163163-23-3

Basic information

• Product Name: CHROMANOL 293B
• Synonyms: TRANS-N-[6-CYANO-3,4-DIHYDRO-3-HYDROXY-2,2-DIMETHYL-2H-1-BENZOPYRAN-4-YL]-N-METHYL-ETHANESULFONAMIDE;CHROMANOL 293B;6-cyano-4-(N-ethylsulfonyl-N-methylamino)-3-hydroxy-2,2-dimethylchromane;N-[(3R,4S)-6-cyano-3-hydroxy-2,2-dimethyl-3,4-dihydrochromen-4-yl]-N-methylethanesulfonamide
• CAS NO: 163163-23-3
• Molecular Formula: C15H20N2O4S
• Molecular Weight: 324.4
• Product Categories: Potassium channel
• Mol File: 163163-23-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 474.1°Cat760mmHg
• Flash Point: 240.6°C
• Appearance: white/solid
• Density: 1.33g/cm³
• Vapor Pressure: 8.52E-10mmHg at 25°C
• Refractive Index: 1.592
• Storage Temp.: −20°C
• Solubility: DMSO: 18 mg/mL
• PKA: 12.96±0.60(Predicted)
• CAS DataBase Reference: CHROMANOL 293B(CAS DataBase Reference)
• NIST Chemistry Reference: CHROMANOL 293B(163163-23-3)
• EPA Substance Registry System: CHROMANOL 293B(163163-23-3)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 36/37-7/9
• WGK Germany: 3
• Hazardous Substances Data: 163163-23-3(Hazardous Substances Data)

Usage

Description

Chromanol 293B is a potent inhibitor of potassium channel protein (KvLQT1), specifically designed to block slowly activating delayed-rectifier K+ current (IKs). It selectively targets IKs channels with high specificity, showing no activity on rat Kv1.1 or Kir2.1 channels at a concentration of 30 μM. CHROMANOL 293B has been found to modulate potassium voltage-gated channel (KCNQ1), which plays a role in glucose-stimulated insulin secretion (GSIS) in the pancreas.

Uses

Used in Cardiology:
Chromanol 293B is used as a research tool for studying the effects of IKs channel inhibition in human atrial myocytes. It helps researchers understand the role of these channels in repolarization and their potential as therapeutic targets for cardiac arrhythmias.
Used in Electrophysiology:
Chromanol 293B is used as a potent blocker in patch-clamp electrophysiology studies, particularly in cardiomyocytes. It aids in investigating the function and regulation of potassium channels in these cells.
Used in Cell Biology:
In Xenopus oocytes expressing rat IKs channels, Chromanol 293B is used to increase the rate and extent of IKs in a dose-dependent manner. This application helps researchers study the mechanisms underlying the regulation of potassium channels and their impact on cellular function.
Used in Cystic Fibrosis Research:
Chromanol 293B is used as an inhibitor of cystic fibrosis transmembrane conductance regulator (CFTR) Clcurrents (ICTFR) in Xenopus oocytes expressing human CFTR. This application assists in understanding the role of CFTR in chloride transport and its implications in cystic fibrosis pathology.
Used in Endocrinology:
Chromanol 293B is used as a modulator of potassium voltage-gated channel (KCNQ1) to improve glucose-stimulated insulin secretion (GSIS) in the pancreas. This application is crucial for studying the relationship between potassium channels and insulin secretion, which can have implications for the development of treatments for diabetes.

Biological Activity

Blocker of the slow delayed rectifier K + current (I Ks ) (IC 50 = 1-10 μ M). Also blocks the CFTR chloride current (I CFTR ) (IC 50 = 19 μ M).

Biochem/physiol Actions

Blocker of the slow delayed rectifier K+ current via KCNQ1 channels

InChI:InChI=1/C15H20N2O4S/c1-5-22(19,20)17(4)13-11-8-10(9-16)6-7-12(11)21-15(2,3)14(13)18/h6-8,13-14,18H,5H2,1-4H3/t13-,14-/m1/s1

Upstream product

• 6601-37-2 N-methyl-ethanesulfonamide 
• 65018-90-8 3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-6-carbonitrile 
• 65018-90-8 (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile 
• 163163-45-9 N-methyl-N-trimethylsilyl-ethanesulfonamide 
• 35794-84-4 2-hydroxy-5-cyanoacetophenone 
• 33143-29-2 6-cyano-2,2-dimethylchromene 
• 121021-88-3 3,4-dihydro-2,2-dimethyl-4-oxo-2H-1-benzopyran-6-carbonitrile 
• 65018-90-8 6-cyano-2,2-dimethylchromene-3,4-epoxide 

Relevant articles and documents

Total synthesis of chromanol 293B and cromakalim via stereoselective amination of chiral benzylic ethers

Stereoselective benzylic amination reaction is important for their further application as pharmaceuticals and agrochemicals, and other chemical entities. Herein, we describe the diastereoselective amination of 1,2-anti-dialkoxychromane on chromane framewo

Stereoselective interactions of the enantiomers of chromanol 293B with human voltage-gated potassium channels

Selective inhibitors of the slow component of the cardiac delayed rectifier K+ current, I(Ks), are of interest as novel class III antiarrhythmic agents and as tools for studying the physiologic roles of the I(Ks) current. Racemic chromanol 293B is an inhibitor of both native I(Ks) and its putative molecular counterpart, the KvLQT1 +minK ion channel complex. We synthesized the (+)-[3S,4R] and (-)-[3R,4S] enantiomers of chromanol 293B using chiral intermediates of known absolute configuration and determined their relative potency to block recombinant human K+ channels that form the basis for the major repolarizing K+ currents in human heart, including KvLQT1+minK, human ether-a-go-go-related gene product (hERG), Kv1.5, and Kv4.3, corresponding to the slow (I(Ks)), rapid (I(Kr)), and ultrarapid (I(Kur)) delayed rectifier currents and the transient outward current (l(To)), respectively. K+ channels were expressed in mammalian cells and currents were recorded using the whole-cell patch-clamp technique. We found that the physicochemical properties and relative potency of the enantiomers differed from those reported previously, with (-)-[3R,4S]293B nearly 7-fold more potent in block of KvLQT1+minK than (+)-[3S,4R]293B, indicating that the original stereochemical assignments were reversed. K+ current inhibition by (-)-293B was selective for KvLQT1+minK over hERG, whereas the stereospecificity of block for KvLQT1+minK and Kv1.5 was preserved, with (-)-293B more potent than (+)-293B for both channel complexes. We conclude that the (-)-[3R,4S] enantiomer of chromanol 293B is a selective inhibitor of KvLQT1+minK and therefore a useful tool for studying I(Ks).