Synthesis, structure, theoretical calculations and biological activity of sulfonate active ester new derivatives

Ghazzali, Mohamed; Khattab, Sherine N.; Elnakady, Yasser A.; Al-Mekhlafi, Fahd A.; Al-Farhan, Khalid; El‐Faham, Ayman

doi:10.1016/j.molstruc.2013.04.025

Cited by 8 publications

(4 citation statements)

References 12 publications

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“…2) showed a moderate anti-proliferative effect against human cancer cell line SW756 for compounds 4 and 5, while the sulfonate ester 6 showed a strong growth inhibition for mosquito Culex pipiens 4th instar larvae. 41) We are extending our work by the synthesis of a series of sulfonate ester derivatives of the recently prepared N-alkylcyanoacetamido oximes 8-11 (Fig. 3), N-hydroxybenzimidoyl cyanide 12, and N-hydroxypicolinimidoyl cyanide 13 (Fig.…”

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confidence: 81%

Synthesis, Characterization and Anti-proliferation Activities of Novel Cyano Oximino Sulfonate Esters

El‐Faham

Elnakdy

Gazzar

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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A series of novel cyano oximino sulfonate derivatives were prepared from the reaction of arylsulfonyl chloride with different cyanoacetamide-based oximes ranging from the simplest unsubstituted amide to analogues containing N-ethyl (mimicking the Oxyma template), N-piperidinyl and N-morpholinyl chains. In addition, the cyano oximes, N-hydroxybenzimidoyl cyanide and N-hydroxypicolinimidoyl cyanide were also used in the synthesis of the novel cyano oximino sulfonate derivatives. The structures of the prepared compounds were confirmed by 1 H-NMR, 13 C-NMR, and elemental analysis. The preliminary bioassays showed that some of the title compounds, such as 2-oxo-2-(piperidin-1-yl)-N-(tosyloxy)acetimidoyl cyanide (TsPipOx), N-(tosyloxy)benzimidoyl cyanide (TsPhOX), N-(naphthalen-2-ylsulfonyloxy)-2-oxo-2-(piperidin-1-yl)acetimidoyl cyanide (NpsPipOx), 2-amino-N-(naphthalen-2-ylsulfonyloxy)-2-oxoacetimidoyl cyanide (NpsAmOx), N-(naphthalen-2-ylsulfonyloxy)benzimidoyl cyanide (NpsPhCN), and N-(naphthalen-2-ylsulfonyloxy)picolinimidoyl cyanide (NpsPyCN), showed anti-proliferation effect on the mouse fibroblast L929. The calculated IC 50 -values were ranging between 36.5 µg/mL and 0.235 mg/mL. However the anti-proliferation effects seem to be cytostatic rather than cytotoxic. The compounds only minimize the growth activity without completely killing the cells.Key words phenylsulfonate; naphthylsulfonate; oxime; anti-proliferation; 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay (MTT-assay) Oximes are one of the most versatile building blocks in organic and organometallic chemistry. The substituent pending at α-position account for the specific properties of each oxime, such as dissociation constant, solubility, chelating ability, etc.1-3) Their multifaceted nature derives in a broad range of applications in chemistry in addition to be biologically relevant moieties. 4-7)Biologically active heterocyclic compounds containing amine moiety, specifically piperidine and morpholine skeletons are attractive targets of organic synthesis owing to their pharmacological activity and wide occurrence in nature. 8,9) Piperidines are known to have central nervous system (CNS) depressant activity at low dosage levels but stimulant activity with increased doses. In addition, the piperidine skeleton possesses analgesic, ganglionic blocking and anesthetic properties.10,11) Morpholine derivatives have been reported to possess antiinflammatory [12][13][14] antimicrobial 15,16) and central nervous system activities. 17,18)The sulfonate ester is considered an important class in the sulfonylation reaction for the synthesis of sulfonamide which exhibits a wide range of biological activities. [19][20][21][22] Sulfonylation is also used as a protection technique for OH and NH functionalities, as it enables crystallization and the protecting group can be selectively cleaved in the presence of acid-labile tert-butyl-based groups by using HCl or HBr in alcohol 23) or in aprotic solvents such as ethylacetate or dimethylformamide. 24,...

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confidence: 81%

Synthesis, Characterization and Anti-proliferation Activities of Novel Cyano Oximino Sulfonate Esters

El‐Faham

Elnakdy

Gazzar

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Given its limited natural abundance within native proteins, tyrosine emerges as an appealing target for biomolecule labelling. [29][30][31] Historically, various methodologies have been employed for tyrosine modification, encompassing Mannich-type reactions, π-allyl Pd complexes, and Ru photocatalysts. [32][33][34][35][36][37] However, the challenge of functionalizing tyrosine with useful moieties in the absence of additives remains formidable.…”

Section: Introductionmentioning

confidence: 99%

Electro-induced O–S bonding reaction targeting biological macromolecules

Jiang,

Xiao,

Pan

et al. 2024

Org. Chem. Front.

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“…These sulfonic ester derivatives are components of various bioactive pharmaceutical structures with a range of biological activities. The representative examples include the inhibition of monoamine oxidase, steroid sulfatase, cysteine protease and protein kinase II, in addition to antitumor, anticancer, antidepressant and bactericidal activities (Roush et al, 1998;Catto et al, 2006;Pisani et al, 2009Pisani et al, , 2013Ghazzali et al, 2013;El-Gamal et al, 2014Park et al, 2015). The presence of various hydrogen and halogen atoms in these molecules makes them suitable for performing comparative analyses of halogen and hydrogen-bonding interactions and of the influence on the different supramolecular architectures.…”

Section: Introductionmentioning

confidence: 99%

A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

et al. 2018

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To explore the operational role of noncovalent interactions in supramolecular architectures with designed topologies, a series of solid-state structures of 2- and 4-formylphenyl 4-substituted benzenesulfonates was investigated. The compounds are 2-formylphenyl 4-methylbenzenesulfonate, CHOS, 3a, 2-formylphenyl 4-chlorobenzenesulfonate, CHClOS, 3b, 2-formylphenyl 4-bromobenzenesulfonate, CHBrOS, 3c, 4-formylphenyl 4-methylbenzenesulfonate, CHOS, 4a, 4-formylphenyl 4-chlorobenzenesulfonate, 4b, CHClOS, and 4-formylphenyl 4-bromobenzenesulfonate, CHBrOS, 4c. The title compounds were synthesized under basic conditions from salicylaldehyde/4-hydroxybenzaldehydes and various aryl sulfonyl chlorides. Remarkably, halogen-bonding interactions are found to be important to rationalize the solid-state crystal structures. In particular, the formation of O...X (X = Cl and Br) and type I X...X halogen-bonding interactions have been analyzed by means of density functional theory (DFT) calculations and characterized using Bader's theory of `atoms in molecules' and molecular electrostatic potential (MEP) surfaces, confirming the relevance and stabilizing nature of these interactions. They have been compared to antiparallel π-stacking interactions that are formed between the arylsulfonates.

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Synthesis, structure, theoretical calculations and biological activity of sulfonate active ester new derivatives

Cited by 8 publications

References 12 publications

Synthesis, Characterization and Anti-proliferation Activities of Novel Cyano Oximino Sulfonate Esters

Synthesis, Characterization and Anti-proliferation Activities of Novel Cyano Oximino Sulfonate Esters

Electro-induced O–S bonding reaction targeting biological macromolecules

A comparative experimental and theoretical investigation of hydrogen-bond, halogen-bond and π–π interactions in the solid-state supramolecular assembly of 2- and 4-formylphenyl arylsulfonates

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