Synthesis and Trace-Level Quantification of Mutagenic and Cohort-of-Concern Ciprofloxacin Nitroso Drug Substance-Related Impurities (NDSRIs) and Other Nitroso Impurities Using UPLC-ESI-MS/MS─Method Optimization Using I-Optimal Mixture Design

ACS Omega, Journal Year: 2024, Volume and Issue: 9(8), P. 8773 - 8788

Published: Feb. 15, 2024

Globally, the pharmaceutical industry has been facing challenges from nitroso drug substance-related impurities (NDSRIs). In current study, we synthesized and developed a rapid new UPLC-MS/MS method for trace-level quantification of ciprofloxacin NDSRIs couple N-nitroso simultaneously. (Q)-SAR methodology was employed to assess categorize genotoxicity all impurities. The projected results were positive, cohort concern (CoC) three indicates potential genotoxicity. AQbD-driven I-optimal mixture design used optimize solvents in method. chromatographic resolution accomplished using an Agilent Poroshell 120 Aq-C18 column (150 mm × 4.6 mm, 2.7 μm) isocratic elution mode with 0.1% formic acid water, acetonitrile, methanol ratio 475:500:25 v/v/v at flow rate 0.5 mL/min. Quantification carried out triple quadrupole mass detection electrospray ionization (ESI) multiple reaction monitoring technique. finalized validated successfully, affording ICH guidelines. All revealed excellent linearity over concentration range 0.00125–0.0250 ppm. Pearson correlation coefficient each impurity >0.999. accuracy recoveries ranged 93.98 108.08% aforementioned N-nitrosamine Furthermore, effectively applied quantify simultaneously commercially available formulated samples, its efficiency recurring trace levels. Thus, is capable determining levels marketed tablet dosage forms commercial release stability testing.

Language: Английский

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Electrochemical Oxidative Cleavage of Alkynes to Carboxylic Acids

Organic Letters, Journal Year: 2023, Volume and Issue: 25(1), P. 293 - 297

Published: Jan. 1, 2023

A sustainable method for converting terminal alkynes into their corresponding carboxylic acids is reported using synthetic electrolysis in an undivided cell at room temperature. This protocol, avoiding transition metal catalysis and stoichiometric chemical oxidants, tolerates a variety of aryl, heteroaryl, alkyl akynes. Preliminary mechanistic studies demonstrate that sodium nitrite serves triple role as the electrolyte, nitryl radical precursor, nitrosating reagent.

Language: Английский

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Electrochemical Nitration with Nitrite

ChemSusChem, Journal Year: 2021, Volume and Issue: 14(22), P. 4936 - 4940

Published: Sept. 28, 2021

Aromatic nitration has tremendous importance in organic chemistry as nitroaromatic compounds serve versatile building blocks. This study represents the electrochemical aromatic with NBu

Language: Английский

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Electrochemical nitration for organic C–N bond formation: a current view on possible N-sources, mechanisms, and technological feasibility

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(19), P. 7508 - 7517

Published: Jan. 1, 2023

Rethinking nitration: sustainable electrochemical C-N functionalization. This work reviews diverse inorganic nitrogen sources for fine chemical production, with a perspective on innovative pathways to harness alternative sources' potential.

Language: Английский

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Raman Study of Intermediates Formed During the Electrochemical N‐Nitrosation of Secondary Amines

Chemistry - Methods, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 5, 2025

Abstract An in situ electrochemical Raman method is described to identify and validate the reaction pathway of amine nitrosations using density functional theory (DFT). In this reaction, sodium nitrite used as an affordable readily available nitrosating reagent, which also serves electrolyte reaction. This a green approach towards it does not require use acids other harsh or toxic solvents chemicals. Intermediate species have been detected spectroscopy are correlated with calculated spectra expected N ‐nitrosamine products.

Language: Английский

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Electrochemical Heteroatom‐Heteroatom Bond Construction

The Chemical Record, Journal Year: 2021, Volume and Issue: 22(1)

Published: Aug. 31, 2021

Heteroatom-heteroatom linkage, with S-S bond as a presentative motif, served crucial role in biochemicals, pharmaceuticals, pesticides, and material sciences. Thus, preparation of the privileged scaffold has always been attracting tremendous attention from synthetic community. However, classic protocols suffered several drawbacks, such toxic unstable agents, poor functional group tolerance, multiple steps, explosive oxidizing regents well transitional metal catalysts. Electrochemical organic synthesis exhibited promising alternative to traditional chemical reaction due sustainable electricity can be employed traceless redox agents. Hence, oxidants and/or metals could discarded under mild high efficiency. In this context, series electrochemical approaches for construction heteroatom-heteroatom were reviewed. Notably, most cases illustrated dehydrogenative feature clean energy molecules hydrogen sole by-product.

Language: Английский

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Flow Electrochemistry for the N‐Nitrosation of Secondary Amines

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 29(32)

Published: March 28, 2023

A flow electrochemical method towards the synthesis of N-nitroso compounds from secondary amines using cheap and readily available sodium nitrite has been developed. Sodium dissolved in aqueous acetonitrile made additional electrolytes unnecessary. This mild straightforward approach use acids or other harsh toxic chemicals redundant. procedure was applied to an assortment cyclic acyclic (27 examples) resulting yields N-nitrosamines as high 99 %. To demonstrate practicality process, scaled-up reactions were performed. Finally, selected products could be purified by in-line acidic extraction.

Language: Английский

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Conversion of nitrogenous small molecules into value-added chemicals by building N–C bonds

Chemical Engineering Journal, Journal Year: 2023, Volume and Issue: 474, P. 145899 - 145899

Published: Sept. 9, 2023

Language: Английский

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Non‐Conventional Methodologies for the Synthesis of N‐Nitrosamines

Chemistry - Methods, Journal Year: 2024, Volume and Issue: 4(4)

Published: March 4, 2024

Abstract N ‐Nitrosamines acting as contaminants in our environment is a topic of increasing concern. Detection methods are required, necessitating analytical standards. Herein, we discuss some conventional methodologies to prepare ‐nitrosamines and compare them with unconventional pathways towards their synthesis. These often more environmentally benign safer.

Language: Английский

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Regioselective synthesis of 3-nitroindoles under non-acidic and non-metallic conditions

RSC Advances, Journal Year: 2023, Volume and Issue: 13(38), P. 26581 - 26586

Published: Jan. 1, 2023

An electrophilic substitution reaction, without acid and metal, of indole with ammonium tetramethylnitrate for accessing 3-nitroindole has been developed.

Language: Английский

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