Crystal structure of 5-methoxy-N′-[(3Z)-5-chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C25H18ClFN4O3 · C2H6OS

Haress, Nadia G.; Ghabbour, Hazem A.; Almutairi, Maha S.; Fun, Hoong‐Kun; Attia, Mohamed I.

doi:10.1515/ncrs-2016-0032

Cited by 3 publications

(1 citation statement)

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“…The stereochemistry of the title conjugates 5a-s was assigned the (Z)-configuration, based on the previously documented X-ray results of structurally related analogous compounds. 43,44 Pharmacological Investigations…”

Section: Results and Discussion Chemistrymentioning

confidence: 99%

New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity

Al-Wabli

Almomen

Almutairi

et al. 2020

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Background: Cancer remains the leading cause of human morbidity universally. Hence, we sought to assess the in vitro antiproliferative activity of new isatin-based conjugates (5a-s) against three human cancer cell lines. Methods: The antiproliferative activities of compounds 5a-s were evaluated in vitro and their ADME (absorption, distribution, metabolism and excretion) was carried out using standard protocols. Subsequently, Western blot analysis was conducted to elucidate the potential antiproliferative mechanism of compounds 5a-s. Results: The in vitro antiproliferative activities of compounds 5a-s against the tested cancer cell lines ranged from 20.3 to 95.9%. Compound 5m had an IC 50 value of 1.17 µM; thus, its antiproliferative potency was approximately seven-fold greater than that of sunitinib (IC 50 = 8.11 µM). In-depth pharmacological testing was conducted with compound 5m to gain insight into the potential antiproliferative mechanism of this class of compounds. Compound 5m caused an increase in the number of cells in the G1 phase, with a concomitant reduction of those in the G2/M and S phases. Additionally, compound 5m significantly and dose-dependently reduced the amount of phosphorylated retinoblastoma protein detected. Compound 5m enhanced expression of B cell translocation gene 1, cell cycle-associated proteins (cyclin B1, cyclin D1, and phosphorylated cyclin-dependent kinase 1), and a pro-apoptotic protein (Bcl-2-associated X protein gene), and activated caspase-3. ADME predictions exposed the oral liability of compounds 5a-s. Conclusion: Herein, we revealed the antiproliferative activity and ADME predictions of the newly-synthesized compounds 5a-s and provided a detailed insight into the pharmacological profile of compound 5m. Thus, compounds 5a-s can potentially be exploited as new antiproliferative lead compounds for cancer chemotherapeutic.

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Section: Results and Discussion Chemistrymentioning

confidence: 99%

New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity

Al-Wabli

Almomen

Almutairi

et al. 2020

DDDT

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Correlations and statistical analysis of solvent molecule hydrogen bonding – a case study of dimethyl sulfoxide (DMSO)

2018

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Synthesis, Spectroscopic Characterization and Antimicrobial Potential of Certain New Isatin-Indole Molecular Hybrids

2017

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Molecular hybridization has a wide application in medicinal chemistry to obtain new biologically active compounds. New isatin-indole molecular hybrids 5a–n have been synthesized and characterized by various spectroscopic tools. The in vitro antimicrobial potential of the prepared compounds 5a–n was assessed using diameter of the inhibition zone (DIZ) and minimum inhibitory concentration (MIC) assays against a panel of Gram-negative bacteria, Gram-positive bacteria and fungi. Most of the synthesized compounds 5a–n showed weak activities against Gram-negative bacteria while compounds 5b and 5c exhibited good activities against Gram-positive bacteria. On the other hand, compound 5j emerged as the most active compound towards Candida albicans (C. albicans), with an MIC value of 3.9 µg/mL, and compound 5g as the most active congener towards Asperagillus niger (A. niger), with an MIC value of 15.6 µg/mL. Moreover, compound 5h manifested the best anti-P. notatum effect, with an MIC value of 7.8 µg/mL, making it equipotent with compound 5g.

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Crystal structure of 5-methoxy-N′-[(3Z)-5-chloro-1-(4-fluorobenzyl)-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C₂₅H₁₈ClFN₄O₃ · C₂H₆OS

Abstract: C 25 H 18 ClFN4O 3 · C 2 H 6 OS, monoclinic, P21 (No. 4), a = 6.0486(2) Å, b = 17.4704(7) Å, c = 11.9215(4) Å, β = 96.327(1)°,

Cited by 3 publications

References 6 publications

<p>New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity</p>

<p>New Isatin–Indole Conjugates: Synthesis, Characterization, and a Plausible Mechanism of Their in vitro Antiproliferative Activity</p>

Correlations and statistical analysis of solvent molecule hydrogen bonding – a case study of dimethyl sulfoxide (DMSO)

Synthesis, Spectroscopic Characterization and Antimicrobial Potential of Certain New Isatin-Indole Molecular Hybrids

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