1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents

Bailey, Denis M.; Mount, Eldridge M.; Siggins, J. E.; Carlson, John A.; Yarinsky, Allen; Slighter, Ralph G.

doi:10.1021/jm00191a031

Cited by 24 publications

(14 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…It is found that several tetrahydroquinolines exhibit analgesic [10], hypertensive [11,12], antiamebic [13], insecticide [14] and fungicide [15][16][17][18][19] activities. Many molecules of natural origin, especially alkaloids, contain quinoline and tetrahydroquinoline rings.…”

Section: Itroductionmentioning

confidence: 99%

Quinolines spiro annulated at heterocyclic fragment: Synthesis and properties

Kouznetsov

2005

Journal of Heterocyclic Chemistry

View full text Add to dashboard Cite

Chemical information of the quinolines spiro annulated at heterocyclic fragment with cycloalkanes or heterocycles is reviewed. Synthetic approaches to three possible spiro-2(1H)-, spiro-3(4H)-and spiro-4(1H)quinoline core derivatives are analysed. Their syntheses are divided into three groups: a) chemical transformations of the substituted quinoline ring, b) construction of spiro structure from the alicyclic precursors, mainly, amine derivatives or imines preformed from cyclic ketones; c) rearrangements of more complex heterocycles leading to the spiro quinolines. Special attention is paid to spiro quinolines that display pharmacological properties. Synthetic routes to the discorhabdin alkaloids are also briefly discussed on in this review.

show abstract

Section: Itroductionmentioning

confidence: 99%

Quinolines spiro annulated at heterocyclic fragment: Synthesis and properties

Kouznetsov

2005

Journal of Heterocyclic Chemistry

View full text Add to dashboard Cite

show abstract

“…As a structural subunit in many natural products, the quinoline ring system is one of the most commonly encountered heterocycles in medicinal chemistry. A literature survey revealed that substituted quinolines possess diverse chemotherapeutic activities including antibacterial , in vitro antifungal , anti‐amoebic , antileishmanial , antimalarial , antitumor , antidiabetic , immunosuppressive , anti‐breast cancer , antiviral , anti‐inflammatory , HIV‐1 integrase inhibitory , antiasthmatic , analgesic, vasorelaxing , antiplasmodial , anticonvulsant, and antihypertensive effects . Halogen‐containing quinolines are of particular interest because halogens play a crucial role in the compounds' bioactivity and provide an avenue for further structure elaboration .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Reactions, and Biological Activities of Some New Thieno[3,2‐c]quinoline and Pyrrolo[3,2‐c]quinoline Derivatives

Abdel-Wadood

Abdel-Monem

Fahmy

et al. 2013

Archiv der Pharmazie

View full text Add to dashboard Cite

2-Bromo-4-fluoroaniline (1) was condensed with ethyl 2-cyano-3-ethoxyacrylate (2) in ethanol to afford 3, which upon refluxing in paraffin oil at 250°C gave 8-bromo-3-cyano-6-fluoroquinoline-4(1H)-one (4). Then, compound 4 was taken as a versatile building block that allows the synthesis of thieno[3,2-c]quinoline, pyrrolo[3,2-c]quinoline, and N-methylpyrrolo[3,2-c]quinoline systems. The newly synthesized compounds and their derivatives were characterized by elemental analysis and spectroscopy (IR, (1)H NMR, (13)C NMR, and mass). Furthermore, some of these synthesized compounds were screened for their biological activities against various pathogenic bacterial and fungal strains. Our results demonstrate that most of the synthesized compounds possess a significant broad antibacterial activity against all strains of both gram-positive and gram-negative bacteria. In addition, compound 5 showed remarkable antifungal activity.

show abstract

“…The heterocyclic quinoline ring building block of many natural compounds is widely used in medicinal chemistry. Substituted quinolines possess diverse biological activities including antibacterial , antifungal , antiamoebic , antileishmanial , antimalarial , and antitumor activities.…”

Section: Introductionmentioning

confidence: 99%

Utility of the Pfitzinger Reaction in the Synthesis of Novel Quinoline Derivatives and Related Heterocycles

Gök

Kasımoğulları

Cengiz

et al. 2013

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

in Wiley Online Library (wileyonlinelibrary.com). 1 3 4 9 12 10a-d2-(2-Amino-3,5-dinitrophenyl)-2-oxoacetic acid (2) was obtained from hydrolysis of 5,7-dinitroisatin (1) in alkaline media. A novel quinoxaline derivative (3) was synthesized from the reaction of the same compound (1) with o-phenylenediamine. Reacting 2 with ethyl 3-oxo-3-phenylpropanoate yields 6,8-dinitro-2-phenylquinoline-3,4-dicarboxylic acid (4). Then, 4 was converted into new quinoline-diacylchloride, quinoline-ester, quinolinedicarboxamide, pyridazine, and pyrroledione derivatives (5, 6a-d, 7a-d, 8, 9, 10a-d, 11a-b, 12) with SOCl 2 , alcohols, amines, and hydrazines, respectively. The structures of synthesized compounds were clarified by 1 H NMR, 13 C NMR, IR, mass and elemental analysis methods.

show abstract

1-(Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinol esters. New potent antiamebic agents

Cited by 24 publications

References 0 publications

Quinolines spiro annulated at heterocyclic fragment: Synthesis and properties

Quinolines spiro annulated at heterocyclic fragment: Synthesis and properties

Synthesis, Reactions, and Biological Activities of Some New Thieno[3,2‐c]quinoline and Pyrrolo[3,2‐c]quinoline Derivatives

Utility of the Pfitzinger Reaction in the Synthesis of Novel Quinoline Derivatives and Related Heterocycles

Contact Info

Product

Resources

About