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Febrifugine

$258

  • Brand : BIOFRON

  • Catalogue Number : AV-H03078

  • Specification : 98%

  • CAS number : 24159-07-7

  • Formula : C16H19N3O3

  • Molecular Weight : 301.34

  • PUBCHEM ID : 115723

  • Volume : 20mg

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Catalogue Number

AV-H03078

Analysis Method

HPLC,NMR,MS

Specification

98%

Storage

2-8°C

Molecular Weight

301.34

Appearance

White powder

Botanical Source

Dichroa febrifuga Lour./Alkaloid from Root and leaves of the Chinese drug Ch'ang Shan (Dichroa febrifuga) and from Hydrangea spp. (Hydrangeaceae)

Structure Type

Category

Standards;Natural Pytochemical;API

SMILES

C1CC(C(NC1)CC(=O)CN2C=NC3=CC=CC=C3C2=O)O

Synonyms

3-{3-[(2S,3R)-3-Hydroxypiperidin-2-yl]-2-oxopropyl}quinazolin-4(3H)-one/3-[b-Keto-g-(3-hydroxy-2-piperidyl)propyl]-4-quinazolone/(2S-trans)-3-[3-(3-Hydroxy-2-piperidinyl)-2-oxopropyl]-4(3H)-quinazolinone/3-{3-[(2S,3R)-3-Hydroxy-2-piperidinyl]-2-oxopropyl}-4(3H)-quinazolinone/b-Dichroine/β-Dichroine/4(3H)-Quinazolinone, 3-[3-[(2S,3R)-3-hydroxy-2-piperidinyl]-2-oxopropyl]-/Febrifugine/febrifungineFebrifugine (8CI)

IUPAC Name

3-[3-(3-hydroxypiperidin-2-yl)-2-oxopropyl]quinazolin-4-one

Density

1.4±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

261.1±32.9 °C

Boiling Point

508.2±60.0 °C at 760 mmHg

Melting Point

139-140°; mp 154-156°

InChl

InChI=1S/C16H19N3O3/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22/h1-2,4-5,10,14-15,17,21H,3,6-9H2/t14-,15+/m0/s1

InChl Key

FWVHWDSCPKXMDB-LSDHHAIUSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:24159-07-7) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

29681487

Abstract

The quinazolinone-containing 2,3-disubstituted piperidines febrifugine and isofebrifugine have been the subject of significant research efforts since their occurrence in Dichroa febrifuga and their anti-malarial actions were first described in the late 1940s. Subsequently they have also been shown to be present in other plants belonging to the hydrangea family and various analogues of febrifugine have been prepared in attempts to tune biological properties. The most notable analogue is termed halofuginone and a substantial body of work now demonstrates that this compound possesses potent human disease relevant activities. This review focuses on the literature associated with efforts dedicated towards uncovering the structures of febrifugine and isofebrifugine, the development of practical methods for their synthesis and the syntheses of structural analogues.

Copyright ? 2018 Elsevier Ltd. All rights reserved.

KEYWORDS

3-hydroxypiperidine; Anti-angiogenic; Anti-fibrotic; Anti-protozoal; Dichroine A and B; Febrifugine; Halofuginone; Isofebrifugine; Isomerization; Quinazolinone

Title

Chemical synthesis of febrifugine and analogues.

Author

Smullen S1, McLaughlin NP1, Evans P2.

