83280-65-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Acetylfuro-1,4-naphthoquinone is used as a cancer cell stemness inhibitor for attenuating the progression of prostate cancer. It reduces the growth of cancer cells enriched for high stemness and decreases the expression of various self-renewal and pro-survival markers in a concentration-dependent manner. In vivo studies have shown that it inhibits tumor growth in mouse xenograft models and prevents tumor regrowth after treatment cessation. Additionally, it has been found to block the formation of spleen and liver metastases, making it a promising candidate for cancer therapy.
Used in Chemical Synthesis:
2-Acetylfuro-1,4-naphthoquinone can be used as a key intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other organic compounds. Its unique structure and reactivity make it a valuable building block for the development of new molecules with potential applications in various fields.
Used in Research and Development:
Due to its unique chemical properties, 2-Acetylfuro-1,4-naphthoquinone can be employed as a research tool in various scientific studies. It can be used to investigate the structure-activity relationships of naphthoquinone-based compounds, explore their potential applications in drug discovery, and study their interactions with biological systems.

References

1) Li et al. (2015), Suppression of cancer relapse and metastasis by inhibiting cancer stemness; Proc. Natl. Acad. Sci. USA, 112 1839 2) Hubbard and Grothey (2017), Napabucasin: an Update on the First-in-Class Cancer Stemness Inhibitor; Drugs, 77 1091 3) Zhang et al. (2016), Suppression of prostate cancer progression by cancer cell stemness inhibitor napabucasin; Cancer Med., 5 1251 4) MacDonagh et al. (2018), BBI608 inhibits cancer stemness and reverses cisplatin resistance in NSCLC; Cancer Lett., 428 117

Upstream product

• 13019-43-7 2-isopropylnaphtho[2,3-b]furan-4,9-dione 
• 83-72-7 2-hydroxynaphtho-1,4-quinone 
• 25109-57-3 3,4-dibromobutan-2-one 
• 147568-55-6 2-acetyl-2,3,4,9-tetrahydronaphtho[2,3-b]furan-4,9-dione 
• 85-44-9 phthalic anhydride 
• 117560-06-2 3-phenyliodonio-1,2,4-trioxo-1,2,3,4-tetrahydronaphthalenide 
• 75-16-1 methylmagnesium bromide 
• 108-24-7 acetic anhydride 
• 92487-46-2 2-(2-furylmethyl)benzoic acid 
• 18633-71-1 2-ethyl-4H,9H-naphtho[2,3-b]furan-4,9-dione 
• 1203-39-0 3-bromolawsone 
• 15441-75-5 2-ethynyl-2-methyl-1,3-dioxolane 
• 130-15-4 [1,4]naphthoquinone 
• 1785-67-7 1,2,4-triacetyloxynaphthalene 

Downstream Products

• 83889-95-6 2-(1-hydroxy-ethyl)-naphtho[2,3-b]furan-4,9-dione 

Relevant academic research and scientific papers

FURANONAPHTHOQUINONES FROM TABEBUIA OCHRACEA

From the trunkwood of Tabebuia ochracea, β-sitosterol, cycloolivil, lapachol, and seven furanonaphthoquinones including the known 2-(1-hydroxyethyl)naphthofuran-4,9-quinone were isolated.The six new furanonaphthoquinones comprise three similar C2 alcohol-ketone pairs at C-2 as proved by oxidations with pyridinium chlorochromate. 2-Acetyl-6-methoxynaphthofuran-4,9-quinone was shown to be different from the synthetic 7-methoxy isomer, while 2-acetyl-8-methoxynaphthofuran-4,9-quinone and 2-acetyl-7,8-dimethoxynaphthofuran-4,9-quinone were identical to the synthetic compounds.

Structure-activity relationship studies of antimicrobial naphthoquinones derived from constituents of tabebuia avellanedae

In this study, based on our previous study, derivatives of naphtho[2,3-b]furan-4,9-diones were synthesized and their antimicrobial activities were evaluated. The screening of these naphthoquinones revealed that the fluorine-containing NQ008 compound exhib

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.

Synthetic method of napabucasin

The invention discloses a synthetic method of napabucasin, and belongs to the technical field of compound preparation, wherein the synthetic method comprises the following steps: (1) in the presence of an organic solvent and a catalyst, carrying out a reaction on a compound 1 with oxalyl chloride to generate a compound 2; (2) in the presence of an organic solvent and an alkali, carrying out a reaction on the compound 2 with N,O-dimethylhydroxylamine hydrochloride to generate a compound 3; and (3) carrying out a reaction on the compound 3 with a Grignard reagent to generate napabucasin. According to the method, the compound 1 is used as the raw material, Weber amide is synthesized firstly, then the Weber amide reacts with the Grignard reagent to prepare napabucasin, the route is short, theyield is high, the cost is low, the operation is simple, and the method is suitable for industrial production.

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

NAPHTHOFURAN DERIVATIVES, PREPARATION, AND METHODS OF USE THEREOF

Provided herein are methods of preparation of I by reacting i with acid where R1 and R2 are each independently a leaving group. Intermediates to make i are also claimed.

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.

BBI608 derivative as well as preparation and application thereof

The invention belongs to the technical field of medicines, and relates to a BBI608 derivative and application of the BBI608 derivative in an anti-tumor medicine. The structures of the derivative and apharmacologically acceptable salt are as follows: as shown in the specification, wherein X, R1, R2 and R3 are as described in claims and the specification. The derivative and the pharmacologically acceptable salt can be used for preparing the anti-tumor medicine, particularly a medicine for treating the stomach cancer (including gastric esophageal cancer) and the pancreatic cancer. An HepG2 cellactivity research finds that the cell inhibition activities of most compounds are obviously higher than that of the anti-tumor medicine BBI608.(Refer to Specification).

METHOD FOR PRODUCING 2-ACETYL-4H,9H-NAPHTHO[2,3-B]FURAN-4,9-DIONE

The invention addresses the problem of providing a method for producing 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione that is suited to industrial production. The invention provides a method for producing 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione by reacting 3-bromo-3-buten-2-one and 2-hydroxy-1,4-naphthoquinone in the presence of a solvent, then obtaining crystals of 2-acetyl-4H,9H-naphtho[2,3-b]furan-4,9-dione by adding an alcohol-based solvent and/or water to the reaction system, and treating the crystals by using a specific adsorbent in the presence of a solvent.

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.