An efficient and green one-pot three-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol)s catalyzed by 2-hydroxy ethylammonium propionate

Zhou, Zhongqiang; Zhang, Yuliang

doi:10.1080/17518253.2014.894142

Cited by 38 publications

(1 citation statement)

References 33 publications

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“…The designed compounds (1) were readily obtained in two steps. The 3/4-(pyridine-4ylmethoxy)benzaldehydes (3) were prepared as previously described 31…”

Section: Docking Of Sdz-88357 In the Hcyp24a1 Model And A Triple Mutamentioning

confidence: 99%

Analysis of the binding sites of vitamin D 1α-hydroxylase (CYP27B1) and vitamin D 24-hydroxylase (CYP24A1) for the design of selective CYP24A1 inhibitors: Homology modelling, molecular dynamics simulations and identification of key binding requirements

Taban

Zhu

DeLuca

et al. 2017

Bioorganic & Medicinal Chemistry

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A homology model of human CYP27B1 was built using MOE and was further optimised by molecular dynamics simulations of the hCYP27B1 homology model and a hCYP27B1-SDZ-88357 complex. Docking results from the hCYP27B1-SDZ-88357 complex showed amino acids Arg107, Asn387 and Asp320 have an important role in binding interaction, with Asp320 part of the important acid-alcohol pair situated in the I-helix with the conserved sequence (A/G) GX (E/D) (T/S), which assumes an essential role in the binding of an oxygen molecule for catalysis. Additional docking experiments with selective hCYP27B1 or hCYP24A1 inhibitors using both the hCYP27B1 model and a triple mutant hCYP24A1 model provided further support for the importance of H-bonding interactions with the three identified active site amino acids. To confirm the role of Arg107, Asn387 and Asp320 in the active site of hCYP27B1 compounds were designed that would form H-bonding interactions, as determined from docking experiments with the hCYP27B1 model. Subsequent synthesis and CYP24A1 and CYP27B1 enzyme assays of the designed compounds 1a and 1b showed a∼5-fold selectivity for CYP27B1 confirming the importance of Asp320 in particular and also Asn387 and Arg107 as important amino acids for CYP27B1 inhibitory activity.

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“…The designed compounds (1) were readily obtained in two steps. The 3/4-(pyridine-4ylmethoxy)benzaldehydes (3) were prepared as previously described 31…”

Section: Docking Of Sdz-88357 In the Hcyp24a1 Model And A Triple Mutamentioning

confidence: 99%

Analysis of the binding sites of vitamin D 1α-hydroxylase (CYP27B1) and vitamin D 24-hydroxylase (CYP24A1) for the design of selective CYP24A1 inhibitors: Homology modelling, molecular dynamics simulations and identification of key binding requirements

Taban

Zhu

DeLuca

et al. 2017

Bioorganic & Medicinal Chemistry

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ZrOCl₂·8H₂O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives

Han

Zhou

2019

Applied Organom Chemis

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A simple, efficient and eco‐friendly procedure has been developed using ZrOCl2·8H2O as catalyst for the synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives in aqueous ethanol at room temperature. The present methodology offers several advantages such as operational simplicity, use of ZrOCl2·8H2O as a green, non‐toxic, inexpensive and reusable catalyst, reusability of reaction media, high yields, mild and environmentally benign reaction conditions.

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Greener and practical synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s through a conventional heating and a mechanochemical procedure

Khaligh

Mihankhah

2020

Journal of Heterocyclic Chem

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A new catalytic application of 4,4′‐trimethylenedipiperidine for the efficient synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s is developed. According to the principles of green chemistry, the reaction was performed by conventional and non‐conventional processes: (a) in the refluxing ethanol using a catalytic amount of organocatalyst; (b) at room temperature in the presence of organocatalyst in a planetary ball mill under solvent‐free conditions. The organocatalyst could be reused up to 10 runs, and a negligible reduction of catalytic activity was detected. A variety of substituted 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s were obtained in good–to‐excellent yields under eco‐friendly conditions. 4,4′‐Trimethylenedipiperidine is commercially available and easy to handle and storage, less toxic, non‐flammable, as well as it shows high thermal stability and good solubility in water. The current methodology has merits including (a) wide substrate‐scope and high yields of the desired products in the short reaction times, (b) avoiding the use of hazardous solvents and acidic and metal‐containing catalysts, (c) minimize the generation of hazardous waste, and (d) simple workup process. Based on great potential as a promising organocatalyst, we hope it can be used as a greener alternative to piperidine for other organic transformations.

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An efficient and green one-pot three-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol)s catalyzed by 2-hydroxy ethylammonium propionate

Cited by 38 publications

References 33 publications

Analysis of the binding sites of vitamin D 1α-hydroxylase (CYP27B1) and vitamin D 24-hydroxylase (CYP24A1) for the design of selective CYP24A1 inhibitors: Homology modelling, molecular dynamics simulations and identification of key binding requirements

Analysis of the binding sites of vitamin D 1α-hydroxylase (CYP27B1) and vitamin D 24-hydroxylase (CYP24A1) for the design of selective CYP24A1 inhibitors: Homology modelling, molecular dynamics simulations and identification of key binding requirements

ZrOCl₂·8H₂O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives

Greener and practical synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s through a conventional heating and a mechanochemical procedure

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An efficient and green one-pot three-component synthesis of 4,4′-(arylmethylene)bis(1H-pyrazol-5-ol)s catalyzed by 2-hydroxy ethylammonium propionate

Cited by 38 publications

References 33 publications

Analysis of the binding sites of vitamin D 1α-hydroxylase (CYP27B1) and vitamin D 24-hydroxylase (CYP24A1) for the design of selective CYP24A1 inhibitors: Homology modelling, molecular dynamics simulations and identification of key binding requirements

Analysis of the binding sites of vitamin D 1α-hydroxylase (CYP27B1) and vitamin D 24-hydroxylase (CYP24A1) for the design of selective CYP24A1 inhibitors: Homology modelling, molecular dynamics simulations and identification of key binding requirements

ZrOCl2·8H2O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives

Greener and practical synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s through a conventional heating and a mechanochemical procedure

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ZrOCl₂·8H₂O as an efficient and recyclable catalyst for the one‐pot multicomponent synthesis of novel [1,3]oxazino[5,6‐c]quinolin‐5‐one derivatives