Abstract
In this work, we describe a simple and easy synthetic approach to variously 4-aryl-2-alkylphosphonomethyl-4-oxobutanenitrile based on the reaction of aromatic aldehydes with phosphorylated Michael’s acceptors in good yields. A general mechanism for the reactions was also proposed. Characterization of the products was carried out by several spectroscopic tools, including Infrared and Nuclear Magnetic Resonance Spectroscopies (1H, 13C, and 31P-NMR). Molecular docking studies were conducted on the synthesized materials against (1UK4) the crystal structure of the SARS Coronavirus Main Proteinase (3CLpro) to study the antiviral activity of these compounds and against (1E3K) the Human Progesterone Receptor to study the anticancer activity of these compounds. We found that compound (5i) was the best one in both antiviral and anticancer activity (according to the binding energy values).
Highlights
Compounds with both a carbonyl and a nitrile function piqued the interest of several researchers due to their potential utility as reagents in organic synthesis [1]
Many of these compounds have several biological activities [2], and numerous methods of synthesis are described in the literature [3,4]
C2.hRemeissutrlyts and Discussion ChemIinstrreycent studies carried out in our laboratory, we showed that dialkylphosphonomethyl-pInrorpeceennetnsitturdilieess 3c,arorbietdaionuetdinfrooumr ltahbeorAatrobruy,zwove srheaocwtieodnthwaittdhiaMlkaynlpnhicohspbhaosneo[m12e,t2h2y]l,(pSrcohpeemneen1it)rbilehs a3v, oebatsaibnieledcftroomphtihliecAargbeunztsov[2r3e,a2c4t]i.oTnhweitrhdMouanbnleicbhobnads,es[t1r2o,n2g2]ly, (Sachtievmateed1) byehthaveeparessbeinleccetorofpthheilincitargileenftusn[c2t3i,o2n4]a.nTdhtehiredpohuobslpehboonnodg,rsotruopn,gelaysialcytiavdadtesdnubcylethoephpirles[e2n5c]e. of the nitrile function and the phosphono group, adds nucleophiles [25]
Summary
Compounds with both a carbonyl and a nitrile function piqued the interest of several researchers due to their potential utility as reagents in organic synthesis [1]. Many of these compounds have several biological activities [2], and numerous methods of synthesis are described in the literature [3,4]. At the start of this year, the world was shocked when severe acute respiratory syndrome (SARS) was discovered in the Chinese province of Hubei and spread rapidly. The structure of 3CLpro from SARS-CoV-2 (PDB code 6LU7) differs from
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