Infractin

CAS# 91147-07-8

Infractin

Catalog No. BCN3652----Order now to get a substantial discount!

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Quality Control of Infractin

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Chemical structure

Infractin

3D structure

Chemical Properties of Infractin

Cas No. 91147-07-8 SDF Download SDF
PubChem ID 5319542 Appearance Cryst.
Formula C15H14N2O2 M.Wt 254.3
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name methyl 3-(9H-pyrido[3,4-b]indol-1-yl)propanoate
SMILES COC(=O)CCC1=NC=CC2=C1NC3=CC=CC=C23
Standard InChIKey IYWBIIGDWQBZJQ-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H14N2O2/c1-19-14(18)7-6-13-15-11(8-9-16-13)10-4-2-3-5-12(10)17-15/h2-5,8-9,17H,6-7H2,1H3
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 Infractin

The barks of Picrasma quassioides

Protocol of Infractin

Structure Identification
Liebigs Annalen der Chemie, 1993, 1993(2).

Synthesis of Manzamine C, Infractine and 6‐Hydroxyinfractine.[Reference: WebLink]


METHODS AND RESULTS:
Manzamine C (1), a β‐carboline alkaloid with antitumor activity isolated from the marine sponge Haliclona sp. was synthesized. The dilithium derivative of 5‐hexynoic acid (6) was alkylated with 7 to give after esterification the methyl 10‐hydroxy‐5‐decynoate (8). The tosylate of 8 was converted into the azide 9 which could be selectively hydrogenated with Lindlar palladium catalyst to give the amino ester 10. Saponification of 10 and acylation with (Boc)2O yielded 11, which was converted with pentafluorophenol into 12. Removal of the Boc group in 12 gave an amino ester as intermediate, which cyclized immediately under high dilution conditions to give the lactam 13 in high yield. Reduction of 13 with LiAlH4 produced the macrocyclic amine 4. The β‐carboline part of 1 was prepared by condensation of N‐benzyltryptamine 14 with the formylacetic acid equivalent 15 to give 16. Dehydrogenation of 16 with Pd‐on‐carbon catalyst led to the orthoester 17, which could be converted into the methyl ester 5 in high overall yield. The 4‐(dimethylamino)pyridine‐catalyzed substitution of the methyl ester function in 5 by the amine 4 gave the amide 29. The analogous reaction of 5 with pyrrolidine or with azacyclotridecane yielded 30 and 31. Reduction of these three amides with LiAlH4 produced 1, 2 and 3.
CONCLUSIONS:
The spectroscopic properties of 1 were identical with those of natural manzamine C. – Condensation of 14 or N‐benzyl‐5‐(benzyloxy)tryptamine (19) with aldehyde 18 yielded the products 20 and 21, which could be dehydrogenated to furnish 22 and 23. From these the methyl esters 24 and 25 with properties identical to those of the known β‐carboline alkaloids Infractine and 6‐hydroxyInfractine could be obtained.

Infractin Dilution Calculator

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Preparing Stock Solutions of Infractin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.9324 mL 19.6618 mL 39.3236 mL 78.6473 mL 98.3091 mL
5 mM 0.7865 mL 3.9324 mL 7.8647 mL 15.7295 mL 19.6618 mL
10 mM 0.3932 mL 1.9662 mL 3.9324 mL 7.8647 mL 9.8309 mL
50 mM 0.0786 mL 0.3932 mL 0.7865 mL 1.5729 mL 1.9662 mL
100 mM 0.0393 mL 0.1966 mL 0.3932 mL 0.7865 mL 0.9831 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 Infractin

[A new indole alkaloid from the stems of Brucea mollis].[Pubmed:24761613]

Yao Xue Xue Bao. 2014 Feb;49(2):225-9.

Eight compounds were isolated from the stems of Brucea mollis by various chromatographic techniques such as column chromatography on silica gel and Sephadex LH-20, and preparative HPLC, and their structures were elucidated as bruceolline O (1), 1-(1-beta-glucopyranosyl)-1H-indole-3-carbaldehyde (2), canthin-6-one (3), 11-hydroxycanthin-6-one (4), 9-methoxycanthin-6-one (5), 4-methoxycanthin-6-one (6), Infractin (7), and beta-carboline-1-propionic acid (8). The cytotoxic activities of compounds 1-8 against HCT-8 and A549 human cell lines were determined, but none of them exhibited significant activity (IC 50 > 10 micromol x L(-1)). Among them, compound 1 is a new indole alkaloid, and compounds 2 and 5-7 were isolated from this plant for the first time.

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