Unprecedented reaction of ninhydrin with ethyl cyanoacetate and diethyl malonate on ultrasonic irradiation

Saini, Yeshwinder; Khajuria, Rajni; Rana, Love Karan; Hundal, Geeta; Gupta, Vivek K.; Kant, Rajni; Kapoor, Kamal K.

doi:10.1016/j.tet.2015.11.022

Cited by 13 publications

(3 citation statements)

References 28 publications

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“…Kapoor et al reported in their study that the reaction of ninhydrin 1 with 2 equivalents of ethyl cyanoacetate resulted in the formation of indenopyran derivative 18 (Scheme 8). 81 The highly reactive C-2 of ninhydrin has been exploited to condense with an active methylene compound, resulting in 18 as the major product. Importantly, the reaction was carried out under an ultrasound condition without using any catalyst.…”

Section: Synthesis Of Indeno-fused Heterocyclesmentioning

confidence: 99%

Recent applications of ninhydrin in multicomponent reactions

Das¹

2020

RSC Adv.

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Section: Synthesis Of Indeno-fused Heterocyclesmentioning

confidence: 99%

Recent applications of ninhydrin in multicomponent reactions

Das¹

2020

RSC Adv.

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“…The process involves hydroxylating L-tyrosine to create L-dihydroxyphenylalanine (L-DOPA), which is further oxidized to form dopaquinone. 20 Tyrosinase and similar proteins are synthesized in the rough endoplasmic reticulum. However, tyrosinase possesses some specificity related to malignant melanoma and enzymatic browning in mammals.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a New Series of Anthraquinone-Linked Cyclopentanone Derivatives: Investigating the Antioxidant, Antibacterial, Cytotoxic and Tyrosinase Inhibitory Activities of the Mushroom Tyrosinase Enzyme Using Molecular Docking

Mullaivendhan,

Akbar,

Ahamed

et al. 2024

DDDT

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New bioactive anthraquinone derivatives are investigated for antibacterial, tyrosinase inhibitory, antioxidant cytotoxic activity, and molecular docking. Methods: The compounds were produced using the grindstone method, yielding 69 to 89%. These compounds were analyzed using IR, 1 H, and 13 C NMR and elemental and mass spectral methods. Additionally, the antibacterial, antioxidant, and tyrosinase inhibitory activities of all the synthesised compounds were evaluated. Results: Compound 2 showed remarkable tyrosinase inhibition activity, with an (IC 50 : 13.45 µg/mL), compared to kojic acid (IC 50 : 19.40 µg/mL). It also exhibited moderate antioxidant and antibacterial activities with respect to the references BHT and ampicillin, respectively. Kinetic analysis revealed that the tyrosinase inhibitory activity of compound 2 was non-competitive and competitive, whereas that of compound 1 was low. All compounds (1-8) were significantly less active than doxorubicin (LC 50 : 0.74±0.01μg/mL). However, compound 2 affinity for the 2Y9X protein was lower than kojic acid, with a lower docking score (−8.6 kcal/mol compared to (−4.7 kcal/mol), making it more effective. Conclusion: All synthesized compounds displayed remarkable antibacterial, tyrosinase inhibitory, antioxidant, and cytotoxic activities, with compound 2 showing exceptional potency as a multitarget agent. Anthraquinone substituent groups may offer the potential for the development of treatments. The derivatives were synthesized using the grindstone method, and their antibacterial, antioxidant, tyrosinase inhibitory, and cytotoxic activities were inspected. Molecular docking and molecular dynamics simulations were performed using compound 2 and kojic acid to validate the results and confirm the stability of the compounds.

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“…Besides the analytical role, the reactivity of ninhydrin molecule has been exploited in many chemical reactions resulting different indanone‐based scaffolds . In fact, indanones core structures are integral part of many natural products .…”

Section: Introductionmentioning

confidence: 99%

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

Das¹,

Dutta

2020

ChemistrySelect

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Ninhydrin (1,2,3‐indanetrione hydrate) is a powerful electrophile having enormousapplications in organic and bio‐organic sciences. In the last few years, reactivity of various ninhydrin adducts have been exploited extensively for the development of diverse organic scaffolds. The present review focuses on the applications of readily accessible ninhydrin adducts as building block towards the synthesis of a variety of compounds including N‐inserted compounds, spiro‐heterocycles, medium ring compounds, polycyclic molecules, propellanes, cycloadducts, allylic anions, axially chiral molecules etc. Interestingly, some of the compounds have profound biological activities and a few display important photophysical properties. Most of the reactions described here are simple and carried out with easily available starting materials under green conditions.

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Unprecedented reaction of ninhydrin with ethyl cyanoacetate and diethyl malonate on ultrasonic irradiation

Cited by 13 publications

References 28 publications

Recent applications of ninhydrin in multicomponent reactions

Recent applications of ninhydrin in multicomponent reactions

Synthesis of a New Series of Anthraquinone-Linked Cyclopentanone Derivatives: Investigating the Antioxidant, Antibacterial, Cytotoxic and Tyrosinase Inhibitory Activities of the Mushroom Tyrosinase Enzyme Using Molecular Docking

Ninhydrin Adducts as Valid Synthon in Organic Synthesis: A Review

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