Crystal structure of 5-methoxy-N′-[(3Z)-1-benzyl-5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C27H25FN4O4S

Almutairi, Maha S.; Ghabbour, Hazem A.; Haress, Nadia G.; Attia, Mohamed I.

doi:10.1515/ncrs-2016-0033

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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

Self Cite

View full text Add to dashboard Cite

show abstract

Crystal structure of 5-methoxy-N′-[(3Z)-1-benzyl-5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene]-1H-indole-2-carbohydrazide-DMSO (1/1), C₂₇H₂₅FN₄O₄S

Abstract: C 27 H 25 FN4O4S, triclinic, P¯ , a = 10.1996(5) CCDC no.: 1430640The crystal structure is shown in the gure. Tables 1 and 2 contain details of the measurement method and a list of

Cited by 1 publication

References 8 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>

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