Synthesis of oxadiazoloquinoxaline, oxathiadiazoloquinoxaline and oxadiazolobenzothiazine derivatives

Fylaktakidou, Konstantina C.; Litinas, Κonstantinos E.; Saragliadis, Athanasios; Adamopoulos, Spyros G.; Nicolaides, D. N.

doi:10.1002/jhet.5570430309

Cited by 15 publications

(6 citation statements)

References 16 publications

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“…Additionally, they are widely known as efficient reactivators of nerve agent inhibited acetylcholinesterases, offering a treatment from poisoning by organophosphorous compounds [38,39,40]. Our team has a continuous interest in the chemistry and biology of oximes [23,41,42,43,44,45,46,47,48,49,50] as well as in the DNA photocleavage caused by oxime derivatives [30,34,35]. We have discovered that p -nitro-benzoyl ester conjugates of pyridine aldoxime and amidoxime [30], as well as p -nitrophenyl sulfonates of pyridine ethanone oxime [34] and amidoxime [35] exemplified, among other conjugates, the best activities.…”

Section: Introductionmentioning

confidence: 99%

Pyridine and p-Nitrophenyl Oxime Esters with Possible Photochemotherapeutic Activity: Synthesis, DNA Photocleavage and DNA Binding Studies

et al. 2016

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Compared to standard treatments for various diseases, photochemotherapy and photo-dynamic therapy are less invasive approaches, in which DNA photocleavers represent promising tools for novel "on demand" chemotherapeutics. A series of p-nitrobenzoyl and p-pyridoyl ester conjugated aldoximes, amidoximes and ethanone oximes were subjected to UV irradiation at 312 nm with supercoiled circular plasmid DNA. The compounds which possessed appropriate properties were additionally subjected to UVA irradiation at 365 nm. The ability of most of the compounds to photocleave DNA was high at 312 nm, whereas higher concentrations were required at 365 nm as a result of their lower UV absorption. The affinity of selected compounds to calf-thymus (CT) DNA was studied by UV spectroscopy, viscosity experiments and competitive studies with ethidium bromide (EB) revealing that all compounds interacted with CT DNA. The fluorescence emission spectra of the pre-treated EB-DNA exhibited a moderate to significant quenching in the presence of the compounds indicating the binding of the compounds to CT DNA via intercalation as concluded also by DNA-viscosity experiments. For the oxime esters the DNA photocleavage and affinity studies aimed to clarify the role of the oxime nature (aldoxime, ketoxime, amidoxime) and the role of the pyridine and p-nitrophenyl moieties both as oxime substituents and ester conjugates.

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Section: Introductionmentioning

confidence: 99%

Pyridine and p-Nitrophenyl Oxime Esters with Possible Photochemotherapeutic Activity: Synthesis, DNA Photocleavage and DNA Binding Studies

et al. 2016

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“…This reaction could be readily scaled up to 5 mmol, and the target product 3 a was obtained in a satisfactorily isolated yield of 74% (0.647 g). Oxime 5 a could be prepared by treatment of 3 a with hydroxylamine hydrochloride . Benzoyl amide 6 a was obtained when 3 a reacted with benzoyl chloride .…”

Section: Figurementioning

confidence: 99%

Direct C(sp²)−H Amination to Synthesize Primary 3‐aminoquinoxalin‐2(1H)‐ones under Simple and Mild Conditions

Yang

Tan

et al. 2019

Adv Synth Catal

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A convenient CÀH amination of quinoxalin-2-ones has been developed. This transformation provides concise access to 3-aminoquinoxalin-2(1H)-ones with a broad tolerance of functional groups, utilizing TMSN 3 as an amino source under simple and mild conditions. The target 3-aminoquinoxalin-2(1H)-ones are important intermediates for the synthesis of biologically active 3-N-substituted quinoxalin-2-one derivatives.

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“…The 3-oxime of 2H-[1,4]benzoxazine-2,3(4H)-dione 99 was obtained by the cyclization of o-aminophenol 98 in the presence of the Z-isomer of ethyl chloro(hydroxyimino)acetate and triethylamine in diethyl ether [91]. The derivatives of o-aminophenol 100 and dicyanogen di-N-oxide in chloroform at 0°C give 1,4-benzoxazine-2,3-dioximes 101 [92].…”

Section: ) Meli Thfmentioning

confidence: 99%

Oximes of six-membered heterocyclic compounds with two or three hetero-atoms: I. Synthesis and structure (review)

Абеле

Lukevics

2009

Chem Heterocycl Comp

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Data on methods for the production of and on the structure of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes, and their derivatives are reviewed.The oximes of heterocyclic compounds with two or three heteroatoms are widely used as intermediates in fine organic synthesis. In this review the basic methods for the synthesis of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes and their derivatives are summarized. The basic methods for investigation of the structure of the oximes of six-membered heterocyclic compounds with two or three heteroatoms are discussed in relation to isomerism. The reactions and biological activity of the oximes of heterocyclic compounds with two or three heteroatoms will be examined in the second part of the review.

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Synthesis of oxadiazoloquinoxaline, oxathiadiazoloquinoxaline and oxadiazolobenzothiazine derivatives

Cited by 15 publications

References 16 publications

Pyridine and p-Nitrophenyl Oxime Esters with Possible Photochemotherapeutic Activity: Synthesis, DNA Photocleavage and DNA Binding Studies

Pyridine and p-Nitrophenyl Oxime Esters with Possible Photochemotherapeutic Activity: Synthesis, DNA Photocleavage and DNA Binding Studies

Direct C(sp²)−H Amination to Synthesize Primary 3‐aminoquinoxalin‐2(1H)‐ones under Simple and Mild Conditions

Oximes of six-membered heterocyclic compounds with two or three hetero-atoms: I. Synthesis and structure (review)

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Synthesis of oxadiazoloquinoxaline, oxathiadiazoloquinoxaline and oxadiazolobenzothiazine derivatives

Cited by 15 publications

References 16 publications

Pyridine and p-Nitrophenyl Oxime Esters with Possible Photochemotherapeutic Activity: Synthesis, DNA Photocleavage and DNA Binding Studies

Pyridine and p-Nitrophenyl Oxime Esters with Possible Photochemotherapeutic Activity: Synthesis, DNA Photocleavage and DNA Binding Studies

Direct C(sp2)−H Amination to Synthesize Primary 3‐aminoquinoxalin‐2(1H)‐ones under Simple and Mild Conditions

Oximes of six-membered heterocyclic compounds with two or three hetero-atoms: I. Synthesis and structure (review)

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Direct C(sp²)−H Amination to Synthesize Primary 3‐aminoquinoxalin‐2(1H)‐ones under Simple and Mild Conditions