SYNTHESIS AND IN-VITRO CYTOTOXIC ACTIVITY OF NOVEL BENZO[b]PHENAZINE-6,11-DIONE AND 1,4- NAPHTHOQUINONE DERIVATIVES

Khalifa, Maha M.; Ismail, Magda M. F.; Noaman, Eman

doi:10.21608/bfsa.2008.64215

Cited by 6 publications

(5 citation statements)

References 9 publications

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“…The same group then patented the preparation of 33 and some derivatives (34-38, Table 8); 61 however, none of the derivatives displayed significantly higher in vitro anticancer activity than 32 (Table 8). Finally, Khalifa et al 62 described the in vitro anticancer activity of 5,12-dihydrobenzo[b]phenazine-6,11-dione (39, Table 8), but this compound was found to be less active than those compounds described by Kim et al 57 and also less active than doxorubicin (Table 8).…”

Section: Phenazine-611-dione and Analogsmentioning

confidence: 98%

Phenazines and cancer

et al. 2012

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Phenazines are a large group of natural and synthesised nitrogen-containing heterocycles, including more than 100 different compounds of natural origin and over 6000 synthetic compounds. Many of these compounds have been investigated as potential anti-cancer agents. Despite a large number of research publications, no recent attempt to summarise and critically evaluate the experimental findings relating to the anti-cancer activity of this class of compounds has been made. The present review fills this gap in the literature and discusses both natural and synthetic phenazines with a critical focus on in vitro, in vivo and available clinical anti-cancer activities of these compounds.

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Section: Phenazine-611-dione and Analogsmentioning

confidence: 98%

Phenazines and cancer

et al. 2012

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“…Quinones are important compounds widely spread in Nature. Compounds containing 1,4-naphthoquinone moiety exhibit a broad spectrum of biological activities such as cytotoxic [ 1 , 2 ] antiviral [ 3 , 4 ] anti-inflammatory [ 5 , 6 ] antimalarial [ 7 ], antibacterial [ 8 , 9 ], antifungal [ 10 ] and antiproliferative properties [ 11 ]. Naphthoquinones are particularly important in dye chemistry, and recently they have been used for new infrared dyes in optical recording media [ 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

et al. 2012

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New 3-substituted 1-(3-hydroxyphenyl)-5-oxopyrrolidine derivatives containing hydrazone, azole, diazole, oxadiazole fragments, as well as 2-phenoxy- and 2,3-diphenoxy-1,4-naphthoquinone derivatives were synthesized. The structure of all compounds has been confirmed by NMR, IR, mass spectra, and elemental analysis data. Methyl 1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarboxylate demonstrated potential antibacterial and antifungal activities as determined by diffusion and serial dilution methods, while N'-[(4-bromophenyl)methylidene]-1-{3-[(3-chloro-1,4-dioxo-1,4-dihydro-2-naphthalenyl)oxy]phenyl}-5-oxo-3-pyrrolidinecarbohydrazide and 2-{3-[4-(1,2,3-oxadiazol-5-yl)-2-oxo-1-pyrrolidinyl]phenoxy}-3-{3-[4-(1,3,4-oxadiazol-2-yl)-2-oxo-1-pyrrolidinyl]phenoxy}naphthoquinone showed antifungal activity against Candida tenuis and Aspergillus niger at low concentrations, as determined by the serial dilution method. The substitution of the methoxy fragment by N-containing substituents in monophenoxy substituted naphthoquinones was found to decrease their activity against Mycobacterium luteum. Besides, introduction of the second phenoxy substituted fragment increased the antifungal activity against Candida tenuis and Aspergillus niger at lower concentrations.

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“…The study on the cytotoxicity of reported compounds revealed that the pyridophenazinediones as tetracyclic hydroquinone analogs with three N-atoms exhibited much better activity than benzophenazinediones. [138] The in vitro assays showed that 9-[(propan-2-yl)oxy]pyrido[2,3b]phenazine-5,12-dione (29, see Figure 4) and 9,10dimethylpyrido[2,3-b]phenazine-5,12-dione (30) had high antitumor activity against different human cancer cell lines, namely, non-small cell lung (A549), the human ovarian tumor cells (SK-OV-3), and colon (HCT 15) with the IC 50 value in the range of 0.12 -0.16 μM or 0.03 -0.13 μM, respectively for both described compounds. [137] Moreover, 6,11-dihydro-3,4-dimethylpyrido[2,3-b]phenazine-6,11-dione exhibited strong cytotoxicity to the human brain CNS cells (XF 498) with the IC 50 value of 0.06 μM, which was 2.6-fold higher than for doxorubicin (IC 50 = 0.16 μM).…”

Section: Phenazine-611-dione Derivativesmentioning

confidence: 99%

“…Suh and coworkers [137] synthesized a series of compounds with a framework of benzo[2,3‐ b ]phenazine‐6,11‐dione or pyrido[2,3‐ b ]phenazine‐5,12‐dione. The study on the cytotoxicity of reported compounds revealed that the pyridophenazinediones as tetracyclic hydroquinone analogs with three N‐atoms exhibited much better activity than benzophenazinediones [138] . The in vitro assays showed that 9‐[(propan‐2‐yl)oxy]pyrido[2,3‐ b ]phenazine‐5,12‐dione ( 29 , see Figure 4) and 9 ,10‐dimethylpyrido[2,3‐ b ]phenazine‐5,12‐dione ( 30 ) had high antitumor activity against different human cancer cell lines, namely, non‐small cell lung (A549), the human ovarian tumor cells (SK‐OV‐3), and colon (HCT 15) with the IC 50 value in the range of 0.12–0.16 μ m or 0.03–0.13 μ m , respectively for both described compounds [137] .…”

Section: Phenazine‐611‐dione Derivativesmentioning

confidence: 99%

The Phenazine Scaffold Used as Cytotoxic Pharmacophore Applied in Bactericidal, Antiparasitic and Antitumor Agents

Miksa

2022

Helvetica Chimica Acta

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Phenazine derivatives are important bactericidal antibiotics and antiparasitic compounds which can be used in synergistic combinations with anticancer drugs in chemotherapy treatments. The development of synthetic phenazines with anticancer activity improves the effectiveness of chemotherapy. Chemical variations introduced at the phenazine core which is known as a chromophore with fluorescent properties provide advanced theranostic agents useful in optical bioimaging techniques and photodynamic anticancer therapy. This review summarizes the field of structural modifications of phenazine derivatives which have been tested against different parasitic and bacterial infections. The report highlights advances in design and biological evaluations of phenazines as anticancer drugs for the development of new chemotherapeutic as well as bio‐imaging reagents.

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SYNTHESIS AND IN-VITRO CYTOTOXIC ACTIVITY OF NOVEL BENZO[b]PHENAZINE-6,11-DIONE AND 1,4- NAPHTHOQUINONE DERIVATIVES

Cited by 6 publications

References 9 publications

Phenazines and cancer

Phenazines and cancer

Synthesis and Microbiological Evaluation of New 2- and 2,3-Diphenoxysubstituted Naphthalene-1,4-diones with 5-Oxopyrrolidine Moieties

The Phenazine Scaffold Used as Cytotoxic Pharmacophore Applied in Bactericidal, Antiparasitic and Antitumor Agents

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