4H-Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine,6,7,12b,13-tetrahydro-
- CAS Number:4312-32-7
- Molecular Formula:C19H17NO4
- Molecular Weight:323.348
- Mol File:4312-32-7.mol
Synonyms:Berbine,2,3:9,10-bis(methylenedioxy)-, (?à)- (8CI); (RS)-Stylopine; (?à)-Stylopine; (?à)-Tetrahydrocoptisine; 2,3:9,10-Bis(methylenedioxy)berbine; Chelidamine;NSC 110382; NSC 404529; Tetrahydrocoptisine; dl-Stylopine;dl-Tetrahydrocoptisine
Physicochemical Properties
- Melting Point:221-222℃
- Boiling Point:466.6°Cat760mmHg
- Density:1.47g/cm3
- Solubility:N/A
- Flash Point:142.5°C
- Vapor Density:N/A
- Refractive Index:N/A
- Sensitive:N/A
- Storage Temp.:N/A
- Appearance/Colour:N/A
4H-Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine,6,7,12b,13-tetrahydro- Safety information and MSDS
·Hazard identification:
| Pictogram(s) | no data available |
|---|---|
| Signal word | no data available |
| Hazard statement(s) | no data available |
| Precautionary statement(s) | |
| Prevention | no data available |
| Response | no data available |
| Storage | no data available |
| Disposal | no data available |
·Composition/information on ingredients:
| Chemical name | Common names and synonyms | CAS number | EC number | Concentration |
|---|---|---|---|---|
| (.+-.)-Tetrahydrocoptisine | (.+-.)-Tetrahydrocoptisine | 4312-32-7 | none | 100% |
·First-aid measures:
General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
·Fire-fighting measures:
Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.
·Accidental release measures:
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.
4H-Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine,6,7,12b,13-tetrahydro- Relevant articles
All total 26 Articles be found
All total 26 Articles be foundSynthesis and Structure-Activity Relationships of Quaternary Coptisine Derivatives as Potential Anti-ulcerative Colitis Agents
Zhang, Zhi-Hui,Zhang, Hai-Jing,Deng, An-Jun,Wang, Bo,Li, Zhi-Hong,Liu, Yang,Wu, Lian-Qiu,Wang, Wen-Jie,Qin, Hai-Lin
, p. 7557 - 7571 (2015/10/05)
Thirty quaternary coptisine derivatives from a synthesized library were found to activate the in vitro transcription of x-box-binding protein 1 (XBP1). Among these, the dihydrocoptisines were demonstrated by in vitro XBP1 transcriptional activity assays and animal experiments to be much more active anti-ulcerative colitis (UC) agents than quaternary coptisines, tetrahydrocoptisines, and the positive control. Unsubstituted dihydrocoptisine exhibited more significant anti-UC efficacy than dihydrocoptisines substituted at the C-8 or C-13 position. The EC50 value of dihydrocoptisine for XBP1 transcriptional activation was 2.25 nM. Dihydrocoptisine exhibited a significant dose-effect relationship, as indicated by biomarkers in in vitro and in vivo experiments. According to this study, the starting material's reductive states and the substitution patterns of the dihydrocoptisines were determined to be the critical parameters for modulating their anti-UC efficacy, and the dihydrocoptisine skeleton was designated as the key pharmacophore. The synthesized dihydrocoptisine is a promising lead for developing anti-UC drugs.
Berberine-based derivative and preparation method thereof, pharmaceutical composition, and antitumor uses of berberine-based derivative and pharmaceutical composition
-
Paragraph 0103, (2018/01/11)
The invention discloses a berberine-based derivative and a synthesis method thereof, and applications of the berberine-based derivative in preparation of products for prevention, alleviation and/or treatment of tumors, wherein the berberine-based derivative is a 12-aminotetrahydroberberine-based derivative represented by a general formula I or a physiologically acceptable salt thereof, a 12-N,N-disubstituted aminotetrahydroberberine-based derivative or a physiologically acceptable salt thereof, a 12-amino berberine quaternary ammonium salt derivative represented by a general formula II or a physiologically acceptable salt thereof, and a 12-N,N-disubstituted amino baterine quaternary ammonium salt derivative or a physiologically acceptable salt thereof. According to the present invention, the solubility of the berberine-based derivative is significantly improved compared to the raw material chlorinated berberine quaternary ammonium salt compound; and the obtained berberine-based derivative can provide inhibition activity on the growth of tumor cell lines, and can be used for preparing products for prevention, alleviation and/or treatment of tumors, wherein the action intensity of the berberine-based derivative is significantly higher than the berberine quaternary ammonium salt raw material, or is comparable to the positive control drug, or is higher than the positive control. The general formulas I and II are defined in the specification.
