An Antimalarial Alkaloid From Hydrangea. Xiv. Synthesis of 5-, 6-, 7-, and 8-Monosubstituted Derivatives

Baker, B. R.; Schaub, Robert E.; Joseph, Joseph P.; McEvoy, Francis J.; Williams, James H.

doi:10.1021/jo01135a014

Cited by 53 publications

(17 citation statements)

References 15 publications

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“…12 Ring opening was carried out by treatment with 30% hydrogen peroxide in 1 N sodium hydroxide to yield 2-aminonaphthalene-1-carboxylic acid. 13 Sulfonamide formation was carried out with in situ protection of the carboxyl group as its TMS ester, followed by reaction with appropriate arylsulfonyl chloride.…”

mentioning

confidence: 99%

Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

Kawai

Bamaung

Fidanze

et al. 2006

Bioorganic & Medicinal Chemistry Letters

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confidence: 99%

Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

Kawai

Bamaung

Fidanze

et al. 2006

Bioorganic & Medicinal Chemistry Letters

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“…Compounds 10a-10f were prepared from the corresponding, commercially available, 2-aminobenzoic (anthranilic) acids 9a-9f in a modified Niementowski reaction involving heating the anthranilic acids with formamide(Scheme 5). 77 In this manner, halocontaining compounds 9a and 9b gave 10a and 10b in reasonable to good yield. 2-Amino-4,5-dimethoxybenzoic acid (9c)only gave 10c in only low yield (19%) which, despite several attempts, could not be improved.…”

Section: Resultsmentioning

confidence: 80%

Stereoselective synthesis of analogues of deoxyfebrifugine

Zaidan

Evans

2022

Journal of Chemical Research

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The preparation of six new optically active analogues of the natural product febrifugine (1) is reported. These analogues, lacking the hydroxy group from the natural product, were prepared from optically active N-protected S-pelletierine (7) and differ in terms of the specific quinazolinone portion included. The required S-7 (80% enantiomeric excess) was prepared from an asymmetric Mannich reaction between piperideine (8) and acetone in the presence of l-proline. The differently substituted quinazolinone used in this study (10a–10g) was either commercially available or was prepared from the corresponding substituted anthranilic acid and were installed via a bromination–alkylation sequence. N-Deprotection of the subsequent adducts (12a–12g) gave target compounds 13a–13f and completed the synthetic sequence.

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“…The oocyst value (0 -40) reflected the amount of oocysts produced by the elder generation of coccidia. The oocyst values in the groups treated with compounds 7b (20), 7c (20), 7e (20) and 7g (20) were lower than the infected non-medicated group (30). This shows that compounds 7b, 7c, 7e and 7g could effectively suppress the generation of oocysts.…”

Section: Introductionmentioning

confidence: 80%

Synthesis and anticoccidial activity of 4-(2-methoxyphenyl) -2-oxo-butyl-quinazolinone derivatives

You¹,

Ye²,

Weng³

et al. 2008

Arkivoc

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A series of 4-(2-methoxyphenyl)-2-oxo-butyl-quinazolinones were designed and synthesized based on the structure of febrifugine. The structures of the new compounds were confirmed by 1 H NMR, 13 C NMR, IR spectra and HRMS. The biological activity test results indicated that they exhibited anticoccidial activities against Eimeria tenella in the chicken diet with a dose of 9 mg/kg. Compared with halofuginone, these compounds have the advantages of shorter synthetic routes and lower cost.

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An Antimalarial Alkaloid From Hydrangea. Xiv. Synthesis of 5-, 6-, 7-, and 8-Monosubstituted Derivatives

Cited by 53 publications

References 15 publications

Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties

Stereoselective synthesis of analogues of deoxyfebrifugine

Synthesis and anticoccidial activity of 4-(2-methoxyphenyl) -2-oxo-butyl-quinazolinone derivatives

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