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

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.

Naphthoquinone Derivatives from Angustimassarina populi CF-097565 Display Anti-Tumour Activity in 3D Cultures of Breast Cancer Cells

“…In previous reports, some naphthoquinone derivatives were reported as cytotoxic against various cancer cell lines [ 35 ], and specifically in breast cancer [ 36 ], but to our knowledge, there are no reports describing the effect of naphthoquinone derivatives in cancer spheroid models. Furthermore, the use of high-content cellular imaging provided additional valuable information.…”

Emerging Oxygen Based Heterocyclic Scaffolds as Potential Anticancer Candidates

“…Natural dihydropyranonaphthoquinones can be obtained from fungi, bacteria, and higher plants. Numerous scaffolds have certainly been found to hold diverse and noticeable biological actions, including antiparasitic, antimicrobial, anticancer and antiviral properties [65]. Eleutherin ( 64) pentalongin (66) and psychorubrin (65) are of compounds, which exhibited an interesting antimicrobial, phytotoxic antiparasitic, and antineoplastic properties.…”

Synthesis, molecular docking analysis and in vitro evaluation of new heterocyclic hybrids of 4-aza-podophyllotoxin as potent cytotoxic agents

“…Heterocycles, a class of cyclic organic compounds containing at least one ring hetero atom, have played an important role in pharmaceutical development due to their variety of biological activities such as anti-fungal, 1 antimicrobial, 2 anti-inflammatory, 3,4 anti-diabetic, 5 cytotoxic, 6,7 anti-tumor, anti-cancer, 8,9 anti-viral, 10 acetylcholinesterase inhibitory, 11 and SARS-CoV2 inhibitory activities. 12 To date, heterocycles have presented themselves as the basic core of most marketed drugs.…”