84-55-9

Basic information

• Product Name: viquidil
• Synonyms: viquidil;1-(6-Methoxy-4-quinolyl)-3-[(3R,4R)-3-vinyl-4-piperidinyl]-1-propanone;Chinicine;Quinotoxine;Quinotoxol;1-(6-methoxy-4-quinolyl)-3-[(3R,4R)-3-vinyl-4-piperidyl]propan-1-one;3-[(3R,4R)-3-ethenylpiperidin-4-yl]-1-(6-methoxyquinolin-4-yl)propan-1-one;d-quinotoxine
• CAS NO: 84-55-9
• Molecular Formula: C₂₀H₂₄N₂O₂
• Molecular Weight: 324.422
• EINECS: 201-540-1
• Mol File: 84-55-9.mol
• Article Data: 9

Chemical Properties

• Melting Point: 60°C
• Boiling Point: 462.75°C (rough estimate)
• Flash Point: 252°C
• Appearance: /
• Density: 1.1294 (rough estimate)
• Vapor Pressure: 7.23E-10mmHg at 25°C
• Refractive Index: 1.6800 (estimate)
• CAS DataBase Reference: viquidil(CAS DataBase Reference)
• NIST Chemistry Reference: viquidil(84-55-9)
• EPA Substance Registry System: viquidil(84-55-9)

Safety Data

• Hazardous Substances Data: 84-55-9(Hazardous Substances Data)

Usage

Originator

Desclidium,Spret ,France,1972

Uses

1-(6-Methoxyquinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)propan-1-one (CAS# 84-55-9) is in intermediate in the synthesis of Quinotoxine Hydrochloride (Q753500), an isomer of quinine; occurs naturally as the d-form. Present in small quantities in cinchona barks. Vasodilator (cerebral).

Manufacturing Process

2.70 g of N-benzoylhomomeroquinene ethyl ester (0.0086 mol) are mixed with 4.0 g of ethyl quininate (0.0173 mol = 100% excess). 1.4 g of absolutely dry pulverulent sodium ethoxide (0.0207 mol -140% excess, based on N- benzoylhomomeroquinene ethyl ester) is added, and the reaction mixture is heated to about 80°C with continuous stirring. As the ethyl quininate melts, and the materials become thoroughly mixed, the initial yellow color changes to brown and then gradually to deep red. The reaction mixture is maintained at about 82°C for fourteen hours with continuous stirring. It is then cooled, and the resulting very hard, dark red mass is decomposed with ice water and benzene. The (not entirely clear) combined aqueous layers are extracted with a small amount of ether. The clear, deep red, aqueous layer is then made just acid to litmus. The precipitated oil is taken up in ether. Evaporation of solvent, finally in vacuo, gives 2.56 g of a red glass. The combined benzene and ether extracts from above, containing largely neutral material, are extracted with 10% aqueous sodium hydroxide. The alkaline extract is made just acid to litmus, and extraction with ether followed by removal of solvent gives a further small quantity of β-ketoester, 0.16 g.Total weight of N-benzoylquinotoxine carboxylic acid ethyl ester thus obtained was 2.72 g, equivalent to 63.4% of the theoretical. 2.72 g of N-benzoylquinotoxine carboxylic acid ethyl ester are dissolved in 30 cc of 1:1 aqueous hydrochloric acid (from 15 cc concentrated hydrochloric acid and 15 cc water). The clear, reddish-orange solution is then boiled under reflux for four hours. The very dark reddish-brown solution is extracted with ether (from this extract 0.50 g of benzoic acid is obtained on evaporation). The aqueous solution is then made strongly alkaline and extracted with ether. 0.23 g of ether-insoluble interface material is dissolved in benzene and set aside. Removal of solvent from the above ether extract gives 1.39 g of crude quinotoxine as a dark red viscous oil.

