Steric effects on the sydnones reactivity. New sydnones and pyrazoles

Dumitraşcu, Florea; Mitan, Carmen Irena; Dumitrescu, Dan; Drăghici, Constantin; Cãproiu, Miron Teodor

doi:10.3998/ark.5550190.0003.209

Cited by 28 publications

(7 citation statements)

References 9 publications

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“…The 5-iodopyrazoles under investigation (Table 1) were synthesized by 1,3-dipolar cycloaddition of the corresponding 4-iodosydnones with dimethyl acetylenedicarboxylate via a previously described procedure [45,[47][48][49][50].…”

Section: Synthesis and Crystal Growthmentioning

confidence: 99%

5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

et al. 2020

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5-Iodo-1-arylpyrazoles are interesting templates for investigating the halogen bond propensity in small molecules other than the already well-known halogenated molecules such as tetrafluorodiiodobenzene. Herein, we present six compounds with different substitution on the aryl ring attached at position 1 of the pyrazoles and investigate them in the solid state in order to elucidate the halogen bonding significance to the crystallographic landscape of such molecules. The substituents on the aryl ring are generally combinations of halogen atoms (Br, Cl) and various alkyl groups. Observed halogen bonding types spanned by these six 5-iodopyrazoles included a wide variety, namely, C–I⋯O, C–I⋯π, C–I⋯Br, C–I⋯N and C–Br⋯O interactions. By single crystal X-ray diffraction analysis combined with the descriptive Hirshfeld analysis, we discuss the role and influence of the halogen bonds among the intermolecular interactions.

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Section: Synthesis and Crystal Growthmentioning

confidence: 99%

5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

et al. 2020

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“…Sydnones, heterocyclic compounds with mesoionic structure, have been synthesized the first time in 1935 [12]. Compounds belonging to this class have been studied in the laboratories of the Centre of Organic Chemistry since 1965 [17], their structure and properties being of continuous interest, fact reflected in a number of published papers, some of them being mentioned here [9][10][11]. The sydnones are interesting because these compounds revealed a variety of biological activities like: antimicrobial, antifungal, antihelmintic, antiinflamatory or analgesic [1].…”

Section: Introductionmentioning

confidence: 99%

Screening of Heterocyclic Substituted Sydnones for Potential Biological Activity

Corneli¹

2018

FARMACIA

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Nowadays, the emergence of bacterial resistance to antibiotics has become a major public health concern; therefore the development of new compounds overcoming the bacterial resistance is essential. Thus, this study evaluates the in vitro antimicrobial activity of some recently synthesized sydnone derivatives, on Gram-positive (Staphylococcus aureus, Bacillus subtilis), Gram-negative (Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa) bacteria and fungi (Candida albicans, Aspergillus niger) and estimates the influence of sub-inhibitory concentrations of these newly synthesized compounds on the expression of some virulence factors by bacterial strains and on adhesion ability to inert substrates. RezumatÎn prezent, apariția rezistenței bacteriene la antibiotice a devenit o problemă majoră de sănătate publică, prin urmare dezvoltarea de antibiotice noi este esențială. Acest studiu evaluează activitatea antimicrobiană in vitro a unor sydnone sintetizate recent, folosind bacterii Gram-pozitive (Staphylococcus aureus, Bacillus subtilis) și Gram-negative (Klebsiella pneumoniae, Escherichia coli, Pseudomonas aeruginosa), dar și fungi (Candida albicans, Aspergillus niger) și determină influenţa concentrațiilor subinhibitoare a acestor compuși nou sintetizați asupra exprimării unor factori de virulență la tulpinile bacteriene şi asupra aderenţei bacteriene.

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“…Sydnones 3 are mesoionic heterocyclic compounds with a 1,2,3-oxadiazole skeleton and their chemistry and biological properties are well represented and documented in the literature [20–26]. The most interesting chemical reactions of sydnones are their electrophilic substitution at C-4 and their participation in 1,3-dipolar cycloaddition reactions with olefinic and acetylenic dipolarophiles to form pyrazoles and functional transformation at C-4 [20–26].…”

Section: Introductionmentioning

confidence: 99%

“…The most interesting chemical reactions of sydnones are their electrophilic substitution at C-4 and their participation in 1,3-dipolar cycloaddition reactions with olefinic and acetylenic dipolarophiles to form pyrazoles and functional transformation at C-4 [20–26]. …”

Section: Introductionmentioning

confidence: 99%

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

Albota

Caira

Drăghici

et al. 2016

Beilstein J. Org. Chem.

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The synthesis of sydnones heteroarylated at C-4 with an indolizine was achieved by Chichibabin (Tschitschibabin) indolizine synthesis starting from the corresponding sydnone-N-pyridinium bromides. The latter compounds were also transformed to sydnone-indolizines connected through a keto group at the C-4 position by refluxing them in 1,2-epoxybutane with an activated alkyne. The structures of the new compounds were assigned by FTIR, NMR spectroscopy and X-ray analysis.

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Steric effects on the sydnones reactivity. New sydnones and pyrazoles

Cited by 28 publications

References 9 publications

5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

5-Iodo-1-Arylpyrazoles as Potential Benchmarks for Investigating the Tuning of the Halogen Bonding

Screening of Heterocyclic Substituted Sydnones for Potential Biological Activity

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

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