127419-05-0

Basic information

• Product Name: (3R,4S)-4-aMino-3-hydroxy-2,2-diMethylchroMan-6-carbonitrile
• Synonyms: (3R,4S)-4-aMino-3-hydroxy-2,2-diMethylchroMan-6-carbonitrile
• CAS NO: 127419-05-0
• Molecular Formula: C₁₂H₁₄N₂O₂
• Molecular Weight: 218.25176
• Mol File: 127419-05-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3R,4S)-4-aMino-3-hydroxy-2,2-diMethylchroMan-6-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-4-aMino-3-hydroxy-2,2-diMethylchroMan-6-carbonitrile(127419-05-0)
• EPA Substance Registry System: (3R,4S)-4-aMino-3-hydroxy-2,2-diMethylchroMan-6-carbonitrile(127419-05-0)

Safety Data

• Hazardous Substances Data: 127419-05-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
DHMC is used as a pharmaceutical candidate for its potential antioxidant and anti-inflammatory properties, which can be beneficial in the treatment of various diseases and conditions.
Used in Neurodegenerative Disease Treatment:
DHMC is used as a potential therapeutic agent for neurodegenerative diseases due to its potential neuroprotective effects and ability to combat oxidative stress and inflammation in the brain.
Used in Cancer Treatment:
DHMC is used as a potential anticancer agent, as it has been investigated for its ability to target and inhibit the growth of cancer cells, making it a promising candidate for further research and development in oncology.

Upstream product

• 65018-90-8 (1aR-cis)-1a,7b-dihydro-2,2-dimethyl-2H-oxireno[c][1]benzopyran-6-carbonitrile 
• 114865-21-3 6-cyano-3,4-dihydro-2,2-dimethyl-trans-3-bromo-4-hydroxy-2H-1-benzopyran 
• 134017-91-7 [3R-[3α,4β(S*)]]-N-(6-Cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl)-α-hydroxybenzeneacetamide 

Downstream Products

• 156590-88-4 (3S-trans)-3-[[[(6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-yl) amino]carbonyl]amino]benzeneacetic acid, methyl ester 
• 94535-51-0 cromakalim 
• 149279-03-8 ethyl N-acetyl-4-fluorobenzimidate 

Relevant articles and documents

Cardioselective antiischemic ATP-sensitive potassium channel (K(ATP)) openers. 5. Identification of 4-(N-aryl)-substituted benzopyran derivatives with high selectivity

This paper describes our studies aimed at the discovery of structurally distinct analogs of the cardioprotective K(ATP) opener BMS-180448 (2) with improved selectivity for the ischemic myocardium. The starting compound 6, derived from the indole analog 4, showed good cardioprotective potency and excellent selectivity compared to 2 and the first-generation K(ATP) opener cromakalim (1). The structure-activity studies indicate that increasing the size of the alkyl ester leads to diminished potency as does its replacement with a variety of other groups (nitrile, methyl sulfone). Replacement of the ethyl ester of 6 with an imidazole gave the best compound 3 (BMS-191095) of this series which maintains the potency and selectivity of its predecessor 6. The results described in this publication further support that there is no correlation between vasorelaxant and cardioprotective potencies of K(ATP) openers. Compound 3 is over 20- and 4000-fold more selective for the ischemic myocardium than 2 and cromakalim (1), respectively. The selectivity for the ischemic myocardium is achieved by reduction of vasorelaxant potency rather than enhancement in antiischemic potency. As for cromakalim (1) and 2, the cardioprotective effects of compound 3 are inhibited by cotreatment with the K(ATP) blocker glyburide, indicating that the K(ATP) opening is involved in its mechanism of cardioprotection. With its good oral bioavailability (47%) and plasma elimination half-life (3 h) in rats, compound 3 offers an excellent candidate to investigate the role of residual vasorelaxant potency of 2 toward its cardioprotective activity in vivo.

Process for preparing benzoypyranol derivatives

A process for the preparation of a pure (3S,4R)-isomer of a compound of formula (A): STR1 wherein the substituents are herein defined in which the pyrrolidonyl or piperidonyl ring is formed by cyclizing an appropriate precursor dihydrobenzopyranol compound that has already been resolved to the (3S,4R)-configuration, or a mixture in which the (3S,4R)-configuration predominates with respect to the (3S,4R)-configuration.