Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles

Zhou, Chenfeng; Li, Jianjun; Su, Weike

doi:10.1016/j.cclet.2016.05.010

Cited by 45 publications

(12 citation statements)

References 36 publications

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“…More than half of all pyrano[2,3-c] pyrazole heterocyclic compound are lipophilic, and their poor water solubility and stability has limited their application in pharmaceutical products [16]. Therefore, strategies are needed to improve the solubility, stability, and in vivo activity.…”

Section: Discussionmentioning

confidence: 99%

“…BCAP-37 and MCF-7 breast cancer cells were generously donated by Dr. Meihua Sui (People’s Hospital of Zhejiang Province); a series of pyrano [2,3-c]pyrazole derivatives were synthesized by Dr. Weike Su’s group (Zhejiang University of Technology) (Figure 1), and have already reported previously [16]. The cell lines were cultivated in RPMI-1640 medium (Gibco, United States), supplemented with 10% fetal bovine serum (Gibco, United States) and antibiotics (10,000 U/mL penicillin and 10μg/mL streptomycin; Gibco, United States).…”

Section: Methodsmentioning

confidence: 99%

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Nanoformulation of a Novel Pyrano[2,3-c] Pyrazole Heterocyclic Compound AMDPC Exhibits Anti-Cancer Activity via Blocking the Cell Cycle through a P53-Independent Pathway

et al. 2019

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Pyrano[2,3-c]pyrazole derivatives have been reported as exerting various biological activities. One compound with potential anti-tumor activity was screened out by MTT assay from series of dihydropyrazopyrazole derivatives we had synthesized before using a one-pot, four-component reaction, and was named as 6-amino-4-(2-hydroxyphenyl)-3-methyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (hereinafter abbreviated as AMDPC). The IC50 of AMDPC against Bcap-37 breast cancer cells was 46.52 μg/mL. Then the hydrophobic AMDPC was encapsulated in PEG-PLGA block copolymers, and then self-assembled as polymeric micelle (mPEG-PLGA/AMDPC) to improve both physiochemical and release profiles. The effect of mPEG-PLGA/AMDPC on BCAP-37 cancer cells showed similar anti-tumor effects as AMDPC. Furthermore, the anti-tumor mechanism of mPEG-PLGA/AMDPC was investigated, which can probably be attributed to stimulating the expression of P21 gene and therefore protein production on BCAP-37 cells, and then blocked the cell cycle through the P53-independent pathway both in S phase and G2 phase. Thus, mPEG-PLGA/AMDPC is a promising therapeutic agent for cancer treatment, and further in vivo studies will be developed.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Nanoformulation of a Novel Pyrano[2,3-c] Pyrazole Heterocyclic Compound AMDPC Exhibits Anti-Cancer Activity via Blocking the Cell Cycle through a P53-Independent Pathway

et al. 2019

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“…64 By applying this eco-friendly, column chromatography-free methodology 13 derivatives were synthesized in good to excellent yield. In 2016, Zhou et al 65 demonstrated morpholine triflate (MorT) as a Lewis acid catalyst in one-pot fourcomponent synthesis of pyrano [2,3-c]pyrazole derivatives 37 from several aldehydes 5, malononitrile 2, hydrazine 39 and ethyl acetoacetate 13 in aqueous ethanolic solution under refluxing condition for 7-12 hours. For optimizing reaction condition, the reaction was performed in presence of different ammonium triflates and different solvent system such as MeOH, EtOH, DMF, THF, H2O, and EtOH/H2O.…”

Section: Acid-catalyzed Synthesismentioning

confidence: 99%

Applications of pyrazolone in multicomponent reactions for the synthesis of dihydropyrano[2,3-c]pyrazoles and spiro-pyrano[2,3-c]pyrazoles in an aqueous medium

Borah¹,

Dwivedi²,

Chowhan³

2021

Arkivoc

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Pyrazolone is an important class of heterocyclic compounds with numerous applications in the fields of organic/material/pharmaceutical chemistry, food/textile industry and cosmetics. Because of these importances, the synthesis of biologically active complex molecules by employing pyrazolone has emerged. Dihydropyrano[2,3-c]pyrazoles and spiro-pyrano[2,3-c]pyrazoles are synthesized from pyrazolone and hold huge potential in the field of medicinal chemistry because of their wide-ranging biological activities. This review article will summarize the up to date advances on the application of pyrazolone in multicomponent reactions for the synthesis of dihydro-and spiro-pyrano[2,3-c]pyrazoles in aqueous medium.

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“…Trityl carbocation (TrCl) 30 , [ 32 ] 1‐(carboxymethyl)pyridinium iodide {[cmpy]I} 31 , [ 33 ] morpholine triflate (MorT) 32 . [ 34 ] and melamine modified chitosan material (Cs‐Pr‐Me). [ 35 ] can also be used as catalysts to synthesize 1,4/2,4‐dihydropyrano[2,3‐c]pyrazoles via four‐component condensation of hydrazine 34 , ethyl 3‐oxobutanoate 22 , malononitrile 23 , and substituted benzaldehydes 33 in different reaction conditions (Figure 4) (Scheme 6).…”

Section: Review Of the Literaturementioning

confidence: 99%

Synthesis of pyrano[2,3‐c]pyrazoles: A review

Sikandar

Zahoor

2020

Journal of Heterocyclic Chem

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One‐pot synthesis of pyrano[2,3‐c]pyrazole derivatives via two or multicomponent condensation of β‐ketoesters, hydrazine monohydrate/phenyl hydrazine, malononitrile, and substituted benzaldehydes is of great interest not only in synthetic chemistry but also in medicinal chemistry because of the tremendous biological activities, such as anticancer, anti‐inflammatory, analgesic, antimicrobial, and enzyme inhibitory activities exhibited by pyranopyrazoles. This review provides extensive knowledge on novel synthetic methodologies of biologically active non‐spiro/spiro‐pyrano[2,3‐c]pyrazole derivatives published recently.

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Morpholine triflate promoted one-pot, four-component synthesis of dihydropyrano[2,3-c]pyrazoles

Cited by 45 publications

References 36 publications

Nanoformulation of a Novel Pyrano[2,3-c] Pyrazole Heterocyclic Compound AMDPC Exhibits Anti-Cancer Activity via Blocking the Cell Cycle through a P53-Independent Pathway

Nanoformulation of a Novel Pyrano[2,3-c] Pyrazole Heterocyclic Compound AMDPC Exhibits Anti-Cancer Activity via Blocking the Cell Cycle through a P53-Independent Pathway

Applications of pyrazolone in multicomponent reactions for the synthesis of dihydropyrano[2,3-c]pyrazoles and spiro-pyrano[2,3-c]pyrazoles in an aqueous medium

Synthesis of pyrano[2,3‐c]pyrazoles: A review

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