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Structural reassignment of a dibenz[

Authors :
Andrew G. Riches
Christopher J. S. Hart
Matthieu Schmit
Emmanuel A. Debele
Snigdha Tiash
Erin Clapper
Tina S. Skinner-Adams
John H. Ryan
Source :
Australian Journal of Chemistry. 75:839-845
Publication Year :
2022
Publisher :
CSIRO Publishing, 2022.

Abstract

A screen for compounds with antigiardial activity in the Compounds Australia Scaffolds library identified SN00797640 (supplied structure being 8-acylaminodibenzoxazepinone 1) as a hit compound with potent anti-parasitic activity (concentration for 50% growth inhibition of Giardia duodenalis, IC50 0.18 μM). To further explore the structure–activity relationships in this series, compound 1 and analogues, including its 7-acylaminodibenzoxazepinone regioisomer (2), were synthesized and assessed for anti-Giardia activity. While regioisomer 2 demonstrated antigiardial activity, resynthesized 1 and other 8-acylaminodibenzoxazepinone analogues were inactive. Comparison of spectroscopic and physical properties demonstrated the correct structure of SN00797640 to be 7-acylamino regioisomer 2. These results highlight the importance of independent synthesis in verifying the structure and activity of screening hits.

Subjects

Subjects :
General Chemistry

Details

ISSN :
14450038 and 00049425
Volume :
75
Database :
OpenAIRE
Journal :
Australian Journal of Chemistry
Accession number :
edsair.doi...........319fc93b45306b9f0060537089e458b3