2009
DOI: 10.1016/j.bmcl.2008.11.005
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Sulfonamido-aryl ethers as bradykinin B1 receptor antagonists

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Cited by 9 publications
(11 citation statements)
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“…For the synthesis of the 9-HC hybrid 5i, featuring the N-(4hydroxy-3-methoxybenzyl)carboxamide moiety of capsaicin linked through a triazolylbutyl tether on position 9 of huprine, we first attempted a copper-catalyzed azide−alkyne cycloaddition (CuAAC) of an O-protected capsaicin-based 3butynamide to the previously reported racemic 9-azidobutylhuprine 13 60,64 capsaicin-based 3-butynamide, generated by coupling amine 6 with 3-butynoic acid, led to an inseparable 25:75 mixture of the desired 3-butynamide and its 2,3-butadienamide isomerization product. Fortunately, the amount of the isomerization byproduct was much lower (12%) when the O-TBDMS-protected amine 11 65 was used instead of 6. The byproduct and the desired 3-butynamide 12 could be separated by silica gel column chromatography, affording the latter in 36% yield.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
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“…For the synthesis of the 9-HC hybrid 5i, featuring the N-(4hydroxy-3-methoxybenzyl)carboxamide moiety of capsaicin linked through a triazolylbutyl tether on position 9 of huprine, we first attempted a copper-catalyzed azide−alkyne cycloaddition (CuAAC) of an O-protected capsaicin-based 3butynamide to the previously reported racemic 9-azidobutylhuprine 13 60,64 capsaicin-based 3-butynamide, generated by coupling amine 6 with 3-butynoic acid, led to an inseparable 25:75 mixture of the desired 3-butynamide and its 2,3-butadienamide isomerization product. Fortunately, the amount of the isomerization byproduct was much lower (12%) when the O-TBDMS-protected amine 11 65 was used instead of 6. The byproduct and the desired 3-butynamide 12 could be separated by silica gel column chromatography, affording the latter in 36% yield.…”
Section: ■ Results and Discussionmentioning
confidence: 99%
“…Use of an O-TIPS-protected capsaicin-based 3-butynamide, generated by coupling amine 6 with 3-butynoic acid, led to an inseparable 25:75 mixture of the desired 3-butynamide and its 2,3-butadienamide isomerization product. Fortunately, the amount of the isomerization byproduct was much lower (12%) when the O-TBDMS-protected amine 11 was used instead of 6 . The byproduct and the desired 3-butynamide 12 could be separated by silica gel column chromatography, affording the latter in 36% yield.…”
Section: Resultsmentioning
confidence: 99%
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“…For the synthesis of the target triazole-based compounds 15 and 16 , the new alkyne 12 was first prepared by amide coupling of the know amine 11 [ 33 ] with 3-butynoic acid ( Scheme 2 ). Copper(I)-catalyzed Huisgen reaction of alkyne 12 with azides 7 and 8 afforded in good yields the O -TBDMS-protected triazole intermediates 13 and 14 , which were finally converted into the target triazole-containing tacrines 15 and 16 upon deprotection with camphorsulfonic acid (CSA) in MeOH or with tetrabutylammonium fluoride (TBAF) in THF, respectively ( Scheme 2 ).…”
Section: Resultsmentioning
confidence: 99%
“…Although the aromatic compounds were generally superior, some of the tetrahydroquinolines displayed activity in the recombinant virus assay (RVA) . Several N -substituted tetrahydroquinoline derivatives (compounds 41 – 45 ) have exhibited potent activities as allosteric inhibitors of the HIV-1 reverse transcriptase and also had good anti-HIV-1 activities. These compounds can thus be regarded as non-nucleoside reverse transcriptase inhibitors (NNRTIs), an increasingly important class of antiviral agents.…”
Section: Tetrahydroquinoline-based Bioactive Compoundsmentioning
confidence: 99%