13252-84-1

Usage

Uses

Used in Pharmaceutical Industry:
4-HYDROXY-6-METHOXYCOUMARIN is used as an intermediate in the synthesis of pharmaceuticals for its potential therapeutic properties, such as antioxidant, anti-inflammatory, and anticancer activities.
Used in Cosmetics and Perfumery Industry:
4-HYDROXY-6-METHOXYCOUMARIN is used as a component in cosmetics and perfumes due to its natural occurrence and diverse applications.
Used in Research and Analysis:
4-HYDROXY-6-METHOXYCOUMARIN is used as a fluorescent dye in biological and chemical analyses, aiding in the visualization and detection of various compounds and biological molecules.
Used in Antimicrobial Applications:
4-HYDROXY-6-METHOXYCOUMARIN is used in the development of antimicrobial agents due to its potential to inhibit the growth of bacteria and fungi, making it a valuable component in creating effective treatments against microbial infections.

InChI:InChI=1/C10H8O4/c1-13-6-2-3-9-7(4-6)8(11)5-10(12)14-9/h2-5,11H,1H3

Upstream product

• 1663-67-8 malonoyl dichloride 
• 150-78-7 1,4-dimethoxybezene 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 105-58-8 Diethyl carbonate 
• 1200-06-2 4-methoxyphenyl acetate 
• 150-76-5 4-methoxy-phenol 
• 58303-20-1 malonic acid mono-(4-methoxy-phenyl) ester 
• 85630-18-8 N,N-diethyl-O-(4-methoxyphenyl)carbamate 
• 255843-61-9 6-methoxy-2-trichloromethyl-chromen-4-one 
• 211449-29-5 Diethyl-carbamic acid 2-acetyl-4-methoxy-phenyl ester 
• 288087-82-1 (Z)-3-Amino-4,4,4-trichloro-1-(2-hydroxy-5-methoxy-phenyl)-but-2-en-1-one 

Downstream Products

• 53666-78-7 4,6-Dimethoxy-cumarin 
• 1337926-60-9 9-methoxy-2,4-diphenylpyrano[3,2-c]chromen-5(4H)-one 
• 1449795-45-2 C₂₄H₁₇NO₃ 
• 40547-03-3 6-Methoxy-4-phenyl-2H-1-benzopyran-2-one 
• 1292297-05-2 4-(3-hydroxy-4-methoxyphenyl)-6-methoxy-2H-chromen-2-one 

Relevant academic research and scientific papers

Discovery and characterization of aminopiperidinecoumarin melanin concentrating hormone receptor 1 antagonists

4-(1-Benzo[1,3]dioxol-5-ylmethylpiperidine-4-ylmethyl)-6-chlorochromen-2- one (7) is a potent, orally bioavailable melanin concentrating hormone receptor 1 (MCHr1) antagonist that causes dose-dependent weight loss in diet-induced obese mice. Further evalu

TRICYCLIC COMPOUNDS ACTING ON CRBN PROTEINS

The present invention discloses a series of tricyclic compounds and use thereof in preparing a medicament for treating a disease related to CRBN protein. Specifically, the present invention discloses a derivative compound of formula (1) or a pharmaceutically acceptable salt thereof.

Copper(II)-Catalyzed Tandem Reaction: Synthesis of Furo[3,2- c]coumarin Derivatives and Evaluation for Photophysical Properties

An efficient protocol for synthesizing furo[3,2-c]coumarin derivatives is described. The novel reaction could afford the desired furocoumarins with good to excellent yields in a mild and rapid manner. Large substrate scope screening and scale-up preparation have also been accomplished, and selected compounds were evaluated for their photophysical properties.

Electrochemical Sulfenylation of 4-Hydroxycoumarins with Aryl Thiols Catalyzed by Potassium Iodide

A KI-catalyzed indirect electrochemical oxidative method for the synthesis of sulfenylated 4-hydroxycoumarins via cross-coupling of 4-hydroxycoumarins and aryl thiols at a low potential has been reported. The electrocatalytic activity of KI for sulfenylat

Synthesis and biological evaluation of bis-N2,N2′-(4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccinodihydrazides

A series of N2,N2′-bis[4-hydroxycoumarin-3-yl)ethylidene]-2,3-dihydroxysuccino-hydrazides, containing 4-hydroxycoumarin, hydrazine and tartaric acid moieties, have been prepared and examined for possible biological activity. Several of these compounds exhibit promising HIV-1 integrase inhibition (IC50 = 3.5 μM), and anti-T. brucei (32% viability) and anti-mycobacterial (Visual MIC90 = 15.63 μM) activity.

