Primary Amine Functionalized Carbon Dots for Dead and Alive Bacterial Imaging DOI Creative Commons
Yuting Liu,

Di Zhong,

Yu Lei

et al.

Nanomaterials, Journal Year: 2023, Volume and Issue: 13(3), P. 437 - 437

Published: Jan. 21, 2023

Small molecular dyes are commonly used for bacterial imaging, but they still meet a bottleneck of biological toxicity and fluorescence photobleaching. Carbon dots have shown high potential bio-imaging due to their low cost negligible anti-photobleaching. However, there is large space enhance the quantum yield carbon clarify mechanisms imaging. Using dyeing alive bacteria difficult because thick density complicated structure cell walls. In this work, both dead or imaging can be achieved using primary amine functionalized based on small size, excellent functional groups. Four types were prepared estimated It was found that spermine as one precursors obviously dots, which showed 66.46% bleaching-resistance (70% maintained upon 3-h-irradiation). Furthermore, mild modifying method employed bound ethylenediamine surface spermine–carbon favorable staining not only cells also ones. Investigations physical chemical groups indicated existence (which own much higher yield) stain visibly. The mechanism studied in detail, provides preliminary reference exploring efficient environment-friendly

Language: Английский

Direct Synthesis of Sulfonamides via Synergetic Photoredox and Copper Catalysis DOI
Mingjun Zhang, Lixia Liu, Beibei Wang

et al.

ACS Catalysis, Journal Year: 2023, Volume and Issue: 13(17), P. 11580 - 11588

Published: Aug. 18, 2023

Despite the frequent occurrence of sulfonamides in contemporary pharmaceuticals and agrochemicals, synthesis these compounds is limited by availability preexisting sulfur functionality, amine nucleophilicity, functional group compatibility. Herein, we report use synergetic photoredox copper catalysis to synthesize from a variety aryl radical precursors, readily available amines, dioxide source air at room temperature. The reactions proceeded smoothly with various electron-rich electron-deficient amines generate single-step process. Oxygen was deemed be essential for both catalytic cycles, acting as catalyst. Experimental studies, including electron paramagnetic resonance spectroscopy, provided insights into possible mechanism.

Language: Английский

Citations

37
Photoredox Catalysis-Enabled Sulfination of Alcohols and Bromides DOI
William Carson, Patrick Sarver, Noelle S. Goudy

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 145(38), P. 20767 - 20774

Published: Sept. 18, 2023

Sulfinates are important lynchpin intermediates in pharmaceutical production; however, their synthesis via photoredox catalysis is challenging because of facile oxidation. We herein disclose a photocatalytic strategy for the direct conversion alcohols and alkyl bromides into sulfinates. These transformations enabled by utilization easily oxidized radical precursors─namely, alcohol N-heterocyclic carbene adducts N-adamantyl aminosupersilane─that facilitate efficient oxidatively labile sulfinate products. A broad range functional groups amenable to reported transformations, providing rapid access sulfonamides, sulfonyl halides, sulfones, sulfonic acids. The utility these methods further demonstrated late-stage diversification natural products drugs pharmaceutically relevant sulfonamides "clickable" fluorides. In summary, this work illustrates potential novel precursors expand breadth transformations.

Language: Английский

Citations

29
Synthesis, in silico ADMET prediction analysis, and pharmacological evaluation of sulfonamide derivatives tethered with pyrazole or pyridine as anti-diabetic and anti-Alzheimer's agents DOI Creative Commons
Nagwa M. Abdelazeem, Wael M. Aboulthana,

Ashraf S. Hassan

et al.

Saudi Pharmaceutical Journal, Journal Year: 2024, Volume and Issue: 32(5), P. 102025 - 102025

Published: March 12, 2024

Based on previous developments of our research programs in trying to find new compounds with multiple biological targets such as antioxidant, anti-diabetic, anti-Alzheimer's, and anti-arthritic agents. In the context, a novel series sulfonamide derivatives based pyrazole or pyridine moieties 3a, b, 7–9, 11–13, 15a, 16 were synthesized from amine sulfonyl chloride derivatives. The structures elucidated via spectroscopy (1H 13C NMR). biologically assessed vitro for their anti-diabetic (α-amylase α-glucosidase inhibition) anti-Alzheimer's (acetylcholinesterase activities. results revealed that compound 15a is powerful enzyme inhibitor α-amylase α-glucosidase. Also, 15b demonstrated activity against acetylcholinesterase enzyme. structure–activity relationship study was accomplished. Furthermore, complementary silico molecular properties, drug-likeness, ADMET prediction, surface properties two more fulfilled computed. These studies recommend candidates modifications before vivo assays.

Language: Английский

Citations

15
Visible-Light-Induced Decarboxylative Aminosulfonylation of (Hetero)aryl Carboxylic Oxime Esters DOI

Zhen Zhuang,

Yuting Sun, Yuanchen Zhong

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(3), P. 713 - 718

Published: Jan. 12, 2024

Sulfonamides are important structures in pharmaceuticals, agrochemicals, and organocatalysts, yet the rapid benign synthesis of these compounds is still a great challenge. Herein we report photoinduced method for synthesizing sulfonamides from (hetero)aryl carboxylic acid oxime esters. This reaction proceeds via one-pot cascade radical–radical cross-coupling by energy-transfer-mediated photocatalysis. A wide substrate scope including substrates late-stage modification pharmaceutical molecular entities reveal its generality.

