Batch and continuous flow mechanochemical synthesis of organic compounds including APIs

Reaction Chemistry & Engineering, Год журнала: 2023, Номер 9(1), С. 10 - 25

Опубликована: Сен. 5, 2023

Mechanochemistry is becoming an enabling technology for the synthesis of organic and inorganic compounds as well polymers it underlines sustainability in a significant manner.

Язык: Английский

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Flow-to-Flow Technology: Amide Formation in the Absence of Traditional Coupling Reagents Using DPDTC

ACS Sustainable Chemistry & Engineering, Год журнала: 2025, Номер 13(18), С. 6646 - 6655

Опубликована: Апрель 29, 2025

Reported herein is the use of a recyclable coupling agent, 2,2'-dipyridyldithiocarbonate (DPDTC), that generates isolable thioesters in plug flow reactor (PFR). If not isolated, can be reintroduced directly into PFR, along with amines, to generate amides "flow-to-flow" sense. Both electron-rich and -poor aromatic acids, as well sterically hindered aliphatic are efficiently coupled variety including formation Weinreb peptides, high yields.

Язык: Английский

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Broad‐Spectrum Antimicrobial and Antibiofilm Activities of Halogenated Anilines Against Uropathogenic Escherichia coli and ESKAPE Pathogens

Microbial Biotechnology, Год журнала: 2025, Номер 18(5)

Опубликована: Май 1, 2025

ABSTRACT Uropathogenic Escherichia coli (UPEC) is one of the leading causes nosocomial infections and urinary tract (UTIs), capable inducing a spectrum conditions ranging from acute bladder cystitis to chronic pyelonephritis. The virulence arsenal UPEC includes factors, such as curli fimbriae, hemolysin, motility elements metallophores. Moreover, can form biofilm‐like communities quiescent intracellular reservoirs within host tissues, contributing recurrent persistent infections. This study investigates antibiofilm antimicrobial activities two halogen‐substituted aniline derivatives, 4‐bromo‐3‐chloroaniline (4B3CA) 3,5‐dibromoaniline (3,5‐DBA), against UPEC. compounds demonstrated minimum inhibitory concentrations (MICs) 200 μg/mL for 4B3CA 100 3,5‐DBA, with both exhibiting biofilm inhibition IC50 value 10 μg/mL. Additionally, these derivatives showed activity ESKAPE pathogens. Treatment 3,5‐DBA led significant downregulation virulence‐ biofilm‐related genes, including those involved in production, fimbrial adhesion, motility, iron acquisition, colony formation, stress response. Interestingly, mild upregulation hlyA , csrA uvrY was noted, alongside marked adenylate cyclase genes cyaA crp . These findings suggest that may be primary mode action, effects. presence halogen atoms appears enhance their binding affinity through stabilising bond interactions. Furthermore, 3D‐QSAR analysis indicates electrostatic favourability at third fourth positions ring critical bioactivity. Finally, silico ADMET profiling cytotoxicity assessments using Caenorhabditis elegans hold promise therapeutic candidates, warranting further investigation.

Язык: Английский

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Recent advances in synthetic approaches for bioactive cinnamic acid derivatives

Beilstein Journal of Organic Chemistry, Год журнала: 2025, Номер 21, С. 1031 - 1086

Опубликована: Май 28, 2025

Cinnamic acid derivatives represent a significant class of biologically active compounds exhibiting broad spectrum activities, such as antifungal, antidengue, antimetastatic, antimicrobial, antibacterial, and anticancer properties. Their preparation has attracted considerable attention due to their versatile applications across the pharmaceutical, food, chemical sectors. This review elucidates functional groups cinnamic that are instrumental in rational design derivatives. A comprehensive representative recent advancements synthetic methodologies over past five years is presented, particularly emphasizing scaffolds bioactive The provides strategic overview alternative routes highlights latest innovations, including more efficient, highly selective, environmentally sustainable approaches. Given widespread incorporation framework various therapeutic agents, this delivers critical insights into molecular for hit-to-lead optimization, offering detailed strategies diverse modifications. By critically examining these methodologies, paper underscores role expanding utility addressing prevailing challenges.

Язык: Английский

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Selective N-functionalization of Arylhydrazines with Primary Alcohols and Acids under PPh₃/DDQ System

The Journal of Organic Chemistry, Год журнала: 2024, Номер 89(14), С. 10054 - 10065

Опубликована: Июль 1, 2024

We present a PPh3/DDQ-mediated regiospecific selective N-functionalization of arylhydrazines with primary benzylic alcohols and aryl carboxylic acids for the synthesis N1-benzyl N2-acyl arylhydrazines, respectively. This metal- base-free approach features very short reaction times (about 10 min), broad substrate scope, good functional group tolerance, mild conditions. Furthermore, N1-benzlated products have also been successfully applied to concise N-substituted indoles anticancer drug MDM2 inhibitor.

Язык: Английский

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Solvent Minimized Synthesis of Amides by Reactive Extrusion

Angewandte Chemie, Год журнала: 2024, Номер unknown

Опубликована: Сен. 9, 2024

Abstract Herein, we report on the translation of a small scale ball‐milled amidation protocol into large continuous reactive extrusion process. Critical components to successful were: a) understanding how different operating parameters twin‐screw extruder should be harnessed control prolonged operation, and b) consideration physical form input materials. The reaction is applied 36 amides spanning variety combinations (liquid‐liquid, solid–liquid solid‐solid). Following this learning process, have developed an for each combination demonstrated 7‐hour process synthesis amide 500 gram (1.3 mols product).

Язык: Английский

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N-Acylation Reactions of Amines

Elsevier eBooks, Год журнала: 2024, Номер unknown

Опубликована: Янв. 1, 2024

Язык: Английский

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Solvent Minimized Synthesis of Amides by Reactive Extrusion

Angewandte Chemie International Edition, Год журнала: 2024, Номер unknown

Опубликована: Сен. 9, 2024

Abstract Herein, we report on the translation of a small scale ball‐milled amidation protocol into large continuous reactive extrusion process. Critical components to successful were: a) understanding how different operating parameters twin‐screw extruder should be harnessed control prolonged operation, and b) consideration physical form input materials. The reaction is applied 36 amides spanning variety combinations (liquid‐liquid, solid–liquid solid‐solid). Following this learning process, have developed an for each combination demonstrated 7‐hour process synthesis amide 500 gram (1.3 mols product).

Язык: Английский

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Continuous Flow Solvent-Free and Catalyst-Free Mechanochemical Production of Rhodamine-B Dyes and its Derivatives

Chemical Communications, Год журнала: 2024, Номер unknown

Опубликована: Дек. 14, 2024

In this communication, we have described a simple and efficient, catalyst free solvent-free protocol for the continuous flow synthesis of rhodamine B dyes developed from 3-diethyl amino phenol phthalic anhydride.

Язык: Английский

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