimized protocol, 28 different fused heterocycles were synthesized in high yields (71-92%). In order to get mechanistic insight into the reaction, a few control experiments were carried out and the role of the copper salt was discussed.
SummaryA facile and efficient synthetic protocol for the synthesis of α-amino amidines has been developed using a molecular iodine-catalyzed three-component coupling reaction of isocyanides, amines, and aldehydes. The presented strategy offers the advantages of mild reaction conditions, low environmental impact, clean and simple methodology, high atom economy, wide substrate scope and high yields.
Anticancer spiro[cyclopropane-1,3′-indolin]-2′-ones are accessible through a transition metal-free diastereoselective cyclopropanation using in situ generated diazo-compounds.
Phenacyl azides were decomposed in basic media to generate N-unsubstituted imines which were reacted with cyclic amino acids to give an azomethine ylide that underwent [3 + 2] cycloaddition with maleimides and N-unsubstituted imines to yield various diastereoselective pyrrolidines and imidazoles respectively in a one-pot three component manner with good to excellent yields.
Abstract. Special aT-rich sequence binding protein 1 (SaTB1) regulates the expression of more than 1,000 genes in tumor cells. SaTB1 expression has been implicated in metastasis, and its silencing results in reduced cancer progression and the reversion of metastatic cells to normal appearance. Therefore, any compound causing down-regulation of SaTB1 expression or activity may be exploited for its therapeutic potential in terms of cancer regression. earlier studies showed that the 3-hydroxy-3-methylglutaryl coenzymea (HMG-coa) reductase inhibitors (statin drugs), which are widely used to treat hypercholesterolemia, possess other pleotropic activities. These are now increasingly gaining attention for their cancer prevention abilities. However, the downstream interplay of the molecular mechanisms of such anti-cancer activities is unclear. Here, we show that SaTB1 is down-regulated by statins in a time-and dose-dependent manner in colo205 cells. This effect was statin-specific as the down-regulation of SATB1 was brought about by hydrophobic statins, such as simvastatin and fluvastatin, but not by hydrophilic pravastatin. Notably, treatment with mevalonate, an intermediate in the cholesterol and isoprenoid biosynthetic pathways, led to the inhibition of SaTB1 down-regulation and cytotoxicity mediated by statins. Treatment with the proteasome inhibitors lactacystine and MG-132 inhibited the statin-mediated down-regulation of SaTB1, suggesting that regulation occurs at the post-translational level. Thus, our results demonstrate a novel molecular mechanism for the anti-cancer activity of statin drugs in colon cancer cells, without invoking significant cytotoxicity.
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