123297-89-2

Upstream product

• 3126-04-3 1-(tributylstannyl)-3-(tributylstanyloxy)-1-butyne 
• 85-44-9 phthalic anhydride 
• 57901-54-9 2-(2-furoyl)benzoic acid 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 
• 130-15-4 [1,4]naphthoquinone 
• 1203-39-0 3-bromolawsone 
• 18633-71-1 2-ethyl-4H,9H-naphtho[2,3-b]furan-4,9-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 29366-43-6 2-hydroxy-3-(1-n-butenyl)-1,4-naphthoquinone 
• 117560-06-2 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide 
• 2028-63-9 but-3-yn-2-ol 
• 2348-79-0 2-dimethylamino-1,4-naphthoquinone 
• 2065-37-4 2-bromo-1,4-naphthoquinone 
• 91394-68-2 2-bromo-3-(dimethylamino)naphthalene-1,4-dione 

Downstream Products

• 83280-65-3 2-acetylnaphtho[2,3-b]furan-4,9-quinone 

Relevant academic research and scientific papers

Synthesis and cytotoxicity on human leukemia cells of furonaphthoquinones isolated from Tabebuia plants

Furonaphthoquinones are promising skeletons for anticancer drug molecules. In particular, methoxylated furonaphthoquinones are characteristic constituents of Tabebuia plants. In this research, we synthesized the furonaphthoquinones by effective one-pot ca

Design, synthesis and activity of BBI608 derivatives targeting on stem cells

STAT3 plays a vital role in maintaining the self-renewal of tumor stem cells. BBI608, a small molecule identified by its ability to inhibit gene transcription driven by STAT3 and cancer stemness properties, can inhibit stemness gene expression and kill stemness-high cancer cells isolated from a variety of cancer types. In order to improve the pharmacokinetic properties of BBI608 and the antitumor activity, a series of BBI608 derivatives were designed and synthesized here. Most of these compounds were more potent than BBI608 on HepG2 cells, compound LD-8 had the most potent inhibitory activity among them and was 5.4-fold more potent than BBI608 (IC50 = 11.2 μM), but had considerable activity on normal liver cells L-02. Compounds LD-17 (IC50 = 3.5 μM) and LD-19 (IC50 = 2.9 μM) were found to possess significant inhibitory activities and good selectivity. The results showed that compound LD-19 was worthy to investigate further as a lead compound according to its potent inhibitory activity, ideal ClogP value and better water solubility.

Efficient synthesis of cytotoxic furonaphthoquinone natural products

An efficient synthesis of furonaphthoquinone natural products 1 and 4 has been carried out starting from 2-hydroxy-1, 4-naphthoquinone (10) and 2,3-dimethoxy-1,3-butadiene (11) in the presence of CAN.

Discovery of napabucasin derivatives for the treatment of tuberculosis

Tuberculosis is the contagious disease responsible for the highest number of deaths worldwide. Here, we screened a commercially available compound library and found napabucasin to possess a moderate anti-tubercular activity against M. tuberculosis H37Ra (MIC 2.5 μg mL-1, 10.4 μM). Three series of napabucasin derivatives were further evaluated for their in vitro anti-tubercular activities against Mtb H37Ra. The activity of most derivatives was either retained or enhanced compared with that of napabucasin. Compound 3s was the most active compound showing a MIC value of 0.3125 μg mL-1 (0.9 μM). Furthermore, several compounds were selected and evaluated against the Mtb H37Rv standard strain and six Mtb clinical isolates. Importantly, these compounds were found to be effective against Mtb clinical isolates with multi-resistance to isoniazid, rifampicin, and ethambutol.

13C NMR of Lapachol and Some Related Naphthoquinones

13C NMR chemical shift assignments for lapachol and nine related naphthoquinones have been measured and interpreted.Data, based on the results of a number of 1D and 2D experiments performed at 9.4 T, correct several previously reported assignments for some of these compounds. KEY WORDS 13C NMR Lapachol Naphthoquinones

One-pot synthesis of naphtho[2,3-b]furan-4,9-diones by sequential coupling/ring closure reactions

Treatment of 3-phenyliodonio-1,2,3,4-tetrahydronaphthalenides with terminal acetylenes in the presence of a bis(triphynylphosphine)palladium chloride-cuprous iodide catalyst or cuprous oxide in N-methylpiperidine or pyridine, respectively, furnished the corresponding 2-substituted naphtho[2,3-b]furan-4,9-diones in moderate to good yields. The utility of this method was demonstrated in the synthesis of a cytotoxic natural product, 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione.

Domino Michael-O-alkylation reaction: One-pot synthesis of 2,4-diacylhydrofuran derivatives and its application to antitumor naphthofuran synthesis

The one-pot synthesis of 2,4-diacylhydrofuran derivatives and its applications to antitumor napthofuran synthesis was discussed. It was found that the reaction of 1,3-dicarbonyl compounds with α-halo-α,β-unsaturated carbonyl compounds afforded 2,4-diacyldihydrofuran derivatives in the presence of DBU in THF. The analysis showed that the applications of the protocol enabled short-step synthesis of antitumor napthofuran natural products.

Ceric ammonium nitrate (CAN)-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds. Efficient synthesis of dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, dihydrofurophenalenones, and furonaphthoquinone natural products

Ceric ammonium nitrate-mediated oxidative cycloaddition of 1,3-dicarbonyls to conjugated compounds afforded substituted dihydrofurans, dihydrofurocoumarins, dihydrofuroquinolinones, and dihydrofurophenalenones in moderate yields. This new synthetic method has been applied to the synthesis of furonaphthoquinone natural products. (C) 2000 Elsevier Science Ltd.

Conjugates Derived from Lapatinib Derivatives with Cancer Cell Stemness Inhibitors Effectively Reversed Drug Resistance in Triple-Negative Breast Cancer

Increasing evidence indicates that the cancer stem cell (CSC) subpopulation contributes to the therapeutic resistance and metastasis of tumors, leading to patient recurrence and death. Herein, we designed and synthesized several compounds by conjugating lapatinib derivatives with different CSC inhibitors to treat with lapatinib-induced MDA-MB-231 drug-resistant cells. In vitro biological studies indicated that 3a showed strong cytotoxicity and EGFR enzyme inhibitory activity and effectively reversed lapatinib-mediated resistance of MDA-MB-231 cells via inhibiting triple-negative breast cancer (TNBC) cell stemness and the AKT/ERK signaling pathway. In addition, 3a was capable of strongly suppressing the invasion and migration of TNBC cells by inhibiting the Wnt/β-catenin signaling pathway and MMP-2 and MMP-9 protein expression. In vivo tumorigenicity tests showed that 3a could inhibit the occurrence of TNBC by inhibiting BCSCs, proving 3a is a potential EGFR and CSC dual inhibitor for TNBC treatment.

METHOD FOR PRODUCING 2-ALKYLCARBONYLNAPHTHO[2,3-b]FURAN-4,9-DIONE-RELATED SUBSTANCE, AND SAID RELATED SUBSTANCE

Provided is a method for producing a 2-alkylcarbonylnaphtho[2,3-b]furan-4,9-dione-related substance, which is suitable for the production on an industrial scale. The present invention provides: a method for producing an intermediate for the production of