Alkylation of NH-, OH-, and SH-acids in the presence of potassium carbonate

Khachatryan, D. S.; Razinov, Anatoly L.; Колотаев, А. В.; Belus, S. K.; Matevosyan, K. R.

doi:10.1007/s11172-015-0875-9

Cited by 11 publications

(2 citation statements)

References 20 publications

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“…Initially, the 4-(Chloromethyl)-7-hydroxy-2H-chromen-2-one (3) was prepared by Pechmenn condensation of resorcinol (1) with ethyl-4-chloroacetoacetate (2) in the presence of sulphuric acid (Benci et al, 2012). Further, compound (3) was treated with substituted morpholine derivatives and offered morpholines linked coumarin intermediates 4a and 4b, which are further involved in the O-alkylation process with propargyl bromide in the presence of potassium carbonate resulted morpholines linked coumarin with terminal alkyne derivatives 5a and 5b (Khachatryan, Razinov, Kolotaev, Belus′, & Matevosyan, 2015). Finally, copper(I)-catalysed 1,3-dipolar cycloaddition of morpholines linked coumarin with terminal alkyne derivatives (5a, 5b) and various benzyl azides furnished the target compounds 6a-6v with moderate to good yields.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of morpholines linked coumarin–triazole hybrids as anticancer agents

et al. 2019

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A series of novel morpholines linked coumarin–triazole hybrids (6a–6v) has been synthesized and evaluated for their anti‐proliferative potential on a panel of five human cancer cell lines, namely bone (MG‐63), lung (A549), breast (MDA‐MB‐231), colon (HCT‐15) and liver (HepG2), using MTT assay. Among all, the compound 6n {7‐((1‐(2,4‐dichlorobenzyl)‐1H‐1,2,3‐triazol‐4‐yl) methoxy)‐4‐((2,6‐dimethylmorpholino) methyl)‐2H‐chromen‐2‐one} showed significant growth inhibition against MG‐63 cells with an IC50 value of 0.80 ± 0.22 μM. Further, induction of apoptosis by 6n of MG‐63 cells confirmed as a result of morphological changes, the sub‐G1 phase arrest, increased percentage of apoptotic cells, and decrease in mitochondrial membrane potential and increase in reactive oxygen species levels. The in vitro Gal‐1 expression in cell culture supernatant of MG‐63 cells treated with compound 6n showed dose‐dependent reduction. The binding constant (Ka) of 6n with Gal‐1 was calculated from the intercept value which was observed as 3.0 × 105 M−1 by fluorescence spectroscopy. Surface plasmon resonance showed that 6n binds to Gal‐1 with binding constant (Ka) of 1.29E+04 1/Ms and equilibrium constant KD value of 7.54E−07 M, respectively. Molecular docking studies revealed the binding interactions of 6n with Gal‐1.

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Section: Chemistrymentioning

confidence: 99%

Synthesis and biological evaluation of morpholines linked coumarin–triazole hybrids as anticancer agents

et al. 2019

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“…The study of the regiochemistry of the alkylation process takes one of the key positions in the development of the organic synthesis methodology [1][2][3][4][5][6][7][8]. A classic synthetic problem that remains unresolved is a reaction that involves the control of N-and / or O-alkylation of ambident anions, in particular, the study of the process of N-and O-alkylation of quinazolinones.…”

Section: Introductionmentioning

confidence: 99%