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.
28923380
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.
Alzheimer's disease; Cholinesterase inhibitors; Deoxyvasicinone derivatives; Inhibition of Aβ(1−42) self-aggregation; Metal chelator.
Novel Deoxyvasicinone Derivatives as Potent Multitarget-Directed Ligands for the Treatment of Alzheimer's Disease: Design, Synthesis, and Biological Evaluation
Fang Ma 1, Hongtao Du 2
2017 Nov 10;
25196325
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.
Deoxyvasicinone; Drug discovery; NEDD8; Pharmacophore; Ubiquitin-like.
Discovery of Deoxyvasicinone Derivatives as Inhibitors of NEDD8-activating Enzyme
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
2015 Jan;
26166311
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.
(S)-vasicinone-1-O-β-d-glucopyranoside; Peganum harmala; Zygophyllaceae; antiproliferative activity; quizonaline alkaloids.
Antitumor Quinazoline Alkaloids From the Seeds of Peganum Harmala
Chun-Hua Wang 1, Hong Zeng, Yi-Hai Wang, Chuan Li, Jun Cheng, Zhi-Jun Ye, Xiang-Jiu He
2015 May;
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