486-64-6

Basic information

• Product Name: VASICINONE
• Synonyms: VASICINONE;(3R)-2,3-Dihydro-3-hydroxypyrrolo[2,1-b]quinazolin-9(1H)-one;(3R)-2,3-Dihydro-3β-hydroxypyrrolo[2,1-b]quinazoline-9(1H)-one;2,3-Dihydro-3-hydroxypyrrolo[2,1-b]quinazolin-9(1H)-one;l-Vasicinone
• CAS NO: 486-64-6
• Molecular Formula: C₁₁H₁₀N₂O₂
• Molecular Weight: 202.21
• Product Categories: Alkaloids
• Mol File: 486-64-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 200-202℃
• Boiling Point: 320.7°C (rough estimate)
• Flash Point: 201.7°C
• Appearance: /
• Density: 1.50
• Vapor Pressure: 1.88E-07mmHg at 25°C
• Refractive Index: 1.5300 (estimate)
• PKA: 12.76±0.20(Predicted)
• Water Solubility: 1.597g/L(25 oC)
• CAS DataBase Reference: VASICINONE(CAS DataBase Reference)
• NIST Chemistry Reference: VASICINONE(486-64-6)
• EPA Substance Registry System: VASICINONE(486-64-6)

Safety Data

• Hazardous Substances Data: 486-64-6(Hazardous Substances Data)

Usage

Description

VASICINONE is an alkaloid found in Adhatoda vasica and Peganum harmala, which forms colorless crystals from 95% ethanol. It has a specific rotation of [α]22D 100° (c 0.5, CHCL3) and exhibits absorption maxima at 227, 272, 302, and 315 nm in the ultraviolet spectrum. The alkaloid can yield a series of crystalline salts with mineral acids, such as hydrochloride, hydro bromide, hydriodide, nitrate, and sulfate. The optically inactive form of the base has been synthesized, with a melting point of 211-2°C. VASICINONE is an active bronchodilator.

Uses

Used in Pharmaceutical Industry:
VASICINONE is used as a bronchodilator for treating respiratory conditions, such as asthma and chronic obstructive pulmonary disease (COPD). Its bronchodilating properties help in relaxing the smooth muscles of the airways, allowing for easier breathing and improved lung function.
Used in Chemical Research:
VASICINONE can be used as a research compound for studying its chemical properties, interactions with other compounds, and potential applications in the development of new drugs and therapies. Its ability to form crystalline salts with mineral acids makes it an interesting subject for chemical investigations.
Used in Drug Synthesis:
The optically inactive form of VASICINONE, which has been synthesized, can be used in the development of new drugs with potential therapeutic applications. Its unique chemical properties and bronchodilating effects may contribute to the creation of novel medications for respiratory and other health conditions.

References

Ghose et al., J. Chem. Soc., 2740 (1932) Morris, Horford, Adams., J. Amer. Chem. Soc., 57,951 (1935) Mehta, Naravane, Desai., J. Org. Chem., 28, 445 (1963)

InChI:InChI=1/C11H10N2O2/c14-9-5-6-13-10(9)12-8-4-2-1-3-7(8)11(13)15/h1-4,9,14H,5-6H2/t9-/m0/s1

Upstream product

• 530-53-0 deoxyvasicinone 
• 182058-08-8 O-tert-butydimethylsilylvasicinone 
• 108-05-4 vinyl acetate 
• 35387-16-7 (+/-)-vasicinone 
• 328571-50-2 (S)-acetylvasicinone 
• 391249-56-2 1-[1(S),3-dihydroxypropyl]quinazolin-4(1H)-one 
• 28144-70-9 anthranilic acid amide 
• 391249-53-9 β(S)-acetoxy-o-amidosuccinanilic acid 
• 391249-54-0 methyl β-(S)-acetoxy-o-amidosuccinanilate 
• 31162-13-7 2-azidobenzoic acid 
• 34897-85-3 o-azidobenzoyl chloride 
• 125659-45-2 1-(2-azidobenzoyl)azacyclopent-2-one 
• 71540-68-6 3-bromo-3-deoxyvasicinone 
• 72710-66-8 (+/-)-acetylvasicinone 

Relevant articles and documents

Antitumor quinazoline alkaloids from the seeds of Peganum harmala

A phytochemical study on the methanol extracts from the seeds of Peganum harmala L. led to a new quizonaline alkaloid (S)-vasicinone-1-O-b-D-glucopyranoside (1) and four known ones, (R)-vasicinone-1-O-b-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.

Reversible P(III)/P(V) redox: Catalytic aza-Wittig reaction for the synthesis of 4(3H)-quinazolinones and the natural product vasicinone

The catalytic aza-Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by-product triphenylphosphine oxide (Ph 3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza-Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)-quinazolinones and the natural product (S)-vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O-i-Pr)4] reductant system (81-95% yields and >99% ee).

Toward new camptothecins. Part 5: On the synthesis of precursors for the crucial Friedl?nder reaction

The synthesis of potential precursors of ketones, which could be used to obtain camptothecin analogs, is described. Noteworthy is the difference of reactivity between indolizinone and pyrrolidinoquinazolinone heterocycle.