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

A further alkaloid present in Adhatoda vasica and Peganum harmala, this base forms colourless crystals from 95 per cent EtOH. It has [α]22D - 100° (c 0.5, CHCL3) and the ultraviolet spectrum has absorption maxima at 227, 272, 302 and 315 mfJ.. The alkaloid yields a series of crystalline salts with mineral acids, e.g. the hydrochloride, m.p. 232-4°C; hydro bromide, m.p. 254-5°C (dec.); hydriodide, m.p. 222-6°C (dec.); nitrate, m.p. 138-9° C (dec.) and the sulphate, m.p. l82-5°C (dec.). The optically inactive form of the base has been prepared synthetically, m.p. 211- 2°C. The alkaloid is an active bronchodilator.

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 
• 226070-17-3 7,8-dihydropyrrolo[2,1-b]quinazoline-6,10-dione 
• 1227263-77-5 (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol 
• 182058-08-8 O-tert-butydimethylsilylvasicinone 
• 6159-55-3 (+)-vasicinol 
• 182058-02-2 (S)-1-(2-Azido-benzoyl)-3-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-one 
• 72710-66-8 (+/-)-acetylvasicinone 
• 71540-68-6 3-bromo-3-deoxyvasicinone 
• 125659-45-2 1-(2-azidobenzoyl)azacyclopent-2-one 
• 34897-85-3 o-azidobenzoyl chloride 
• 31162-13-7 2-azidobenzoic acid 
• 28144-70-9 anthranilic acid amide 
• 391249-56-2 1-[1(S),3-dihydroxypropyl]quinazolin-4(1H)-one 
• 108-05-4 vinyl acetate 

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.