Berberine type alkaloid production (by machine translation)
-
Paragraph 0076, (2018/05/29)
[Problem] to efficiently produce the alkaloid production-type alkaloid berberine berberine. 2, 6 - Di - tert - butyl -4 - methylpyridine [solution] trifluoromethanesulfonic anhydride with certain compound after the intramolecular cyclization reaction, after reduction, de-bromo, quinone oxidants including a step of the manufacturing method of an aromatic ring. Figure 1 [drawing] (by machine translation)
A unified total synthesis of benzo[: D] [1,3]dioxole-type benzylisoquinoline alkaloids of aporphines, coptisines, and dibenzopyrrocolines
Lv, Jie,Li, Zhi-Hong,Deng, An-Jun,Qin, Hai-Lin
, p. 658 - 666 (2022/01/28)
The first total synthesis of (S)-(+)-ovigerine, (S)-(+)-N-formylovigerine, and (6aS,6a'S)-(+)-ovigeridimerine of aporphine alkaloids with a benzo[d][1,3]dioxole structure feature was established. The strategy was based upon the well-known Pd-catalyzed arylation to set the aporphine framework, and Noyori asymmetric hydrogenation followed by diastereoselective resolution to achieve excellent enantioselectivity. By slightly modifying the total synthetic route and strategically combining it with a aza-Michael addition, Bischler-Napieralski reaction and N-arylation, this methodology was also applied to the total syntheses of benzo[d][1,3]dioxole-type benzylisoquinoline alkaloids of coptisines and dibenzopyrrocolines, including two impatiens, tetrahydrocoptisine, and quaternary coptisine bromide of coptisines and two dibenzopyrrocoline analogues, with the syntheses of all of these target compounds being efficient. Among the nine synthesized compounds, the total syntheses of the three aporphines and the two impatiens, all with ee values of greater than 99%, were reported for the first time. This work also represents the first unification of synthetic routes for the total synthesis of benzo[d][1,3]dioxole-type aporphines, coptisines, and dibenzopyrrocolines. This journal is
A General, Concise Strategy that Enables Collective Total Syntheses of over 50 Protoberberine and Five Aporhoeadane Alkaloids within Four to Eight Steps
Zhou, Shiqiang,Tong, Rongbiao
supporting information, p. 7084 - 7089 (2016/05/19)
A concise, catalytic, and general strategy that allowed efficient total syntheses of 22 natural 13-methylprotoberberines within four steps for each molecule is reported. This synthesis represents the most efficient and shortest route to date, featuring three catalytic processes: CuI-catalyzed redox-A3 reaction, Pd-catalyzed reductive carbocyclization, and PtO2-catalyzed hydrogenation. Importantly, this new strategy to the tetracyclic framework has also been applied to the collective concise syntheses of >30 natural protoberberines (without 13-methyl group) and five aporhoeadane alkaloids.
