110865-03-7

Basic information

• Product Name: Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)- (9CI)
• Synonyms: Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)- (9CI);Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)-;2-Chloro-1-(2,4,6-trihydroxyphenyl)-ethanone
• CAS NO: 110865-03-7
• Molecular Formula: C₈H₇ClO₄
• Molecular Weight: 202.59178
• Product Categories: ACETYLHALIDE
• Mol File: 110865-03-7.mol
• Article Data: 23

Chemical Properties

• Appearance: /
• Solubility: Dichloromethane (Partially); Methanol
• CAS DataBase Reference: Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)- (9CI)(110865-03-7)
• EPA Substance Registry System: Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)- (9CI)(110865-03-7)

Safety Data

• Hazardous Substances Data: 110865-03-7(Hazardous Substances Data)

Usage

Description

Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)(9CI) is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique molecular structure, which includes a chloro group and three hydroxyl groups attached to a phenyl ring, all connected to an ethanone backbone.

Uses

Used in Pharmaceutical Synthesis:
Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)(9CI) is used as an intermediate in the synthesis of Diosmetin 3’,7-Diglucuronide-d3 (D485042), a labelled Diosmetin 3’,7-Diglucuronide (D485040). Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)(9CI) is a metabolite of Diosmetin (D485000), a flavonoid that has significant therapeutic applications.
Used in the Treatment of Chronic Venous Insufficiency:
In the medical industry, Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)(9CI) contributes to the development of treatments for chronic venous insufficiency, a condition characterized by the inadequate functioning of the veins, leading to various symptoms such as leg pain, swelling, and skin changes.
Used in the Treatment of Hemorrhoids:
Ethanone, 2-chloro-1-(2,4,6-trihydroxyphenyl)(9CI) also plays a role in the synthesis of compounds used for the treatment of hemorrhoids, which are swollen veins in the rectal area that can cause discomfort and bleeding.
Used in the Treatment of Related Affective Disorders:
Furthermore, this compound is utilized in the development of treatments for other related affections, which may include conditions that are affected by or associated with chronic venous insufficiency and hemorrhoids, enhancing the overall well-being of patients suffering from these conditions.

Synthesis Reference(s)

Journal of the American Chemical Society, 64, p. 382, 1942 DOI: 10.1021/ja01254a044

Upstream product

• 108-73-6 3,5-dihydroxyphenol 
• 107-14-2 chloroacetonitrile 
• 79-04-9 chloroacetyl chloride 

Downstream Products

• 354128-70-4 5,7-diisopropoxy-2-(4-isopropoxyphenyl)-4H-benzopyran-4-one 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 152969-67-0 2-(4-fluorophenyl)-5’,7’-dihydroxy-chromen-4-one 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 4225-35-8 4,6-dimethoxycoumaranone 
• 89971-01-7 2-(2,3-dimethoxyphenyl)-5,7-dihydroxy-4H-chromen-4-one 

Relevant articles and documents

An efficient synthesis of 4,6 dimethoxyaurones

4,6-Dimethoxybenzofuran-3(2H)-one was synthesized in two steps starting from phloroglucinol and used as a useful starting block for the synthesis of aurones by condensation with benzaldehyde derivatives.

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Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer

Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.

Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens

A set of variously substituted aurones was synthesized and evaluated against Methicillin-Resistant S. aureus (MRSA) and P. aeruginosa. Several analogues were found active against MRSA, but no effect was recorded against P. aeruginosa. Compounds 27, 30 and 33 showed low cytotoxicity, and were tested against a full range of bacterial (Gram-positive and Gram-negative) and fungal species, including resistant strains. These aurones displayed a selective inhibition of Gram-positive bacteria with excellent Therapeutic Index values, while showing no significant action on several Gram-negative strains, H. pylori and V. alginolyticus being the only susceptible strains among the Gram-negative bacteria tested. A permeabilization assay showed that the antibacterial activity of at least some of the aurones could be linked to alterations of the bacterial membrane. Overall, this study endorses the use of the aurone scaffold for the development of new potent and selective antibacterial agents.

Structure-activity relationship of the inhibitory effects of flavonoids on nitric oxide production in RAW264.7 cells

We isolated flavonoids from herbal specimens from the Tibetan region (Sophora yunnanensis and Rhodiola sacra) that suppress nitric oxide (NO) production in macrophages stimulated by lipopolysaccharide and interferon-γ. The isolated flavonoids carry symmetric substitutions in the B ring (R3′= R5′). We analyzed the quantitative structure-activity relationship of the inhibitory activity by comparative molecular field analysis (CoMFA) using this series of flavonoids. Use of flavonoids with symmetrical substitutions in the B ring made it simpler to align molecules because it was not necessary to consider a huge number of combinations due to the B-ring conformation. The CoMFA model, whose cross-validated q2value was 0.705, suggested the existence of a hydroxy group at the 5-position, the choice of the A/C-ring scaffold (chromane or chromene) and electrostatic field around the B ring are important for NO inhibitory activity. Flavonoids synthesized based on the CoMFA model exhibited significant inhibitory potential against NO production, validating the predictive capability of the CoMFA model.