A new route for the synthesis of phenazine di-N-oxides

Elhalim, M. S. Abd; El-Ahl, Abdel-Aziz S.; Etman, H. A.; Ali, M. M.; Fouda, Ahmed M.; Fadda, Ahmed A.

doi:10.1007/bf00824300

Cited by 7 publications

(3 citation statements)

References 2 publications

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“…The compounds 1a – d and 3a , 3c obtained have been previously described [28,47]. Compound 2a was first synthesized according to a previously reported method [50]. It was a spontaneous reaction that gives the desired compound in good yield.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Structure-Activity Relationships of New Quinoxaline Derivatives as Anti-Plasmodium falciparum Agents

et al. 2014

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Section: Resultsmentioning

confidence: 99%

Synthesis, Biological Evaluation and Structure-Activity Relationships of New Quinoxaline Derivatives as Anti-Plasmodium falciparum Agents

et al. 2014

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“…-3-methylquinoxaline-1,4-dioxide 2-A mixture of benzofurazan-1-oxide 1 (0.05 mol), acetylacetone (0.55 mol), triethylamine (5 mL) and ethanol (20 mL) was stirred at room temperature for 24 h. The resultant precipitate was collected by filtration, dried and recrystallized from ethanol to give 2, mp 154 °C (lit. 22 Aryl-2-propenyl)-3-methylquinoxaline-1,4-dioxides 3a-l-A mixture of 2-acetyl-3-methylquinoxaline-1,4-dioxide 2 (0.003 mol) and an aryl aldehyde (0.0035 mol) in methanolic sodium hydroxide solution (5% w/v, 10 mL) was stirred at 5-10 °C for 5-10 min. The solid which deposited was collected, washed with water and recrystallized from chloroform-ethanol to provide the compounds in series 3.…”

Section: Chemistrymentioning

confidence: 99%

“…-2-(3-phenyl-2-propenoyl)-quinoxaline-1,4-dioxide (3a): Yield: 62%, mp 172-173 °C (lit. 22 1.2.6. 3-Methyl-2-[3-(4-methylphenyl)-2-propenoyl]-quinoxaline-1,4- 2-[3-(4-Chlorophenyl)-2-propenoyl]-3-methyl-quinoxaline-1,4- 25 with the exception of the 3,4-methylenedioxy sigma value which was obtained from another source.…”

Section: Chemistrymentioning

confidence: 99%

2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: A novel cluster of tumor-specific cytotoxins which reverse multidrug resistance

Das

Pati

Panda

et al. 2009

Bioorganic & Medicinal Chemistry

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A series of 2-(3-aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides 3a-l were prepared by condensation of various aryl aldehydes with 2-acetyl-3-methylquinoxaline-1,4-dioxide 2. These compounds inhibit the growth of human Molt 4/C8 and CEM T-lymphocytes and the IC 50 values are mainly in the 5-30 μM range. The quinoxaline 1,4-dioxide 3j inhibited the growth of 58 human tumor cell lines, particularly leukemic and breast cancer neoplasms. All of the compounds 3a-l reversed the multidrug resistance (MDR) properties of murine L-5178Y leukemic cells which were transfected with the human MDR1 gene. The MDR-reversing effect may be due to the conjugated π-electron system forming a weak electron charge transfer complex with the Pglycoprotein-mediated efflux pump. The compounds in series 2 and 3 were assessed against HL-60, HSC-2, HSC-3 and HSC-4 malignant cells as well as HGF, HPC and HPLF normal cell lines which revealed that the majority of the compounds displayed a greater toxicity to neoplastic than normal cells. Various ways in which the project may be expanded are presented.

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Nitroxide‐Derived N‐Oxide Phenazines for Noncovalent Spin‐Labeling of DNA

Júlíusson

Sigurdsson

2020

ChemBioChem

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Two o‐benzoquinone derivatives of isoindoline were synthesized for use as building blocks to incorporate isoindoline nitroxides into different compounds and materials. These o‐quinones were condensed with a number of o‐phenylenediamines to form isoindoline‐phenazines in high yields. Subsequent oxidation gave phenazine‐di‐N‐oxide isoindoline nitroxides that were evaluated for noncovalent and site‐directed spin‐labeling of duplex DNA and RNA that contained abasic sites. Although only minor binding was observed for RNA, the unsubstituted phenazine‐N,N‐dioxide tetramethyl isoindoline nitroxide showed high binding affinity and selectivity towards abasic sites in duplex DNA that contained cytosine as the orphan base.

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A new route for the synthesis of phenazine di-N-oxides

Cited by 7 publications

References 2 publications

Synthesis, Biological Evaluation and Structure-Activity Relationships of New Quinoxaline Derivatives as Anti-Plasmodium falciparum Agents

Synthesis, Biological Evaluation and Structure-Activity Relationships of New Quinoxaline Derivatives as Anti-Plasmodium falciparum Agents

2-(3-Aryl-2-propenoyl)-3-methylquinoxaline-1,4-dioxides: A novel cluster of tumor-specific cytotoxins which reverse multidrug resistance

Nitroxide‐Derived N‐Oxide Phenazines for Noncovalent Spin‐Labeling of DNA

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