Total Syntheses and Absolute Configuration Assignment of (+)-Sootepdienone, (−)-Jambolanin C, (−)-Jambolanin I, and (−)-Gibberodione

2021 ◽  
Vol 86 (3) ◽  
pp. 3074-3080
Author(s):  
Kevin Ng ◽  
Michael Khoury ◽  
Thomas Gerard Minehan
Keyword(s):  
Absolute Configuration ◽  
Total Syntheses ◽  
Configuration Assignment

Synthesis, Chiral Separation, Absolute Configuration Assignment, and Biological Activity of Enantiomers of Retro-1 as Potent Inhibitors of Shiga Toxin

ChemMedChem ◽  
2015 ◽  
Vol 10 (7) ◽  
pp. 1153-1156 ◽  
Author(s):  
Hajer Abdelkafi ◽  
Aurélien Michau ◽  
Alexandra Clerget ◽  
David-Alexandre Buisson ◽  
Ludger Johannes ◽  
...  
Keyword(s):  
Biological Activity ◽  
Absolute Configuration ◽  
Chiral Separation ◽  
Shiga Toxin ◽  
Configuration Assignment

scholarly journals Absolute Configuration Sensing of Chiral Aryl- and Aryloxy-Propionic Acids by Biphenyl Chiroptical Probes

Chemosensors ◽  
2021 ◽  
Vol 9 (7) ◽  
pp. 154
Author(s):  
Stefania Vergura ◽  
Stefano Orlando ◽  
Patrizia Scafato ◽  
Sandra Belviso ◽  
Stefano Superchi
Keyword(s):  
Circular Dichroism ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Environmental Pollutants ◽  
Red Shift ◽  
Electronic Circular Dichroism ◽  
Configuration Assignment ◽  
Clear Sign ◽  
The Absolute ◽  
Circular Dichroïsm

The absolute configuration of chiral 2-aryl and 2-aryloxy propionic acids, which are among the most common chiral environmental pollutants, has been readily and reliably established by either electronic circular dichroism spectroscopy or optical rotation measurements employing suitably designed 4,4′-disubstituted biphenyl probes. In fact, the 4,4′-biphenyl substitution gives rise to a red shift of the diagnostic electronic circular dichroism signal of the biphenyl A band employed for the configuration assignment, removing its overlap with other interfering dichroic bands and allowing its clear sign identification. The largest A band red shift, and thus the most reliable results, are obtained by employing as a probe the 4,4′-dinitro substituted biphenylazepine 3c. The method was applied to the absolute configuration assignment of 2-arylpropionic acids ibuprofen (1a), naproxen (1b), ketoprofen (1c) and flurbiprofen (1d), as well as to the 2-aryloxypropionic acids 2-phenoxypropionic acid (2a) and 2-naphthoxypropionic acid (2b). This approach, allowing us to reveal the sample’s absolute configuration by simple optical rotation measurements, is potentially applicable to online analyses of both the enantiomeric composition and absolute configuration of these chiral pollutants.

scholarly journals Chiral Resolution, Absolute Configuration Assignment, and Genotoxicity Evaluation of Racemic 3,4-Dihydroquinazoline as a Novel Anticancer Agent

2021 ◽  
Vol 2021 ◽  
pp. 1-8
Author(s):  
Junseong Ahn ◽  
Dohyeong Ko ◽  
Seyoung Yang ◽  
Kwang H. Moon ◽  
Jiwon Woo ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Anticancer Agent ◽  
Metabolic Activation ◽  
Chiral Resolution ◽  
Drug Candidate ◽  
Bacterial Strains ◽  
Configuration Assignment ◽  
Preclinical And Clinical Studies ◽  
Human A549 ◽  
A549 Lung

If a new drug candidate will be a mixture of enantiomers, both enantiomers should be separately studied for at least latent genotoxicity as early as possible since the thalidomide tragedy. Our group has recently reported that KCP-10043F (OZ-001) as a racemate (±)-3,4-dihydroquinazoline derivative strongly represses the proliferation of human A549 lung cancer cells by caspase-mediated apoptosis via STAT3 inactivation. To investigate the possible teratological effects of the two enantiomers of a racemic KCP-10043F, therefore chiral resolution of (±)-KCP-10043F was performed and subsequently followed by a series of chemical processes to afford the corresponding chiral diastereomers. By using 1H NMR anisotropy method, the absolute configuration (+)-KCP-10043F and (−)-KCP-10043F could be assigned as S and R configuration, respectively. The bacterial reverse mutation test (Ames test) for racemate (±)-KCP-10043F and its two enantiomers exhibited that all three stereoisomers were found to be nongenotoxic against five bacterial strains with/without metabolic activation. In addition, (R)-(−)-KCP-10043F displayed almost equal anticancer activity to (S)-(+)-KCP-10043F against three cancer cell lines. Based on these overall results, racemate KCP-10043F (OZ-001) could be used for our ongoing preclinical and clinical studies without the expensive asymmetric process and/or chiral separation.

scholarly journals Enantiomeric Mixtures in Natural Product Chemistry: Separation and Absolute Configuration Assignment

Molecules ◽  
2018 ◽  
Vol 23 (2) ◽  
pp. 492 ◽  
Author(s):  
Andrea N. L. Batista ◽  
Fernando M. dos Santos ◽  
João Batista ◽  
Quezia Cass
Keyword(s):  
Natural Product ◽  
Absolute Configuration ◽  
Natural Product Chemistry ◽  
Configuration Assignment ◽  
Product Chemistry

Absolute configuration assignment to anticancer Amaryllidaceae alkaloid jonquailine

Fitoterapia ◽  
2018 ◽  
Vol 129 ◽  
pp. 78-84 ◽  
Author(s):  
Stefania Vergura ◽  
Ernesto Santoro ◽  
Marco Masi ◽  
Antonio Evidente ◽  
Patrizia Scafato ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Configuration Assignment
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