Acridinedione-phthalimide conjugates: Intramolecular electron transfer and singlet oxygen generation studies for optical and photodynamic therapy applications DOI Creative Commons
Mohamed E. El‐Khouly, Hassan A. Khatab,

Ayamn A. Abdel-Shafi

et al.

Photochemical & Photobiological Sciences, Journal Year: 2024, Volume and Issue: 23(8), P. 1445 - 1455

Published: June 27, 2024

We reported herein the synthesis, characterization of hybrid conjugates composed phthalimide (Phth) and acridine-1,8-diones (Acr) for optical medical applications. For synthetic procedure, a three-step strategy has been utilized. The properties examined 1,8-acridinedione-phthalimide connected molecules (AcrPhth 1-5) have utilizing various spectroscopic techniques, e.g., steady-state absorption fluorescence, time-correlated single photon counting. studies showed that AcrPhth 1-5 absorbs light in UV visible region. fluorescence exhibited significant quenching compared to acridinedione control compounds (Acr suggesting occurrence electron-transfer reactions from electron donating moiety accepting (Phth). rate efficiency were determined lifetime measurements indicating fast processes covalently conjugates. Computational supported intramolecular reaction using ab initio B3LYP/6-311G methods. In optimized structures, HOMO was found be entirely located on Acr entity, while LUMO Phth entity. Further, synthesized tested as photosensitizers generating singlet oxygen species, which is key factor photodynamic therapy (PDT) nanosecond laser flash enable us detect triplet-excited states conjugates, determining triplet quantum yields, direct detecting an accurate way. From this observation, yields range 0.12-0.27 (for 0.07-0.19 conjugates). molecular docking revealed compound 2 high binding affinity with genes (p53, TOP2B, p38, EGFR) its potential targeted anticancer therapy.

Language: Английский

Photodecarboxylative C–H Alkylation of Azauracils with N-(Acyloxy)phthalimides DOI

Satya Prakash Panda,

Sudhir Kumar Hota,

Rupashri Dash

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3739 - 3744

Published: May 15, 2023

We disclose a transition-metal-free NaI/PPh3-mediated direct C-H alkylation of azauracils using N-(acyloxy)pthalimides (NHPIs) as readily available alkyl surrogates under visible light irradiation. Detailed mechanistic studies reveal formation photoactivated electron donor-acceptor (EDA) complex between NaI/PPh3, TMEDA, and NHPI ester establish the crucial role TMEDA in increasing activity photoredox system. The reaction demonstrates broad scope, scalability, appreciable functional group tolerance. A variety are shown to undergo by primary, secondary, tertiary esters mild conditions, furnishing desired products good excellent yields.

Language: Английский

Citations

38
A General Electron Donor–Acceptor Photoactivation Platform of Diaryliodonium Reagents: Arylation of Heterocycles DOI

Prahallad Meher,

Satya Prakash Panda,

Sanat Kumar Mahapatra

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(46), P. 8290 - 8295

Published: Nov. 14, 2023

We report a photoredox system comprising sodium iodide, triphenyl phosphine, and N,N,N',N'-tetramethylethylenediamine (TMEDA) that can form self-assembled tetrameric electron donor-acceptor (EDA) complex with diaryliodonium reagents (DAIRs) furnish aryl radicals upon visible light irradiation. This practical mode of activation DAIRs enables arylation an array heterocycles under mild conditions to provide the respective heteroaryl-(hetero)aryl assembly in moderate excellent yields. Detailed mechanistic investigations photophysical DFT studies provided insight into reaction mechanism.

Language: Английский

Citations

29
Organophotoredox-Catalyzed Arylation and Aryl Sulfonylation of Morita–Baylis–Hillman Acetates with Diaryliodonium Reagents DOI

Sudip Senapati,

Sushanta Kumar Parida,

Sayali Sunil Karandikar

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(43), P. 7900 - 7905

Published: Oct. 26, 2023

We report an organophotoredox-catalyzed stereoselective allylic arylation of MBH acetates with a palette diaryliodonium triflates (DAIRs) to provide the corresponding trisubstituted alkenes in moderate good yields. The method could be extended three-component coupling involving 1,4-diazabicyclo[2.2.2]octane bis(sulfur dioxide) adduct (DABSO) as sulfur dioxide surrogate for synthesis biologically relevant sulfones. Both these reactions were carried out under mild conditions featuring broad scope, robustness, and appreciable functional group tolerance.

