2. Academic Validation
  3. Synthesis and anticancer properties of new (dihydro)pyranonaphthoquinones and their epoxy analogs

Synthesis and anticancer properties of new (dihydro)pyranonaphthoquinones and their epoxy analogs

  • Bioorg Med Chem Lett. 2015 Aug 15;25(16):3355-8. doi: 10.1016/j.bmcl.2015.05.051.
Tuyet Anh Dang Thi 1,  Thu Ha Vu Thi 1,  Hoang Thi Phuong 1,  Thanh Ha Nguyen 1,  Chinh Pham The 1,  Cuong Vu Duc 1,  Yves Depetter 2,  Tuyen Van Nguyen 3,  Matthias D'hooghe 2
Affiliations

Affiliations

  • 1 Institute of Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, CauGiay, Hanoi, Vietnam.
  • 2 SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
  • 3 Institute of Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, CauGiay, Hanoi, Vietnam. Electronic address: [email protected].
PMID: 26081288 DOI: 10.1016/j.bmcl.2015.05.051
Abstract

1,4-Dihydroxy-2-naphthoic acid was used as a substrate for a straightforward five-step synthesis of 3-substituted 1H-benzo[g]isochromene-5,10-diones, with a Michael addition of N-acylmethylpyridinium ylides across 2-hydroxymethyl-1,4-naphthoquinone and a subsequent acid-mediated dehydratation of intermediate hemiacetals as the key steps. The obtained benzo[g]isochromene-5,10-diones were subsequently deployed for further synthetic elaboration to produce new 3,4-dihydrobenzo[g]isochromene-5,10-diones and (3,4-dihydro-)4a,10a-epoxybenzo[g]isochromene-5,10-diones. All compounds were screened for their cytotoxic and antimicrobial effects, revealing an interesting cytotoxic activity of 1H-benzo[g]isochromene-5,10-diones against different Cancer cell lines.

Keywords

Cytotoxicity; Epoxides; Pyranonaphthoquinones.

Figures