ScandineCAS# 24314-59-8 |
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| Cas No. | 24314-59-8 | SDF | Download SDF |
| PubChem ID | 12082288 | Appearance | Powder |
| Formula | C21H22N2O3 | M.Wt | 350.4 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | methyl (1S,10R,12S,19S)-12-ethenyl-9-oxo-8,16-diazapentacyclo[10.6.1.01,10.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate | ||
| SMILES | COC(=O)C12CC3(C=CCN4C3C1(CC4)C5=CC=CC=C5NC2=O)C=C | ||
| Standard InChIKey | JTSSMMKHJYRYEG-VRXWPRPYSA-N | ||
| Standard InChI | InChI=1S/C21H22N2O3/c1-3-19-9-6-11-23-12-10-20(16(19)23)14-7-4-5-8-15(14)22-17(24)21(20,13-19)18(25)26-2/h3-9,16H,1,10-13H2,2H3,(H,22,24)/t16-,19-,20+,21+/m0/s1 | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | Standard reference |
| Structure Identification | J Nat Prod. 2013 Dec 27;76(12):2322-9.Melosuavines A-H, cytotoxic bisindole alkaloid derivatives from Melodinus suaveolens.[Pubmed: 24274642]
J Org Chem. 2014 Apr 4;79(7):3173-84.Intramolecular cycloaddition reactions of furo[3,4-b]indoles for alkaloid synthesis.[Pubmed: 24617539]Model studies dealing with the Cu(II)- or Rh(II)-catalyzed carbenoid cyclization/cycloaddition cascade of several α-diazo indolo amido esters have been carried out as an approach to the alkaloid Scandine.
Beilstein J Org Chem. 2012;8:107-11.Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy.[Pubmed: 22423277]
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Scandine Dilution Calculator
Scandine Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.8539 mL | 14.2694 mL | 28.5388 mL | 57.0776 mL | 71.347 mL |
| 5 mM | 0.5708 mL | 2.8539 mL | 5.7078 mL | 11.4155 mL | 14.2694 mL |
| 10 mM | 0.2854 mL | 1.4269 mL | 2.8539 mL | 5.7078 mL | 7.1347 mL |
| 50 mM | 0.0571 mL | 0.2854 mL | 0.5708 mL | 1.1416 mL | 1.4269 mL |
| 100 mM | 0.0285 mL | 0.1427 mL | 0.2854 mL | 0.5708 mL | 0.7135 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Intramolecular cycloaddition reactions of furo[3,4-b]indoles for alkaloid synthesis.[Pubmed:24617539]
J Org Chem. 2014 Apr 4;79(7):3173-84.
Model studies dealing with the Cu(II)- or Rh(II)-catalyzed carbenoid cyclization/cycloaddition cascade of several alpha-diazo indolo amido esters have been carried out as an approach to the alkaloid Scandine. The Cu(II)-catalyzed reaction of an alpha-diazo indolo diester that contains a tethered oxa-pentenyl side chain was found to give rise to a reactive benzo[c]furan which undergoes a subsequent [4 + 2]-cycloaddition across the tethered pi-bond. The reaction proceeds by the initial generation of a copper carbenoid intermediate which cyclizes onto the adjacent carbonyl group to give a reactive benzo[c]furan which in certain cases can be isolated. Disappointingly, the analogous reaction with the related amido indolo ester failed to take place, even when the tethered pi-bond contained an electron-withdrawing carbomethoxy group. It would seem that the geometric requirements for the intramolecular cycloaddition of the furo[3,4-b]indole system with the tethered pi-bond imposes distinct restrictions upon the bond angles of the reacting centers to prevent the cycloaddition reaction from occurring. However, the incorporation of another carbonyl group on the nitrogen atom of the tethered alkenyl diazo amido indolo ester seemingly provides better orbital overlap between the reacting pi-systems and allows the desired cycloaddition reaction to occur.
Melosuavines A-H, cytotoxic bisindole alkaloid derivatives from Melodinus suaveolens.[Pubmed:24274642]
J Nat Prod. 2013 Dec 27;76(12):2322-9.
Eight new bisindole alkaloids, melosuavines A-C (1-3), having an aspidosperma-Scandine linkage, melosuavines D-F (4-6), possessing an aspidosperma-aspidosperma skeleton, and melosuavines G and H (7 and 8) of the aspidosperma-venalatonine type, tenuicausine (9), and melodinine J (10) were isolated from the twigs and leaves of Melodinus suaveolens. The structures of 1-8 were elucidated by extensive spectroscopic methods, and compounds 9 and 10 were identified by comparison with data in the literature. The relative configuration 9 was determined from the ROESY spectrum, and some NMR signals were reassigned. Compounds 1, 2, 4-6, 8, and 10 exhibited low micromolar cytotoxicity against one or more of five human cancer cell lines.
Synthesis of fused tricyclic amines unsubstituted at the ring-junction positions by a cascade condensation, cyclization, cycloaddition then decarbonylation strategy.[Pubmed:22423277]
Beilstein J Org Chem. 2012;8:107-11.
Heating aldehydes that contain a protected hydroxymethyl group, a tethered alkyl chloride and a tethered alkenyl group at the alpha-position of the aldehyde with an amine sets up a cascade (tandem) reaction sequence involving condensation to an intermediate imine, then cyclization and formation of an intermediate azomethine ylide and then intramolecular dipolar cycloaddition. The fused tricyclic products are formed with complete or very high stereochemical control. The hydroxymethyl group was converted into an aldehyde - which could be removed to give the tricyclic amine products that are unsubstituted at the ring junction positions - or was converted into an alkene, which allowed the formation of the core ring system of the alkaloids Scandine and meloscine.
