Home Quinolines 6020-18-4
6020-18-4,MFCD00016676
Catalog No.:AA00IKIN

6020-18-4 | Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium, 6,7-dihydro-, chloride

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1mg
98%
in stock  
$24.00   $17.00
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5mg
98%
in stock  
$58.00   $41.00
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10mg
98%
in stock  
$74.00   $52.00
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25mg
98%
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$95.00   $67.00
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50mg
98%
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$122.00   $86.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA00IKIN
Chemical Name:
Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium, 6,7-dihydro-, chloride
CAS Number:
6020-18-4
Molecular Formula:
C19H14ClNO4
Molecular Weight:
355.7718
MDL Number:
MFCD00016676
SMILES:
C1Oc2c(O1)cc1c(c2)CC[n+]2c1cc1ccc3c(c1c2)OCO3.[Cl-]
NSC Number:
119754
Properties
Properties
 
BP:
601.5°C at 760 mmHg  
Form:
Solid  
MP:
>258°C (dec.)  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
502  
Covalently-Bonded Unit Count:
2  
Heavy Atom Count:
25  
Hydrogen Bond Acceptor Count:
5  

Downstream Synthesis Route

[1]Tetrahedron,2002,vol.58,p.5053-5059

[1]Kadam,ShivajiS.;Toušek,Jaromír;Maier,Lukáš;Pipíška,Matej;Sklenář,Vladimír;Marek,Radek[JournalofMolecularStructure,2012,vol.1028,p.31-38]

6020-18-4    111-13-7   
C27H29NO5 

[1]CurrentPatentAssignee:CHINESEACADEMYOFMEDICALSCIENCES-EP2789612,2014,A1Locationinpatent:Paragraph0055

[2]CurrentPatentAssignee:CHINESEACADEMYOFMEDICALSCIENCES-US2015/31717,2015,A1Locationinpatent:Paragraph0030;0085;0086

[3]Zhang,Zhi-Hui;Yan,Yu;Deng,An-Jun;Zhang,Hai-Jing;Li,Zhi-Hong;Yuan,Tian-Yi;Fang,Lian-Hua;Wu,Lian-Qiu;Du,Guan-Hua;Qin,Hai-Lin[ChineseChemicalLetters,2018,vol.29,#1,p.131-135]

821-55-6    6020-18-4   
C28H31NO5 

[1]CurrentPatentAssignee:CHINESEACADEMYOFMEDICALSCIENCES-EP2789612,2014,A1Locationinpatent:Paragraph0056

[2]CurrentPatentAssignee:CHINESEACADEMYOFMEDICALSCIENCES-US2015/31717,2015,A1Locationinpatent:Paragraph0030;0087;0088

[3]Zhang,Zhi-Hui;Yan,Yu;Deng,An-Jun;Zhang,Hai-Jing;Li,Zhi-Hong;Yuan,Tian-Yi;Fang,Lian-Hua;Wu,Lian-Qiu;Du,Guan-Hua;Qin,Hai-Lin[ChineseChemicalLetters,2018,vol.29,#1,p.131-135]

2879-20-1    6020-18-4   
8-(1-(3,4-ethylenedioxybenzoyl)ethene-1-yl)-13-methylcoptisinechloride 

[1]Patent:EP2789612,2014,A1

[2]ChineseChemicalLetters,2018,vol.29,p.131-135

Literature

Title: Quality evaluation and species differentiation of Rhizoma coptidis by using proton nuclear magnetic resonance spectroscopy.

Journal: Analytica chimica acta 20121017

Title: Analysis of four alkaloids of Coptis chinensis in rat plasma by high performance liquid chromatography with electrochemical detection.

Journal: Analytica chimica acta 20120806

Title: Design, synthesis and multidrug resistance reversal activity evaluation of 8-oxocoptisine derivatives.

Journal: Medicinal chemistry (Shariqah (United Arab Emirates)) 20120701

Title: Coptisine exert cardioprotective effect through anti-oxidative and inhibition of RhoA/Rho kinase pathway on isoproterenol-induced myocardial infarction in rats.

Journal: Atherosclerosis 20120501

Title: Determination of protoberberine alkaloids in Rhizoma Coptidis by ERETIC ¹H NMR method.

Journal: Journal of pharmaceutical and biomedical analysis 20120223

Title: Coptisine inhibits RANKL-induced NF-κB phosphorylation in osteoclast precursors and suppresses function through the regulation of RANKL and OPG gene expression in osteoblastic cells.

Journal: Journal of natural medicines 20120101

Title: Analysis of the mechanisms underlying the vasorelaxant action of coptisine in rat aortic rings.

Journal: The American journal of Chinese medicine 20120101

Title: [Preparation and stuctural behavior of the inclusion complex of beta-cyclodextrin and coptisine hydrochloride].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20120101

Title: Comparative pharmacokinetics of dehydroevodiamine and coptisine in rat plasma after oral administration of single herbs and Zuojinwan prescription.

Journal: Fitoterapia 20111201

Title: Ionic liquid sensitized fluorescence determination of four isoquinoline alkaloids.

Journal: Talanta 20110715

Title: [Quantitative analysis of four alkaloids in Xianglian preparations by QAMS method].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20110601

Title: Differential gene expression in rat vascular smooth muscle cells following treatment with coptisine exerts a selective antiproliferative effect.

Journal: Journal of natural products 20110425

Title: Application of 1H-NMR spectroscopy to validation of berberine alkaloid reagents and to chemical evaluation of Coptidis Rhizoma.

