11-Phenylundeca-5Z,9Z-dienoic Acid: Stereoselective Synthesis and Dual Topoisomerase I/IIα Inhibition

Vladimir A. D’yakonov; Lilya U. Dzhemileva; Aleksey A. Makarov; Alfiya R. Mulyukova; Dmitry S. Baevd; Elza K. Khusnutdinova; Tatiana G. Tolstikova; Usein M. Dzhemilev

doi:10.2174/1568009615666150506093155

ISSN: 1568-0096
E-ISSN: 1873-5576

11-Phenylundeca-5Z,9Z-dienoic Acid: Stereoselective Synthesis and Dual Topoisomerase I/IIα Inhibition
By Vladimir A. D’yakonov, Lilya U. Dzhemileva, Aleksey A. Makarov, Alfiya R. Mulyukova, Dmitry S. Baevd, Elza K. Khusnutdinova, Tatiana G. Tolstikova and Usein M. Dzhemilev
Source: Current Cancer Drug Targets, Volume 15, Issue 6, Jul 2015, p. 504 - 510
DOI: https://doi.org/10.2174/1568009615666150506093155
- Available online: 01 Jul 2015

Abstract

(5Z,9Z)-11-Phenylundeca-5,9-dienoic acid was stereoselectively synthesized, based on original cross-cyclomagnesiation of 2-(hepta-5,6-dien-1-yloxy)tetrahydro-2H-pyran and buta-2,3-dien-1-ylbenzene with EtMgBr in the presence of the Cp2TiCl2 catalyst giving 2,5-dialkylydenemagnesacyclopentane in 86% yield. The acid hydrolysis of the product and Jones oxidation of the resulting 2-{[(5Z,9Z)-11-phenylundeca-5,9-dien-1-yl]oxy}tetrahydro-2Н-pyran afforded (5Z,9Z)-11-phenylundeca-5,9-dienoic acid in an overall yield of 75%. A high inhibitory activity of the synthesized acid with respect to human topoisomerase I (hTop1) and II (hTop2α) was detected. Resorting to the data of molecular docking, a mechanism of inhibition was proposed.

Article metrics loading...

/content/journals/ccdt/10.2174/1568009615666150506093155

2015-07-01

2025-05-21

From This Site

/content/journals/ccdt/10.2174/1568009615666150506093155

dcterms_title,dcterms_subject,pub_keyword

-contentType:Contributor -contentType:Concept -contentType:Institution

10

5

Full text loading...

/content/journals/ccdt/10.2174/1568009615666150506093155

Article Type: Research Article

Keyword(s): 9Z-dienoic acid; Cyclomagnesiation; docking; fatty acids; homogeneous catalysis; novel topoisomerase I and IIα inhibitors; stereoselective synthesis of 5Z

Most Cited Most Cited RSS feed

- Luteolin, a Flavonoid with Potential for Cancer Prevention and Therapy
  
  Authors: Yong Lin, Ranxin Shi, Xia Wang and Han-Ming Shen
- The Role of Snail in EMT and Tumorigenesis
  
  Authors: Yifan Wang, Jian Shi, Kequn Chai, Xuhua Ying and Binhua P. Zhou
- The PTEN/PI3K/AKT Signalling Pathway in Cancer, Therapeutic Implications
  
  Authors: Amancio Carnero, Carmen Blanco-Aparicio, Oliver Renner, Wolfgang Link and Juan F.M. Leal
- Bortezomib as the First Proteasome Inhibitor Anticancer Drug: Current Status and Future Perspectives
  
  Authors: D. Chen, M. Frezza, S. Schmitt, J. Kanwar and Q. P. Dou
- P-glycoprotein Inhibition as a Therapeutic Approach for Overcoming Multidrug Resistance in Cancer: Current Status and Future Perspectives
  
  Authors: Ziyad Binkhathlan and Afsaneh Lavasanifar
- Taxanes: Microtubule and Centrosome Targets, and Cell Cycle Dependent Mechanisms of Action
  
  Authors: M. Abal, J.M. Andreu and I. Barasoain
- Paclitaxel Resistance: Molecular Mechanisms and Pharmacologic Manipulation
  
  Authors: R.Z. Yusuf, Z. Duan, D.E. Lamendola, R.T. Penson and M.V. Seiden
- The Role of Fibroblast Growth Factors in Tumor Growth
  
  Authors: M. Korc and R. E. Friesel
- Garlic [Allium sativum]: A Review of its Potential Use as an Anti-Cancer Agent
  
  Authors: M. Thomson and M. Ali
- Oxidative Stress and Cancer: The Role of Nrf2
  
  Authors: Soraya Sajadimajd and Mozafar Khazaei
More Less

11-Phenylundeca-5Z,9Z-dienoic Acid: Stereoselective Synthesis and Dual Topoisomerase I/IIα Inhibition

Abstract

Most Read This Month

Most Cited Most Cited RSS feed