Syntheses of 3-Cyano-3-methyl-4-thiochromanone and 3-Carbomethoxy-3-methyl-4-thiochromanone

Moriwake, Tosio

doi:10.1021/jm00319a048

Cited by 9 publications

(3 citation statements)

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“…The resulting acid was reacted with polyphosphoric acid (PPA) at 65 °C for 6 h to afford 4-oxothiochromane derivative 6 . 36 Reaction of ketone 6 with commercially available ( R )-(+)-2-methyl-2-propane sulfinamide in the presence of Ti(OEt) 4 in THF at 70 °C furnished sulfinyl imins 7 . 37,38 Imine derivative 7 was reduced with NaBH 4 in a mixture of THF and water at −50 °C to afford a mixture (3:1) of diastereomeric sulfonamides 8 and 9 in 78% combined yield.…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, and X-ray studies of potent HIV-1 protease inhibitors incorporating aminothiochromane and aminotetrahydronaphthalene carboxamide derivatives as the P2 ligands

Ghosh

Jadhav

Simpson

et al. 2018

European Journal of Medicinal Chemistry

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We describe the design, synthesis, and biological evaluation of a series of novel HIV-1 protease inhibitors with carboxamide derivatives as the P2 ligands. We have specifically designed aminothiochromane and aminotetrahydronaphthalene-based carboxamide ligands to promote hydrogen bonding and van der Waals interactions in the active site of HIV-1 protease. Inhibitors 4e and 4j have shown potent enzyme inhibitory and antiviral activity. High resolution X-ray crystal structures of 4d- and 4k-bound HIV-1 protease revealed molecular insights into the ligand-binding site interactions.

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Section: Resultsmentioning

confidence: 99%

Design, synthesis, and X-ray studies of potent HIV-1 protease inhibitors incorporating aminothiochromane and aminotetrahydronaphthalene carboxamide derivatives as the P2 ligands

Ghosh

Jadhav

Simpson

et al. 2018

European Journal of Medicinal Chemistry

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show abstract

“…The most efficient route to generate a 1,3-dicarbonyl system from a thiochroman-4-one unit relies upon the base catalysed condensation of thiochroman-4-one with ethyl formate to afford 3-formylthiochroman-4-one, which exists exclusively as its 3-hydroxymethylene tautomer. 9 Application of this methodology to several substituted thiochroman-4-ones 1 10,11 gave a range of 3-hydroxymethylenethiochroman-4-ones 2 as bright yellow oils in good yield (Scheme 2).…”

Section: Discussionmentioning

confidence: 99%