Antiviral Activity of Glyoxals and Derivatives

Anderson, Elvin L.; Casey, John E.; Emas, Morton; Force, Elizabeth E.; Jensen, Elizabeth; Matz, Ralph S.; Rivard, Donald E.

doi:10.1021/jm00342a035

Cited by 10 publications

(4 citation statements)

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“…For the general synthetic procedure, see: Matiychuk et al (2010). For the biologial activity of arylthiophenes, see: Reddy et al (2005); Anderson et al (1963); Bohlmann et al (1984); Michaelides et al (1997); Tanaka et al (1998) and for their applications, see Masui et al (2004); Roncali (1992Roncali ( , 1997. For methods of obtaining arylthiophenes via cross-coupling reactions, see: Stanforth (1998).…”

Section: Related Literaturementioning

confidence: 99%

“…(2011). E67, o585 (Roncali, 1992;Roncali, 1997), liquid crystals (Masui et al, 2004, ligands and molecules of medicinal interest (Michaelides et al, 1997;Tanaka et al, 1998;Reddy et al, 2005;Anderson et al, 1963). In view of the arylthiophenes importance a number of catalytic methods of these compounds formation from precursors in a cross-coupling reactions have been developed over the last two decades (Stanforth, 1998).…”

Section: Sup-1mentioning

confidence: 99%

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1-{5-[2-Chloro-5-(trifluoromethyl)phenyl]thiophen-2-yl}ethanone

et al. 2011

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In the title molecule, C13H8ClF3OS, the dihedral angle between the mean planes of 2-chloro-5-(trifluoromethyl)phenyl and tiophene rings is 54.37 (5)°. The acethyl group is twisted by 8.1 (2)° with respect to the thiophene ring. The CF3 group is disordered over two sets of sites with occupations of 0.49 (3) and 0.51 (3). The crystal packing features C—H⋯F and C—H⋯O hydrogen bonds, forming dimers which are connected into chains along the c axis by C—H⋯O hydrogen bonds and C—Cl⋯π [Cl⋯π = 3.415 (1) Å and C—Cl⋯π = 151.56 (5)°] interactions. The chains are further connected into layers perpendicular to the a axis by C—H⋯O interactions.

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Section: Related Literaturementioning

confidence: 99%

Section: Sup-1mentioning

confidence: 99%

1-{5-[2-Chloro-5-(trifluoromethyl)phenyl]thiophen-2-yl}ethanone

et al. 2011

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“…The chemistry of α-ketoacetal compounds is incredibly versatile. − Specifically, α-ketoacetals, and their derivatives, are frequently employed in the synthesis of pharmaceutically important heterocycles, − natural products, porphyrins, antiviral or antitumor agents, , and bioactive molecules . As a “protected glyoxal”, α-ketoacetals strategically direct nucleophiles to the less reactive carbonyl while protecting the more reactive aldehyde as an acetal; ,, furthermore, the acetal-protecting group, at the α-position, has even been reported to increase the reactivity of the adjacent carbonyl .…”

Section: Introductionmentioning

confidence: 99%

Rapid, One-Step Synthesis of α-Ketoacetals via Electrophilic Etherification

et al. 2021

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Herein, we report a rapid, one-step synthesis of α-ketoacetals via electrophilic etherification of α-alkoxy enolates and monoperoxyacetals. Methyl, primary, and secondary α-ketoacetals were obtained in 44–63% yields from tetrahydropyranyl substrates; using methyl tetrahydropyranyl, alkyl tetrahydropyranyl, or methyl tetrahydrofuranyl peroxyacetals, however, methyl and primary products were isolated in 66–90% yields. The present method is applied to C–O bond formation at tertiary carbons, via alkyl and methyl peroxyacetals, with yields of 25–65%. Intermolecular “alkoxyl” transfer, from peroxyacetal to α-alkoxy enolate, relies heavily on decreased steric bulk surrounding the peroxide bond and site of etherification; additionally, we found the α-OCH3 group to be critical in ensuring product formation. α-Ketoacetals demonstrated excellent reactivity, as selective, nucleophilic attack at the unprotected carbonyl furnished α-hydroxy acetals in 80–100% yields; subsequent hydrolysis of the foregoing compounds provided α-hydroxy aldehydes in yields of 58–90%.

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“…Thio-oxanilic acid (17) was prepared according to the method of Reissert (1904). 4,41-Diglyoxalyldiphenyl ether monohydrate (20) was prepared according to the method of Cavallini (1964), whilst dibenzofuran-2,8-bisglyoxal monohydrate (21) and dibenzofuran-2-glyoxal monohydrate (22) were prepared according to the method of Anderson, Casey, Emas, Force, Jensen, Matz & Rivard (1963). p-Nitrophenylglyoxal monohydrate (23) and m-nitrophenylglyoxal monohydrate (24) were prepared by the method of Steinbach & Becker (1954).…”

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confidence: 99%