Efficient atom-economic one-pot multicomponent synthesis of benzylpyrazolyl coumarins and novel pyrano[2,3-c]pyrazoles catalysed by 2-aminoethanesulfonic acid (taurine) as a bio-organic catalyst

Chate, Asha V.; Shaikh, Badrodin Ayyub; Bondle, Giribala M.; Sangle, Sunil M.

doi:10.1080/00397911.2019.1619772

Cited by 22 publications

(15 citation statements)

References 60 publications

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“…Taurine (Tau) is an essential amino acid which its positive effects on bone metabolism and formation have been reported 17 – 19 . It is a sulfurated β-amino acid that is found in free form in animal sources 20 , 21 . It is documented that Tau is involved in calcium modulation, osmoregulation, antioxidation, membrane stabilization, neuromodulation, protein phosphorylation regulation 19 , 22 , 23 .…”

Section: Introductionmentioning

confidence: 99%

A tailored polylactic acid/polycaprolactone biodegradable and bioactive 3D porous scaffold containing gelatin nanofibers and Taurine for bone regeneration

Samadian

Farzamfar

Vaez

et al. 2020

Sci Rep

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The focus of the current study was to develop a functional and bioactive scaffold through the combination of 3D polylactic acid (PLA)/polycaprolactone (PCL) with gelatin nanofibers (GNFs) and Taurine (Tau) for bone defect regeneration. GNFs were fabricated via electrospinning dispersed in PLA/PCL polymer solution, Tau with different concentrations was added, and the polymer solution converted into a 3D and porous scaffold via the thermally-induced phase separation technique. The characterization results showed that the scaffolds have interconnected pores with the porosity of up to 90%. Moreover, Tau increased the wettability and weight loss rate, while compromised the compressive strengths. The scaffolds were hemo- and cytocompatible and supported cell viability and proliferation. The in vivo studies showed that the defects treated with scaffolds filled with new bone. The computed tomography (CT) imaging and histopathological observation revealed that the PLA/PCL/Gel/Tau 10% provided the highest new bone formation, angiogenesis, and woven bone among the treatment groups. Our finding illustrated that the fabricated scaffold was able to regenerate bone within the defect and can be considered as the effective scaffold for bone tissue engineering application.

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Section: Introductionmentioning

confidence: 99%

A tailored polylactic acid/polycaprolactone biodegradable and bioactive 3D porous scaffold containing gelatin nanofibers and Taurine for bone regeneration

Samadian

Farzamfar

Vaez

et al. 2020

Sci Rep

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“…In the same year, several novel dihydropyrano[2,3-c]pyrazole derivatives 67 in 80-90% yield has been synthesized by Chate et al from the reaction of aldehydes 10, malononitrile 2, ethyl acetoacetate 13, and isoniazid 66 in the presence of 2-aminoethanesulfonic acid (taurine) as a bio-organic catalyst in water medium at 70 °C (Scheme 38c). 87 Another achievement has also been gained by Valiey et al in 2019, who synthesized and fully characterized the melamine modified chitosan (Cs-Pr-Me) materials as a reusable bifunctional organocatalyst, and then the efficacy of the catalyst was tested by applying it in the fourcomponent reaction of aldehydes 10, malononitrile 2, hydrazine hydrate 39 and ethyl acetoacetate 13 in the aqueous ethanolic solution as the solvent under reflux condition. Under this condition, several dihydropyrano[2,3-c]pyrazole derivatives 50 was prepared within 25 to 50 minutes and the prepared catalyst was found to be very effective for this transformation.…”

Section: Organocatalyzed 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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“…To date, only a few methodologies have been reported for the development of such benzylpyrazolyl coumarin derivatives. However, the major disadvantages of these protocols are the use of corrosive and unrecyclable homogeneous acid catalysts like glacial acetic acid, 42 2-aminoethanesulfonic acid, 43 Ca-(OTf) 2 , 44 and NbCl 5 45 and the use of expensive heterogeneous catalysts like ZrO 2 nanoparticles 28 and Nb-Zr/KIT-6. 46 Therefore, the synthesis of such aforementioned biologically relevant heterocyclic compounds by the combination of MCR and carbon-based metal-free catalysts would be highly desirable.…”

Section: ■ Introductionmentioning

confidence: 99%

Versatile and Sustainable Approach to Access Biologically Relevant Chromeno[2,3-b]pyridine and Benzylpyrazolyl Coumarin Derivatives Using Graphitic Carbon Nitride as a Reusable Heterogeneous Catalyst

Gajurel

Sarkar

et al. 2022

ACS Omega

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Herein, the synthesis of graphitic carbon nitride (g-C3N4) via the simple heating of cheap and readily available urea as the starting material has been reported. The catalytic activity of the prepared g-C3N4 was investigated for the synthesis of chromeno[2,3-b]pyridine and benzylpyrazolyl coumarin derivatives in an ethanol medium. The reactions were performed under mild conditions to achieve widely functionalized target products in a one-pot operation. The as-synthesized g-C3N4, being a heterogeneous catalyst, demonstrates excellent recyclability up to the 5th consecutive run without a significant decrease in its catalytic activity and yield of the product. A gram-scale reaction was performed to demonstrate the industrial applications of the present protocol. The green chemistry metrics such as environmental factor (E-factor), atom economy (AE), carbon efficiency (CE), and reaction mass efficiency (RME) were calculated and found to be very close to the ideal values. Additionally, operation simplicity, wide substrate scope, easy reusability of the catalyst, and avoidance of metal contamination in the products drive the process toward green and sustainable development.

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Efficient atom-economic one-pot multicomponent synthesis of benzylpyrazolyl coumarins and novel pyrano[2,3-c]pyrazoles catalysed by 2-aminoethanesulfonic acid (taurine) as a bio-organic catalyst

Cited by 22 publications

References 60 publications

A tailored polylactic acid/polycaprolactone biodegradable and bioactive 3D porous scaffold containing gelatin nanofibers and Taurine for bone regeneration

A tailored polylactic acid/polycaprolactone biodegradable and bioactive 3D porous scaffold containing gelatin nanofibers and Taurine for bone regeneration

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

Versatile and Sustainable Approach to Access Biologically Relevant Chromeno[2,3-b]pyridine and Benzylpyrazolyl Coumarin Derivatives Using Graphitic Carbon Nitride as a Reusable Heterogeneous Catalyst

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