Recent Developments on Catalyst‐Free, Visible‐Light‐Triggered Synthesis of Heterocyclic Scaffolds and Their Mechanistic Study

Goswami, Munmee; Dutta, Arup; Paul, Pooja; Nongkhlaw, Rishanlang

doi:10.1002/slct.202102696

Cited by 9 publications

(5 citation statements)

References 72 publications

(101 reference statements)

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“…Taking inspiration from our earlier work, [5,6,21–23] herein, we have synthesized some of the thiazolo[3,2‐ b ]‐[1,2,4]triazoles 6 a – t using visible light as a green energy source and water as a solvent [24–26] . Visible‐light photocatalysis provides additional merits to the reaction condition such as: high yields, inexpensive and readily available visible‐light sources, simple workup procedures, environmentally benign reaction conditions, efficient synthesis with safety and sustainability.…”

Section: Resultsmentioning

confidence: 99%

“…Taking inspiration from our earlier work, [5,6,[21][22][23] herein, we have synthesized some of the thiazolo[3,2-b]-[1,2,4]triazoles 6 a-t using visible light as a green energy source and water as a solvent. [24][25][26] Visible-light photocatalysis provides additional merits to the reaction condition such as: high yields, inexpensive and readily available visible-light sources, simple workup procedures, environmentally benign reaction conditions, efficient synthesis with safety and sustainability. Starting materials, 1,3-diketones 1 was prepared according to the conventional claisen condensation reaction, [27] however, 3mercapto-[1,2,4]triazoles 5 were prepared as per the literature multistep procedure [28] via the intermediacy of hydrazides, which on treatment with thiocyanate salt and refluxing in basic medium afforded cyclized 3-mercaptotriazole derivatives.…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and In vitro‐In silico Evaluation of Thiazolo‐triazole Hybrids as Anticancer Candidates

et al. 2023

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To meet the growing need for stable and clinically effective chemotherapeutic agents, herein, we have synthesized a series of acyl‐functionalized thiazolo[3,2‐b]‐[1,2,4]triazole derivatives in highly efficient and regioselective manner. The structure of newly synthesized regioisomeric products was unambiguously characterized by multinuclear 2D‐NMR [(1H−13C) HMBC, (1H−13C) HMQC] spectroscopic data. To assess the anticancer and pharmacokinetic profile of the synthesized compounds, we performed in silico, and ex vivo binding studies of compounds with calf‐thymus deoxyribonucleic acid (ct‐DNA) and bovine serum albumin (BSA), respectively, and also tested their efficacy against five human cancer cell lines. viz., MCF‐7 (breast cancer), BT‐474 (breast cancer), A549 (lung cancer), MOLT4 (acute lymphoblastic leukemia), and BxPC3 (pancreatic cancer). Compounds (2‐(4‐chlorophenyl)‐6‐methylthiazolo[3,2‐b][1,2,4]triazol‐5‐yl)(4‐fluorophenyl)methanone 6 l, (4‐chlorophenyl)(2‐(4‐chlorophenyl)‐6‐methylthiazolo[3,2‐b][1,2,4]triazol‐5‐yl)methanone 6 m and (2‐(4‐chlorophenyl)‐6‐methylthiazolo[3,2‐b][1,2,4]triazol‐5‐yl)(4‐methoxyphenyl) methanone 6 q exhibited excellent anticancer potential among the screened derivatives. Furthermore, ex‐vivo mechanistic investigations showed the static mode of quenching and moderate bindings between the ligand and biomolecules; DNA (Kq=2.01‐2.24*1012 M−1 s−1) and BSA (Kq=2.25‐.2.72*1012 M−1 s−1). Moreover, fluorescence displacement assay demonstrated a groove binding mode of interaction with ct‐DNA, which was supported by UV‐Visible absorption spectrum, circular dichroism, and viscosity analysis.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Synthesis and In vitro‐In silico Evaluation of Thiazolo‐triazole Hybrids as Anticancer Candidates

et al. 2023

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“…On the same line, eco-friendly approaches based on the reaction of 2-aminothiophenol with an aldehyde and isocyanide in ethanol/water under visible light irradiation have been recently reviewed (Figure 2, path l). In particular, yields > 90% were observed even in the absence of photocatalysists under 22 W irradiation with compact fluorescence light for 4.5 h [34].…”

