Synthesis, antimicrobial activities and cytogenetic studies of newer diazepino quinoline derivatives via Vilsmeier–Haack reaction

Nandhakumar, Raju; Suresh, T.; Jude, A.L. Calistus; Kannan, V.; Mohan, P. S.

doi:10.1016/j.ejmech.2007.01.004

Cited by 44 publications

(8 citation statements)

References 27 publications

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“…Quinoline scaffold has been used to develop new molecules possessing antimicrobial, antiproliferative,antineoplastic, antimalarial, anticonvulsant, anti‐inflammatory, and other activities . Particularly, anticancer drugs containing quinoline cycle give rise to anticancer activities through different mechanisms involving apoptosis, cell cycle arrest, inhibition of angiogenesis, and disruption of cell migration .…”

Section: Introductionmentioning

confidence: 99%

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Köprülü

Ökten

Teki̇n³

et al. 2018

J Biochem & Molecular Tox

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Due to a great deal of biological activities, quinoline derivatives have drawn attention for synthesis and biological activities in the search for new anticancer drug development. In this work, a variety of substituted (phenyl, nitro, cyano, N‐oxide, and methoxy) quinoline derivatives (3‐13) were tested in vitro for their biological activity against cancer cell lines, including rat glioblastoma (C6), human cervical cancer cells (HeLa), and human adenocarcinoma (HT29). 6‐Bromo‐5‐nitroquinoline (4), and 6,8‐diphenylquinoline (compound 13) showed the greatest antiproliferative activity as compared with the reference drug, 5‐fluorouracil (5‐FU), while the other compounds showed low antiproliferative activity. 6‐Bromo‐5‐nitroquinoline (4) possesses lower cytotoxic activity than 5‐FU in HT29 cell line. Due to its the apoptotic activity 6‐Bromo‐5‐nitroquinoline (4) has the potential to cause cancer cell death.

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Section: Introductionmentioning

confidence: 99%

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Köprülü

Ökten

Teki̇n³

et al. 2018

J Biochem & Molecular Tox

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“…The commercially available ethyl acetoacetate was condensed with 4-substituted anilines in the presence of ammonium ceric nitrate at 40 °C leading to the formation of 4a–b [9]. Treatment of 4a–b in diphenyl ether at 250 °C for 20 min yielded compounds 5a–b , which were then chlorinated with phosphoryl chloride to afford 4-chloro-2-methylquinolines 6a–b in 97–98% yields [10,11]. Subsequent alkylation of 6a–b with an excess of the corresponding aliphatic amines at reflux gave rise to the key intermediates 7a–f [12].…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Antiproliferative Activity of Novel 2-Substituted-4-amino-6-halogenquinolines

Jiang

Zhai

et al. 2012

Molecules

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Two series of novel 2-substituted-4-amino-6-halogenquinolines 8a-l and 13a-h were designed, synthesized and evaluated for their antiproliferative activity against H-460, HT-29, HepG2 and SGC-7901 cancer cell lines in vitro. The pharmacological results indicated that most compounds with 2-arylvinyl substituents exhibited good to excellent antiproliferative activity. Among them, compound 8e was a considered promising lead for further structural modifications with IC 50 values of 0.03 μM, 0.55 μM, 0.33 μM and 1.24 μM, which was 2.5-to 186-fold more active than gefitinib and compound 1.

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“…The newly formed aldehydes can be reacted under base-catalyzed condensation reactions, such as the Perkin transformation, leading to styryl type compounds. Like Nandhakumar et al we isolated the product from the reaction between the electrophilic Vilsmeier's reagent generated in situ and the methyl group located at the R position in the quinoline ring [12]. After hydrolysis a moderate yield of (Z)-8-hydroxy-2-(2-hydroxyvinyl)quinoline-5-carbaldehyde (2l) was isolated (Scheme 4).…”

Section: Compoundmentioning

confidence: 96%

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

et al. 2020

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A new approach to the synthesis of selected quinolinecarbaldehydes with carbonyl groups located at C5 and/or in C7 positions is presented in this paper in conjunction with spectroscopic characterization of the products. The classical Reimer-Tiemann, Vilsmeier-Haack and Duff aldehyde synthesis methods were compared due to their importance. Computational studies were carried out to explain the preferred selectivity of the presented formylation transformations. A carbene insertion reaction based on Reimer-Tiemann methodology is presented for making 7-bromo-8-hydroxyquinoline-5-carbaldehyde. Additionally, Duff and Vilsmeier-Haack reactions were used in the double formylation of quinoline derivatives and their analogues benzo[h]quinolin-10-ol, 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde, 8-(dimethylamino) quinoline-5,7-dicarbaldehyde and 10-hydroxybenzo[h]quinoline-7,9-dicarbaldehyde. Four Schiff base derivatives of 2,6-diisopropylbenzenamine were prepared from selected quinoline-5-carbaldehydes and quinoline-7-carbaldehyde by an efficient synthesis protocol. Their properties have been characterized by a combination of several techniques: MS, HRMS, GC-MS, FTIR, electronic absorption spectroscopy and multinuclear NMR. The electrochemical properties of 8-hydroxy-quinoline-5-carbaldehyde, 6-(dimethylamino)quinoline-5-carbaldehyde and its methylated derivative were investigated, and a strong correlation between the chemical structure and obtained reduction and oxidation potentials was found. The presence of a methyl group facilitates oxidation. In contrast, the reduction potential of methylated compounds was more negative comparing to non-methylated structure. Calculations of frontier molecular orbitals supported the finding. The structures of 8-hydroxy-2-methylquinoline-5,7-dicarbaldehyde and four Schiff bases were determined by single-crystal X-ray diffraction measurements.

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Synthesis, antimicrobial activities and cytogenetic studies of newer diazepino quinoline derivatives via Vilsmeier–Haack reaction

Cited by 44 publications

References 27 publications

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Biological evaluation of some quinoline derivatives with different functional groups as anticancer agents

Design, Synthesis and Antiproliferative Activity of Novel 2-Substituted-4-amino-6-halogenquinolines

Synthesis, Electrochemical and Spectroscopic Characterization of Selected Quinolinecarbaldehydes and Their Schiff Base Derivatives

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