Publish date

2018 May 15;

PMID

29552823

Abstract

A quantitative nuclear magnetic resonance method(qNMR) was established for determination of the absolute content of febrifugine. Proton nuclear magnetic resonance spectroscopy of febrifugine was obtained in DMSO-d? with hydroquinone as the internal standard substance on a Bruker Ascend 600 MHz superconducting nuclear resonance spectrometer at 298 K. The specific parameters were as follows: the observing frequency was 600 MHz,spectra width was 7 211 Hz, pulse width was 9.70 μs, pulse sequence was zg30,scan times was 32 and relaxation time was 2 s. The proton signal peaked at δ 7.71 for febrifugine and δ 6.55 for hydroquinone were selected as the quantification peaks. Linear regression of quantitative peak area ratio of febrifugine-hydroquinone versus their mass ratio yielded a correlation coefficient of 0.999 6 and a regression equation of Y=0.083 3X+0.008 6.The linear range of febrifugine was 2.17-17.07 g·L?¹,the precision RSD was 0.78%(n=6),the repeatability RSD was 1.2%(n=6),and the contents of three batches of febrifugine sample were 94.91%,95.09% and 95.52%,respectively. The content of febrifugine was 96.44% determined by high performance liquid chromatography(HPLC). The relative error of the content of febrigugine determinted by qNMR and HPLC methods was 1.27%. The results showed that the internal standard method of proton nuclear magnetic resonance spectroscopy could be used to determine the absolute content of febrifugine.

Copyright? by the Chinese Pharmaceutical Association.

KEYWORDS

absolute content ; febrifugine ; quantitative nuclear magnetic resonance method

Title

[Quantitative determination of febrifugine by proton nuclear magnetic resonance spectroscopy with internal standard method].

Author

Zhang JY1,2,3, Fan XR1,2, Liu XQ1,2, Yu XW4, Yang LX1,2, Guo ZT5, Feng WH1,2, Wang ZM1,2, Li C1,2.

Publish date

2018 Jan;

PMID

29171238

Abstract

To investigate the stability and degradation kinetics of febrifugine. The results showed that within 24 hours, febrifugine content was decreased by only 1% in mobile phase solvent, but its content was decreased to be 90% of the initial content in the water, methanol, 50% methanol and 10% acetonitrile solution. When the pH value of the solution was between 3 and 7, the retention rate of febrifugine in 24 hours was over 98%, but its content was decreased by about 12% in alkaline solution (pH 9.0). The higher the temperature, the worse the stability of febrifugine. At 40-80 ℃, the content of febrifugine was decreased to be 60% of its initial content in 10 hours, but the content was decreased by only 5% in 10 h at 20 ℃.However, no matter 40 ℃or 60 ℃, febrifugine was mainly transformed into isofebrifugine, and the total content of febrifugine and isofebrifugine was equal to their initial total content in 10 hours, while incase of 80 ℃, the total content was decreased to be 83.33% in 10 h, which suggested that the structure of febrifugine was absolutely changed, not just isomerized to be isofebrigugine at high temperature. Light had a significant impact on the stability of febrifugine. Under bright light, the content of febrifugine was reduced by about 23% in 108 h, but it only decreased by about 10% in the natural light or darkness. In artificial gastric fluid (pH 1.4) and artificial intestinal fluid (pH 6.8), the content of febrifugine was decreased by less than 5% in 10 h. After storage at high temperature(60 ℃), high humidity [(75±1)%] and strong light (3 000 lx) conditions for 10 d, the content of solid febrifugine was decreased by 0.27%, 7.6% and 5.39%, respectively. The degradation of febrifugine basically complied with the first-order reaction kinetic process in the following conditions: in water, methanol, 50%methanol and 10% acetonitrile solvents, alkaline solution (pH>7), different light intensity and different temperatures (20,40 ℃). Therefore, no matter the isolation and purification of febrifugine or the production of the related preparations, it should be done fast in the acidic solution, low temperature and dark conditions, while the febrifugine solid should be kept in dry and dark conditions.

Copyright? by the Chinese Pharmaceutical Association.

KEYWORDS

HPLC ; febrifugine ; stability

Title

[Investigation on stability and degradation kinetics of febrifugine].

Author

Zhang JY1,2,3, Liu XQ2,3, Yang LX2,3, Feng WH2,3, Wang ZM2,3, Li C2,3.

Publish date

2017 Aug


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