Leuconolam

CAS# 93710-27-1

Leuconolam

Catalog No. BCN4482----Order now to get a substantial discount!

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Quality Control of Leuconolam

Number of papers citing our products

Chemical structure

Leuconolam

3D structure

Chemical Properties of Leuconolam

Cas No. 93710-27-1 SDF Download SDF
PubChem ID 125060 Appearance Powder
Formula C19H22N2O3 M.Wt 326.4
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CCC12CCCN3C1(C(=CC3=O)C4=CC=CC=C4NC(=O)CC2)O
Standard InChIKey OXDBJKLQCGAPQX-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H22N2O3/c1-2-18-9-5-11-21-17(23)12-14(19(18,21)24)13-6-3-4-7-15(13)20-16(22)8-10-18/h3-4,6-7,12,24H,2,5,8-11H2,1H3,(H,20,22)
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 Leuconolam

The herbs of Alstonia scholaris

Biological Activity of Leuconolam

DescriptionStandard reference
In vitro

Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve.[Pubmed: 28282127]

J Nat Prod. 2017 Apr 28;80(4):1007-1014

Three new monoterpene indole alkaloids (1-3) have been isolated from the bark of Geissospermum laeve, together with the known alkaloids (-)-Leuconolam (4), geissolosimine (5), and geissospermine (6).
METHODS AND RESULTS:
The structures of 1-3 were elucidated by analysis of their HRMS and NMR spectroscopic data. The absolute configuration of geissolaevine (1) was deduced from the comparison of experimental and theoretically calculated ECD spectra. The isolation workflow was guided by a molecular networking-based dereplication strategy using an in-house database of monoterpene indole alkaloids. In addition, five known compounds previously undescribed in the Geissospermum genus were dereplicated from the G. laeve alkaloid extract network and were assigned with various levels of identification confidence. The antiparasitic activities against Plasmodium falciparum and Leishmania donovani as well as the cytotoxic activity against the MRC-5 cell line were determined for compounds 1-5.

Protocol of Leuconolam

Structure Identification
J Nat Prod. 2014 Feb 28;77(2):327-38.

Transformations of the 2,7-Seco Aspidosperma alkaloid leuconolam, structure revision of epi-leuconolam, and partial syntheses of leuconoxine and leuconodines A and F.[Pubmed: 24428198]


METHODS AND RESULTS:
Several transformations of the seco Aspidosperma alkaloid Leuconolam were carried out. The based-induced reaction resulted in cyclization to yield two epimers, the major product corresponding to the optical antipode of a (+)-meloscine derivative. The structures and relative configuration of the products were confirmed by X-ray diffraction analysis. Reaction of Leuconolam and epi-Leuconolam with various acids, molecular bromine, and hydrogen gave results that indicated that the structure of the alkaloid, previously assigned as epi-Leuconolam, was incorrect.
CONCLUSIONS:
This was confirmed by an X-ray diffraction analysis, which revealed that epi-Leuconolam is in fact 6,7-dehydroleuconoxine. Short partial syntheses of the diazaspiro indole alkaloid leuconoxine and the new leuconoxine-type alkaloids leuconodines A and F were carried out.

Org Lett. 2014 Dec 5;16(23):6216-9.

Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.[Pubmed: 25412144]


METHODS AND RESULTS:
Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, Leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton.
CONCLUSIONS:
The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.

Leuconolam Dilution Calculator

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Leuconolam Molarity Calculator

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Preparing Stock Solutions of Leuconolam

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0637 mL 15.3186 mL 30.6373 mL 61.2745 mL 76.5931 mL
5 mM 0.6127 mL 3.0637 mL 6.1275 mL 12.2549 mL 15.3186 mL
10 mM 0.3064 mL 1.5319 mL 3.0637 mL 6.1275 mL 7.6593 mL
50 mM 0.0613 mL 0.3064 mL 0.6127 mL 1.2255 mL 1.5319 mL
100 mM 0.0306 mL 0.1532 mL 0.3064 mL 0.6127 mL 0.7659 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 Leuconolam

Transformations of the 2,7-Seco Aspidosperma alkaloid leuconolam, structure revision of epi-leuconolam, and partial syntheses of leuconoxine and leuconodines A and F.[Pubmed:24428198]

J Nat Prod. 2014 Feb 28;77(2):327-38.

Several transformations of the seco Aspidosperma alkaloid Leuconolam were carried out. The based-induced reaction resulted in cyclization to yield two epimers, the major product corresponding to the optical antipode of a (+)-meloscine derivative. The structures and relative configuration of the products were confirmed by X-ray diffraction analysis. Reaction of Leuconolam and epi-Leuconolam with various acids, molecular bromine, and hydrogen gave results that indicated that the structure of the alkaloid, previously assigned as epi-Leuconolam, was incorrect. This was confirmed by an X-ray diffraction analysis, which revealed that epi-Leuconolam is in fact 6,7-dehydroleuconoxine. Short partial syntheses of the diazaspiro indole alkaloid leuconoxine and the new leuconoxine-type alkaloids leuconodines A and F were carried out.

Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve.[Pubmed:28282127]

J Nat Prod. 2017 Apr 28;80(4):1007-1014.

Three new monoterpene indole alkaloids (1-3) have been isolated from the bark of Geissospermum laeve, together with the known alkaloids (-)-Leuconolam (4), geissolosimine (5), and geissospermine (6). The structures of 1-3 were elucidated by analysis of their HRMS and NMR spectroscopic data. The absolute configuration of geissolaevine (1) was deduced from the comparison of experimental and theoretically calculated ECD spectra. The isolation workflow was guided by a molecular networking-based dereplication strategy using an in-house database of monoterpene indole alkaloids. In addition, five known compounds previously undescribed in the Geissospermum genus were dereplicated from the G. laeve alkaloid extract network and were assigned with various levels of identification confidence. The antiparasitic activities against Plasmodium falciparum and Leishmania donovani as well as the cytotoxic activity against the MRC-5 cell line were determined for compounds 1-5.

Biosynthetically inspired divergent approach to monoterpene indole alkaloids: total synthesis of mersicarpine, leuconodines B and D, leuconoxine, melodinine E, leuconolam, and rhazinilam.[Pubmed:25412144]

Org Lett. 2014 Dec 5;16(23):6216-9.

Inspired by their potential biosynthesis, we have developed divergent total syntheses of seven monoterpene indole alkaloids including mersicarpine, leuconodines B and D, leuconoxine, melodinine E, Leuconolam, and rhazinilam, and one unnatural analogue with an unprecedented structural skeleton. The key steps involve a Witkop-Winterfeldt oxidative indole cleavage followed by transannular cyclization. The transannular cyclization product was then converted to the corresponding structural skeletons by pairing its functional groups into different reaction modes.

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