17388-17-9

Basic information

• Product Name: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin- 9-ol,5,8,13,13a-tetrahydro-10-methoxy-
• Synonyms: Tetrahydroberberrubine;Nandinine DL-form;Nandinine ,(+/-)-;6H-Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizin-9-ol,5,8,13,13a-tetrahydro-10-methoxy-;(+/-)-Nandinine;(RS)-Nandinine;(+/-)-5,6,13,14-Tetrahydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-8H-dibenzo(a,g)quinolizine;Nandinine,DL-
• CAS NO: 17388-17-9
• Molecular Formula: C19H19NO4
• Molecular Weight: 325.364
• Mol File: 17388-17-9.mol
• Article Data: 5

Chemical Properties

• Melting Point: 183-185°
• CAS DataBase Reference: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin- 9-ol,5,8,13,13a-tetrahydro-10-methoxy- (CAS DataBase Reference)
• NIST Chemistry Reference: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin- 9-ol,5,8,13,13a-tetrahydro-10-methoxy- (17388-17-9)
• EPA Substance Registry System: 6H-Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizin- 9-ol,5,8,13,13a-tetrahydro-10-methoxy- (17388-17-9)

Safety Data

• Hazardous Substances Data: 17388-17-9(Hazardous Substances Data)

Usage

Structure

Contains a benzodioxole ring system fused to a quinolizinone ring, creating a polycyclic structure.
Includes a methoxy group (-OCH3) and a tetrahydroquinoline moiety.

Functional Groups

Benzodioxole ring system
Quinolizinone ring
Methoxy group (-OCH3)

Solubility

The presence of the methoxy group may influence solubility characteristics.

Potential Activity

Structural complexity suggests potential pharmaceutical or biological activity.
Methoxy group can influence interactions with biological systems.

Applications

Pharmaceutical research: Potential medicinal applications due to structural complexity.
Industrial research: Investigation for potential industrial applications.

Research Importance

Further characterization needed to understand its properties fully.
Investigation may yield insights into medicinal or industrial uses.

Upstream product

• 1485-00-3 5-(2-nitrovinyl)benzo[1,3]dioxole 
• 1429118-90-0 (R)-(2-(benzyloxy)-3-methoxy-6-((5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl)phenyl)methanol 
• 1429118-70-6 (R)-2-(benzyloxy)-3-methoxy-6-((5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl)benzyl acetate 
• 1422431-44-4 2-(benzyloxy)-6-((7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)methyl)-3-methoxybenzyl acetate 
• 1422431-37-5 6-(2-(2-(benzo[d][1,3]dioxol-5-yl)ethylamino)-2-oxoethyl)-2-(benzyloxy)-3-methoxybenzyl acetate 
• 1422431-30-8 N-(2-(benzo[d][1,3]dioxol-5-yl)ethyl)-2-(3-(benzyloxy)-2-(hydroxymethyl)-4-methoxyphenyl)acetamide 
• 120-57-0 piperonal 
• 56201-87-7 8-hydroxy-7-methoxyisobenzofuranyltetrahydropyran-3-one 
• 1131-94-8 homoisovanillic acid 
• 19626-36-9 methyl 2-(3-bromo-4-methoxyphenyl)acetate 
• 34918-57-5 methyl 3-bromo-4-hydroxyphenylacetate 
• 14199-15-6 Methyl 4-hydroxyphenylacetate 
• 1484-85-1 3,4-methylenedioxyphenylethylamine 
• 1429118-98-8 14-(R)-9-benzyloxy-2,3-methylenedioxy-10-methoxytetrahyrdooxyprotoberberine 

Downstream Products

• 1095271-57-0 C₂₅H₂₁ClFNO₆S 
• 572-76-9 tetrahydroberberrubine 
• 572-76-9 5,6,13,14-tetrahydro-9-hydroxy-10-methoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine 
• 1416047-00-1 C₂₈H₂₅NO₇ 
• 749793-14-4 (+/-)-5,6,13,14-tetrahydro-9-((3-phenyl)acryloxy)-10-methoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine 
• 1416047-01-2 (+/-)-5,6,13,14-tetrahydro-9-[3-(3-methoxyl-4-acetoxy)phenyl]acryloxy-10-methoxy-2,3-(methylenedioxy)-8H-dibenzo[a,g]quinolizine 
• 1095271-62-7 10-methoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinolin-9-yl (phenylmethoxy)formate 
• 1095271-69-4 10-methoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinolin-9-yl 3-nitrobenzenesulfonate 
• 1095271-57-0 10-methoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinolin-9-yl 2-chloro-4-fluorobenzenesulfonate 
• 1095271-46-7 10-methoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinolin-9-yl 4-phenylbenzenesulfonate 
• 723752-25-8 10-methoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinolin-9-yl benzoate 
• 1095271-68-3 (10-methoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinolin-9-yloxy)-N-benzamide 
• 1095271-37-6 10-methoxy-9-(phenylmethoxy)-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinoline 
• 1095271-47-8 10-methoxy-5,6,7,8,13,13a-hexahydro-2H-1,3-dioxolano[4,5-g]isoquinolino[3,2-a]isoquinolin-9-yl 4-(tert-butyl)benzenesulfonate 

