2019
DOI: 10.1039/c9ra00118b
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A methanol and protic ionic liquid Ugi multicomponent reaction path to cytotoxic α-phenylacetamido amides

Abstract: The Ugi reaction (aldehyde, amine, isocyanide and an ethanoic acid) in the protic ionic liquids ethylammonium nitrate (EAN) and propylammonium nitrate (PAN) gave excellent yields of α-phenylacetamido amides.

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Cited by 9 publications
(14 citation statements)
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“…Biologically active α-amino amide analogs (RS)-N-(2-(Cyclohexylamino)-2-oxo-1-phenylethyl)-N-phenylpropiolamide (α-AAA-A) and (RS)-N-(2-(Cyclohexylamino)-2-oxo-1-phenylethyl)-N-phenylbut2-enamide (α-AAA-B) were synthesized using linear Ugi multicomponent reaction (batch reaction with methanol) as published previously ( 12 ). Briefly, for the synthesis of α-AAA-A, a solution was prepared using methanol (5 ml), aniline (0.09 ml; 1 mmol) and benzaldehyde (0.1 ml; 1 mmol).…”
Section: Methodsmentioning
confidence: 99%
See 1 more Smart Citation
“…Biologically active α-amino amide analogs (RS)-N-(2-(Cyclohexylamino)-2-oxo-1-phenylethyl)-N-phenylpropiolamide (α-AAA-A) and (RS)-N-(2-(Cyclohexylamino)-2-oxo-1-phenylethyl)-N-phenylbut2-enamide (α-AAA-B) were synthesized using linear Ugi multicomponent reaction (batch reaction with methanol) as published previously ( 12 ). Briefly, for the synthesis of α-AAA-A, a solution was prepared using methanol (5 ml), aniline (0.09 ml; 1 mmol) and benzaldehyde (0.1 ml; 1 mmol).…”
Section: Methodsmentioning
confidence: 99%
“…Some important molecules, such as Brentuximab Vedotin, Gemtuzumab Ozogamicin, Ado-trastuzumab emtansine, polatuzumab vedotin-piiq, and inotuzumab ozogamicin, are combined with monoclonal antibodies specific to surface antigens present on particular tumor cells and are used as combinationaltargeted cancer therapies (11). There are a number of newly synthesized a-amino amide derivatives, which show potent anticancer and cytotoxic activities against a wide range of cancer cell lines (12). Derivatives of 3-cyano pyridine also exhibited cytotoxic activities against many human MCF-7, HCT-116, and HepG-2 cancer cell lines (13).…”
Section: Introductionmentioning
confidence: 99%
“…For our system, gelation only occurred at 60 °C. It is known that at higher temperatures, the reaction yield is increased granting faster connectivity of the network [18,29] …”
Section: Figurementioning
confidence: 99%
“…It is known that at higher temperatures, the reaction yield is increased granting faster connectivity of the network. [18,29] The aldehyde and the isocyanide are very important components for the Ugi reaction. The poor choice of the aldehyde can lead to a low concentration of the iminium ion, which is critical to yield the Ugi scaffold because, without the nucleophilic attack of the isocyanide to the iminium ion, the scaffold is not formed.…”
mentioning
confidence: 99%
“…These extensive applications of ILs are attributed to their unique properties including, low vapor pressure, non-flammability, wide liquid-state temperature range, high thermal and chemical stability, favorable solvating capability, large electrochemical window, and ability to catalyze different kinds of organic reactions. In particular, acidic ILs possess useful characteristics of solid acids and mineral liquid acids, and have been designed to replace conventional mineral liquid acids like sulfuric acid and hydrochloric acid to catalyze chemical transformations [1][2][3][4][5][6][7][8][9][10][11][12].…”
Section: Introductionmentioning
confidence: 99%