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Improved synthesis, resolution, absolute configuration determination and biological evaluation of HLM006474 enantiomers
- Source :
- Bioorganic and Medicinal Chemistry Letters, Bioorganic and Medicinal Chemistry Letters, Elsevier, 2019, 29, pp.380-382. ⟨10.1016/j.bmcl.2018.12.037⟩, Bioorganic and Medicinal Chemistry Letters, 2019, 29, pp.380-382. ⟨10.1016/j.bmcl.2018.12.037⟩
- Publication Year :
- 2019
- Publisher :
- HAL CCSD, 2019.
-
Abstract
- International audience; An improved green synthesis of the E2F inhibitor HLM0066474 is described, using solvent-free and microwave irradiation conditions. The two enantiomers are separated using semi-preparative separation on Chiralpak ID and their absolute configuration is determined by vibrational circular dichroism (VCD) analysis. Biological evaluation of both enantiomers on E2F1 transcriptional activity reveals that the (+)-R, but not the (−)-S enantiomer is biologically active in repressing E2F1 transcriptional activity.
- Subjects :
- endocrine system
Resolution (mass spectrometry)
Stereochemistry
Clinical Biochemistry
Pharmaceutical Science
Aminopyridines
Solvent-free reaction
01 natural sciences
Biochemistry
Structure-Activity Relationship
[CHIM.GENI]Chemical Sciences/Chemical engineering
Drug Discovery
Humans
[SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM]
Molecular Biology
Biological evaluation
Transcriptional activity
Dose-Response Relationship, Drug
Molecular Structure
010405 organic chemistry
Chemistry
[CHIM.ORGA]Chemical Sciences/Organic chemistry
Betti reaction
Circular Dichroism
Biological activity
Organic Chemistry
Absolute configuration
Stereoisomerism
[SDV.BBM.BM]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Molecular biology
0104 chemical sciences
3. Good health
[SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biomolecules [q-bio.BM]
Absolute configuration determination
010404 medicinal & biomolecular chemistry
HEK293 Cells
Vibrational circular dichroism
Hydroxyquinolines
Molecular Medicine
HLM006474 enantiomers
Enantiomer
biological phenomena, cell phenomena, and immunity
Microwave assisted synthesis
E2F1 Transcription Factor
Subjects
Details
- Language :
- English
- ISSN :
- 0960894X
- Database :
- OpenAIRE
- Journal :
- Bioorganic and Medicinal Chemistry Letters, Bioorganic and Medicinal Chemistry Letters, Elsevier, 2019, 29, pp.380-382. ⟨10.1016/j.bmcl.2018.12.037⟩, Bioorganic and Medicinal Chemistry Letters, 2019, 29, pp.380-382. ⟨10.1016/j.bmcl.2018.12.037⟩
- Accession number :
- edsair.doi.dedup.....3cf7becf201ecaac7886aca72aaa0a14
- Full Text :
- https://doi.org/10.1016/j.bmcl.2018.12.037⟩