182570-28-1

Basic information

• Product Name: 2H-1-Benzopyran-3-carboxylic acid, 3,4-dihydro-6-Methoxy-, (3S)-
• Synonyms: 2H-1-Benzopyran-3-carboxylic acid, 3,4-dihydro-6-Methoxy-, (3S)-;(S)-6-Methoxychroman-3-carboxylic acid;Methoxy-, (3S)-
• CAS NO: 182570-28-1
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21058
• Mol File: 182570-28-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2H-1-Benzopyran-3-carboxylic acid, 3,4-dihydro-6-Methoxy-, (3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-1-Benzopyran-3-carboxylic acid, 3,4-dihydro-6-Methoxy-, (3S)-(182570-28-1)
• EPA Substance Registry System: 2H-1-Benzopyran-3-carboxylic acid, 3,4-dihydro-6-Methoxy-, (3S)-(182570-28-1)

Safety Data

• Hazardous Substances Data: 182570-28-1(Hazardous Substances Data)

Usage

General Description

2H-1-Benzopyran-3-carboxylic acid, 3,4-dihydro-6-Methoxy-, (3S)-, is a chemical compound with the molecular formula C11H12O4. It is a type of benzopyran, which is a class of organic compounds containing a benzene ring fused to a pyran ring. This specific compound has a carboxylic acid group attached to the benzopyran ring, as well as a methoxy group at the 6 position. The "S" stereochemistry indicates that the compound has a specific three-dimensional arrangement of atoms. 2H-1-Benzopyran-3-carboxylic acid, 3,4-dihydro-6-Methoxy-, (3S)- has potential applications in pharmaceuticals, as the benzopyran structure is found in many bioactive natural products, and the methoxy group can influence the compound's properties and reactivity.

Upstream product

• 57543-62-1 3-caboxy-6-methoxy-2H-1-benzopyran 
• 182570-26-9 6-methoxy-3,4-dihydro-2H-1-benzopyran-3-carboxylic acid 
• 672-13-9 2-hydroxy-5-methoxybenzaldehyde 
• 57543-71-2 6-methoxy-2H-chromene-3-carbonitrile 

Relevant articles and documents

Discovery of (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide as potent and isoform selective ROCK2 inhibitors

ROCK1 and ROCK2 are highly homologous isoforms. Accumulated studies indicate that they have distinct different functions, and the development of isoform selective ROCK inhibitors will pave new roads for the treatment of various diseases. In this work, a series of amide-chroman derivatives were synthesized and biologically evaluated in order to develop potent and isoform selective ROCK2 inhibitors. Remarkably, (S)-6-methoxy-chroman-3-carboxylic acid (4-pyridin-4-yl-phenyl)-amide ((S)-7c) possessed ROCK2 inhibitory activity with an IC50 value of 3 nM and 22.7-fold isoform selectivity (vs. ROCK1). Molecular docking indicated that hydrophobic interactions were the key element for the high potency and isoform selectivity of (S)-7c. The binding free energies predicted by MM/GBSA were in good agreement with the experimental bioactivities, and the analysis of individual energy terms suggested that residue Lys105 in ROCK1 or Lys121 in ROCK2 was the key residue for the isoform selectivity of (S)-7c.

Preparation method of optically pure (R)-6-methoxychroman-3-carboxylic acid

The invention discloses a preparation method of optically pure (R)-6-methoxychroman-3-carboxylic acid. The preparation method specifically comprises the following steps: adding acetonitrile and a decomposition agent into racemic 6-methoxychroman-3-carboxylic acid, dropwise adding ethanol at a heating reflux state until the solution is clarified, carrying out cooling, crystallization and separationso as to obtain an ammonium salt compound, carrying out acidolysis on the ammonium salt compound by virtue of acid so as to dissociate optically pure (R)-6-methoxychroman-3-carboxylic acid; and carrying out recrystallization on the obtained (R)-6-methoxychroman-3-carboxylic acid, so as to obtain high-optically pure (R)-6-methoxychroman-3-carboxylic acid. The preparation method has the advantagesthat the raw materials are cheap and easily available, conditions are mild, a synthetic process is simple, the decomposition agent can be circularly utilized, the cost is low, and the like.