Apparicine

CAS# 2122-36-3

Apparicine

Catalog No. BCN4008----Order now to get a substantial discount!

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Quality Control of Apparicine

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Chemical structure

Apparicine

3D structure

Chemical Properties of Apparicine

Cas No. 2122-36-3 SDF Download SDF
PubChem ID 5281349 Appearance Powder
Formula C18H20N2 M.Wt 264.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC=C1CN2CCC1C(=C)C3=C(C2)C4=CC=CC=C4N3
Standard InChIKey LCVACABZTLIWCE-CRAFIKPXSA-N
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.
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.
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.

Source of Apparicine

The herbs of Voacanga africana

Biological Activity of Apparicine

DescriptionStandard reference
In vitro

Anti-malarial activity of indole alkaloids isolated from Aspidosperma olivaceum.[Pubmed: 24731256 ]

Malar J. 2014 Apr 14;13:142.

Several species of Aspidosperma (Apocynaceae) are used as treatments for human diseases in the tropics.
METHODS AND RESULTS:
Aspidosperma olivaceum, which is used to treat fevers in some regions of Brazil, contains the monoterpenoid indole alkaloids (MIAs) aspidoscarpine, uleine, Apparicine, and N-methyl-tetrahydrolivacine. Using bio-guided fractionation and cytotoxicity testing in a human hepatoma cell line, several plant fractions and compounds purified from the bark and leaves of the plant were characterized for specific therapeutic activity (and selectivity index, SI) in vitro against the blood forms of Plasmodium falciparum.

Protocol of Apparicine

Structure Identification
J Org Chem. 2014 Jul 3;79(13):6389-93.

Convergent approach to the tetracyclic core of the apparicine class of indole alkaloids via a key intermolecular nitrosoalkene conjugate addition.[Pubmed: 24927230]


METHODS AND RESULTS:
Readily available methyl 3-formylindol-2-ylacetate and N-tosyl-4-chloro-3-piperidone oxime have been used to construct the tetracyclic skeleton of the Apparicine class of monoterpene indole alkaloids in only four steps in 80% overall yield.
CONCLUSIONS:
Key transformations in this convergent approach involve use of an intermolecular ester enolate/nitrosoalkene conjugate addition to form the C-15/16 bond, followed by a reductive cyclization to construct the C-ring of the tetracycle.

J Org Chem. 2009 Nov 6;74(21):8359-68.

Total synthesis of the bridged indole alkaloid apparicine.[Pubmed: 19824689]


METHODS AND RESULTS:
An indole-templated ring-closing metathesis or a 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid Apparicine. From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents.

Apparicine Dilution Calculator

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Preparing Stock Solutions of Apparicine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.7821 mL 18.9107 mL 37.8215 mL 75.643 mL 94.5537 mL
5 mM 0.7564 mL 3.7821 mL 7.5643 mL 15.1286 mL 18.9107 mL
10 mM 0.3782 mL 1.8911 mL 3.7821 mL 7.5643 mL 9.4554 mL
50 mM 0.0756 mL 0.3782 mL 0.7564 mL 1.5129 mL 1.8911 mL
100 mM 0.0378 mL 0.1891 mL 0.3782 mL 0.7564 mL 0.9455 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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References on Apparicine

Anti-malarial activity of indole alkaloids isolated from Aspidosperma olivaceum.[Pubmed:24731256]

Malar J. 2014 Apr 14;13:142.

BACKGROUND: Several species of Aspidosperma (Apocynaceae) are used as treatments for human diseases in the tropics. Aspidosperma olivaceum, which is used to treat fevers in some regions of Brazil, contains the monoterpenoid indole alkaloids (MIAs) aspidoscarpine, uleine, Apparicine, and N-methyl-tetrahydrolivacine. Using bio-guided fractionation and cytotoxicity testing in a human hepatoma cell line, several plant fractions and compounds purified from the bark and leaves of the plant were characterized for specific therapeutic activity (and selectivity index, SI) in vitro against the blood forms of Plasmodium falciparum. METHODS: The activity of A. olivaceum extracts, fractions, and isolated compounds was evaluated against chloroquine (CQ)-resistant P. falciparum blood parasites by in vitro testing with radiolabelled [3H]-hypoxanthine and a monoclonal anti-histidine-rich protein (HRPII) antibody. The cytotoxicity of these fractions and compounds was evaluated in a human hepatoma cell line using a 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyl tetrazolium bromide (MTT) assay, and the SI was calculated as the ratio between the toxicity and activity. Two leaf fractions were tested in mice with Plasmodium berghei. RESULTS: All six fractions from the bark and leaf extracts were active in vitro at low doses (IC50 < 5.0 mug/mL) using the anti-HRPII test, and only two (the neutral and basic bark fractions) were toxic to a human cell line (HepG2). The most promising fractions were the crude leaf extract and its basic residue, which had SIs above 50. Among the four pure compounds evaluated, aspidoscarpine in the bark and leaf extracts showed the highest SI at 56; this compound, therefore, represents a possible anti-malarial drug that requires further study. The acidic leaf fraction administered by gavage to mice with blood-induced malaria was also active. CONCLUSION: Using a bio-monitoring approach, it was possible to attribute the anti-P. falciparum activity of A. olivaceum to aspidoscarpine and, to a lesser extent, N-methyl-tetrahydrolivacine; other isolated MIA molecules were active but had lower SIs due to their higher toxicities. These results stood in contrast to previous work in which the anti-malarial activity of other Aspidosperma species was attributed to uleine.

The first total synthesis of (+/-)-apparicine.[Pubmed:19503874]

Chem Commun (Camb). 2009 Jun 21;(23):3372-4.

The first total synthesis of the indole alkaloid Apparicine has been developed through a sequence that includes an indole-templated ring-closing metathesis and a vinyl halide Heck cyclization.

Total synthesis of the bridged indole alkaloid apparicine.[Pubmed:19824689]

J Org Chem. 2009 Nov 6;74(21):8359-68.

An indole-templated ring-closing metathesis or a 2-indolylacyl radical cyclization constitute the central steps of two alternative approaches developed to assemble the tricyclic ABC substructure of the indole alkaloid Apparicine. From this key intermediate, an intramolecular vinyl halide Heck reaction accomplished the closure of the strained 1-azabicyclo[4.2.2]decane framework of the alkaloid with concomitant incorporation of the exocyclic alkylidene substituents.

Convergent approach to the tetracyclic core of the apparicine class of indole alkaloids via a key intermolecular nitrosoalkene conjugate addition.[Pubmed:24927230]

J Org Chem. 2014 Jul 3;79(13):6389-93.

Readily available methyl 3-formylindol-2-ylacetate and N-tosyl-4-chloro-3-piperidone oxime have been used to construct the tetracyclic skeleton of the Apparicine class of monoterpene indole alkaloids in only four steps in 80% overall yield. Key transformations in this convergent approach involve use of an intermolecular ester enolate/nitrosoalkene conjugate addition to form the C-15/16 bond, followed by a reductive cyclization to construct the C-ring of the tetracycle.

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