Synthesis, Structural and Antioxidant Studies of Some Novel N-Ethyl Phthalimide Esters

Kumar, C. S. Chidan; Loh, Wan-Sin; Chandraju, S.; Win, Yip-Foo; Tan, Weng Kang; Quah, Ching Kheng; Fun, Hoong‐Kun

doi:10.1371/journal.pone.0119440

Cited by 13 publications

(1 citation statement)

References 18 publications

(22 reference statements)

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“…N ‐Functionalized azaheterocyclic compounds with N ‐alkyl ester groups possess important biological and pharmaceutical properties, including antitumor, [1] antibacterial, [2] anthelmintic, [3] anti‐inflammatory, [4] and antioxidant [5] activities. Such N ‐functionalized azaheterocyclic motifs are also found in natural products [6] and material additives [7] .…”

Section: Entry 2 a (Equiv) Base Solvent Temp Time (H) Yield (%)[B]mentioning

confidence: 99%

Transition‐Metal‐Free N‐Functionalization of Benzimidazoles and Related Azaheterocycles with α‐Acyloxy Sulfides

et al. 2022

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Direct N‐functionalization of benzimidazoles and related azaheterocycles has been achieved using readily accessible α‐acyloxy sulfides under transition metal‐free conditions. In the presence of the base, potassium carbonate, a variety of N‐functionalized azaheterocyclic compounds bearing an N‐alkyl ester moiety were synthesized from corresponding heterocyclic precursors. The present reaction does not use transition metals, is operationally simple, and has broad substrate scope.

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Section: Entry 2 a (Equiv) Base Solvent Temp Time (H) Yield (%)[B]mentioning

confidence: 99%

Transition‐Metal‐Free N‐Functionalization of Benzimidazoles and Related Azaheterocycles with α‐Acyloxy Sulfides

et al. 2022

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Quantification of microbiota-related phenols and aromatic acids in mouse feces of a diabetic nephropathy model by simultaneous BDAPE derivatization using ultra-performance liquid chromatography-tandem mass spectrometry

Zheng

Duan

et al. 2020

Anal Bioanal Chem

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Insights into the spontaneity of hydrogen bond formation between formic acid and phthalimide derivatives

2016

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We evaluated a group of phthalimide derivatives, which comprise a convenient test set for the study of the multiple factors involved in the energetics of hydrogen bond formation. Accordingly, we carried out quantum chemical calculations on the hydrogen bonded complexes formed between a sample of phthalimide derivatives with formic acid with the intent of identifying the most important electronic and structural factors related to how their strength and spontaneity vary across the series. The geometries of all species considered were fully optimized at DFT B3LYP/6-31++G(d,p), RM1, RM1-DH2, and RM1-D3H4 level, followed by frequency calculations to determine their Gibbs free energies of hydrogen bond formation using Gaussian 2009 and MOPAC 2012. Our results indicate that the phthalimide derivatives that form hydrogen bond complexes most favorably, have in their structures only one C=O group and at least one NH group. On the other hand, the phthalimide derivatives predicted to form hydrogen bonds least favorably, possess in their structures two carbonyl groups, C=O, and no NH group. The ability to donate electrons and simultaneously receive one acidic hydrogen is the most important property related to the spontaneity of hydrogen bond formation. We further chose two cyclic compounds, phthalimide and isoindolin-1-one, in which to study the main changes in molecular, structural and spectroscopic properties as related to the formation of hydrogen bonds. Thus, the greatest ability of the isoindolin-1-one compound in forming hydrogen bonds is evidenced by the larger effect on the structural, vibrational, and chemical shifts properties associated with the O-H group. In summary, the electron-donating ability of the hydrogen bond acceptor emerged as the most important property differentiating the spontaneity of hydrogen bond formation in this group of complexes.

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Synthesis, Structural and Antioxidant Studies of Some Novel N-Ethyl Phthalimide Esters

Cited by 13 publications

References 18 publications

Transition‐Metal‐Free N‐Functionalization of Benzimidazoles and Related Azaheterocycles with α‐Acyloxy Sulfides

Transition‐Metal‐Free N‐Functionalization of Benzimidazoles and Related Azaheterocycles with α‐Acyloxy Sulfides

Quantification of microbiota-related phenols and aromatic acids in mouse feces of a diabetic nephropathy model by simultaneous BDAPE derivatization using ultra-performance liquid chromatography-tandem mass spectrometry

Insights into the spontaneity of hydrogen bond formation between formic acid and phthalimide derivatives

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