Language: Английский

Citations

13
Single-Electron-Transfer-Generated Aryl Sulfonyl Ammonium Salt: Metal-Free Photoredox-Catalyzed Modular Construction of Sulfonamides DOI
Fengying Yan, Qing Li,

Shanshan Fu

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(7), P. 5227 - 5235

Published: March 21, 2024

Sulfonamides are prominently featured in organic synthesis and medicinal chemistry. Yet, a general synthetic platform for the modular construction of aryl sulfonamides remains elusive. Herein, metal-free photoredox-catalyzed three-component via an sulfonyl ammonium salt intermediate, which was generated situ SET event, has been established. A variety structurally diverse primary, secondary, tertiary were synthesized rapidly from abundant amines or sodium azide under mild conditions. Notably, primary aliphatic amine, challenging Cu-catalyzed protocols, worked well this approach. Moreover, fluoride can be accessed smoothly as well, using potassium hydrogen nucleophile. The potential utility conversion is demonstrated facile three bioactive drug compounds. Preliminary mechanistic studies have revealed that radical key intermediates mechanistically innovative methodology.

Language: Английский

Citations

12
Selective Synthesis of Sulfonamides and Sulfenamides from Sodium Sulfinates and Amines DOI

Rong Feng,

Zhongyu Li, Yue‐Jin Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(3), P. 1736 - 1747

Published: Jan. 12, 2024

An effective method was explored for the selective synthesis of sulfonamides and sulfenamides using sodium sulfinates amines as starting materials. This offers mild reaction conditions, a broad substrate scope, high efficiency, readily accessible materials, making it suitable an alternative strategy preparation variety biologically or pharmaceutically active compounds.

Language: Английский

Citations

8
Exploring photo-excited states of aromatic sulfones for efficient near-infrared-activated photothermal cancer therapy DOI
Kazuya Yoshida, Toshiaki Suzuki, Yasuko Osakada

et al.

Bulletin of the Chemical Society of Japan, Journal Year: 2025, Volume and Issue: 98(1)

Published: Jan. 1, 2025

Abstract Near-infrared light activation enhances phototherapeutic efficacy due to deep-tissue penetration and minimal invasion. While near-infrared-phototherapeutic agents are widely studied, conventional designs often increase molecular size, affecting pharmacokinetics. This study elucidates the photo-excited states of sulfone-containing aromatic compounds as efficient near-infrared-activated photothermal for cancer therapy. We synthesized sulfone-rosamine (3 4) exhibiting strong optical absorption around 700 nm, attributed a unique orbital in LUMO. Compound 4, 35% smaller than near-infrared-dye molecules, such Cy5.5 (0.86 nm3/molecule), intracellular mobility. Upon photoexcitation, 4 undergoes rapid non-radiative relaxation, resulting remarkable effects photostability. Transient spectroscopy density functional theory calculations revealed mechanism involving deactivation after illumination, efficiently converting heat. The near-infrared-induced effect effectively killed various cell lines, including HeLa, MDA-MB-231, PCI-55. provides guidelines designing novel photodrugs with improved mobility, near-infrared responsiveness, photostability, introduces advancement treatment.

Language: Английский

Citations

1
Synthesis, structure elucidation, and in vitro pharmacological evaluation of novel polyfluoro substituted pyrazoline type sulfonamides as multi-target agents for inhibition of acetylcholinesterase and carbonic anhydrase I and II enzymes DOI
Cem Yamalı, Halise İnci Gül, Cavit Kazaz

et al.

Bioorganic Chemistry, Journal Year: 2020, Volume and Issue: 96, P. 103627 - 103627

Published: Jan. 27, 2020

Language: Английский

Citations

66
Sequential C–S and S–N Coupling Approach to Sulfonamides DOI
Kai Chen, Wei Chen, Bing Han

et al.

Organic Letters, Journal Year: 2020, Volume and Issue: 22(5), P. 1841 - 1845

Published: Feb. 19, 2020

A one-pot three-component reaction involving nitroarenes, (hetero)arylboronic acids, and potassium pyrosulfite leading to sulfonamides was described. broad range of bearing different reactive functional groups were obtained in good excellent yields through sequential C-S S-N coupling that does not require metal catalysts.

Language: Английский

Citations

64
Nickel‐Catalyzed Cross‐Coupling of Sulfonamides With (Hetero)aryl Chlorides DOI

Ryan T. McGuire,

Connor M. Simon,

Arun A. Yadav

et al.

Angewandte Chemie International Edition, Journal Year: 2020, Volume and Issue: 59(23), P. 8952 - 8956

Published: March 12, 2020

Abstract The development of Ni‐catalyzed C−N cross‐couplings sulfonamides with (hetero)aryl chlorides is reported. These transformations, which were previously achievable only Pd catalysis, are enabled by use air‐stable ( L )NiCl( o ‐tol) pre‐catalysts (L= PhPAd‐DalPhos and PAd2‐DalPhos ), without photocatalysis. collective scope (pseudo)halide electrophiles (X=Cl, Br, I, OTs, OC(O)NEt 2 ) demonstrated herein unprecedented for any reported catalyst system sulfonamide cross‐coupling (Pd, Cu, Ni, or other). Preliminary competition experiments relevant coordination chemistry studies also presented.

Language: Английский

Citations

55