A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

Ibad, Afshan; Waseem, Malik A.; Ibad, Farah; Ansari, Khursheed; Lone, Ali Mohd; Watal, Geeta; Siddiqui, I. R.

doi:10.1002/slct.201700229

Cited by 25 publications

(6 citation statements)

References 41 publications

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“…Moreover, it has been found that in different types of tumor cells, neuropilins (NRPs) such as NRP2 facilitate tumor metastasis 30,31 . Increased expression of NRP2 leads to an elevated rate of cell proliferation in melanoma cells and enhances cell metastasis 32–38 . In the present study, invasive potential of Kyse‐270 and EC9706 cells showed a pronounced decrease on incubation with TDFPT compared with the control cultures.…”

Section: Discussionsupporting

confidence: 46%

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Tretinoin (2,4‐difluoro‐phenyl) triazole activates proapoptotic protein expression and targets NRP2 protein to inhibit esophageal carcinoma cell growth

Alotaibi

2023

Environmental Toxicology

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The present study investigated the effect of tretinoin (2,4‐difluoro‐phenyl) triazole (TDFPT) on the growth and proliferation of Kyse‐270 and EC9706 esophageal carcinoma cells and explored the underlying mechanism. The results demonstrated that TDFPT treatment of Kyse‐270 and EC9706 cells led to a dose‐dependent reduction in cell proliferation. Colony formation was significantly (p < .05) reduced in Kyse‐270 and EC9706 cells on treatment with various concentrations of TDFPT. In TDFPT‐treated Kyse‐270 and EC9706 cells, the expression of Bcl‐2 protein showed a remarkable decrease, whereas the level of Bax protein was found to be higher compared with the control cells. Cell invasion showed a prominent decrease in Kyse‐270 and EC9706 cells on treatment with TDFPT. Treatment with TDFPT led to a prominent suppression in the expression of MMP‐9 and NRP2 in Kyse‐270 and EC9706 cells. In silico studies using the AutoDock Vina and discovery studio software revealed that various confirmations of TDFPT bind to NRP2 protein with the affinity ranging from −8.6 to −6.1 kcal/mol. It was found that the TDFPT interacts with NRP2 protein by binding to alanine (ALA A:295), proline (PRO A:306), glutamine (GLN A:307), and isoleucine (ILE A:293) amino acid residues. In summary, TDFPT exposure suppresses esophageal carcinoma cell proliferation, inhibits colony formation ability, and activates apoptotic pathway. Thus, TDFPT acts as an effective antiproliferative agent for esophageal carcinoma cells and needs to be investigated further as chemotherapeutic molecule.

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Section: Discussionsupporting

confidence: 46%

“…30,31 Increased expression of NRP2 leads to an elevated rate of cell proliferation in melanoma cells and enhances cell metastasis. [32][33][34][35][36][37][38] In the present study, invasive…”

Section: Discussionmentioning

confidence: 95%

Tretinoin (2,4‐difluoro‐phenyl) triazole activates proapoptotic protein expression and targets NRP2 protein to inhibit esophageal carcinoma cell growth

Alotaibi

2023

Environmental Toxicology

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“…Researchers have effectively explored the visible lightmediated synthesis of pyrano[2,3-d]pyrimidine compounds. Ibad et al (2017) used ethylene glycol as a green solvent and promoter to synthesize tetrahydro-1H-pyrano[2,3-d] pyrimidine derivatives, achieving high yields under mild conditions. Mohamadpour developed a green method for making pyrano[2,3-d] pyrimidine scaffolds using visible light irradiation to promote Knoevenagel-Michael cyclocondensation without a catalyst or solvent.…”

Section: Visible Light-mediated Synthesis Of Pyrano[23d]pyrimidine Co...mentioning

confidence: 99%

“…Using ethylene glycol as a green solvent and promoter, Ibad et al [77] synthesized tetrahydro-1H-pyrano[2,3-d] pyrimidine 60 derivatives in 2017 by performing Knoevenagel condensation and [4 + 2] cycloaddition. The method was metal-free and base-free and achieved high yields under mild conditions with good functional group compatibility.…”

