Microwave-assisted Döbner Synthesis of 2-Phenylquinoline-4-carboxylic Acids and their Antiparasitic Activities
TL;DR: A series of twelve substituted 2-phenylquinoline-4-carboxylic acids analogous to antimalarial and antileishmanial natural products was developed via the Dobner reaction employing microwave irradiation and evaluated in vitro against the parasites responsible for malaria, leishmaniasis and trypanosomiasis diseases.
About: This article is published in Journal of Heterocyclic Chemistry.The article was published on 2008-03-01. It has received 27 citations till now. The article focuses on the topics: Leishmania infantum.
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11 Feb 2020
TL;DR: This exploration reported the design and synthesis of a novel ionically tagged magnetic nanoparticles bearing urea linkers, namely, Fe3O4@SiO2@(CH2)3–urea–thiazole sulfonic acid chloride, which was fully characterized by using several techniques.
Abstract: In this exploration, we reported the design and synthesis of a novel ionically tagged magnetic nanoparticles bearing urea linkers, namely, Fe3O4@SiO2@(CH2)3-urea-thiazole sulfonic acid chloride. The structure of the mentioned compound was fully characterized by using several techniques including Fourier transform infrared spectroscopy, energy-dispersive X-ray analysis, elemental mapping analysis, thermogravimetric analysis/differential thermal analysis, scanning electron microscopy, transmission electron microscopy, and vibrating sample magnetometer. In the presence of the novel reusable catalyst, applied starting materials including aryl aldehydes, pyruvic acid, and 1-naphthylamine condensed to afford the desired 2-aryl-quinoline-4-carboxylic acid derivatives via an anomeric-based oxidation pathway under solvent-free conditions.
48 citations
TL;DR: New quinoline / chalcone hybrids containing 1,2,4-triazole moiety have been designed, synthesized and their structures elucidated and confirmed by various spectroscopic techniques.
47 citations
TL;DR: The progress of selected quinolines through pre-clinical development and phase I/II trials, and the lead quinoline drugs sitamaquinine and Imiquimod are discussed in conjunction with delivery systems and combination therapies.
Abstract: The development of leishmanicidal quinolines and their in vitro (promastigote and amastigote) and, where applicable, in vivo activities are reviewed. This survey provides a direct comparison of bioactivity across different species(e.g. L. donovani, L. amazonensis, L. chagasi, L infantum), and in different animal models (e.g. L. donovani Balb/c mice and L. donovani infected hamsters). The progress of selected quinolines through pre-clinical development and phase I/II trials, and the lead quinoline drugs sitamaquinine and Imiquimod, are discussed in conjunction with delivery systems and combination therapies.
46 citations
TL;DR: A series of novel quinolines incorporating 1,2,4-triazole/oxime hybrids showed remarkable anti-inflammatory activity and exhibited very low incidence of gastric ulceration, compared to indomethacin.
38 citations
TL;DR: Findings support the antitumor potential of quinoline-chalcone derivatives for NSCLC and CML by inhibiting the PI3K/Akt/mTOR pathway by inhibition of the phosphorylation ofPI3K, Akt, mTOR, as well as GSK-3β in both A549 and K562 cells.
37 citations
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1,179 citations
TL;DR: In this article, two general synthetic routes based on the utilization of mono-substituted or ortho-subtituted anilines are discussed and their major methods and modifications are analyzed.
Abstract: New developments in the chemistry of quinoline derivatives are reviewed. Two general synthetic routes based on the utilization of mono-substituted or ortho-substituted anilines are discussed. Their major methods and modifications are analyzed. syntheses. These classical syntheses are well-known and still frequently used for the preparation of pharmaceutical agents, ligands and functional materials bearing a quinoline backbone. However, current methods for quinoline synthesis often do not allow for adequate diversity and substitution on the quinoline ring system (19). Recent developments in the chemistry of quinoline derivatives have demonstrated that new metal-catalyzed coupling cyclizations or acid catalyzed cycloaddition of appropriate precursors could compete with classical syntheses in the efficacy and rapidity of the quinoline construction. These new developments have prompted us to review and analyze their major methods and modifications.
412 citations
TL;DR: The quantitative in vitro antimalarial activities of a set of 13 aminoquinolines and quinoline methanols were found to correlate significantly with beta-hematin inhibition values determined using the assay, showing good agreement with alternative assay methods reported by four laboratories.
205 citations
TL;DR: It is suggested that chimanine B may be chosen as a lead molecule in the development of oral therapy against leishmaniasis.
Abstract: The antileishmanial efficacies of 2-n-propylquinoline, chimanines B and D, 2-n-pentylquinoline, 2-phenylquinoline, 2-(3,4-methylenedioxyphenylethyl) quinoline, and two total alkaloidal extracts of Galipea longiflora were evaluated in BALB/c mice infected with Leishmania amazonensis or Leishmania venezuelensis. Animals were treated for 4 to 6 weeks postinfection with a quinoline by the oral route at 50 mg/kg of body weight twice daily for 15 days or by five intralesional injections at intervals of 4 days with a quinoline at 50 mg/kg of body weight. The reference drug, N-methylglucamine antimonate (Glucantime), was administered by subcutaneous or intralesional injection (regimens of 14, 28, or 56 mg of pentavalent antimony [Sbv] per kg of body weight daily). Twice-daily oral treatment with chimanine B at 50 mg/kg resulted in a decrease in lesion weight by 70% (P < 0.001) and a decrease in the parasite loads by 95% (P < 0.001). Five injections of chimanine B at intervals of 4 days reduced the lesion weight by 74% and the parasite loads in the lesion by 90% compared with the values for the group of untreated mice. Subcutaneous administration of N-methylglucamine antimonate at 28 mg of Sbv kg per day for 15 days reduced the parasite burden by 95% (P < 0.001), and five intralesional injections at the same concentration reduced the parasite burden by 96% (P < 0.001). Other 2-substituted quinolines, 2-n-propylquinoline administered by the oral and intralesional routes, 2-phenylquinoline administered by the oral route, 2-n-pentylquinoline administered by intralesional injection, and two total alkaloidal extracts of G. longiflora administered by the oral route, had intermediate effects. These findings suggest that chimanine B may be chosen as a lead molecule in the development of oral therapy against leishmaniasis.
124 citations
TL;DR: A series of substituted quinolines was developed via the Friedlander reaction employing microwave irradiation (MW), in the presence of a catalytic amount of hydrochloric acid.
105 citations