17112-93-5

Upstream product

• 110271-51-7 2-hydroxy-3-[(1E)-prop-1-en-1-yl]naphthalene-1,4-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 29366-41-4 2-hydroxy-3-(prop-1-en-1-yl)naphthalene-1,4-dione 
• 195156-60-6 2-methyl-2,3-dihydrolnaphthol[1,2-b]furan-4,5-dione 
• 40815-76-7 3-allyl-2-hydroxy-1,4-naphthoquinone 
• 40815-72-3 2-allyloxy-1,4-naphthoquinone 
• 858019-87-1 2-(1,2-dibromo-propyl)-3-hydroxy-[1,4]naphthoquinone 

Relevant academic research and scientific papers

A novel tanshinone analog exerts anti-cancer effects in prostate cancer by inducing cell apoptosis, arresting cell cycle at G2 phase and blocking metastatic ability

Prostate cancer (PCa), an epithelial malignant tumor, is the second common cause of cancer death among males in western countries. Thus, the development of new strategies is urgently needed. Tanshinones isolated from Salvia miltiorrhiza and its synthetic analogs show various biological activities including anticancer effects. Among them, the tanshinone analog 2-((Glycine methyl ester)methyl)-naphtho (TC7) is the most effective, with better selectivity and lower toxicity. Therefore, in this work, the effect of TC7 against PCa was investigated through assessing the molecular mechanisms regulating the growth, metastasis, and invasion of PCa cells. Human PCa cells, PC3 and LNCAP, were used to evaluate TC7 mechanisms of action in vitro, while male BALB/c nude mice were used for in vivo experiments by subjecting each mouse to a subcutaneous injection of PC3 cells into the right flank to evaluate TC7 effects on tumor volume. Our in vitro results showed that TC7 inhibited cell proliferation by arresting the cell cycle at G2/M through the regulation of cyclin b1, p53, GADD45A, PLK1, and CDC2/cyclin b1. In addition, TC7 induced cell apoptosis by regulating apoptosis-associated genes such as p53, ERK1, BAX, p38, BCL-2, caspase-8, cleaved-caspase-8, PARP1, and the phosphorylation level of ERK1 and p38. Furthermore, it decreased DNA synthesis and inhibited the migration and invasion ability by regulating VEGF-1 and MMP-9 protein expression. Our in vivo evidence supports the conclusion that TC7 could be considered as a potential promising chemotherapeutic candidate in the treatment of PCa.

Potent cytotoxicity of novel L-shaped ortho-quinone analogs through inducing apoptosis

Twenty-seven L-shaped ortho-quinone analogs were designed and synthesized using a one pot double-radical synthetic strategy followed by removing methyl at C-3 of the furan ring and introducing a diverse side chain at C-2 of the furan ring. The synthetic derivatives were investigated for their cytotoxicity activities against human leukemia cells K562, prostate cancer cells PC3, and melanoma cells WM9. Compounds TB1, TB3, TB4, TB6, TC1, TC3, TC5, TC9, TC11, TC12, TC14, TC15, TC16, and TC17 exhibited a better broad-spectrum cytotoxicity on three cancer cells. TB7 and TC7 selectively displayed potent inhibitory activities on leukemia cells K562 and prostate cancer cells PC3, respectively. Further studies indicated that TB3, TC1, TC3, TC7, and TC17 could significantly induce the apoptosis of PC3 cells. TC1 and TC17 significantly induced apoptosis of K562 cells. TC1, TC11, and TC14 induced significant apoptosis of WM9 cells. The structure-activity relationships evaluation showed that removing methyl at C-3 of the furan ring and introducing diverse side chains at C-2 of the furan ring is an effective strategy for improving the anticancer activity of L-shaped ortho-quinone analogs.

Design, synthesis and biological evaluation of tanshinone IIA-based analogues: Potent inhibitors of microtubule formation and angiogenesis

We report the structural optimization of tanshinone IIA, a natural product which possesses anti-tumor properties but low water-solubility, weak antiproliferative activity and poor PK properties. A new series of ring A/C/D modified tanshinone analogues were synthesized and studied for their antiproliferative capacities against six human cancer cell lines. SAR study revealed that ring A cleavage of tanshinone IIA led to improved anti-cancer activity. Introduction of a methoxy group to the phenyl ring could enhance the anti-cancer activity even further. Compound 2f with methoxy group at C-8 position was selected as an early lead with IC50 values of 0.28–3.16 μM against six tested cell lines. 2f could bind to tubulin colchicine site, inhibit tubulin assembly and disrupt the normal formation of microtubule networks. Cellular mechanistic studies revealed that 2f induced apoptotic cell death of A549 cells in a dose-dependent manner. In vitro investigations showed that 2f impeded the tubule-formation of HUVECs and potently inhibited the proliferation, migration and invasion of A549 cells as well as HUVECs. Furthermore, the in vivo anti-angiogenic effect of 2f was confirmed via a zebrafish model test. The satisfactory physicochemical property and metabolic stability of 2f, as well as improved water-solubility, further suggested that 2f could serve as a promising tubulin inhibitor and anti-angiogenic agent.

