Synthesis of aminovinyl derivatives of quinoline- and isoquinoline-5,8-diones*

Batenko, Nelli; Попова, О. С.; Belyakov, Sergey; Valters, Raimonds

doi:10.1007/s10593-012-1071-6

Cited by 7 publications

(3 citation statements)

References 8 publications

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“…The 1,4-quinones 7 – 9 were obtained according to literature methods [ 12 , 43 ]. The 2,3-dichloro-1,4-naphthoquinon 10 was purchased in Merck (Darmstadt, German).…”

Section: Methodsmentioning

confidence: 99%

Hybrids of 1,4-Quinone with Quinoline Derivatives: Synthesis, Biological Activity, and Molecular Docking with DT-Diaphorase (NQO1)

et al. 2022

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Hybrids 1,4-quinone with quinoline were obtained by connecting two active structures through an oxygen atom. This strategy allows to obtain new compounds with a high biological activity and suitable bioavailability. Newly synthesized compounds were characterized by various spectroscopic methods. The enzymatic assay used showed that these compounds were a suitable DT-diaphorase (NQO1) substrates as evidenced by increasing enzymatic conversion rates relative to that of streptonigrin. Hybrids were tested in vitro against a panel of human cell lines including melanoma, breast, and lung cancers. They showed also a high cytotoxic activity depending on the type of 1,4-quinone moiety and the applied tumor cell lines. It was found that cytotoxic activity of the studied hybrids was increasing against the cell lines with higher NQO1 protein level, such as breast (MCF-7 and T47D) and lung (A549) cancers. Selected hybrids were tested for the transcriptional activity of the gene encoding a proliferation marker (H3 histone), cell cycle regulators (p53 and p21) and the apoptosis pathway (BCL-2 and BAX). The molecular docking was used to examine the probable interaction between the hybrids and NQO1 protein.

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“…The 1,4-quinones 7 – 9 were obtained according to literature methods [ 12 , 43 ]. The 2,3-dichloro-1,4-naphthoquinon 10 was purchased in Merck (Darmstadt, German).…”

Section: Methodsmentioning

confidence: 99%

Hybrids of 1,4-Quinone with Quinoline Derivatives: Synthesis, Biological Activity, and Molecular Docking with DT-Diaphorase (NQO1)

et al. 2022

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“…Heterocyclic compounds have been widely studied and developed as potent biological compounds . The 5,8-quinolinediones derived from 8-hydroxyquinoline have demonstrable anticancer activity and are used as anticancer, antifungal, and antimalarial agents. − Additionally, several 7-aminoquinoline quinones, Streptonigrin, and clioquinol derivatives, − and their Ni(II), Yb(III), Sm(III), and La(III) complexes have shown activity against senile dementia, intestinal amebiasis, and cancer. − …”

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confidence: 99%

Novel Quinoline-based Ir(III) Complexes Exhibit High Antitumor Activity in Vitro and in Vivo

Yang

Bin

Qin

et al. 2019

ACS Med. Chem. Lett.

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Eight novel Ir(III) complexes listed as [Ir(H–P)2(P)]PF6 (PyP-Ir), [Ir(H–P)2(dMP)]PF6 (PydMP-Ir), [Ir(H–P)2(MP)]PF6 (PyMP-Ir), [Ir(H–P)2(tMP)]PF6 (PytMP-Ir), [Ir(MPy)2(P)]PF6 (MPyP-Ir), [Ir(MPy)2(dMP)]PF6 (MPydMP-Ir), [Ir(MPy)2(MP)]PF6 (MPyMP-Ir), [Ir(MPy)2((tMP)]PF6 (MPytMP-Ir) with 2-phenylpyri-dine (H–P) and 3-methyl-2-phenylpyridine (MPy) as ancillary ligands and pyrido-[3,2-a]-pyrido[1′,2′:1,2]imidazo[4,5-c]phenazine (P), 12,13-dimethyl pyrido-[3,2-a]-pyrido[1′,2′:1,2]-imidazo-[4,5-c]-phenazine (dMP), 2-methylpyrido [3,2-a]-pyrido-[1′,2′:1,2]-imidazo-[4,5-c]-phenazine (MP), and 2,12,13-trimethylpyrido-[3,2-a]-pyrido-[1′,2′:1,2]-imidazo-[4,5-c]-phenazine (tMP) as main ligands, respectively, were designed and synthesized to fully characterize and explore the effect of their toxicity on cancer cells. Cytotoxic mechanism studies demonstrated that the eight Ir(III) complexes exhibited highly potent antitumor activity selectively against cancer cell lines NCI-H460, T-24, and HeLa, and no activity against HL-7702, a noncancerous cell line. Among the eight Ir(III) complexes, MPytMP-Ir exhibited the highest cytotoxicity with an IC50 = 5.05 ± 0.22 nM against NCI-H460 cells. The antitumor activity of MPytMP-Ir in vitro could be contributed to the steric or electronic effect of the methyl groups, which induced telomerase inhibition and damaged mitochondria in NCI-H460 cells. More importantly, MPytMP-Ir displayed a superior inhibitory effect on NCI-H460 xenograft in vivo than cisplatin. Our work demonstrates that MPytMP-Ir could potentially be developed as a novel potent Ir-based antitumor drug.