Novel conjugates of podophyllotoxin and coumarin: Synthesis, cytotoxicities, cell cycle arrest, binding CT DNA and inhibition of Topo IIβ

A series of conjugates of podophyllotoxin and coumarin were prepared using the click reaction, and their cytotoxicities against A549, HepG2, HeLa, and LoVo cells were evaluated. Among them, compound 14e exhibited the strongest cytotoxicities against these cancer cells with IC50 values of 4.9–17.5 μM. Furthermore, 14e disrupted microtubules and induced cell cycle arrest at G1 phase by regulating P21 and Cyclin D1 in LoVo cells. In addition, 14e bond CT DNA and selectively inhibited Topo IIβ over Topo IIα. Molecular docking model showed that 14e appeared to form stable hydrogen bonds with several DNA bases and residue Gln778. Taken together, these conjugates have the potential to be developed as anti-tumor drugs.

Discovery of a C-8 hydroxychromene as a potent degrader of estrogen receptor alpha with improved rat oral exposure over GDC-0927

Phenolic groups are responsible for the high clearance and low oral bioavailability of the estrogen receptor alpha (ERα) clinical candidate GDC-0927. An exhaustive search for a backup molecule with improved pharmacokinetic (PK) properties identified several metabolically stable analogs, although in general at the expense of the desired potency and degradation efficiency. C-8 hydroxychromene 30 is the first example of a phenol-containing chromene that not only maintained excellent potency but also exhibited 10-fold higher oral exposure in rats. The improved in vivo clearance in rat was hypothesized to be the result of C-8 hydroxy group being sterically protected from glucuronide conjugation. The excellent potency underscores the possibility of replacing the presumed indispensable phenolic group at C-6 or C-7 of the chromene core. Co-crystal structures were obtained to highlight the change in key interactions and rationalize the retained potency.

Stereoselective synthesis of carbohydrate fused pyrano[3,2-c]pyranones as anticancer agents

Pyrano[3,2-c]pyranone is an important structural motif present in many natural products exhibiting diverse biological activities. Two series of carbohydrate fused pyrano[3,2-c]pyranone derivatives (n = 20) were efficiently synthesized starting from 2-C-formyl galactal and 2-C-formyl glucal, reacting with various 4-hydroxycoumarins in a very short reaction time (10 min) under microwave assisted conditions. The anticancer activity of these synthesized pyrano[3,2-c]pyranones was determined in detail through cellular assays against MCF-7 (breast), MDA-MB-231 (breast) and HepG2 (liver) cancer cell lines. The newly synthesized pyrano[3,2-c]pyranones were screened for their cell-viability and anti-proliferative activity against MCF-7, MDA-MB-231 and HepG2 cell lines. Compounds 12, 13 and 14 exhibited high growth inhibitory potencies selectively against MCF-7 cells with half-maximal inhibitory concentration (IC50) values of 19.9, 14.5 and 10.9 μM respectively. Compounds 12, 13, 14, 15 and 19 inhibited the growth of MDA-MB-231 cells (breast) by 43, 44, 37, 31 and 45% respectively. However, no inhibitory effect was observed for these compounds in the human liver cancer cell line (HepG2) and normal cell lines (HEK293, human embryonic kidney cells). Mechanistic studies showed that these compounds alter the cell morphology and cause G2/M arrest in MCF-7. Further studies showed that compounds 12, 13 and 14 significantly inhibited cell migration which was accompanied by altered microtubule distribution. An enhanced accumulation of these compounds in cells was observed as compared to the 4-hydroxycoumarins precursor in the intracellular uptake assay. These findings confirm that carbohydrate fused pyrano[3,2-c]pyranones are better candidates for anticancer activity.

Synthesis of furo[3,2-c]coumarins via I2/TBHP-mediated reaction of 4-hydroxycoumarins with terminal alkynes

An efficient I2/TBHP-mediated process for the formation of furo[3,2-c]coumarins from readily available materials has been developed. This process for the formation of furo[3,2-c]coumarins is quite environmental friendly and atom-economical.

One-pot two-step synthesis of 3-iodo-4-aryloxy coumarins and their Pd/C-catalyzed annulation to coumestans

An efficient protocol for the synthesis of various coumestans from the intramolecular annulation of 3-iodo-4-aryloxy coumarins through C-H activation has been developed. When 3-iodo-4-aryloxy coumarins were treated with 10% Pd/C (0.3 mol% Pd) in the presence of sodium acetate, the corresponding coumestans were produced in good to excellent yield. Reusability of the palladium catalyst was investigated in up to three consecutive cycles and it was found that the yield of the reaction was almost unaltered. Sequential iodination and O-arylation of 4-hydroxy coumarins leading to the 3-iodo-4-aryloxy coumarins were also achieved in a one-pot two-step process starting from aryl iodides in high yield. Pivalic acid was revealed to be the most effective additive for the later method to produce 3-iodo-4-phenoxy coumarins. Different functional groups bearing electron-donating as well as withdrawing groups are also tolerant to the reaction conditions.