Section: Visible Light-mediated Synthesis Of Pyrano[23d]pyrimidine Co...mentioning

confidence: 99%

Furo, Pyrano, and Pyrido[2,3‐d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications

Rezaeifard,

Bakherad,

Navidpour

et al. 2024

ChemistrySelect

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Due to their extensive applications in pharmaceuticals and natural substances, organic synthesis and heterocyclic compounds have been at the forefront of research for many years. Pyrimidine is one of the heterocyclic compounds that have various derivatives with promising biological and pharmacological properties. This review article covers the synthesis and biological effects of pyrimidine derivatives, such as pyrano[2,3‐d]pyrimidines, pyrido[2,3‐d]pyrimidines, and furo[2,3‐d]pyrimidines. The compounds discussed in this review have a wide range of biological activities. Recent advances in green chemistry have led to the development of eco‐friendly synthetic methods for producing these bioactive heterocycles. This review aims to present various synthetic methods and biological effects of these compounds and provide new opportunities for organic chemists to develop potent nitrogen‐ and oxygen‐containing heterocycles for future applications. The review highlights examples of successful syntheses and applications of pyrimidine derivatives in the fields of antibacterial, antifungal, anticancer, enzyme inhibition, and antiviral research.

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“…Ibad et al 161 reported a novel and green synthetic route to afford tetrahydro-1 H -pyrano[2,3- d ]-pyrimidine 123 by heterocyclization through Knoevenagel condensation of 2-thiobarbituric acid 11a (2 mmol) and 1 (2 mmol) to form cyclic adduct 5-arylidine thiobarbituric acid which then undergo [4+2] cycloaddition with internal alkynes’ derivatives 83 / 83b / 83c / 83d / 83e (2 mmol) in the presence of ethylene glycol acting as a catalyst as well as solvent under visible blue-LED light irradiation (24 W) ( Scheme 86 ). 1 carrying electron-releasing substituents gave higher yields of 123 in lower reaction time than those carrying electron-withdrawing substituents and also symmetrical alkynes produced a higher yield of the product than asymmetrical alkynes.…”

Section: Synthesis Of 5-aryl-substituted Pyrano[23- D ...mentioning

confidence: 99%

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

2023

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The pyranopyrimidine core is a key precursor for medicinal and pharmaceutical industries due to its broader synthetic applications as well as its bioavailability. Among its four possible isomers, we found that 5H-pyrano[2,3-d]pyrimidine scaffolds have a wide range of applicability, and in recent years, they have been intensively investigated, but the development of the main core is found to be more challenging due to its structural existence. In this review article, we cover all of the synthetic pathways that are employed for the development of substituted 4-aryl-octahydropyrano/hexahydrofuro[2,3-d]pyrimidin-2-one (thiones) and 5-aryl-substituted pyrano[2,3-d]pyrimidindione (2-thiones) derivatives through a one-pot multicomponent reaction using diversified hybrid catalysts such as organocatalysts, metal catalysts, ionic liquid catalysts, nanocatalysts, green solvents, catalyst-/solvent-free conditions, and miscellaneous catalysts as well as the mechanism and recyclability of the catalysts. This review mainly focuses on the application of hybrid catalysts (from 1992 to 2022) for the synthesis of 5H-pyrano[2,3-d]pyrimidine scaffolds. This review will definitely attract the world’s leading researchers to utilize broader catalytic applications for the development of lead molecules.

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A Green Access to Tetrahydro-1H-pyrano[2,3-d]pyrimidines: Visible-Light-Triggered and Ethylene-Glycol-Mediated Multicomponent One-Pot Process.

Cited by 25 publications

References 41 publications

Tretinoin (2,4‐difluoro‐phenyl) triazole activates proapoptotic protein expression and targets NRP2 protein to inhibit esophageal carcinoma cell growth

Tretinoin (2,4‐difluoro‐phenyl) triazole activates proapoptotic protein expression and targets NRP2 protein to inhibit esophageal carcinoma cell growth

Furo, Pyrano, and Pyrido[2,3‐d]Pyrimidines: A Comprehensive Review of Synthesis and Medicinal Applications

Importance of Hybrid Catalysts toward the Synthesis of 5H-Pyrano[2,3-d]pyrimidine-2-ones/2,4-diones (Thiones)

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