Next Article in Journal
Quantitative Phosphoproteomic Analysis Provides Insight into the Response to Short-Term Drought Stress in Ammopiptanthus mongolicus Roots
Next Article in Special Issue
Vitamin D in Pain Management
Previous Article in Journal
The Specific Mitogen- and Stress-Activated Protein Kinase MSK1 Inhibitor SB-747651A Modulates Chemokine-Induced Neutrophil Recruitment
Previous Article in Special Issue
Long-Term Therapy Outcomes When Treating Chronic Kidney Disease Patients with Paricalcitol in German and Austrian Clinical Practice (TOP Study)
Article

Seco-B-Ring Steroidal Dienynes with Aromatic D Ring: Design, Synthesis and Biological Evaluation

1
Department of Chemistry, University of Warsaw, Pasteura 1, 02-093 Warsaw, Poland
2
Department of Biotechnology, University of Wroclaw, Joliot-Curie 14a, 50-383 Wroclaw, Poland
*
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2017, 18(10), 2162; https://doi.org/10.3390/ijms18102162
Received: 28 September 2017 / Revised: 13 October 2017 / Accepted: 14 October 2017 / Published: 17 October 2017
Continuing our structure-activity studies on the vitamin D analogs with the altered intercyclic seco-B-ring fragment, we designed compounds possessing dienyne system conjugated with the benzene D ring. Analysis of the literature data and the docking experiments seemed to indicate that the target compounds could mimic the ligands with a good affinity to the vitamin D receptor (VDR). Multi-step synthesis of the C/D-ring building block of the tetralone structure was achieved and its enol triflate was coupled with the known A-ring fragments, possessing conjugated enyne moiety, using Sonogashira protocol. The structures of the final products were confirmed by NMR, UV and mass spectroscopy. Their binding affinities for the full-length human VDR were determined and it was established that compound substituted at C-2 with exomethylene group showed significant binding to the receptor. This analog was also able to induce monocytic differentiation of HL-60 cells. View Full-Text
Keywords: steroidal dienynes; B-seco steroids; Sonogashira reaction; vitamin D receptor; HL-60 cell differentiation steroidal dienynes; B-seco steroids; Sonogashira reaction; vitamin D receptor; HL-60 cell differentiation
Show Figures

Graphical abstract

MDPI and ACS Style

Szybinski, M.; Brzeminski, P.; Fabisiak, A.; Berkowska, K.; Marcinkowska, E.; Sicinski, R.R. Seco-B-Ring Steroidal Dienynes with Aromatic D Ring: Design, Synthesis and Biological Evaluation. Int. J. Mol. Sci. 2017, 18, 2162. https://doi.org/10.3390/ijms18102162

AMA Style

Szybinski M, Brzeminski P, Fabisiak A, Berkowska K, Marcinkowska E, Sicinski RR. Seco-B-Ring Steroidal Dienynes with Aromatic D Ring: Design, Synthesis and Biological Evaluation. International Journal of Molecular Sciences. 2017; 18(10):2162. https://doi.org/10.3390/ijms18102162

Chicago/Turabian Style

Szybinski, Marcin, Pawel Brzeminski, Adrian Fabisiak, Klaudia Berkowska, Ewa Marcinkowska, and Rafal R. Sicinski 2017. "Seco-B-Ring Steroidal Dienynes with Aromatic D Ring: Design, Synthesis and Biological Evaluation" International Journal of Molecular Sciences 18, no. 10: 2162. https://doi.org/10.3390/ijms18102162

Find Other Styles
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

1
Back to TopTop