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

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

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 
• 125659-45-2 1-(2-azidobenzoyl)azacyclopent-2-one 
• 226070-17-3 7,8-dihydropyrrolo[2,1-b]quinazoline-6,10-dione 
• 6159-55-3 (+)-vasicinol 
• 1227263-77-5 (3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol 
• 182058-08-8 O-tert-butydimethylsilylvasicinone 
• 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 
• 34897-85-3 o-azidobenzoyl chloride 
• 31162-13-7 2-azidobenzoic acid 
• 391249-54-0 methyl β-(S)-acetoxy-o-amidosuccinanilate 
• 391249-53-9 β(S)-acetoxy-o-amidosuccinanilic acid 
• 28144-70-9 anthranilic acid amide 

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.

Redox Condensations of o-Nitrobenzaldehydes with Amines under Mild Conditions: Total Synthesis of the Vasicinone Family

A total synthesis of the vasicinone family of natural products from bulk chemicals was developed. Reductive condensation of o-nitrobenzaldehydes with amines utilizing iron pentacarbonyl as a reducing agent followed by subsequent oxidation leads to a great variety of polycyclic nitrogen-containing heterocycles under mild conditions. Enantiomerically pure vasicinone, rutaecarpine, isaindigotone, and luotonin were synthesized from readily available starting materials like hydroxyproline, nitrobenzaldehyde, pyrrolidine, and piperidine in two to four operational steps without chromatography. The antifungal activity of all products was tested.

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).

Natural (-)-vasicine as a novel source of optically pure 1-benzylpyrrolidin-3-ol

A facile and scalable methodology for the preparation of optically active (3S)-1-benzylpyrrolidin-3-ol (3), an important drug precursor, is reported. Starting from the naturally occurring alkaloid (-)-vasicine (1), a major alkaloid of the plant Adhatoda vasica, 3 was obtained in 84% overall yield (Scheme 3). Copyright

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.

A polymer-assisted solution-phase strategy for the synthesis of fused [2,1-b]quinazolinones and the preparation of optically active vasicinone

An efficient preparation of fused [2,1-b]quinazolinones has been developed utilizing polymer-supported reagents. (±)- Vasicinone was converted into its dione by oxidation with poly (4-vinylpyridiniumdichromate). An efficient method has been developed for the synthesis of (d)- and (l)-vasicinone via asymmetric reduction of pyrrolo[2,1-b]quinazoline-3,9-dione by employing NaBH4/Me3SiCl as the reducing agent and polymer-supported chiral sulfonamide as catalyst. Georg Thieme Verlag Stuttgart.

Chemoenzymatic synthesis of pyrrolo[2,1-b]quinazolinones: Lipase-catalyzed resolution of vasicinone

A facile synthesis of bronchodilatory pyrrolo[2,1-b]quinazoline alkaloids by azidoreductive cyclization strategy employing TMSCl-NaI and bakers' yeast is described. Both the chemical and enzymatic methods are mild and take place at room temperature in good yields. Further, synthesis and resolution of vasicinone has been carried out by employing different lipases. It has been observed that lipase PS provides acetate of (S)-vasicinone in 98% ee.

Synthesis of optically active vasicinone based on intramolecular aza-Wittig reaction and asymmetric oxidation

Both optical isomers of a quinazoline alkaloid, vasicinone, were synthesized by two different methods. The first method used (3S)-3-hydroxy-γ-lactam as a chiral synthon, which was, after O-TBDMS protection, o-azidobenzoylated followed by treatment with tri-n-butylphosphine to afford (S)-(-)-vasicinone via the tandem Staudinger/intramolecular aza-Wittig reaction. The second method utilized asymmetric oxygenation of deoxyvasicinone with (1S)-(+)- or (1R)-(-)-(10-camphorsulfonyl)oxaziridine (the Davis reagent), respectively. The aza-enolate anion of deoxyvasicinone was treated with (S)-(+)-reagent to afford (R)-(+)-vasicinone in 71% ee, while the reaction with (R)-(-)-reagent gave (S)-(-)-vasicinone in 62% ee. The optical purity was analyzed by HPLC on specially modified cellulose as a stationary phase. These results provided a facile method to prepare both optical isomers of vasicinone and confirmed the recently reversed stereochemistry of natural (-)-vasicinone.