Use of 1-β-naphthalenesulfonyloxybenzotriazole as coupling reagent in solid phase peptide synthesis

Kundu, Bijoy; Shukla, Sushma; Shukla, Mukesh

doi:10.1016/0040-4039(94)88525-7

Cited by 13 publications

(8 citation statements)

References 7 publications

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“…3 Sulfonate ester of 1-hydroxybenzotriazole (HOBt 2) derivatives has been synthesized and used for peptide coupling. 9,10 The reactivity of these sulfonate esters was affected by the presence of electron-withdrawing substituent in both the benzotriazole and the sulfonic acid moieties. [11][12][13][14] Later, 7-Aza-1-hydroxybenzotriazole (HOAt 3)has been reported to be more efficient than HOBt 2 due to the electronic effect caused by the pyridine ring.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystallographic characterization, DFT and TD-DFT studies of Oxyma-sulfonate esters

et al. 2017

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Three oxyma sulfonate esters were prepared using dichloromethane-water (two-phase method) in the presence of sodium carbonate for scavenging HCl. The products were characterized by FT-IR, NMR ( 1 H and 13 C), UV-Vis spectra and elemental analysis. X-ray single crystal diffraction experiments proved the molecular structures of three esters. Their molecular structures were also calculated using DFT/B3LYP method. The optimized structures agreed well with the X-ray structures. Time-dependent density functional theory (TD-DFT) was used to assign the electronic absorption bands observed experimentally. Pyridine derivative showed two bands at shorter λmax compared to the others, both experimentally and theoretically. The NMR chemical shifts were computed for protons and carbons using GIAO method, which correlated well with the experimental data. Natural charges, dipole moments and chemical reactivity of these molecules, as well as their non-linear optical activity, were computed and compared.

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Section: Introductionmentioning

confidence: 99%

Synthesis, crystallographic characterization, DFT and TD-DFT studies of Oxyma-sulfonate esters

et al. 2017

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“…The active esters are well known precursors in peptide bond reaction for both liquid-and solid-state synthesis [1,2]. An important step in peptide bond formation is the development of N-protected amino acid derivatives that are reactive enough to combine with amine groups when both are mixed.…”

Section: Introductionmentioning

confidence: 99%

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

Ghazzali¹,

Khattab²,

Elnakady³

et al. 2013

Journal of Molecular Structure

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Section: 18)mentioning

confidence: 99%

“…24,25) Esters of sulfonic acids and 1-hydroxybenzotriazole (HOBt, 1) have been used for peptide coupling. [26][27][28][29][30] The reactivity of these sulfonate esters was shown to be directly related to the presence of electron-withdrawing substituents in both the HOBt 1 and the sulfonic acid moieties. [31][32][33][34][35][36] 1-Hydroxy-7-azabenzotriazole (HOAt, 2) has been reported to be more efficient than HOBt 1 because of the anchimeric assistance effect caused by the pyridine ring.…”

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confidence: 99%

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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Use of 1-β-naphthalenesulfonyloxybenzotriazole as coupling reagent in solid phase peptide synthesis

Cited by 13 publications

References 7 publications

Synthesis, crystallographic characterization, DFT and TD-DFT studies of Oxyma-sulfonate esters

Synthesis, crystallographic characterization, DFT and TD-DFT studies of Oxyma-sulfonate esters

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

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

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