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“…[7][8][9][10] Similarly isoquinoline methobisulphate play active role in photographic improvement. 5 Other unique and special uses of some isoquinoline derivatives are their utilization as organic semiconductors 11,12 and catalysts in the ring opening or polymerization reaction of epoxides. 13 Isoquinolines have also been found useful in environmental monitoring activities.…”

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confidence: 99%

Detailed Electrochemical Probing of a Biologically Active Isoquinoline

Shah

Ullah

Rehman

et al. 2013

J. Electrochem. Soc.

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The detailed electrochemistry of a biologically active isoquinoline, 2-benzoyl-7-methoxy-2,3-dihydroisoquinoline-4(1H)-one (IQN) was carried out in different pH media with the objective of elucidating its redox mechanism. Cyclic voltammetry was used to determine pka, diffusion coefficient and heterogeneous electron transfer rate constant. The involvement of protons in redox mechanism was confirmed from a shift in peak potential as a function of pH. Differential pulse voltammetry was used to verify the number of electrons involved in the redox process. The reversibility of the redox process was decided on the basis of the results obtained from square wave voltammetry. The existence of IQN in keto and enol forms was evidenced by UV-Vis spectroscopy. The redox mechanism proposed on the basis of voltammetric and electronic absorption spectroscopic investigations was supported by theoretical calculations. These mechanistic pathways are expected to present a key in understanding the hidden routes by which isoquinolines exert their biochemical action.Isoquinoline is a structural isomer of quinoline. A number of isoquinoline derivatives bestowed with remarkable biological activities have been identified. Andreas et al. have reported the inhibitory properties of some isoquinolines against gastric acid secretion. 1 Literature survey reveals the cytotoxicity of isoquinolines against cancer cells. Won et al. reported indeno [1,2-c]isoquinoline to have strong potency against tumor cells. 2 The same group further investigated that such compounds exert their cytotoxic effect by inhibiting topoisomerase I. Berberine, a medicinally important isoquinoline derivative was found to have strong antidiarrheal activity 3 and ability of preventing the adherence of E coli to the host cells without producing any harm in the intestinal layer. 4 The role of isoquinoline is not only limited to medicines but have significantly important role in agricultural as well. 2-dodecylisoquinolinium bromide has been reported to have pesticidal and insecticidal activities. 5 Some quaternary isoquinolinium salts are used as disinfectants or micellar catalysts of wide industrial applications. 6 A few isoquinoline derivatives are used as additives in metal plating for improving the brightness of metal surfaces. 5 Isoquinolinium quaternary salts are industrially used as demulsifiers and flocculating agents in petroleum industry. 7-10 Similarly isoquinoline methobisulphate play active role in photographic improvement. 5 Other unique and special uses of some isoquinoline derivatives are their utilization as organic semiconductors 11,12 and catalysts in the ring opening or polymerization reaction of epoxides. 13 Isoquinolines have also been found useful in environmental monitoring activities. One of its derivative, bis(isoquinoline N-oxide) has been identified as fluorosensor with significant sensitivity toward Li +1 , Ca +2 and Mg +2 ions. 14 As most of the isoquinolines applications like their role as semiconductors and catalysts involve electron transfer rea...

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Synthesis of aminovinyl derivatives of quinoline- and isoquinoline-5,8-diones*

Cited by 7 publications

References 8 publications

Hybrids of 1,4-Quinone with Quinoline Derivatives: Synthesis, Biological Activity, and Molecular Docking with DT-Diaphorase (NQO1)

Hybrids of 1,4-Quinone with Quinoline Derivatives: Synthesis, Biological Activity, and Molecular Docking with DT-Diaphorase (NQO1)

Novel Quinoline-based Ir(III) Complexes Exhibit High Antitumor Activity in Vitro and in Vivo

Detailed Electrochemical Probing of a Biologically Active Isoquinoline

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