1025716-65-7

Basic information

• Product Name: (S)-2-(8-((4-fluorophenoxy)carbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid
• Synonyms: (S)-2-(8-((4-fluorophenoxy)carbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid
• CAS NO: 1025716-65-7
• Molecular Weight: 500.504
• Mol File: 1025716-65-7.mol

Chemical Properties

• CAS DataBase Reference: (S)-2-(8-((4-fluorophenoxy)carbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(8-((4-fluorophenoxy)carbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid(1025716-65-7)
• EPA Substance Registry System: (S)-2-(8-((4-fluorophenoxy)carbonylamino)dibenzo[b,d]furan-3-sulfonamido)-3-methylbutanoic acid(1025716-65-7)

Safety Data

• Hazardous Substances Data: 1025716-65-7(Hazardous Substances Data)

Upstream product

• 1025718-87-9 (S)-2-(8-amino-dibenzofuran-3-sulfonylamino)-3-methyl-butyric acid tert-butyl ester 
• 1025718-85-7 (S)-3-methyl-2-(8-nitro-dibenzofuran-3-sulfonylamino)-butyric acid tert-butyl ester 
• 1025718-83-5 8-nitrodibenzo[b,d]furan-3-sulfonyl chloride 
• 4106-66-5 3-aminodibenzofuran 

Relevant articles and documents

Synthesis of radioiodinated probes targeted toward matrix metalloproteinase-12

Matrix metalloproteinase-12 (MMP-12, macrophage elastase) is a member of the MMP family that is responsible for the degradation of extracellular matrix, and is associated with the inflammatory process of chronic obstructive pulmonary disease (COPD). COPD, characterized by progressive and irreversible airflow obstruction, is recently a major cause of mortality and morbidity worldwide. Herein, to develop radioiodinated probes for the early diagnosis of COPD, we designed and synthesized novel MMP-12-targeted dibenzofuran compounds (1–3) with a variety of linker structures (carbamate, amide, and sulfonamide). In competitive enzyme activity assays, it was revealed that the linker structures significantly affected the inhibitory activity against and selectivity for MMP-12. Compound 1, with carbamate linker, demonstrated potent MMP-12 inhibitory activity (IC50 = 8.5 nM) compared to compound 2, with amide linker, and compound 3, with sulfonamide linker. Using bromo-substituted carbamate 13 as a radioiodination precursor, [125I]1 was successfully prepared to high radiochemical purity (over 98%) and good specific radioactivity (4.1 GBq/μmol). These results suggest that radioiodinated compound 1 is potent as a novel MMP-12-targeted probe.

A selective matrix metalloprotease 12 inhibitor for potential treatment of chronic obstructive pulmonary disease (COPD): Discovery of (S)- 2-(8-(Methoxycarbonylamino)dibenzo[b,d]furan- 3-sulfonamido)-3-methylbutanoic acid (MMP408)

Matrix metalloprotease 12 plays a significant role in airway inflammation and remodeling. Increased expression and production of MMP-12 have been found in the lung of human COPD patients. MMP408 (14), a potent and selective MMP-12 inhibitor, was derived from a potent matrix metalloprotease 2 and 13 inhibitor via lead optimization and has good physical properties and bioavailability. The compound blocks rhMMP-12-induced lung inflammation in a mouse model and was advanced for further development for the treatment of COPD.

TRICYCLIC COMPOUNDS AS MATRIX METALLOPROTEINASE INHIBITORS

The present invention relates to compositions of the formula (I): and pharmaceutically acceptable salts, hydrates, or esters thereof, wherein R1, R2, R3, R4, R5, X, and Y are as defined herein. The present teachings also provide methods of making the compounds of formula I, and methods of treating pathologic conditions or disorders mediated wholly or in part by matrix metalloproteinases, such as asthma and chronic obstructive pulmonary disease, comprising administering a therapeutically effective amount of a compound of formula (I) to a mammal (e.g., a human) in need thereof.