The Total Synthesis of Streptonigrin and Related Antitumor Antibiotic Natural Products.

Bringmann, Gerhard; Reichert, Yanina; Kane, Vinayak V.

doi:10.1002/chin.200426239

Cited by 4 publications

(3 citation statements)

References 1 publication

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“…The 5,8-quinolinedione derivatives were among the first compounds to be systematically modified in order to find products with higher biological activities, such as anticancer, anti-inflammatory or antibacterial [1][2][3][4][5][6][7][8][9]. For example, it was found that substitution of the electron-withdrawing groups at the 6-or 7-positions of the 5,8-quinolinedione led to an increase in the DNA degradation [8][9][10][11][12][13].…”

Section: Introductionmentioning

confidence: 99%

New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity

et al. 2017

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Acetylenic amine derivatives of the 5,8-quinolinedione were synthesized and characterized by the 1 H and 13 C NMR, IR spectroscopy and MS spectra. Additionally, the 6-and 7-substituted allylamine-5,8-quinolinediones were synthesized for comparison purposes. The crystal structure was determined for the 6-chloro-7-propargylamine-5,8-quinolinedione and 7-chloro-6-propargylamine-5,8-quinolinedione. Additionally, the IR spectral analysis supplemented by the density functional theory (DFT) calculations were carried out. It was found that different positions of the propargylamine side chain had a distinct influence on crystal structure, formation of H-bonds and the carbonyl stretching IR bands. Correlation between the frequency separation ∆ν of the carbonyl IR bands and the position of the 6-and 7-substituents was found. The 7-substituted derivatives exhibited a higher frequency separation ∆ν. The observed correlation could provide an opportunity to use the IR spectroscopy to study substitution reactions. Cytotoxic activities against three human cancer cell lines for the 5,8-quinolinedione derivatives with different amine substituents, i.e., propargylamine, N-methylpropargylamine, 1,1-dimethylpropargylamine, allylamine and propylamine were also analysed with respect to their molecular structure.

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Section: Introductionmentioning

confidence: 99%

New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity

et al. 2017

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“…Therefore, nucleophilic attack takes place at the 2-and 4-positions. Quinolines and their derivatives are very important compounds because of their wide occurrence in natural products [1,2] and biologically active compounds [3][4][5][6][7][8]. These derivatives are also used for the preparation of nano-and meso structures having enhanced electronic and photonic properties [9,10] and are known to have applications as pharmaceuticals, agrochemicals and synthetic building blocks [11].…”

Section: Introductionmentioning

confidence: 99%

Antibacterial Screening of some Heterocyclic Compounds Containing Quinoline Nucleus

Baluja

Godvani

Chanda

2017

ILCPA

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Abstract. In this work, some novel derivatives of Cyanopyridines and Isoxazoles were synthesized using Vilsmeier-Haack reagent and their structures were confirmed by FTIR, 1 H NMR and mass spectroscopic methods. The antibacterial activities of these synthesized compounds were studied in DMSO and DMF by agar well diffusion method against some Gram positive and Gram negative bacteria. It is observed that activity depends upon three S: solvent, strain and structure.

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“…On the other hand, quinoline derivatives are known to possess diverse pharmacological properties such as antioxidant 18,19 , antibiotic 20,21 , cardiovascular 22 , anti-TB 23 , antiplatelet 24 , anticancer 25,26 , receptor antagonists 27 , NK3 receptor antagonists-II 28 , anti-inflammatory 29 , antimicrobial 30,31 , selective estrogen receptor modulators (SERMs) 32 and protein kinase inhibitor 33 . Keeping above in mind, we decided to synthesize conjugates of the above-mentioned moieties to study the biological profile of the resulting product.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

Verbanac

Malik

Chand

et al. 2016

Journal of Enzyme Inhibition and Medicinal Chemistry

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C NMR, and finally mass spectrometry. All the synthesized compounds were evaluated in vitro for their potential antibacterial activity and their preliminary safety profile was assessed through cytotoxicity assay. Additionally, six selected conjugates were evaluated for their antioxidative properties on the basis of density functional theory calculations, using radical scavenging assay (DPPH) and cellular antioxidant assay. The reported results encourage further investigation of selected compounds and are shading light on their potential pharmacological use.

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The Total Synthesis of Streptonigrin and Related Antitumor Antibiotic Natural Products.

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 4 publications

References 1 publication

New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity

New Acetylenic Amine Derivatives of 5,8-Quinolinediones: Synthesis, Crystal Structure and Antiproliferative Activity

Antibacterial Screening of some Heterocyclic Compounds Containing Quinoline Nucleus

Synthesis and evaluation of antibacterial and antioxidant activity of novel 2-phenyl-quinoline analogs derivatized at position 4 with aromatically substituted 4H-1,2,4-triazoles

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