75491-93-9

Basic information

• Product Name: dehydrodiscretine
• Synonyms: dehydrodiscretine
• CAS NO: 75491-93-9
• Molecular Formula: C20H20ClNO4
• Molecular Weight: 373.8301
• Mol File: 75491-93-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: dehydrodiscretine(CAS DataBase Reference)
• NIST Chemistry Reference: dehydrodiscretine(75491-93-9)
• EPA Substance Registry System: dehydrodiscretine(75491-93-9)

Safety Data

• Hazardous Substances Data: 75491-93-9(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H19NO4.ClH/c1-23-18-10-15-12(7-17(18)22)4-5-21-11-14-9-20(25-3)19(24-2)8-13(14)6-16(15)21;/h6-11H,4-5H2,1-3H3;1H

Upstream product

• 40225-82-9 (+/-)-discretine 
• 3213-30-7 5-(2-amino-ethyl)-2-methoxy-phenol 
• 322474-09-9 2-(3-hydroxy-4-methoxyphenyl)-1-nitroethane 
• 39816-35-8 2-(3-hydroxy-4-methoxyphenyl)-1-nitroethene 
• 621-59-0 isovanillin 

Relevant articles and documents

Thalifaurine and dehydrodiscretine, new quaternary protoberberines from Thalictrum fauriei

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Synthesis and biological evaluation of berberine analogues as novel up-regulators for both low-density-lipoprotein receptor and insulin receptor

Berberine (BBR) is a natural compound with up-regulating activity on both low-density-lipoprotein receptor (LDLR) and insulin receptor (InsR). This one-drug-multiple-target characteristic might be suitable for the treatment of metabolic syndrome. In searching for up-regulators effective for both LDLR and InsR expression, the structure-activity relationship (SAR) analysis for BBR analogues was done. Fourteen BBR analogues were designed, synthesized and biologically evaluated. SAR analysis revealed that appropriate modifications on the phenyl ring A or D of BBR might retain the up-regulatory activities on the expression of both LDLR and InsR. Among these compounds, compound 13a bearing 9-methoxy and 10-hydroxyl on the ring D showed promising activities on either LDLR or InsR gene expression. The 10-hydroxyl of 13a could be an arm to connect proper chemical groups for optimizing drug-bioavailability in vivo. Thus, 13a could be considered to be a parent compound to make pro-drugs for either blood lipids or glucose.