Reaction pathway of POCl<sub>3</sub>-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione

Sandeep, Mohanty; Roy, Amrendra Kumar; Reddy, Sandeep G.; Kumar, K. P. Vinay; Karmakar, Arun

doi:10.1080/10426507.2015.1073277

Cited by 4 publications

(1 citation statement)

References 11 publications

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“…[7] Although they were eventually phased out, they have recently regained interest, particularly as a "solid surrogate" to aldehydes in specific organic reactions. Bertagnini's salts [8] exhibit a reactivity comparable to aldehydes yet they offer enhanced stability against moisture and air exposure, maintaining their integrity over extended periods. Furthermore, their scope has been expanded to encompass specific ketones, enabling access to bisulfite-adducts with a greater reactivity than their corresponding carbonyl counterparts.…”

Section: Introductionmentioning

confidence: 99%

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Behera,

Kanti Bera,

Basoccu

et al. 2024

Adv Synth Catal

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Our research has demonstrated that mechanochemical activation is more effective with solid reagents. We have showcased the practicality of Bertagnini's salts, also called aldehyde‐bisulfite adducts, which are crystalline, simplifying preparation and storage. These salts are stable substitutes for liquid aldehydes and ketones that have been effectively employed in reductive amination, synthesizing aza‐heterocycles and hydrazones within mechanochemistry. The technique's effectiveness broadens the substrate scopes, simplifies purification, reduces reaction times, and delivers good product yields. Additionally, the thermal stability of the bisulfite adducts has been confirmed through TGA (Thermogravimetric analysis) analysis.

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Section: Introductionmentioning

confidence: 99%

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Behera,

Kanti Bera,

Basoccu

et al. 2024

Adv Synth Catal

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Reactions of Aldehydes and Ketones and Their Derivatives

Murray

2020

Organic Reaction Mechanisms · 2016

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Synthesis of Thiazolidinedione‐ and Triazole‐Linked Organoselenocyanates and Evaluation of Anticancer Activities Against Breast Cancer with Mechanistic Investigations

Pal,

Banerjee,

Sarkar

et al. 2024

Chemistry A European J

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Organoselenocyanates are important classes of organoselenium compounds having potential pharmaceutical applications in cancer biology. In the present study, two different series of organoselenocyanates (15a‐15c and 16a‐16c) incorporating crucial heterocyclic pharmacophores such as 2,4‐thiazolidine‐1,3‐dione and 1,2,3‐triazole were rationally designed. The organoselenocyanates were synthesized using multi‐step organic synthesis and investigated for their anticancer activities against triple‐negative breast cancer cells. Based on the preliminary anti‐proliferative activities and the selectivity index towards cancer cells over the normal cells, 2,4‐thiazolidine‐1,3‐dione‐based selenocyanate 15a was identified as the lead analogue for detailed investigations. In addition to the anti‐migratory activity, compound 15a induced G1‐phase arrest of the cell cycle and led to early apoptosis. Further studies on the redox balance of MDA‐MB‐231 cells indicated the antioxidant nature of 15a with the quenching of ROS level and upregulation of TrxR1 expression. Detailed mechanistic investigations with the expression levels of key‐cancer marker proteins revealed that the selenocyanate 15a induced the activation of ERK pathway by upregulating p‐ERK expression with the subsequent downregulation of p‐Akt and c‐Myc levels leading to the inhibition of cellular proliferation. Therefore, the primary outcomes of the study would be valuable in the development of chemotherapeutic agents towards the treatment of triple‐negative breast cancer.

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Reaction pathway of POCl₃-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione

Cited by 4 publications

References 11 publications

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Reactions of Aldehydes and Ketones and Their Derivatives

Synthesis of Thiazolidinedione‐ and Triazole‐Linked Organoselenocyanates and Evaluation of Anticancer Activities Against Breast Cancer with Mechanistic Investigations

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Reaction pathway of POCl3-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione

Cited by 4 publications

References 11 publications

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Application of Bertagnini's Salts in a Mechanochemical Approach Toward Aza‐Heterocycles and Reductive Aminations via Imine Formation

Reactions of Aldehydes and Ketones and Their Derivatives

Synthesis of Thiazolidinedione‐ and Triazole‐Linked Organoselenocyanates and Evaluation of Anticancer Activities Against Breast Cancer with Mechanistic Investigations

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Product

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Reaction pathway of POCl₃-mediated Knoevenagel condensation of bisulfite adducts with 2,4-thiazolidinedione