Journal: Journal of natural medicines 20110401

Title: Intestinal absorption mechanisms of berberine, palmatine, jateorhizine, and coptisine: involvement of P-glycoprotein.

Journal: Xenobiotica; the fate of foreign compounds in biological systems 20110401

Title: [Simultaneous determination of six alkaloids in Coptis chinensis of different regions by RP-HPLC].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20101001

Title: Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.

Journal: Bioorganic & medicinal chemistry letters 20100801

Title: Selective regulation of multidrug resistance protein in vascular smooth muscle cells by the isoquinoline alkaloid coptisine.

Journal: Biological & pharmaceutical bulletin 20100101

Title: Investigation of the anti-fungal activity of coptisine on Candida albicans growth by microcalorimetry combined with principal component analysis.

Journal: Journal of applied microbiology 20091001

Title: Purification of alkaloids from Corydalis yanhusuo W. T. Wang using preparative 2-D HPLC.

Journal: Journal of separation science 20090501

Title: [Effect of additives on absorption of Coptis chinensis total alkaloids and pharmacokinetics in mice].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20090201

Title: Development of a rapid resolution liquid chromatographic method for simultaneous analysis of four alkaloids in Rhizoma coptidis under different cultivation conditions.

Journal: Journal of AOAC International 20090101

Title: Simple and reliable methods for the determination of sixteen marker components for quality control of Daochi pill by HPLC coupled with diode array detection.

Journal: Phytochemical analysis : PCA 20090101

Title: Covalent bonding of azoles to quaternary protoberberine alkaloids.

Journal: Magnetic resonance in chemistry : MRC 20081201

Title: [Studies on chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo].

Journal: Zhong yao cai = Zhongyaocai = Journal of Chinese medicinal materials 20081101

Title: Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.

Journal: Biopharmaceutics & drug disposition 20071201

Title: [Absorption of coptisine chloride and berberrubine across human intestinal epithelial by using human Caco-2 cell monolayers].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20071201

Title: Analysis of Central European Corydalis species by nonaqueous capillary electrophoresis-electrospray ion trap mass spectrometry.

Journal: Journal of chromatography. A 20070803

Title: High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.

Journal: Journal of separation science 20070401

Title: Selective inhibition of vascular smooth muscle cell proliferation by coptisine isolated from Coptis rhizoma, one of the crude drugs composing Kampo medicines Unsei-in.

Journal: Phytomedicine : international journal of phytotherapy and phytopharmacology 20060501

Title: Simultaneous determination of four active alkaloids from a traditional Chinese medicine Corydalis saxicola Bunting. (Yanhuanglian) in plasma and urine samples by LC-MS-MS.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20060202

Title: [Studies on the alkaloids from herb of Corydalis adunca].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20051101

Title: [Quality assessment of Coptis chinensis in China].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20050401

Title: [Establishment of the control substance of plant drug and fingerprints of Coptis chinensis].

Journal: Zhongguo yi xue ke xue yuan xue bao. Acta Academiae Medicinae Sinicae 20041201

Title: Improved detection of Coptidis alkaloids by field-amplified sample stacking in capillary electrophoresis.

Journal: Journal of pharmaceutical and biomedical analysis 20040921

Title: Cytotoxic effects of Coptis chinensis and Epimedium sagittatum extracts and their major constituents (berberine, coptisine and icariin) on hepatoma and leukaemia cell growth.

Journal: Clinical and experimental pharmacology & physiology 20040101

Title: [Study on the solubility changes of Rhizoma Coptidis' main chemical constituents influenced by the proportion of Rhizoma Coptidis and Fructus Evodiae].

Journal: Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica 20030701

Title: Potentiation of nerve growth factor-induced neurite outgrowth in PC12 cells by a Coptidis Rhizoma extract and protoberberine alkaloids.

Journal: Bioscience, biotechnology, and biochemistry 20021101

Title: Inhibition of type A monoamine oxidase by coptisine in mouse brain.

Journal: Life sciences 20011228

Title: Gastric-mucous membrane protection activity of coptisine derivatives.

Journal: Biological & pharmaceutical bulletin 20011101

Title: In vitro cytotoxicity of the protoberberine-type alkaloids.

Journal: Journal of natural products 20010701

Title: Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine.

Journal: Farmaco (Societa chimica italiana : 1989) 20010101

Title: Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.

Journal: Cell biology and toxicology 20010101

Title: Analysis of coptisine, berberine and palmatine in adulterated Chinese medicine by capillary electrophoresis-electrospray ion trap mass spectrometry.

Journal: Journal of chromatography. A 20000114

Title: Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.

Journal: Journal of natural products 19910101

Title: Yu D, et al. The IDO inhibitor coptisine ameliorates cognitive impairment in a mouse model of Alzheimer's disease. J Alzheimers Dis. 2015;43(1):291-302.

Title: He K, et al. The safety and anti-hypercholesterolemic effect of coptisine in Syrian golden hamsters. Lipids. 2015 Feb;50(2):185-94.

Title: Rao PC, et al. Coptisine-induced cell cycle arrest at G2/M phase and reactive oxygen species-dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells. Tumour Biol. 2017 Mar;39(3):1010428317694565.

Title: Zhou X, et al. Inhibition activity of a traditional Chinese herbal formula Huang-Lian-Jie-Du-Tang and its major components found in its plasma profile on neuraminidase-1. Sci Rep. 2017 Nov 14;7(1):15549.

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SDS
Tags:6020-18-4 Molecular Formula|6020-18-4 MDL|6020-18-4 SMILES|6020-18-4 Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizinium, 6,7-dihydro-, chloride