664366-11-4

Basic information

• Product Name: (5-Methyl-7-oxo-3-phenyl-7H-furo[3,2-g]chromen-6-yl)-acetic acid
• Synonyms: (5-Methyl-7-oxo-3-phenyl-7H-furo[3,2-g]chromen-6-yl)-acetic acid
• CAS NO: 664366-11-4
• Molecular Formula: C20H14O5
• Molecular Weight: 334.32216
• Mol File: 664366-11-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (5-Methyl-7-oxo-3-phenyl-7H-furo[3,2-g]chromen-6-yl)-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (5-Methyl-7-oxo-3-phenyl-7H-furo[3,2-g]chromen-6-yl)-acetic acid(664366-11-4)
• EPA Substance Registry System: (5-Methyl-7-oxo-3-phenyl-7H-furo[3,2-g]chromen-6-yl)-acetic acid(664366-11-4)

Safety Data

• Hazardous Substances Data: 664366-11-4(Hazardous Substances Data)

Upstream product

• 70-11-1 α-bromoacetophenone 
• 1115-30-6 diethyl acetylsuccinate 
• 108-46-3 recorcinol 
• 5852-03-9 ethyl 2-(7-hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)acetate 
• 10420-33-4 dimethyl 2-acetylsuccinate 
• 95903-37-0 7-hydroxy-3-methoxycarbonylmethyl-4-methyl-2H-chromen-2-one 
• 664365-91-7 methyl 2-[4-methyl-7-(2-oxo-2-phenylethoxy)-2-oxo-2H-3-chromenyl]acetate 

Relevant articles and documents

Design, Synthesis, and Biological Evaluation of Novel Psoralen-Based 1,3,4-Oxadiazoles as Potent Fungicide Candidates Targeting Pyruvate Kinase

Pyruvate kinase (PK) has been considered as a promising fungicide target discovered in our previous studies. Natural compounds are important sources for discovery and development of new pesticides. To continue our ongoing studies on the discovery of novel PK-targeted fungicides, a series of novel psoralen derivatives including a 1,3,4-oxadiazole moiety were designed by a computer-aided pesticide molecular design method, synthesized, and evaluated for their fungicidal activity. The bioassay results indicated that compounds 11d, 11e, 11g, 11i, and 12a showed excellent in vitro fungicidal activity against Botrytis cinerea with EC50values of 4.8, 3.3, 6.3, 5.4, and 3.9 μg/mL, respectively. They were more active than the corresponding positive control YZK-C22 [3-(4-methyl-1,2,3-thiadiazol-5-yl)-6-(trichloromethyl)-[1,2,4]-triazolo-[3,4-b][1,3,4]-thiadiazole] (with an EC50value of 13.4 μg/mL). Compounds 11g and 11i displayed promising in vivo fungicidal activity against B. cinerea with 80 and 70% inhibition at a concentration of 200 μg/mL, respectively. They possessed much higher fungicidal activity than the positive control psoralen and comparable activity with the positive control pyrisoxazole. Enzymatic assays indicated that 11i showed good BcPK inhibition with an IC50value of 39.6 μmol/L, comparable to the positive control YZK-C22 (32.4 μmol/L). Molecular docking provided a possible binding mode of 11i in the BcPK active site. Our studies suggested that the psoralen-based 1,3,4-oxadiazole 11i could be used as a new fungicidal lead targeting PK for further structural optimization.

Targeting Tumor Associated Carbonic Anhydrases IX and XII: Highly Isozyme Selective Coumarin and Psoralen Inhibitors

A small library of psoralen carboxylic acids and their corresponding benzenesulfonamide derivatives were designed and synthesized to evaluate their activity and selectivity toward tumor associated human carbonic anhydrase (hCA) isoforms IX and XII. Both p

Nonpeptidic Selective Inhibitors of the Chymotrypsin-Like (β5 i) Subunit of the Immunoproteasome

Elevated expression of the immunoproteasome has been associated with autoimmune diseases, inflammatory diseases, and various types of cancer. Selective inhibitors of the immunoproteasome are not only scarce, but also almost entirely restricted to peptide-based compounds. Herein, we describe nonpeptidic reversible inhibitors that selectively block the chymotrypsin-like (β5i) subunit of the human immunoproteasome in the low micromolar range. The most potent of the reversibly acting compounds were then converted into covalent, irreversible, nonpeptidic inhibitors that retained selectivity for the β5i subunit. In addition, these inhibitors discriminate between the immunoproteasome and the constitutive proteasome in cell-based assays. Along with their lack of cytotoxicity, these data point to these nonpeptidic compounds being suitable for further investigation as β5i-selective probes for possible application in noncancer diseases related to the immunoproteasome.

PSORALEN DERIVATIVES AS NON-PEPTIDIC INHIBITORS OF CHYMOTRYPSIN-LIKE ACTIVITY OF THE IMMUNOPROTEASOME

This invention relates to new inhibitors of chymothrypsin-like activity of the immunoproteasome (inhibitors of β5? or LMP7 subunit) with the general formula (I), where substituents are described in patent description. Compounds can be in the form of pure enantiomers or as racemic mixtures, or in the form of pharmaceutically acceptable salts. The present invention relates to the use of these inhibitors for the treatment of diseases where immunoproteasome activity is increased.

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.