Therapeutic Function

Vasodilator, Antiarrhythmic

InChI:InChI=1/C20H24N2O2/c1-3-14-13-21-10-8-15(14)4-7-20(23)17-9-11-22-19-6-5-16(24-2)12-18(17)19/h3,5-6,9,11-12,14-15,21H,1,4,7-8,10,13H2,2H3/t14-,15+/m0/s1

Upstream product

• 6119-70-6 quinine; hydrogen sulfate dihydrate 
• 84-55-9 rac-6'-methoxy-1,8-seco-cinchonan-9-one 
• 56-54-2 9-epiquinine 
• 64-19-7 acetic acid 
• 56-54-2 quinidine 
• 130-95-0 quinine 
• 5345-57-3 6-methoxyquinoline-4-carboxylic acid ethyl ester 
• 130-95-0 Quinine 
• 113807-66-2 3-((3R,4R)-1-Acetyl-3-vinyl-piperidin-4-yl)-1-(6-methoxy-quinolin-4-yl)-propan-1-one 
• 64-17-5 ethanol 
• 71-43-2 benzene 
• 56-81-5 glycerol 
• 26847-66-5 3-((4R)-1-benzoyl-3c-vinyl-[4r]piperidyl)-propionic acid ethyl ester 
• 47342-58-5 epiquinidine 

Downstream Products

• 87-69-4 L-Tartaric acid 
• 86-68-0 6-methoxyquinoline-4-carboxylic acid 
• 1422160-60-8 C₃₄H₄₁N₃O₅ 
• 1422160-59-5 C₂₇H₂₈N₂O₃ 
• 233746-47-9 C₂₈H₃₀N₂O₄ 

Relevant articles and documents

Combinatorial synthesis of novel 9R-acyloxyquinine derivatives as insecticidal agents

Background: It is one of the effective ways for pesticide innovation to develop new insecticides from natural products as lead compounds. Quinine, the main alkaloid in the bark of cinchona tree as well as in plants in the same genus, is recognized as a safe and potent botanical insecticide to many insects. The structural modification of quinine into 9R-acyloxyquinine derivatives is a potential approach for the development of novel insecticides, which showed more toxicity than quinine. However, there are no reports on the insecticidal activity of 9R-acyloxyquinine derivatives to control Mythimna separata. Methods: Endeavor to discover biorational natural products-based insecticides, 20 novel 9R-acyloxyquinine derivatives were prepared and assessed for their insecticidal activity against M. separata in vivo by the leaf-dipping method at 1 mg/mL. Results: Among all the compounds, especially derivatives 5i, 5k and 5t exhibited the best insecticidal activity with final mortality rates of 50.0%, 57.1%, and 53.6%, respectively. Conclusion: Overall, a free 9-hydroxyl group is not a prerequisite for insecticidal activity and C9-substitution is well tolerated; modification of out-ring double-bond is acceptable, and hydrogenation of double-bond enhances insecticidal activity; Quinine ring is essential and open of it is not acceptable. These preliminary results will pave the way for further modification of quinine in the development of potential new insecticides.

COMPLEX AND STRUCTURALLY DIVERSE COMPOUNDS

The invention provides a novel, general, and facile strategy for the creation of small molecules with high structural and stereochemical complexity. Aspects of the methods include ring system distortion reactions that are systematically applied to rapidly convert readily available natural products to structurally complex compounds with diverse molecular architectures. Through evaluation of chemical properties including fraction of sp3 carbons, ClogP, and the number of stereogenic centers, these compounds are shown to be significantly more complex and diverse than those in standard screening collections. This approach is demonstrated with natural products (gibberellic acid, adrenosterone, and quinine) from three different structural classes, and methods are described for the application of this strategy to any suitable natural product.

Selenophene-containing inhibitors of type IIA bacterial topoisomerases

Figure Presented. We investigated compounds related to the previously reported antistaphyloccocal agent AVE6971 in an effort to attenuate inhibition of hERG potassium channel current that has been noted for this and related antibacterial drug classes. While most modifications of the original thiophene group compromised antibacterial activity, one selenophene analogue displayed (i) improved activity against the primary target enzyme DNA gyrase, (ii) similar activities against a panel of MRSA clinical isolates, and (iii) reduced hERG channel inhibition.