Green Approach to the Design of Functionalized Medicinally Privileged 4‐Aryl‐1,4‐dihydropyrano[2,3‐<i>c</i>]‐pyrazole‐5‐carbonitrile Scaffold

Ilovaisky, Alexey I.; Medvedev, Michael G.; Merkulova, Valentina M.; Elinson, Michaïl N.; Nikishin, G. I.

doi:10.1002/jhet.1737

Cited by 15 publications

(5 citation statements)

References 14 publications

(24 reference statements)

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“…In 2013, Ilovaisky's group reported the "on water" one-pot three-component reaction of aromatic aldehyde 10, malononitrile 2, and pyrazolone 16 in presence of sodium hydroxide (NaOH) as a basic catalyst at 100 °C for the synthesis of several pyrano[2,3-c]pyrazole derivatives 37 in 85-98% yield (Scheme 22). 72 The methodology displays several advantages such as mild reaction conditions, short reaction time, wide substrate scope, high yield of the product, eco-friendly as well as environmentally friendly protocol. By applying this green synthetic protocol, seven compounds possessing electron-rich as well as electron-poor substituents were synthesized in good to excellent yield mainly ranging from 85-98% within a very short reaction time.…”

Section: Scheme 19 Secondary Amine Catalyzed Synthesis Of Dihydropyrano[23-c]pyrazolesmentioning

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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Section: Scheme 19 Secondary Amine Catalyzed Synthesis Of Dihydropyrano[23-c]pyrazolesmentioning

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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“…Furthermore, four-component reactions of aldehyde, malononitrile, β-keto ester and hydrazine hydrate derivatives have also been reported ( Scheme 1(c) ) [ 25–29 ]. These reactions were catalysed using various basic catalysts [ 23–25 , 29 ], ionic liquid catalysts [ 30 ], and metal catalysts [ 22 , 26 , 31 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis of N-(4-chlorophenyl) substituted pyrano[2,3-c]pyrazoles enabling PKBβ/AKT2 inhibitory and in vitro anti-glioma activity

et al. 2022

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A series of N -(4-chlorophenyl) substituted pyrano[2,3-c]pyrazoles was synthesised and screened for their potential to inhibit kinases and exhibit anticancer activity against primary patient-derived glioblastoma 2D cells and 3D neurospheres. A collection of 10 compounds was evaluated against glioma cell lines, with compound 4j exhibiting promising glioma growth inhibitory properties. Compound 4j was screened against 139 purified kinases and exhibited low micromolar activity against kinase AKT2/PKBβ. AKT signalling is one of the main oncogenic pathways in glioma and is often targeted for novel therapeutics. Indeed, AKT2 levels correlated with glioma malignancy and poorer patient survival. Compound 4j inhibited the 3D neurosphere formation in primary patient-derived glioma stem cells and exhibited potent EC 50 against glioblastoma cell lines. Although exhibiting potency against glioma cells, 4j exhibited significantly less cytotoxicity against non-cancerous cells even at fourfold–fivefold the concentration. Herein we establish a novel biochemical kinase inhibitory function for N -(4-chlorophenyl) substituted pyrano[2,3-c]pyrazoles and further report their anti-glioma activity in vitro for the first time. KEY MESSAGE Anti-glioma pyrano[2,3-c]pyrazole 4j inhibited the 3D neurosphere formation in primary patient-derived glioma stem cells. 4j also displayed PKBβ/AKT2 inhibitory activity. 4j is nontoxic towards non-cancerous cells.

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“…Nevertheless, continued efforts are being made to explore new MCR strategies for organic reactions. MCR methodology has been extensively used for the synthesis of heterocyclic compounds such as 4 H ‐chromene, 2 H ‐chromen‐2‐one, 7,8‐dihydro‐4 H ‐chromen‐5(6 H )‐one, pyrano[3,2‐c]pyran‐5(4H)‐one, and 1,4‐dihydropyrano[2,3‐c]pyrazole using different catalysts and reaction conditions.…”

Section: Introductionmentioning

confidence: 99%

Zn(L‐proline)₂ as an efficient and reusable catalyst for the multi‐component synthesis of pyran‐annulated heterocyclic compounds

Tahmassebi

Blevins

Gerardot

2019

Applied Organom Chemis

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We have developed a simple, straightforward and highly efficient multi‐component one‐pot synthesis of 2‐amino‐3‐cyano‐4H‐pyrans and pyran‐annulated heterocyclic compounds. Zn(L‐proline)2 has been utilized as a mild and efficient Lewis acid catalyst for the three‐component reaction of aromatic aldehydes, malononitrile and enolizable C‐H acids or activated phenols to synthesize pyran‐annulated scaffolds. 3‐Methyl‐1‐phenyl‐2‐pyrazolin‐5‐one, 4‐hydroxycoumarine, dimedone, 4‐hydroxy‐6‐methyl‐2‐pyrone, resorcinol, 1‐naphthol and 2‐naphthol were used as activated C‐H acids. The products were isolated in high yields via vacuum filtration and without using any chromatography. The Zn(L‐proline)2 was recovered and reused in another reaction (three times) without significant loss of activity.

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Green Approach to the Design of Functionalized Medicinally Privileged 4‐Aryl‐1,4‐dihydropyrano[2,3‐c]‐pyrazole‐5‐carbonitrile Scaffold

Cited by 15 publications

References 14 publications

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

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 N-(4-chlorophenyl) substituted pyrano[2,3-c]pyrazoles enabling PKBβ/AKT2 inhibitory and in vitro anti-glioma activity

Zn(L‐proline)₂ as an efficient and reusable catalyst for the multi‐component synthesis of pyran‐annulated heterocyclic compounds

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Green Approach to the Design of Functionalized Medicinally Privileged 4‐Aryl‐1,4‐dihydropyrano[2,3‐c]‐pyrazole‐5‐carbonitrile Scaffold

Cited by 15 publications

References 14 publications

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

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 N-(4-chlorophenyl) substituted pyrano[2,3-c]pyrazoles enabling PKBβ/AKT2 inhibitory and in vitro anti-glioma activity

Zn(L‐proline)2 as an efficient and reusable catalyst for the multi‐component synthesis of pyran‐annulated heterocyclic compounds

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Zn(L‐proline)₂ as an efficient and reusable catalyst for the multi‐component synthesis of pyran‐annulated heterocyclic compounds