Language: Английский

Citations

27
Electrochemical C–H Alkylation of Azauracils Using N-(Acyloxy)phthalimides DOI

Rupashri Dash,

Satya Prakash Panda,

Kuldeep Singh Bhati

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(34), P. 7227 - 7232

Published: Aug. 20, 2024

We present an electrochemical alkylation of azauracils using N-(acyloxy)phthalimides (NHPI esters) as readily available alkyl radical progenitors under metal- and additive-free conditions. Several are shown to undergo with array NHPI esters (1°, 2°, 3°, sterically congested), providing the desired products in good excellent yields. This operationally simple method is robust, scalable, suitable for both batch flow setups.

Language: Английский

Citations

9
Visible light photoredox-catalyzed arylative cyclization to access benzimidazo[2,1-a]isoquinolin-6(5H)-ones DOI

Prahallad Meher,

Raj Kumar Samanta,

Sourav Manna

et al.

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(40), P. 6092 - 6095

Published: Jan. 1, 2023

An efficient Ru( ii )-photoredox-catalyzed radical cascade between N -substituted 2-arylbenzoimidazoles and diaryliodonium triflates furnishing a variety of arylated-benzimidazo[2,1- ]isoquinolin-6(5 H )-ones is achieved.

Language: Английский

Citations

20
Photodecarboxylative Radical Cascade Involving N-(Acyloxy)phthalimides for the Synthesis of Pyrazolones DOI

Satya Prakash Panda,

Rupashri Dash,

Sudhir Kumar Hota

et al.

Organic Letters, Journal Year: 2024, Volume and Issue: 26(17), P. 3667 - 3672

Published: April 24, 2024

We disclose

Language: Английский

Citations

8
EDA Complex-Enabled Annulation to Access CF2-Containing Tetralones and Quinazolinones Using Persulfates as Electron Donors DOI
Shupeng Zhang, Dawei Guo,

Mei-Ling Yang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(15), P. 10614 - 10623

Published: July 25, 2024

A photocatalyst-free and EDA complex-enabled radical cascade cyclization reaction of inactive alkenes with bromodifluoroacetamides was reported for the divergent synthesis fluorine-containing tetralones quinazolinones. In this transformation, persulfates as electron donors difluoro bromamide acceptors generate complex. This is a promising photochemical method advantages such mild conditions, simple operation, being metal-free, excellent functional group tolerance.

Language: Английский

Citations

6
C‐H alkylation of heterocycles via light‐mediated palladium catalysis DOI Creative Commons

Sudip Senapati,

Sudhir Kumar Hota,

Lennard Kloene

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 28, 2024

Methods enabling direct C-H alkylation of heterocycles are fundamental importance in the late-stage modification natural products, bioactive molecules, and medicinally relevant compounds. However, there is a scarcity general strategy for variety using commercially available alkyl surrogates. We report an operationally simple palladium-catalyzed halides under visible light irradiation with good scalability functional group tolerance. Our studies suggest that photoinduced proceeds through cascade events comprising, site-selective radical addition, base-assisted deprotonation, oxidation. A combination experiments computations was employed generalization this strategy, which successfully translated towards products pharmaceuticals.

Language: Английский

Citations

5
Metal- and Photocatalyst-Free, Visible-Light-Initiated C3 α-Aminomethylation of Quinoxalin-2(1H)-ones via Electron Donor–Acceptor Complexes DOI
Devidas A. More, Sachin R. Shirsath,

M. Muthukrishnan

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(18), P. 13339 - 13350

Published: Aug. 31, 2023

We report a metal- and photocatalyst-free C3 α-aminomethylation of quinoxalin-2(1H)-ones with N-alkyl-N-methylanilines. The reaction proceeds through the formation photoactivated electron donor–acceptor complex between present method provides mild environmentally friendly protocol that exhibits good atom economy excellent functional group tolerance to obtain library biologically significant α-aminomethylated in yields.

Language: Английский

Citations

12
Electron Donor‐Acceptor (EDA) Complex Enabled C−C Cross‐Coupling Reactions of α‐Amino Radicals DOI

Padmanava Barik,

Subhra Sriharsa Behera,

Santosh K. Nanda

et al.

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(6)

Published: April 18, 2024

Abstract Electron‐donor acceptor (EDA) complex has been an integral part of visible‐light photocatalysis and is different from the traditional photoredox catalysis, which requires exogenous photocatalyst, typically a colored compound to initiate photocatalytic cycle. Interestingly, EDA‐complex photochemistry found profound use in activating inert α‐C−H bonds amines. The strategy relied upon formation between donor (amine) (Lewis acid), harvesting light energy perform SET process generate radical cation anion intermediates. then loses activated acidic proton (because SET, acidity α‐proton increases by lowering BDE) form α‐amino radical, participates various C−C coupling cascades. In this review, conceptual approaches for generation radicals their bond‐forming reaction under triggered will be discussed with particular emphasis on mechanism 2018 onwards.

Language: Английский

Citations

4