Synthesis and cytotoxic activity of 7-methoxy-1H-pyrrolo[3,2-c]-quinoline-6,9-dione and 3-methoxy-11H-indolo[3,2-c]quinoline-1,4-diones

Helissey, Philippe; Parrot‐Lopez, Hélène; Renault, Jean; Cros, S.

doi:10.1016/0223-5234(87)90276-5

Cited by 24 publications

(11 citation statements)

References 4 publications

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“…Quinones 23a, b and 26a, b have in vitro antileukemic activity at the following micromolar IC 50 concentrations: (23a) = 2.01´10 -6 M, (23b) = 4.51´10 -6 M, (26a) = 0.86´10 -6 M, (26b) = 33.2´10 -6 M. Thus, in this case the absence of the methyl group leads to small increases in cytotoxicity as in the conversion of 23a to 26a [7,15].…”

Section: Oxidation and Dehydrationmentioning

confidence: 95%

“…Quinones 21a -d were found to have in vitro antileukemic activity at micromolar concentrations and IC 50 of (1.66 -12.2)´10 -6 M. This approach was used for the synthesis of derivatives 23a and 26a by oxidation of indolo [3,2-c]quinoline derivatives 22a and 25a [7]. In the cases of 22b and 25b, treatment with monobasic potassium phosphate and Fremy's salt produced a mixture of quinones 23b and 26b and quinoneimines 24b and 27b respectively.…”

Section: Oxidation and Dehydrationmentioning

confidence: 99%

See 1 more Smart Citation

Carbolines. Part 2: Comparison of some of the properties of α-, γ-, and δ-carbolines (Review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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Published data on the chemical and biological properties of a-, g-, and d-carbolines are reviewed.Key words: Pyridoindoles (carbolines), chemical and biological properties of carbolines, pK a values of carbolines.Continuing our studies of the properties of carbolines [1], the present study reviews published data on the properties of a-, g-, and d-carbolines. Compounds belonging to different classes of carboline derivatives include many substances with marked biological activity [2, 3].The chemical and physicochemical properties of carbolines have as yet received only fragmentary and insufficient study.The ionization constants of a number of carbolines have been reported [4]. pK a values reflecting the ability of a proton to attach to the pyridine nitrogen atom were obtained, along with constants showing the extent of deprotonation of the indole NH group in carbolines. Table 1 shows that there are significant variations in the ionization constant depending on the structures of the carbolines studied.Information obtained from studies of ionization constants are important for comparing different carbolines. In relation to basicity (protonation of the pyridine nitrogen), it is important to note that the most basic compound in this series is g-carboline. This appears to be due to the greatest level of stabilization of the pyridinium cation due to delocalization of the positive charge by the electron pair of the indole nitrogen:The lowest level of basicity of a-carboline is probably associated with the appearance in the corresponding cation of non-binding interactions between the protons of the pyridinium and indole fragments which destabilize the forming cation.The greatest acidity of g-carboline probably arises by a similar mechanism (increased stabilization of the anion). 389 0091-150X/11/4507-0389

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Section: Oxidation and Dehydrationmentioning

confidence: 95%

Section: Oxidation and Dehydrationmentioning

confidence: 99%

Carbolines. Part 2: Comparison of some of the properties of α-, γ-, and δ-carbolines (Review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

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“…1) have been known for several years as one of the most widely used motifs in medicinal chemistry. Several derivatives of such heterocycles possess a wide spectrum of biological activities, including most notably antitumor 5 and hypotensive 6 properties, gastric (H þ /K þ )-ATPase inhibition, [7][8][9] anti-inflammatory activities, 10 and 5-HT 3 agonism [11][12][13] (Fig. 1).…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted multi-step synthesis of novel pyrrolo-[3,2-c]quinoline derivatives

et al. 2008

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A new approach for the synthesis of original substituted pyrrolo-[3,2-c]quinoline derivatives using microwave-assisted chemistry is described. The use of microwave activation in this synthesis resulted in high yielding and clean steps. The key step for introducing diversity is the amination or the Pd-catalyzed cross-coupling of an imidoyl chloride derivative, obtained in a straightforward manner and in good yield.

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“…To our surprise, the compound, after the reductive cleavage, underwent a unique rearrangement to furnish a novel class of pyrroloquinoline derivative 6a . The prevalence of pyrroloquinoline in bioactive molecules and natural products makes this class of molecules particularly attractive for synthesis . Given this, we performed the reaction employing a series of electronically varied spiro-isoxazolidine-oxindoles bearing halo and methyl substitutions and, though, in moderate yields, the products were obtained in high diastereoselectivity (Scheme ).…”

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confidence: 99%

Additive-Free Three-Component Synthesis of Spiro-isoxazolidine-oxindoles Employing Trifluorodiazoethane

et al. 2018

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An efficient three-component protocol for the synthesis of trifluoromethylated spiro-isoxazolidine-oxindoles has been developed. This approach employs the 1,3-dipolar cycloaddition of trifluoromethyl nitrone, generated in situ from trifluorodiazoethane and nitrosoarene, with phenacylideneoxindoles. A range of phenacyclideneoxindoles and nitrosoarenes can be subjected to this reaction to generate the spiro-isoxazolidine-oxindole derivatives. The reductive ring-opening reaction of isoxazolidines carried out to demonstrate the synthetic potential of our strategy resulted in an interesting rearrangement to yield pyrroloquinoline derivatives.

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Synthesis and cytotoxic activity of 7-methoxy-1H-pyrrolo[3,2-c]-quinoline-6,9-dione and 3-methoxy-11H-indolo[3,2-c]quinoline-1,4-diones

Cited by 24 publications

References 4 publications

Carbolines. Part 2: Comparison of some of the properties of α-, γ-, and δ-carbolines (Review)

Carbolines. Part 2: Comparison of some of the properties of α-, γ-, and δ-carbolines (Review)

Microwave-assisted multi-step synthesis of novel pyrrolo-[3,2-c]quinoline derivatives

Additive-Free Three-Component Synthesis of Spiro-isoxazolidine-oxindoles Employing Trifluorodiazoethane

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