Photo-Oxidation Coupled Kabachnik–Fields and Bigenelli Reactions for Direct Conversion of Benzyl alcohols to α-Aminophosphonates and Dihydropyrimidones

Ali, G.; Dangroo, Nisar A.; Raheem, Shabnam; Naqvi, Tahira; Ara, Tabassum; Rizvi, Masood Ahmad

doi:10.17344/acsi.2019.5348

Cited by 11 publications

(3 citation statements)

References 31 publications

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“…. 7H 2 O, 20 ionic liquids, 21,22 TBAB, 23 visible light, 24,25 chitosan silica sulfate, 26 molybdic acid-functionalized nano-Fe 3 O 4 @TiO 2 , 27 HClO 4 -SiO 2 , 28 microwave-assisted, 29 PW/SiO 2 , 30 solar thermal, 31 I2, 32 sulfonic acid, 33 Fe 3 O 4 @SiO 2 @OSO 3 H, 34 heteropolyacids, 35 silica gel/NaHSO 4 , 36 organocatalysis, 37 AlCl 3…”

Section: Introductionmentioning

confidence: 99%

Efficient One-Pot Synthesis of 1,4-Dihydropyridines Catalyzed by Magnetic MnFe2O4 Nanoparticles

Moradi

Moradian

Naeimi

2022

ACSi

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The efficient one-pot synthesis of some 1,4-dihydropyridines is described by a condensation reaction of some aldehyde derivatives, ethyl acetoacetate and ammonium acetate in the presence of superparamagnetic manganese ferrite nanoparticles at 80 °C. The advantages of this protocol include selectivity, high purity of the products, excellent yields, short reaction times, ease of processing, and environmentally friendly conditions for the synthesis of 1,4-dihydropyridines. In addition, the catalyst can be recovered and reused in multiple runs without significantly reducing the product yield.

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Section: Introductionmentioning

confidence: 99%

Efficient One-Pot Synthesis of 1,4-Dihydropyridines Catalyzed by Magnetic MnFe2O4 Nanoparticles

Moradi

Moradian

Naeimi

2022

ACSi

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“…Bioactive molecules containing 3-substituted pyrrolidine moiety. Thus, keeping in view importance of 1-benzylpyrrolidin-3-ol moiety in medicinal chemistry and in continuation of our research interests in designing synthetic methodologies and chemical biology, [12][13][14][15][16][17][18][19][20][21][22][23][24] we envisaged diversity-oriented synthesis of 1-benzylpyrrolidin-3-ol analogues via Ugi multi component reaction (Ugi-4CR). As an initial screening step, the synthesized library of the compounds (5a-p) was screened for ability to induce cytotoxicity towards a panel of human cancer cell lines.…”

Section: Introductionmentioning

confidence: 99%

In vitro and In silico Evaluation of Structurally Diverse Benzyl-pyrrolidine-3-ol Analogues as Apoptotic Agents via Caspase Activation

Naqvi¹,

Amin

Ali

et al. 2021

ACSi

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The activation of caspases is central to apoptotic process in living systems. Defects in apoptosis have been implicated with carcinogenesis. Need to develop smart agents capable of inducing apoptosis in tumor cells is obvious. With this motive, diversity oriented synthesis of 1-benzylpyrrolidin-3-ol analogues was envisaged. The multi component Ugi reaction synthesized library of electronically diverse analogues was explored for cytotoxic propensity towards a panel of human cancer cell lines at 10 μM. The lead compounds exhibit a selective cytotoxicity towards HL-60 cells as compared to cell lines derived from solid tumors. Besides, their milder cytotoxic effect on non-cancerous cell lines reaffirm their selective action towards cancer cells only.The lead molecules were tested for their ability to target caspase-3, as a vital protease triggering apoptosis. The lead compounds were observed to induce apoptosis in HL-60 cells around 10 μM concentration. The lead compounds exhibited various non-covalent supra type interactions with caspase-3 key residues around the active site. The binding ability of lead compounds with caspase-3 was studied via molecular docking and molecular dynamic (MD) simulations. MD simulations indicated the stability of compound-caspase-3 complex throughout the 50 ns simulation run. The stability and bio-availability of the lead compounds under physiological conditions was assessed by their interaction with Bovine Serum Albumin (BSA) as model protein. BSA interactions of lead compounds were studied by various bio-physical methods and further substantiated with in silico MD simulations.

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“…Therefore, the development of a new and milder Biginelli-like reactions employing new carbonyl component to construct DHMPs is highly desirable. [2] In continuation of our research work on designing novel and green synthesis, [27][28][29][30] herein we have explored the two-step synthesis of dihydropyrimidones from benzyl halides in a onepot tandem approach. The method involves in situ generation of benzaldehydes from benzyl halides under catalyst-free conditions which are subsequently converted into dihydropyrimidones in a one-pot manner under microwave irradiation using dimethyl sulfoxide (DMSO) as an oxidant/catalyst, scheme I.…”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Tandem Kornblum Oxidation and Biginelli Reaction for the Synthesis of Dihydropyrimidones

2020

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A simple and straightforward approach for the synthesis of dihydropyrimidones via sequential Kornblum oxidation/Biginelli reaction has been developed. The protocol involves an in situ oxidation of benzyl halides which serve as a carbonyl equivalents followed by cyclocondensation with (thio) urea and ethylacetoacetate to furnish dihydropyrimidones under catalyst and base free conditions in a one-pot tandem manner under microwave irradiation. Further, the product purification using aqueous recrystallization avoids large quantities of volatile and a toxic organic solvent usually required for work-up and very less time required for this process makes the method environmental-and nature-friendly.

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Photo-Oxidation Coupled Kabachnik–Fields and Bigenelli Reactions for Direct Conversion of Benzyl alcohols to α-Aminophosphonates and Dihydropyrimidones

Cited by 11 publications

References 31 publications

Efficient One-Pot Synthesis of 1,4-Dihydropyridines Catalyzed by Magnetic MnFe2O4 Nanoparticles

Efficient One-Pot Synthesis of 1,4-Dihydropyridines Catalyzed by Magnetic MnFe2O4 Nanoparticles

In vitro and In silico Evaluation of Structurally Diverse Benzyl-pyrrolidine-3-ol Analogues as Apoptotic Agents via Caspase Activation

Microwave‐Assisted Tandem Kornblum Oxidation and Biginelli Reaction for the Synthesis of Dihydropyrimidones

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