Domino-reactions of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide, hetarenecarbaldehydes and active methylene nitriles in the construction of new 2-amino-4H-pyrans and the study of their antimicrobial properties

Grygoriv, G. V.; Lega, Dmitry A.; Chernykh, V. P.; Осолодченко, Т. П.; Shemchuk, L. A.

doi:10.24959/ophcj.18.931

Cited by 3 publications

(2 citation statements)

References 8 publications

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“…The antimicrobial activity of the compounds tested was moderate and more pronounced against grampositive bacteria than gram-negative ones and fungi [49][50][51][52].…”

Section: Resultsmentioning

confidence: 98%

“…The use of hetarene-, cycloalkanecarbaldehydes and aliphatic aldehydes in the reaction with benzoxathiinone 1 and ethyl cyanoacetate (114) was also equivocal. In case of hetarenecarbaldehydes three different product types were isolated again depending on the aldehyde used [52]; propanal and butanal were the only aliphatic aldehydes for which ethyl 2-amino-4H-pyran-3-carboxylates were obtained [50]; cycloalkanecarbaldehydes gave no the target pyranes 115 [51] (Scheme 42).…”

Section: Resultsmentioning

confidence: 99%

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1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Hryhoriv

Lega

Shemchuk

2021

J. org. pharm. chem.

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Aim. To analyze the available literature data on the methods of synthesis, chemical transformations and the biological activity of derivatives containing a sultone core – 1,2-benzoxathiin-4(3H)-one 2,2-dioxide – and to show the possibilities of their further use in the construction of new molecular systems with attractive pharmacological properties. Results and discussion. The most widespread method for the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides is the cyclization of salicylic acid derivatives. The known chemical transformations of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides deal with all reaction centers of the heterocyclic fragment of the condensed system – C=O and CH2 groups, SO2–O bond, CH2CO fragment as a whole. It should be noted that the oxathiine nucleus is prone to undergo recyclizations. The use of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides in multicomponent transformations still remains hardly explored. The “abnormal” course of some classical transformations involving 1,2-benzoxathiine 2,2-dioxides is also noteworthy. The study of the pharmacological properties of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide derivatives is scarce and mainly based on their structural similarity to the coumarin core, which led to the study of anticoagulant, antimicrobial and antitumor properties for the sultone derivatives. Conclusions. The analysis has shown a limited number of studies in each aspect – approaches to the synthesis of 1,2-benzoxathiin-4(3H)-one 2,2-dioxides, their chemical transformations and the study of their pharmacological activity. In addition to a small number of publications on this heterocyclic system, there have been almost no sultone studies in the last 20 years. Taking this into account 1,2-benzoxathiin-4(3H)-one 2,2-dioxide and its derivatives deserve close attention as objects of research for experimental chemistry and pharmacology.

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“…The antimicrobial activity of the compounds tested was moderate and more pronounced against grampositive bacteria than gram-negative ones and fungi [49][50][51][52].…”

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Hryhoriv

Lega

Shemchuk

2021

J. org. pharm. chem.

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Effect of anion structure on the network of hydrogen bonds formed between counter ions in salts composed of triethylamine and derivatives of 2,1-benzothiazine 2,2-dioxide and 1,2-benzoxathiine 2,2-dioxide

Wieczorek-Dziurla

Łapiński

Mizera

et al. 2023

Journal of Molecular Structure

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Spiro[benzo[е]pyrano[3,2-c][1,2]oxathiin-4,3’-indolil]-3-carbonitrile 5,5-dioxides: synthesis and the biological activity study

Grygoriv

Lega

Зупанец

et al. 2019

J. org. pharm. chem.

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Spiro[benzo[е]pyrano[3,2-c][1,2]oxathiin-4,3'-indolil]-3-carbonitrile 5,5-dioxides: synthesis and the biological activity study The development of medicines with several pharmacological activities, including the analgesic, anti-inflammatory and antimicrobial properties, is one of the challenging tasks of modern medicinal chemistry. Aim. To expand the range of novel spiro-condensed derivatives of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide, and study the biological activity of the substances obtained. Results and discussions. The target compounds were synthesized as a result of the interaction of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide, malononitrile and isatins. When using ethyl cyanoacetate the interaction appeared to be much more complicated and requires further research. The study of the biological activity has revealed the compounds with the analgesic properties and the antimicrobial effect against gram-positive strains. Experimental part. Two new 2-amino-2'-oxospiro[4H-pyrano[3,2-c][1,2]benzoxathiine-4,3'-indoline]-3-carbonitrile 5,5-dioxides were synthesized by the three-component reaction based on 1,2-benzoxathiin-4(3H)-one 2,2-dioxide. The anti-inflammatory activity was studied on the model of the carrageenan induced paw edema, and the analgesic activity was assessed on the model of the local inflammatory hyperalgesia. The study of the antimicrobial activity of the compounds obtained was performed by the agar well diffusion method. Conclusions. New spiro[benzo[е]pyrano[3,2-c][1,2]oxathiin-4,3'-indolil]-3-carbonitrile 5,5-dioxides have been synthesized. The compounds obtained have revealed high levels of the analgesic properties and the antimicrobial activity. The latter exceeds the activity of the reference drugs, and has appeared to be higher against grampositive bacteria.

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Domino-reactions of 1,2-benzoxathiin-4(3H)-one 2,2-dioxide, hetarenecarbaldehydes and active methylene nitriles in the construction of new 2-amino-4H-pyrans and the study of their antimicrobial properties

Cited by 3 publications

References 8 publications

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

1,2-Benzoxathiin-4(3H)-one 2,2-dioxide – an underinvestigated building block with a high synthetic and pharmacological potential: synthesis, chemical properties, biological activity

Effect of anion structure on the network of hydrogen bonds formed between counter ions in salts composed of triethylamine and derivatives of 2,1-benzothiazine 2,2-dioxide and 1,2-benzoxathiine 2,2-dioxide

Spiro[benzo[е]pyrano[3,2-c][1,2]oxathiin-4,3’-indolil]-3-carbonitrile 5,5-dioxides: synthesis and the biological activity study

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