A Complete and Unambiguous 1H and 13C NMR Signals Assignment of para?Naphthoquinones, ortho- And para-Furanonaphthoquinones

A complete and unambiguous assignment of 1H and 13C nuclear magnetic resonance (NMR) signals of 29 naphthoquinones is reported on the basis of one- and two-dimensional NMR techniques (1H, 13C, 1H-sup

Synthesis, anti-proliferative activity evaluation and 3D-QSAR study of naphthoquinone derivatives as potential anti-colorectal cancer agents

Colorectal cancer (CRC) is a disease with high incidence and mortality, constituting the fourth most common cause of death from cancer worldwide. Naphthoquinones are attractive compounds due to their biological and structural properties. In this work, 36 naphthoquinone derivatives were synthesized and their activity evaluated against HT-29 cells. Overall, high to moderate anti-proliferative activity was observed in most members of the series, with 15 compounds classified as active (1.73 50 2 = 0.99 and q2 = 0.625). This model allowed proposing five new compounds with two-fold higher theoretical anti-proliferative activity, which would be worthwhile to synthesize and evaluate. Further investigations will be needed to determine the mechanism involved in the effect of most active compounds which are potential candidates for new anticancer agents.

Method for synthesizing coumarone naphthoquinone derivative

The invention discloses a method for synthesizing a coumarone naphthoquinone derivative. The method comprises the following steps that 2-hydroxyl-3-substituted ethylene-1,4-naphthoquinone is used as raw materials, and the angular coumarone naphthoquinone derivative is synthesized in an organic solvent under the effect of iodine; or the 2-hydroxyl-3-substituted ethylene-1,4-naphthoquinone is used as raw materials, the angular coumarone naphthoquinone derivative is firstly synthesized in an organic solvent under the effect of the iodine, and then, the angular coumarone naphthoquinone derivative is used for synthesizing the straight coumarone naphthoquinone derivative under the acid condition. The method has the advantages that the experiment steps are few; the operation is simple; the selectivity is high; the yield is high; a higher application value is realized.

The iodine-mediated highly regioselective synthesis of angular and linear naphthofuroquinones

Naphthofuroquinones are of great value in medicinal chemistry. In this letter, a facile method for highly regioselective synthesis of both linear and angular naphthofuroquinones has been developed via iodine mediated cyclization of 2-hydroxy-3-substituted

PHARMACEUTICAL COMPOSITION FOR TREATMENT AND PREVENTION OF RESTENOSIS

Provided is a pharmaceutical composition for the treatment and/or prevention of restenosis including (a) a therapeutically effective amount of a particular compound represented by Formula 1 and 2, or a pharmaceutically acceptable salt, prodrug, solvate or isomer thereof, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

PHARMACEUTICAL COMPOSITION FOR THE TREATMENT AND PREVENTION OF DISEASES INVOLVING IMPOTENCE

Disclosed is a pharmaceutical composition for the treatment and/or prevention of erectile dysfunction, comprising (a) a therapeutically effective amount of a compound represented by Formula 1 or 2, and (b) a pharmaceutically acceptable carrier, a diluent or an excipient, or any combination thereof.

Antitumor Agents. 89. Psychorubrin, a New Cytotoxic Naphthoquinone from Psychotria rubra and Its Structure-Activity Relationships

A new naphthoquinone, isolated from the alcoholic extract of Psychotria rubra, exhibited significant cytotoxicity in the KB cell assay (ED50=3.0 μg/ml).Spectral data was used to assign the structure of psychorubrin as 2.Naphthoquinone derivatives 6, 8, 13, and 14 were prepared and exhibited superior cytotoxic activity to that of psychorubrin.All were potential Michael acceptors whose conjugation had been extended.However, when a hydrophilic hydroxy group was present in such compounds, reduced in vitro activity was observed.