Acid Dissociation Constants of Some Novel Isatin Thiosemicarbazone Derivatives

Ozkutuk, Muejgan; Öğretır, Cemi̇l; Arslan, Taner; Kandemi̇rlı, Fatma; Köksoy, Baybars

doi:10.1021/je9009738

Cited by 11 publications

(2 citation statements)

References 16 publications

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“…Furthermore, the pKa value is also a useful parameter to optimize separation procedures [33][34][35][36][37]. Potentiometric and spectrophotometric titration methods are the oldest and most widely used methods to determine pKa values [38,39].…”

Section: Researchmentioning

confidence: 99%

Naphthoquinone–thiazole hybrids bearing adamantane: Synthesis, antimicrobial, DNA cleavage, antioxidant activity, acid dissociation constant, and drug-likeness

Yalçin¹

2021

jrp

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In this study, four novel naphthoquinone-thiazole hybrids bearing adamantane were synthesized by reaction of naphthoquinone-aroylthiourea derivatives with 1-adamantyl bromomethyl ketone in 75-85% yield and were characterized using 1 H/ 13 C NMR, FT-IR, and HRMS techniques. Various biological activities of the synthesized compounds, such as antibacterial, antifungal, DNA cleavage, and antioxidant activities, were screened. The compounds showed antibacterial activity against Escherichia coli, Bacillus cereus, Staphylococcus aureus, Pseudomonas aeruginosa, Enterococcus hirae, and Legionella pneumophila subsp. pneumophila strains with MIC values in the range of 4-64 µg/mL and antifungal activity against Candida albicans strains with MIC values in the range of 16-64 µg/mL. The compounds had DNA cleavage activity at 250 and 500 µg/mL. Additionally, the antioxidant activity of the compounds was assessed based on the radical scavenging effect of the stable DPPH (2,2-diphenyl-1-picrylhydrazyl) free radical and the compounds exhibited acceptable antioxidant activity. The acid dissociation constants (pKa) of the compounds were determined potentiometrically in 30% (v/v) dimethyl sulfoxide-water at an ionic background of 0.1 mol L -1 NaCl, at 25 ± 0.1 °C, and the HYPERQUAD computer program was used to calculate the pKa values from the data obtained from potentiometric titrations. Prediction of the drug-likeness properties of the compounds was performed with the use of the MolSoft website, and the compounds had promising drug-likeness model scores within a range of 1.09-1.56.

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Section: Researchmentioning

confidence: 99%

Naphthoquinone–thiazole hybrids bearing adamantane: Synthesis, antimicrobial, DNA cleavage, antioxidant activity, acid dissociation constant, and drug-likeness

Yalçin¹

2021

jrp

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“…Isatin (1H-Indole-2,3-dione) is an indole oxidized derivative belonging to the class of heterocyclic molecules [4]. It possesses several biological activities viz.…”

Section: Introductionmentioning

confidence: 99%

Small Heterocyclic Molecules as Anticancer Agents: Design, Syntheses and Evaluation Against MCF-7 Cell Lines

Varshney

Kumar

Fatima

et al. 2022

Preprint

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Isatin and substituted isatin derivatives possess a broad spectrum of biological activities. These moieties also have a wide scope for substitution, particularly at positions N-1 and C-3. Therefore, the study focused at synthesizing some novel isatin/substituted isatin Schiff’s bases and screening them for anti-cancer activity against MCF-7 cell lines. All the compounds were synthesized by conventional methods in a two-step synthesis. Mannich bases of isatin were synthesized by reacting secondary amines and 37% formalin, which were then reacted with primary aromatic amines in the presence of glacial acetic acid to yield the title compounds. All the compounds were characterized by physical, chromatographic and spectroscopic methods. The synthesized analogues showed good activity against MCF-7 cell lines when compared to the standard drug, Doxorubicin. At a concentration of 10µg/ml, the analogues IDF 3B, IDF 3G, IDF 3H and IDF 3I showed percentage cell viability of 35.46227 ± 12.92, 34.37412 ± 5.39, 35.81035 ± 5.25, 36.19748 ± 3.27 respectively compared to percentage cell viability of 22.36828 ± 2.35 for the standard. The obtained data indicated that the analogues were effective against breast cancer, and therefore the isatin moiety could serve as the lead to the development of new anti-breast cancer agents.

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Recent advances in isatin‐based chemosensors: A comprehensive review

Khan,

Shaily

2024

Luminescence

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A comprehensive review presents an illuminating exploration of the vast potential of isatin, an easily accessible organic compound. This review is a valuable resource, offering a concise yet comprehensive account of the recent breakthroughs in isatin applications in medicinal chemistry, fluorescence sensing, and organic synthesis. Moreover, it dives into the exciting advancements in isatin‐based chemosensors, demonstrating their remarkable ability to detect and recognize diverse cations and anions with exceptional precision. Researchers and scientists in the fields of sensing and organic chemistry will find this review indispensable for sparking innovation and developing cutting‐edge technologies with significant real‐world impact.

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Acid Dissociation Constants of Some Novel Isatin Thiosemicarbazone Derivatives

Cited by 11 publications

References 16 publications

Naphthoquinone–thiazole hybrids bearing adamantane: Synthesis, antimicrobial, DNA cleavage, antioxidant activity, acid dissociation constant, and drug-likeness

Naphthoquinone–thiazole hybrids bearing adamantane: Synthesis, antimicrobial, DNA cleavage, antioxidant activity, acid dissociation constant, and drug-likeness

Small Heterocyclic Molecules as Anticancer Agents: Design, Syntheses and Evaluation Against MCF-7 Cell Lines

Recent advances in isatin‐based chemosensors: A comprehensive review

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