Section: Other Synthetic Routesmentioning

confidence: 97%

The Multifaceted Opportunities Provided by the Pheomelanin-Inspired 1,4-Benzothiazine Chromophore: A Still-Undervalued Issue

Alfieri,

Panzella

2023

Molecules

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1,4-Benzothiazines are the main building blocks of the naturally occurring pheomelanin pigments, and their chromophoric properties have been strongly related to the well-known phototoxicity of these pigments, partly responsible for the high incidence of melanoma and other skin cancers in red-haired people. However, some peculiar features of the 1,4-benzothiazine chromophore could be functionally exploited in several sectors. Within this context, in this perspective, an overview of the very recently reported applications of the 1,4-benzothiazine chromophore in pH sensing, filter permeability control, smart packaging, electrochromic device fabrication, bioimaging, photocatalysis, and HPLC detection systems is provided, together with a brief presentation of recently developed synthetic approaches to the 1,4-benzothiazine scaffold, with the aim of emphasizing the still-undervalued multifunctional opportunities offered by this class of compounds.

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“…[74] Visible light photoredox catalyzed synthesis of therapeutically relevant heterocyclic compounds was devised by P. Singh et al [75] Nongkhlaw et al, also disclosed the facile synthesis of heterocyclic compounds employing catalyst-free photo-induced chemistry. [76] However, the expoitation of visible-light as an alternative clean, energetically and environmentally benign energy source for the stereoselective synthesis of spirocyclic oxindoles are still limited and ample attention needs to be paid in the future. Herein, we have demonstrated a recent outlook on the visible light accelerated rapid construction of structurally functionalized spirooxindoles and covered the reports from 2015 to date.…”

Section: Introductionmentioning

confidence: 99%

Visible‐Light‐Mediated Direct Expeditious Photochemical Construction of Spirocyclic‐Oxindoles

2023

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Spirocyclic compounds, particularly spirooxindoles that comprise a tetrahedral sp3‐hybridized carbon atom at the C‐3 position of an orthogonally shaped bicyclic structure have recently received increasing attention in drug discovery and development, besides their major potential in natural products and synthetic organic chemistry. They are found to be the major structural constituents of many alkaloids, and key active building blocks for the construction of various pharmaceutically significant molecules. On the other hand, with the increasing awareness of people about protecting their health and the living environment from the pollution caused by chemical laboratories and industry, the development of a synthetic method that provides alternatives to the traditional one by introducing atom economical sustainable processes is of scientifically and technically demanding but challenging. To address these concerns and inspired by the natural photosynthesis process, recently visible light‐induced chemistry appears to be a highly economic, sustainable, and alternative approach to organic synthesis. The present mini‐review aims to highlight the recent progress accomplished in the straightforward construction of spirooxindoles accelerated by visible light irradiation from the period of 2015 to date. Besides reviewing the advantages achieved in this field, we also attempt to find out the drawback, mechanistic rationalization, and scopes of future applications.

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Recent Developments on Catalyst‐Free, Visible‐Light‐Triggered Synthesis of Heterocyclic Scaffolds and Their Mechanistic Study

Cited by 9 publications

References 72 publications

Synthesis and In vitro‐In silico Evaluation of Thiazolo‐triazole Hybrids as Anticancer Candidates

Synthesis and In vitro‐In silico Evaluation of Thiazolo‐triazole Hybrids as Anticancer Candidates

The Multifaceted Opportunities Provided by the Pheomelanin-Inspired 1,4-Benzothiazine Chromophore: A Still-Undervalued Issue

Visible‐Light‐Mediated Direct Expeditious Photochemical Construction of Spirocyclic‐Oxindoles

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