20716-41-0

Basic information

• Product Name: 1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone
• CAS NO: 20716-41-0
• Molecular Formula: C₉H₉NO₅
• Molecular Weight: 211.1715
• Mol File: 20716-41-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 316.4°C at 760 mmHg
• Flash Point: 145.1°C
• Density: 1.36g/cm³
• Vapor Pressure: 0.000222mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: 1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone(20716-41-0)
• EPA Substance Registry System: 1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone(20716-41-0)

Safety Data

• Hazardous Substances Data: 20716-41-0(Hazardous Substances Data)

Usage

General Description

1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone is a chemical compound with the molecular formula C9H9NO5. It is a yellow solid with potential applications in pharmaceuticals and as a building block in organic synthesis. 1-(4-hydroxy-3-methoxy-5-nitrophenyl)ethanone contains a nitro group, a hydroxyl group, and a methoxy group attached to a phenyl ring, as well as a ketone group attached to an ethyl chain. These functional groups may give the compound various chemical and biological activities. The compound could be used in the development of novel drugs or as an intermediate in the synthesis of more complex organic molecules. However, further research is needed to determine its specific properties and potential applications.

Upstream product

• 498-02-2 1-(3-methoxy-4-hydroxyphenyl)ethanone 

Downstream Products

• 134610-32-5 1-(3,4-dimethoxy-5-nitrophenyl)ethan-1-one 

Relevant articles and documents

Structure modification and biological evaluation of indole-chalcone derivatives as anti-tumor agents through dual targeting tubulin and TrxR

Microtubule target agents (MTAs) are widely-used clinical anti-cancer drugs for decades, but the acquired drug resistance severely restricted their application. Thioredoxin reductases (TrxR) was reported to be overexpressed in most tumors and closely related to high risk of cancer recurrence and drug resistance, making it a potential target for anticancer drug discovery. Multi-target-directed ligands (MTDLs) by a single molecule provide a logical and alternative approach to drug combinations. In this work, based on the structure-activity relationships obtained in our previous study, some structure modifications were performed. On one hand, the retained skeleton structure of MTAs endowed its tubulin polymerization inhibition activity, on the other hand, the selenium-containing structure and α,β-unsaturated ketone moiety endowed the TrxR inhibition activity. As results, the newly obtained compounds exhibited superior anti-proliferative activities towards various human cancer cells and drug-resistance cells, and displayed high selectivity towards various human normal cells. The mechanism study revealed that the dual effect of cell cycle arrest triggered by targeting tubulin and the abnormal accumulation of ROS caused by TrxR inhibition eventually lead to cell apoptosis. Notably, compared with the MTA agents CA-4P, and the TrxR inhibitor Ethaselen, the optimized compound 14c, which served as dual-targeting inhibitor of tubulin and TrxR, exerted greatly improved in vivo anti-tumor activity. In summary, 14c deserved further consideration for cancer therapy.

Discovery of Novel Benzimidazole and Indazole Analogues as Tubulin Polymerization Inhibitors with Potent Anticancer Activities

Novel indazole and benzimidazole analogues were designed and synthesized as tubulin inhibitors with potent antiproliferative activities. Among them, compound 12b exhibited the strongest inhibitory effects on the growth of cancer cells with an average IC50 value of 50 nM, slightly better than colchicine. 12b exhibited nearly equal potency against both, a paclitaxel-resistant cancer cell line (A2780/T, IC50 = 9.7 nM) and the corresponding parental cell line (A2780S, IC50 = 6.2 nM), thus effectively overcoming paclitaxel resistance in vitro. The crystal structure of 12b in complex with tubulin was solved to 2.45 ? resolution by X-ray crystallography, and its direct binding was confirmed to the colchicine site. Furthermore, 12b displayed significant in vivo antitumor efficacy in a melanoma tumor model with tumor growth inhibition rates of 78.70% (15 mg/kg) and 84.32% (30 mg/kg). Collectively, this work shows that 12b is a promising lead compound deserving further investigation as a potential anticancer agent.

Derivative of Kutkin dimer analog JJA-D0 or its pharmaceutically acceptable salt, preparation method and use thereof

The invention relates to a derivative of Kutkin dimer analog JJA-D0 or its pharmaceutically acceptable salt, a preparation method and use thereof. The compound has a structure shown as a general formula (I). According to the invention, an alkyl group, an aryl group, a heteroaryl group, an alkoxycarbonylalkyl group, an acyl group, a sulfonate group, an antioxidant group such as a lipoic acid group,a H2S donor group such as a cysteine group, and a NO donor group such as a nitrate group are introduced to JJA-D0, and a series of structurally novel compounds can be synthesized and disclosed. The compounds inhibit NADPH oxidase and have superior anti-oxidation and anti-inflammatory pharmacological mechanisms by comparing with Kutkin, the compounds also have donor groups that provide NO and H2S,can further enhance pharmacological activity, and can be a new class of multifunctional compounds. The disclosed JJA-D0 derivative can be used for preparing health products or drugs for prevention ortreatment of diseases associated with NADPH oxidase, diseases associated with free radicals, diseases associated with inflammation, diseases associated with NO, and diseases associated with H2S.