433703-81-2

Basic information

• Product Name: Methyl (7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate
• Synonyms: Methyl (7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate;methyl 2-(7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate
• CAS NO: 433703-81-2
• Molecular Formula: C₁₄H₁₄O₅
• Molecular Weight: 262.25796
• Mol File: 433703-81-2.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl (7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate(433703-81-2)
• EPA Substance Registry System: Methyl (7-hydroxy-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate(433703-81-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 433703-81-2(Hazardous Substances Data)

Upstream product

• 10420-33-4 dimethyl 2-acetylsuccinate 
• 608-25-3 2-methylbenzene-1,3-diol 

Downstream Products

• 664365-92-8 methyl 2-[4,8-dimethyl-7-(2-oxo-2-phenylethoxy)-2-oxo-2H-3-chromenyl]acetate 
• 664365-98-4 methyl 2-[7-[2-(4-bromophenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 664365-94-0 methyl 2-[7-[2-(4-fluorophenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 664365-96-2 methyl 2-[7-[2-(4-chlorophenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 664366-00-1 methyl 2-[7-[2-(4-methoxyphenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 694516-04-6 methyl 2-(4,8-dimethyl-7-methoxy-2-oxo-2H-benzopyran-3-yl)acetate 
• 1339937-05-1 DL-2-[2'-(3''-tert-butyl-5'',9''-dimethyl-7''-oxo-7H-furo[3,2-g][1]benzopyran-6''-yl)-acetylamino]-3-phenylpropionic acid 
• 840515-76-6 methyl 2-(7-((3-chlorobenzyl)oxy)-4,8-dimethyl-2-oxo-2H-chromen-3-yl)acetate 
• 664366-02-3 methyl 2-[4,8-dimethyl-2-oxo-7-(2-oxocyclohexyloxy)-2H-3-chromenyl]acetate 
• 500204-29-5 methyl 2-[7-[2-(3-methoxyphenyl)-2-oxoethoxy]-4,8-dimethyl-2-oxo-2H-3-chromenyl]acetate 
• 664365-90-6 methyl 2-[4,8-dimethyl-7-(1-methyl-2-oxo-2-phenylethoxy)-2-oxo-2H-3-chromenyl]acetate 
• 664366-12-5 2-(5,9-dimethyl-3-phenyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic acid 
• 664366-06-7 2-(3-tert-butyl-5,9-dimethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic acid 
• 664366-08-9 2-(2,3,5,9-tetramethyl-7-oxo-7H-furo[3,2-g]chromen-6-yl)acetic acid 

Relevant articles and documents

4,8-Dimethylcoumarin Inhibitors of Intestinal Anion Exchanger slc26a3 (Downregulated in Adenoma) for Anti-Absorptive Therapy of Constipation

The chloride/bicarbonate exchanger SLC26A3 (downregulated in adenoma) is expressed mainly in colonic epithelium, where it dehydrates the stool by facilitating the final step of chloride and fluid absorption. SLC26A3 inhibition has predicted efficacy in various types of constipation including that associated with cystic fibrosis. We previously identified, by high-throughput screening, 4,8-dimethylcoumarin inhibitors of murine slc26a3 with IC50 down to a150 nM. Here, we synthesized a focused library of forty-three 4,8-dimethylcoumarin analogues. Structure-activity studies revealed the requirement of 4,8-dimethylcoumarin-3-acetic acid for activity. The most potent inhibitors were produced by replacements at C7, including 3-iodo- (4az) and 3-trifluoromethyl- (4be), with IC50 of 40 and 25 nM, respectively. Pharmacokinetics in mice showed predicted therapeutic concentrations of 4az for >72 h following a single 10 mg/kg oral dose. 4az at 10 mg/kg fully normalized stool water content in a loperamide-induced mouse model of constipation. The favorable inhibition potency, selectivity within the SLC26 family, and pharmacological properties of 4az support its further preclinical development.

Modified coumarins. 10. Synthesis of substituted 2-(7-oxofuro[3,2-g] chromen-6-yl) acetic acids

Substituted 2-(7-oxofuro[3,2-g]chromen-6-yl) acetic acids, modified psoralen analogs, were synthesized by linear fusion of a furan ring to the coumarin system.