The first synthesis of (&amp;plusmn;)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative

Silva, Alcides J. M. da; Netto, Chaquip D.; Costa, Paulo R. R.

doi:10.1590/s0103-50532004000600029

Cited by 12 publications

(3 citation statements)

References 4 publications

(4 reference statements)

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“…The results from this study are promising for further development of these compounds for potential application in cancer chemotherapy. 254 The pentacyclic 1,4-naphthoquinones of type 1 36 were designed as molecular hybrids of the cytotoxic naphthoquinones, lapachol and a-lapachone and natural pterocarpan [255][256][257] (Fig. 34).…”

Section: Naphthoquinone-based Stat3 Inhibitorsmentioning

confidence: 99%

Understanding cancer and the anticancer activities of naphthoquinones – a review

2015

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The non-communicable disease, cancer, is one of the major causes of death across the world and is forecast to increase by 75% to reach close to 25 million cases over the next two decades. Radiotherapy and surgical approaches have been unsuccessful in controlling the incidence of most cancers. The development of chemotherapeutic strategies involving novel small molecule antitumour agents has therefore been the focus area of cancer chemotherapy for several decades as another strategy to combat and control the incidence of cancer. Many natural products as well as several synthetic drugs have a naphthoquinone chromophore. The anticancer activities of naphthoquinones have been the focus of much research to discover novel anticancer agents. The naturally occurring 1,2-naphthoquinone-based compound, ß-Lapachone (ARQ 761), is currently being assessed for its anti-tumour activity against advanced solid tumours. This review describes the most recent applications of naphthoquinones and their derivatives in cancer drug discovery. The biology relevant to the design of novel naphthoquinone anticancer agents is also discussed. Furthermore, the discussion of the biology will contribute to understanding cancer as well as the applications of naphthoquinones as anticancer agents.

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Section: Naphthoquinone-based Stat3 Inhibitorsmentioning

confidence: 99%

Understanding cancer and the anticancer activities of naphthoquinones – a review

2015

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“…These compounds were designed as molecular hybrids of the cytotoxic naphthoquinones lapachol (2) and α-lapachone (3), isolated from Tabebuia spp. [1,2] and natural pterocarpan (4), a cytotoxic isoflavonoid isolated from Petalostemon purpureus [19][20][21]. These pentacyclic 1,4-naphthoquinones were cytotoxic to MCF-7, a breast cancer cell line (Table 1), whereas α-lapachone (3) was inactive on these cells [18,22].…”

Section: Introductionmentioning

confidence: 99%

Comparison of the cytotoxic effect of lapachol, α-lapachone and pentacyclic 1,4-naphthoquinones on human leukemic cells

et al. 2009

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The pentacyclic 1,4-naphthoquinones 1a-d were cytotoxic (IC(50) approximately 2-7 microM) to human leukemic cell lines K562 (oxidative stress-resistant), Lucena-1 (MDR phenotype) and Daudi. Fresh leukemic cells obtained from patients, some with the MDR phenotype, were also sensitive to these compounds. The pentacyclic 1,4-naphthoquinones 1a and 1c induced apoptotic cell death in cells from leukemic patients as determined by flow cytometry. Conversely, the cell lines were highly insensitive to lapachol (2) and alpha-lapachone (3). Mitomycin-C inhibited cell proliferation at concentrations as low as 0.5 microM. The low toxicity against lymphocytes activated by phytohemagglutinin shows that these compounds are selective for the cancer cells studied. Previous data suggest that these compounds (1a-d) can be bioactivated in situ by reduction followed by rearrangement leading to enones, which are powerful alkylating agents. In contrast, lapachol (2) and beta-lapachone (3), which cannot be bioactivated by reduction, showed little activity against the same cell lines.

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“…Compound 6. Compound 1 (200 mg, 0.704 mmol) dissolved in DCM (25 mL) was treated with DDQ (60 mg) [ 17 ]. The mixture was left at room temperature for 12 h under constant stirring.…”

Section: Methodsmentioning

confidence: 99%

Antifungal activity against anthracnose-causing species of homopterocarpin derivatives

Martinez

Ramirez

González

et al. 2023

Heliyon

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The first synthesis of (±)-3,4-dihydroxy-8,9-methylenedioxypterocarpan, an antitumoral agent and its coumestan derivative

Cited by 12 publications

References 4 publications

Understanding cancer and the anticancer activities of naphthoquinones – a review

Understanding cancer and the anticancer activities of naphthoquinones – a review

Comparison of the cytotoxic effect of lapachol, α-lapachone and pentacyclic 1,4-naphthoquinones on human leukemic cells

Antifungal activity against anthracnose-causing species of homopterocarpin derivatives

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