2. Academic Validation
  3. Synthesis of new spirooxindole-pyrrolothiazole derivatives: Anti-cancer activity and molecular docking

Synthesis of new spirooxindole-pyrrolothiazole derivatives: Anti-cancer activity and molecular docking

  • Bioorg Med Chem. 2017 Feb 15;25(4):1514-1523. doi: 10.1016/j.bmc.2017.01.014.
Gehad Lotfy 1,  Mohamed M Said 1,  El Sayed H El Ashry 2,  El Sayed H El Tamany 3,  Abdullah Al-Dhfyan 4,  Yasmine M Abdel Aziz 1,  Assem Barakat 5
Affiliations

Affiliations

  • 1 Pharmaceutical Organic Chemistry Department, Faculty of Pharmacy, Suez Canal University, Ismailia 41522, Egypt.
  • 2 Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt.
  • 3 Department of Chemistry, Faculty of Science, Suez Canal University, Ismailia, Egypt.
  • 4 Stem Cell Therapy & Tissue Re-engineering Program, King Faisal Specialized Hospital and Research Center, MBC-03, P.O. Box 3354, Riyadh 11211, Saudi Arabia.
  • 5 Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. Electronic address: ambarakat@ksu.edu.sa.
PMID: 28126436 DOI: 10.1016/j.bmc.2017.01.014
Abstract

The 1,3-dipolar cycloadditions of an azomethine ylide generated from isatin and thiazolidinecarboxylic acid to a series of 2,6-bis[(E)-arylmethylidene]cyclohexanones afforded new di-spiro heterocycles incorporating pyrrolidine and oxindole rings in quantitative yields and chemo-, regio-, and stereoselectively. The newly synthesized compounds were characterized using spectroscopic techniques. Furthermore, the molecular structures of 4a, 4e, and 4n were confirmed by X-ray crystallography. These newly synthesized compounds were screened for their in vitro activity against breast Cancer cell line MCF-7 and K562-leukemia. 4k was found to be the most potent compound of this series in targeting MCF-7 breast Cancer cells and K562-leukemia, with IC50 values of 15.32±0.02 and 14.74±0.7μM, respectively. The molecular studies of the synthesized compounds were investigated.

Keywords

1,3-Dipolar cycloaddition; Atom economy; Azomethine ylide; Breast cancer; Leukemia; Molecular docking; Oxindole; Pyrrolidine; Spirocyclohexanone.

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