A New Strategy for the Synthesis of Nonsymmetrical 3,3’-(Aryl/alkyl- methylene) bis-2-hydroxy-1,4-naphthoquinones and Their Cytotoxic Effects in PC3 Prostate Cancer Cells

Abstract

A novel method for the synthesis of nonsymmetrical 3,3'-(aryl/alkyl-methylene)bis-2-hydroxy-1,4-naphthoquinones was developed by using the Mannich adduct of naphthoquinone and the reaction with another moiety of 2-hydroxy-1,4-naphthoquinone. This novel method produces for the first time nonsymmetrical 3,3'-(aryl/alkyl-methylene)bis-2-hydroxy-1,4-naphthoquinones. In a preliminary study, these compounds (15c, 15f and 15h) were evaluated regarding their effect over the viability of PC3 metastatic prostate cancer cell using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assays at 100 μM. Three of these compounds presented relevant cytotoxic effects at 72 h posttreatment.

Surface-Modified Lyotropic Crystalline Nanoconstructs Bearing Doxorubicin and Buparvaquone Target Sigma Receptors through pH-Sensitive Charge Conversion to Improve Breast Cancer Therapy

“…Treatment with a single medicine cannot effectively deliver the desired therapeutic results due to the pathological complexity of cancer. The naphthoquinone group is the largest subclass of chemicals in the quinone family . Lapachol, atovaquone, and buparvaquone, as well as other compounds that are now being tested in clinical trials, such as lapachone, are examples of natural and synthetic compounds with the naphthoquinone nucleus that were developed into medicines and sold on the pharmaceutical market.…”

“…The naphthoquinone group is the largest subclass of chemicals in the quinone family. 9 Lapachol, atovaquone, and buparvaquone, as well as other compounds that are now being tested in clinical trials, such as lapachone, are examples of natural and synthetic compounds with the naphthoquinone nucleus that were developed into medicines and sold on the pharmaceutical market. Buparvaquone (BPQ), a hydroxynaphthoquinone derivative, has been investigated for treating many veterinary infections, including leishmaniasis, pneumonia, and cryptosporidiosis, but it also has anticancer activity.…”