4H-Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine,6,7,12b,13-tetrahydro- Synthetic route And Reaction conditions
- 41431-72-5
rac-7-methyl-2,3;9,10-bis-methylenedioxy-berbinium; chloride
| Conditions | Yield |
|---|---|
unter vermindertem Druck; |
- 65826-53-1
14-bromo-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline
| Conditions | Yield |
|---|---|
Withpalladium 10% on activated carbon;
hydrogen;
triethylamine;Inmethanol;
chloroform;at 20 ℃;
for 24h; | 99% |
- 6020-18-4
coptisine chloride
| Conditions | Yield |
|---|---|
| 85% | |
| 73.3% | |
| 73.3% | |
Withhydrogenchloride;
zinc; | |
Withhydrogenchloride;
zinc; | |
- 113557-44-1
7,8-methylenedioxy-2-(3,4-methylenedioxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one
| Conditions | Yield |
|---|---|
Withsodium tetrahydroborate;
trichlorophosphate;Yield given. Multistep reaction; | |
Multi-step reaction with 2 steps 1: POCl3; K2CO3 / acetonitrile / 0.67 h / 60 °C 2: NaBH4 / methanol / 1 h / Heating Withsodium tetrahydroborate;
potassium carbonate;
trichlorophosphate;Inmethanol;
acetonitrile;1: Bischler-Napieralski reaction / 2: Reduction; |
- 87167-71-3
N-<2-(3,4-methylenedioxyphenyl)ethyl>(3,4-methylenedioxy-2-hydroxymethyl)-phenylacetamide
| Conditions | Yield |
|---|---|
Withsodium tetrahydroborate;
phosphorus pentachloride;Yield given. Multistep reaction;
1) CHCl3, room t., 20 min; 2) MeOH, 1.5 h; | |
Multi-step reaction with 2 steps 1: trichlorophosphate / acetonitrile / 1.67 h / 20 °C / Inert atmosphere; Reflux 2: methanol; sodium tetrahydroborate / 6.25 h / 0 °C |
- 106544-66-5
2-(2,3-(methylenedioxy)-6-((trimethylsilyl)methyl)benzyl)-6,7-(methylenedioxy)-3,4-dihydroisoquinolinium perchlorate
| Conditions | Yield |
|---|---|
| 61% |
- 76177-42-9
(±)-8-oxostylopine
| Conditions | Yield |
|---|---|
| 86% |
| Conditions | Yield |
|---|---|
2,3,9,10-Tetrahydroxyberberin-methobromid 21, DMSO, CH2Cl2, NaOH, Δ; | |
aus methanol. Extrakt von Glaucium carniculum Curt durch Red. mit Zn/HCl; | |
Oxy-coptisin - elektrolyt. Red.; | |
Coptisin, Zn, wss. HCl; | |
2,3,9,10-Bis-methylendioxy-dihydroprotoberberin, Pt/H2; | |
Coptisin-chlorid; | |
Dehydrocoptisin-chlorid (Syst.Nr. 4482), Platin, Me., Hydrierung; | |
(yield)50percent; | |
Coptisin,H2 in konz. Essigsaeure (PtO2); | |
Coptisin,NaBH4 in wss. Me.; | |
Aus Fumaria indica; | |
Coptisin, Zn, HCl; | |
(3-14C;9,9-3H2)Reticulin; | |
- 75-09-2
dichloromethane
| Conditions | Yield |
|---|---|
Withsodium methylate;
at 100 ℃;
im Rohr; |
| Conditions | Yield |
|---|---|
Withsulfuric acid;
zinc; |
4H-Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine,6,7,12b,13-tetrahydro- Raw materials
- 41431-72-5
rac-7-methyl-2,3;9,10-bis-methylenedioxy-berbinium; chloride
- 65826-53-1
14-bromo-6,7,12b,13-tetrahydro-4H-[1,3]dioxolo[4,5-g][1,3]dioxolo[4',5':7,8]isoquino[3,2-a]isoquinoline
- 6020-18-4
coptisine chloride
- 113557-44-1
7,8-methylenedioxy-2-(3,4-methylenedioxyphenethyl)-1,2,3,4-tetrahydroisoquinolin-3-one
- 87167-71-3
N-<2-(3,4-methylenedioxyphenyl)ethyl>(3,4-methylenedioxy-2-hydroxymethyl)-phenylacetamide
4H-Bis[1,3]benzodioxolo[5,6-a:4',5'-g]quinolizine,6,7,12b,13-tetrahydro- Target Products
Business Type:
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Certificate:
- Product LicenseEnterprise AuthenticationISOGMPFDAHALAL
Country :
China (Mainland)(38)
United States(1)
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