Chiral Resolution and Absolute Configuration of a Pair of Rare Racemic Spirodienone Sesquineolignans from Xanthium sibiricum

2014 ◽  
Vol 16 (20) ◽  
pp. 5406-5409 ◽  
Author(s):  
Yusheng Shi ◽  
Yunbao Liu ◽  
Yong Li ◽  
Li Li ◽  
Jing Qu ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Chiral Resolution ◽  
Xanthium Sibiricum

Enantiopure methoxetamine stereoisomers: chiral resolution, conformational analysis, UV-circular dichroism spectroscopy and electronic circular dichroism

2021 ◽  
Author(s):  
Kun Won Lee ◽  
Ahmed H. E. Hassan ◽  
Youngdo Jeong ◽  
Seolmin Yoon ◽  
Seung-Hwan Kim ◽  
...  
Keyword(s):  
Circular Dichroism ◽  
Conformational Analysis ◽  
Absolute Configuration ◽  
Circular Dichroism Spectroscopy ◽  
Chiral Resolution ◽  
Treatment Resistant Depression ◽  
Treatment Resistant ◽  
Electronic Circular Dichroism ◽  
Resistant Depression ◽  
Circular Dichroïsm

Enantioseparation and assignment of absolute configuration of methoxetamine (MXE) enantiopure stereoisomers; a promising novel antidepressant for management of treatment-resistant depression.

Synthesis, Chiral Resolution, and Absolute Configuration of Functionalized Tröger’s Base Derivatives: Part II

ChemPlusChem ◽  
2012 ◽  
Vol 77 (5) ◽  
pp. 396-403 ◽  
Author(s):  
Christian Benkhäuser-Schunk ◽  
Boris Wezisla ◽  
Kirstin Urbahn ◽  
Ulf Kiehne ◽  
Jörg Daniels ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Chiral Resolution ◽  
Troger's Base

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 Chiral Resolution and Absolute Configuration of 3α,6β-Dicinnamoyloxytropane and 3α,6β-Di(1-ethyl-1H-pyrrol-2-ylcarbonyloxy)tropane, Constituents of Erythroxylum Species

2014 ◽  
Vol 9 (1) ◽  
pp. 1934578X1400900 ◽  
Author(s):  
Marcelo A. Muñoz ◽  
Solange Arriagada ◽  
Pedro Joseph-Nathan
Keyword(s):  
Stationary Phase ◽  
Natural Product ◽  
Absolute Configuration ◽  
Optical Rotation ◽  
Normal Phase ◽  
Vibrational Circular Dichroism ◽  
Chiral Resolution ◽  
Case Characteristic ◽  
The Absolute

Chiral resolution of (±)-3α,6β-dicinnamoyloxytropane (1) and (±)-3α,6β-di(1-methyl-1 H-pyrrol-2-ylcarbonyloxy)tropane (2), prepared by esterification of (±)-3α,6β-tropanediol (3), was achieved using an amylose-derived HPLC stationary phase and normal phase conditions. The corresponding vibrational circular dichroism (VCD) spectra provided the absolute configuration of the enantiomers as (-)-(3 R,6 R)-1, (+)-(3S,6S)- 1, (-)-(3 R,6 R)-2 and (+)-(3S,6S)- 2. In each case, characteristic VCD bands for the absolute configuration determination of the 3α,6β-tropandiol esters were observed. While the absolute configuration of natural 1, previously isolated from Erythroxylum hypericifolium, could not be established due to the lack of literature optical rotation values, that of catuabine E, previously isolated from E. vacciniifolium, is now assigned as (-)-(3 R,6 R)-2 by comparison with the optical rotation values of the prepared samples and the reported rotation of the natural product.

scholarly journals Chiral Resolution and Absolute Configuration of the Enantiomers of the Psychoactive “Designer Drug” 3,4-Methylenedioxypyrovalerone

Chirality ◽  
2015 ◽  
Vol 27 (4) ◽  
pp. 287-293 ◽  
Author(s):  
Masaki Suzuki ◽  
Jeffrey R. Deschamps ◽  
Arthur E. Jacobson ◽  
Kenner C. Rice
Keyword(s):  
Absolute Configuration ◽  
Chiral Resolution ◽  
Designer Drug

scholarly journals Novel Enantiopure Sigma Receptor Modulators: Quick (Semi-)Preparative Chiral Resolution via HPLC and Absolute Configuration Assignment

Molecules ◽  
2016 ◽  
Vol 21 (9) ◽  
pp. 1210 ◽  
Author(s):  
Marta Rui ◽  
Annamaria Marra ◽  
Vittorio Pace ◽  
Markus Juza ◽  
Daniela Rossi ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Chiral Resolution ◽  
Sigma Receptor ◽  
Configuration Assignment ◽  
Receptor Modulators

Chiral resolution, absolute configuration determination, and stereo-activity relationship study of IDO1 inhibitor NLG919

Tetrahedron ◽  
2018 ◽  
Vol 74 (24) ◽  
pp. 3045-3051 ◽  
Author(s):  
Wen-Qiang Liu ◽  
Fang-Fang Lai ◽  
Jie Zhang ◽  
Li Sheng ◽  
Yan Li ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Chiral Resolution ◽  
Activity Relationship ◽  
Relationship Study

scholarly journals Insight into GEBR-32a: Chiral Resolution, Absolute Configuration and Enantiopreference in PDE4D Inhibition

Molecules ◽  
2020 ◽  
Vol 25 (4) ◽  
pp. 935 ◽  
Author(s):  
Valeria Cavalloro ◽  
Katia Russo ◽  
Francesca Vasile ◽  
Luca Pignataro ◽  
Archimede Torretta ◽  
...  
Keyword(s):  
Absolute Configuration ◽  
Catalytic Domain ◽  
Memory Loss ◽  
Cyclic Adenosine Monophosphate ◽  
Adenosine Monophosphate ◽  
Chiral Resolution ◽  
Regulatory Domains ◽  
Downstream Effectors ◽  
Configuration Assignment ◽  
Ic50 Values

Alzheimer’s disease is the most common type of dementia, affecting millions of people worldwide. One of its main consequences is memory loss, which is related to downstream effectors of cyclic adenosine monophosphate (cAMP). A well-established strategy to avoid cAMP degradation is the inhibition of phosphodiesterase (PDE). In recent years, GEBR-32a has been shown to possess selective inhibitory properties against PDE type 4 family members, resulting in an improvement in spatial memory processes without the typical side effects that are usually correlated with this mechanism of action. In this work, we performed the HPLC chiral resolution and absolute configuration assignment of GEBR-32a. We developed an efficient analytical and semipreparative chromatographic method exploiting an amylose-based stationary phase, we studied the chiroptical properties of both enantiomers and we assigned their absolute configuration by 1H-NMR (nuclear magnetic resonance). Lastly, we measured the IC50 values of both enantiomers against both the PDE4D catalytic domain and the long PDE4D3 isoform. Results strongly support the notion that GEBR-32a inhibits the PDE4D enzyme by interacting with both the catalytic pocket and the regulatory domains.

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