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Deoxyvasicinone

$960

  • Brand : BIOFRON

  • Catalogue Number : BN-O1523

  • Specification : 99%(HPLC)

  • CAS number : 530-53-0

  • Formula : C11H10N2O

  • Molecular Weight : 186.2

  • PUBCHEM ID : 68261

  • Volume : 5mg

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Catalogue Number

BN-O1523

Analysis Method

HPLC,NMR,MS

Specification

99%(HPLC)

Storage

-20℃

Molecular Weight

186.2

Appearance

Powder

Botanical Source

This product is isolated and purified from the herbs of Galium aparine L.

Structure Type

Alkaloids

Category

Standards;Natural Pytochemical;API

SMILES

C1CC2=NC3=CC=CC=C3C(=O)N2C1

Synonyms

Pyrrolo[2,1-b]quinazolin-9(1H)-one, 2,3-dihydro-/Deoxyvasicinone/2,3-Dihydropyrrolo[2,1-b]quinazolin-9(1H)-one/Pyrrolo(2,1-b)quinazolin-9(1H)-one, 2,3-dihydro-/Deoxypeganine/3H-Quinazolin-4-one,2,3-trimethyleno/desoxyvascinone/2,3-Trimethylene-4-quinazolone

IUPAC Name

2,3-dihydro-1H-pyrrolo[2,1-b]quinazolin-9-one

Density

1.4±0.1 g/cm3

Solubility

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

Flash Point

162.6±23.2 °C

Boiling Point

345.3±25.0 °C at 760 mmHg

Melting Point

InChl

InChI=1S/C11H10N2O/c14-11-8-4-1-2-5-9(8)12-10-6-3-7-13(10)11/h1-2,4-5H,3,6-7H2

InChl Key

VARHXCYGZKSOOO-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:530-53-0) 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

28923380

Abstract

A series of multitarget ligands was designed by introducing several structurally diverse aminoacetamide groups at position 6 of the deoxyvasicinone group, with the aim of obtaining novel multifunctional anti-Alzheimer’s disease agents using deoxyvasicinone as the substrate. In vitro studies showed that almost all of the derivatives were potent inhibitors of human recombinant acetylcholinesterase (hAChE) and human serum butyrylcholinesterase (hBChE), with IC50 values in the low nanomolar range, and exhibited moderate to high inhibition of Aβ1-42 self-aggregation. In particular, compounds 12h, 12n, and 12q showed promising inhibitory activity for hAChE, with IC50 values of 5.31 ± 2.8, 4.09 ± 0.23, and 7.61 ± 0.53 nM, respectively. Compounds 12h and 12q also exhibited the greatest ability to inhibit hBChE, with IC50 values of 4.35 ± 0.32 and 2.35 ± 0.14 nM, respectively. Moreover, enzyme kinetics confirmed that compound 12q caused a mixed type of AChE inhibition, by binding to both the active sites (PAS and CAS) of AChE. Remarkably, compound 12q also demonstrated the highest potential inhibitory activity for Aβ1-42 self-aggregation (63.9 ± 4.9%, 10 μM), and it was also an excellent metal chelator.

KEYWORDS

Alzheimer's disease; Cholinesterase inhibitors; Deoxyvasicinone derivatives; Inhibition of Aβ(1−42) self-aggregation; Metal chelator.

Title

Novel Deoxyvasicinone Derivatives as Potent Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease: Design, Synthesis, and Biological Evaluation

Author

Fang Ma 1, Hongtao Du 2

Publish date

2017 Nov 10;

PMID

25196325

Abstract

NEDD8-activating enzyme (NAE) controls the specific degradation of proteins regulated by cullin-RING ubiquitin E3 ligases, and has been considered as an attractive molecular target for the development of drugs against cancer. A pharmacophore model constructed from a training set of deoxyvasicinone derivatives was used to screen 376 compounds from an analogue database. From the initial screening, the valine-linked deoxyvasicinone derivative 9 and the N-isopropyl-linked deoxyvasicinone derivative 10 emerged as the top scoring candidates. Compounds 9 and 10 showed micromolar potencies in both cell-free and cell-based systems, with selectivity for NAE over the related enzymes SAE and UAE. Molecular modelling analysis suggested that 9 and 10 may inhibit NAE by blocking the ATP-binding domain. Thus, these deoxyvasicinone derivatives could be considered as promising lead molecules for the development of more potent inhibitors of NAE.

KEYWORDS

Deoxyvasicinone; Drug discovery; NEDD8; Pharmacophore; Ubiquitin-like.

Title

Discovery of Deoxyvasicinone Derivatives as Inhibitors of NEDD8-activating Enzyme

Author

Hai-Jing Zhong 1, Ka-Ho Leung 2, Sheng Lin 2, Daniel Shiu-Hin Chan 2, Quan-Bin Han 3, Sharon Lai-Fung Chan 4, Dik-Lung Ma 5, Chung-Hang Leung 6

Publish date

2015 Jan;

PMID

26166311

Abstract

A phytochemical study on the methanol extracts from the seeds of Peganum harmala L. led to a new quizonaline alkaloid (S)-vasicinone-1-O-β-d-glucopyranoside (1) and four known ones, (R)-vasicinone-1-O-β-d-glucopyranoside (2), (S)-vasicinone (3), vasicine (4), and deoxyvasicinone (5). Their structures were elucidated by spectroscopic analysis including IR, HR-ESI-MS, 1D and 2D NMR, and specific rotation as well as by comparison of the data with those in the literature. All of the alkaloids were screened for antiproliferative activity against human gastric cancer cells MCG-803 with MTT method. Compounds 1 and 3 exhibited moderate inhibitory activity.

KEYWORDS

(S)-vasicinone-1-O-β-d-glucopyranoside; Peganum harmala; Zygophyllaceae; antiproliferative activity; quizonaline alkaloids.

Title

Antitumor Quinazoline Alkaloids From the Seeds of Peganum Harmala

Author

Chun-Hua Wang 1, Hong Zeng, Yi-Hai Wang, Chuan Li, Jun Cheng, Zhi-Jun Ye, Xiang-Jiu He

Publish date

2015 May;


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