84-55-9 Usage
Description
Viquidil, also known as 1-(6-Methoxyquinolin-4-yl)-3-((3R,4R)-3-vinylpiperidin-4-yl)propan-1-one, is an organic compound with the CAS number 84-55-9. It is an intermediate in the synthesis of Quinotoxine Hydrochloride (Q753500), an isomer of quinine, and occurs naturally as the d-form. Viquidil is found in small quantities in cinchona barks and is known for its vasodilator properties, particularly in the cerebral region.
Uses
Used in Pharmaceutical Industry:
Viquidil is used as an intermediate in the synthesis of Quinotoxine Hydrochloride, a compound with potential pharmaceutical applications.
Used in Neurological Applications:
Viquidil is used as a vasodilator for improving blood flow in the cerebral region, which can be beneficial for various neurological conditions and treatments.
Originator
Desclidium,Spret ,France,1972
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
Check Digit Verification of cas no
The CAS Registry Mumber 84-55-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 4 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 84-55:
(4*8)+(3*4)+(2*5)+(1*5)=59
59 % 10 = 9
So 84-55-9 is a valid CAS Registry Number.
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
84-55-9Relevant articles and documents
Combinatorial synthesis of novel 9R-acyloxyquinine derivatives as insecticidal agents
Che, Zhiping,Chen, Genqiang,Jiang, Jia,Lin, Xiaomin,Liu, Shengming,Sun, Di,Tian, Yuee,Yang, Jinming
, p. 111 - 118 (2020/04/29)
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
-
Paragraph 0267; 0268, (2015/12/20)
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
Wiles, Jason A.,Phadke, Avinash S.,Bradbury, Barton J.,Pucci, Michael J.,Thanassi, Jane A.,Deshpande, Milind
scheme or table, p. 3418 - 3425 (2011/06/27)
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.