Synthesis of azolylalkylquinolines with cytotoxic activity

Abel, M; Luu, H. T.; Micetich, Ronald G.; Nguyen, Dai Q.; Oreski, A. B.; Tempest, M. L.; Daneshtalab, Mohsen

doi:10.1002/jhet.5570330233

Cited by 12 publications

(6 citation statements)

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“…For medical and pharmaceutical applications of chiral tricyclic compounds, see: Abel et al (1996); Salvati et al (2005). For the synthesis of the starting reagent, 2-(p-tolyl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione, see: Andrade & Evilazio (2004).…”

Section: Related Literaturementioning

confidence: 99%

Crystal structure ofrac-3-hydroxy-2-(p-tolyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindol-1-one

Aslantaş

Çelik

et al. 2015

Acta Cryst E

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In the title compound, C16H17NO2, the cyclohexene ring adopts a boat conformation, and the five-membered rings have envelope conformations with the bridging atom as the flap. Their mean planes are oriented at a dihedral angle of 86.51 (7)°. The molecular structure is stabilized by a short intramolecular C—H⋯O contact. In the crystal, molecules are linked by O—H⋯O hydrogen bonds forming chains propagating along [100]. The chains are linked by C—H⋯π interactions, forming slabs parallel to (001).

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Section: Related Literaturementioning

confidence: 99%

Crystal structure ofrac-3-hydroxy-2-(p-tolyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindol-1-one

Aslantaş

Çelik

et al. 2015

Acta Cryst E

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“…The derivatives of exo-5,6-dehydronorcantharidin are of great pharmacological interest and have attracted considerable attention (Abel et al, 1996;Deng et al, 2005). Furthermore, molecules of this type containing nitrogen have become a hot topic in heterocyclic chemistry because of their antitumour, antiviral, analgesic, sedative and fungicidal activities (Salvati et al, 2005).…”

Section: Commentmentioning

confidence: 99%

Supramolecular structure of racemic 5-hydroxy-4-(4-methoxyphenyl)-10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-en-3-one

et al. 2008

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The structure of the title compound, C(15)H(15)NO(4), comprises a racemic mixture of chiral molecules containing five stereogenic centres. The cyclohexane ring tends towards a boat conformation and the two tetrahydrofuran rings adopt envelope conformations. Molecules are linked into sheets parallel to (100) by a combination of O-H...O, C-H...O and C-H...pi hydrogen bonds, leading to a two-dimensional supramolecular structure.

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“…A series of azolylalkylquinilines have been previously reported as potent and selective cytotoxic agents in vitro 10. Recently, further research on this class of compounds reported that a series of novel cytotoxic azolylthioalkyl‐ureidoquinoline derivatives named SRA‐HX‐(1‐3) (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of New Quinoline Derivatives as Inhibitors of Human Tumor Cells Growth

Rashad

El‐Sayed

Mohamed

et al. 2010

Archiv der Pharmazie

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A series of new 8-[(2H-tetrazol-5-yl)methoxy]quinoline derivatives, their sugar hydrazones, and their N-glycoside derivatives were synthesized. Furthermore, the 1,2,4-triazole-3-one derivatives 3 and 4 were synthesized from the amidrazone derivative 2. Some of the newly prepared compounds demonstrated inhibitory effects on the growth of MCF-7 human breast cancer cells as compared with the activity of the commonly used anticancer drug, cisplatin. The results of antitumor evaluation revealed that compounds 2-5, 8b, and 12 inhibited the growth of cancer cells through their effect as free-radical regulators by increasing the activity of superoxide dismutase and depletion of intracellular levels of reduced glutathione, catalase and glutathione peroxidase activities, accompanied with a high production of hydrogen peroxide, nitric oxide, and other free radicals causing the killing of tumor cells. The results suggested that the prepared compounds possess significant anticancer activity comparable to cisplatin and the antitumor activity of these prepared compounds was accompanied with a reduction in the levels of protein and nucleic acids.

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Synthesis of azolylalkylquinolines with cytotoxic activity

Cited by 12 publications

References 1 publication

Crystal structure ofrac-3-hydroxy-2-(p-tolyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindol-1-one

Crystal structure ofrac-3-hydroxy-2-(p-tolyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindol-1-one

Supramolecular structure of racemic 5-hydroxy-4-(4-methoxyphenyl)-10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-en-3-one

Synthesis of New Quinoline Derivatives as Inhibitors of Human Tumor Cells Growth

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Synthesis of azolylalkylquinolines with cytotoxic activity

Cited by 12 publications

References 1 publication

Crystal structure ofrac-3-hydroxy-2-(p-tolyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindol-1-one

Crystal structure ofrac-3-hydroxy-2-(p-tolyl)-2,3,3a,4,7,7a-hexahydro-1H-4,7-methanoisoindol-1-one

Supramolecular structure of racemic 5-hydroxy-4-(4-methoxyphenyl)-10-oxa-4-azatricyclo[5.2.1.02,6]dec-8-en-3-one

Synthesis of New Quinoline Derivatives as Inhibitors of Human Tumor Cells Growth

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Supramolecular structure of racemic 5-hydroxy-4-(4-methoxyphenyl)-10-oxa-4-azatricyclo[5.2.1.0^2,6]dec-8-en-3-one