Relevant articles and documents

Significantly different effects of tetrahydroberberrubine enantiomers on dopamine D1/D2 receptors revealed by experimental study and integrated in silico simulation

Tetrahydroberberrubine (TU), an active tetrahydroprotoberberines (THPBs), is gaining increasing popularity as a potential candidate for treatment of anxiety and depression. One of its two enantiomers, l-TU, has been reported to be an antagonist of both D1 and D2 receptors, but the functional activity of the other enantiomer, d-TU, is still unknown. In this study, experiments were combined with in silico molecular simulations to (1) confirm and discover the functional activities of l-TU and d-TU, and (2) systematically evaluate the molecular mechanisms beyond the experimental observations. l-TU proved to be an antagonist of both D1 and D2 receptors (IC50 = 385?nM and 985?nM, respectively), while d-TU shows no affinity against either D1 or D2 receptor, based on the cAMP assay (D1 receptor) and calcium flux assay (D2 receptor). Results from both flexible-ligand docking studies and molecular dynamic (MD) simulations provided insights at the atomic level. The l-TU-bound structures predicted by MD (1) undergo an outward rotation of the extracellular helical bundles; (2) have an enlarged orthosteric binding pocket; and (3) have a central toggle switch that is prevented from rotating freely. These features are unique to the l-TU enantiomer and provide an explanation for its antagonistic behavior toward both D1 and D2 receptors. The present study provides new sight on the structural and functional relationships of l-TU and d-TU binding to dopamine receptors, and provides guidance to the rational design of novel molecules targeting these two dopamine receptors in the future.

Chemical and microbial semi-synthesis of tetrahydroprotoberberines as inhibitors on tissue factor procoagulant activity

To discover new inhibitors on tissue factor procoagulant activity, 21 tetrahydroprotoberberines were screened on the model of human THP-1 cells stimulated by lipopolysaccharide. Among these tetrahydroprotoberberines, several unique compounds were synthesized through microbial transformation: compound 6 (l-corydalmine) was obtained through regio-selective demethylation by Streptomyces griseus ATCC 13273, whereas compounds 4a, 4b, 5h, and 5i were microbial glycosylation products by Gliocladium deliquescens NRRL1086. The bioassay results showed that compounds 3 (tetrahydroberberine), 10 (tetrahydroberberrubine), and 5f (cinnamyl ester of 5) and 5i (glycosidic product of 5), exhibited the most potential effects, with IC50 values of 8.35, 6.75, 3.75, and 8.79 nM, respectively. The preliminary structure and activity relationship analysis revealed that the 2,3-methylenedioxy group of the A ring was essential for the strong inhibitory effects, and the R configuration of the chiral center C-14 showed higher activity than S-form products. The formation of fatty acid or aromatic acid esters of compound 5, except the cinnamyl esters, would weaken its effects. It is also interesting to note that the glycosylation of tetrahydroprotoberberines will maintain and even enhance the inhibitory effects. Because of the importance of glycochemistry in new drug discovery and development, this deserves further exploration and may provide some guide on the semi-synthesis of tetrahydroprotoberberines as tissue factor pathway inhibitors. Our findings also provide some potential leading compounds for tissue factor-related diseases, such as cancer and cardiovascular diseases.

CORYDALINE DERIVATIVES USEFUL FOR REDUCING LIPID LEVELS

The present technology relates to compounds of Formulas (V) and (VI) and methods of making and using such compounds. Methods of use include prevention and treatment of hyperlipidemia, hypercholesterolemia, hypertriglyceridemia, hepatic steatosis, and metabolic syndrome. Compounds disclosed herein also lower total cholesterol, LDL- cholesterol, and triglycerides and increase hepatic LDL receptor expression, inhibit PCSK9 expression, and activate AMP-activated potein kinase.