Synthesis and Anticancer Evaluation of Novel Indole Based Arylsulfonylhydrazides against Human Breast Cancer Cells

Gaur, Aysha; Peerzada, Mudasir Nabi; Khan, Parvez; Ali, Imran; Peerzada, Mudasir Nabi

doi:10.1021/acsomega.2c03908

Cited by 26 publications

(7 citation statements)

References 42 publications

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“…Indole‐sulfonylhydrazide hybrid 57 (IC 50 : 13.2 and 8.2 µM) exhibited strong anti‐MCF‐7 and anti‐MDA‐MB‐231 cell activity and was nontoxic (IC 50 : >100 µM) to normal HEK 293 cells. [ 97 ] The SAR revealed that morpholine at the N‐1 position of indole moiety was unnecessary for the activity, while the introduction of chloro into the C‐5 position increased the activity, as evidenced by the high anti‐MCF‐7 and anti‐MDA‐MB‐231 cell activity of hybrid 58 (IC 50 : 0.5 and 0.9 µM). [ 98 ]…”

Section: Indole/isatin‐sulfonamide/sulfonate/sulfonylhydrazide Hybridsmentioning

confidence: 99%

The anti‐breast cancer potential of indole/isatin hybrids

Wang,

Huang,

Yuan

et al. 2023

Archiv der Pharmazie

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Breast cancer (BC) is one of the most prevalent malignancies and the major contributor to cancer mortality in women globally, with a high degree of heterogeneity and a dismal prognosis. As drug resistance is responsible for most BC fatalities and advanced BC is currently considered incurable, finding innovative anti‐BC chemotherapeutics is urgently required. Indole and its analog isatin (indole‐1H‐2,3‐dione) are prominent pharmacophores in the development of novel medications, and their derivatives exhibit strong anticancer activities, also against BC. In particular, indole/isatin hybrids exhibit significant potency against BC including multidrug‐resistant forms and excellent selectivity by influencing a variety of biological targets associated with the disease, supplying helpful building blocks for the identification of potential new BC treatment options. This review includes articles from 2020 to the present and provides insights into the in vitro and in vivo anti‐BC potential, molecular mechanisms, and structure–activity relationships (SARs) of indole/isatin hybrids that may be helpful in the development of innovative anti‐BC chemotherapeutics.

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Section: Indole/isatin‐sulfonamide/sulfonate/sulfonylhydrazide Hybridsmentioning

confidence: 99%

The anti‐breast cancer potential of indole/isatin hybrids

Wang,

Huang,

Yuan

et al. 2023

Archiv der Pharmazie

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“…Molecular hybridization synergizes the individual therapeutic potential of constituent moieties and upsurges the capacity to inhibit multiple biotargets. Several heterocyclic frameworks containing indole and thiadiazole motifs exhibit notable anti‐breast cancer efficacy, as shown in Figure 2 [32–37] . Considering the remarkable anti‐breast cancer efficacy of indole and thiadiazole derivatives, a new class of indole‐linked 1, 3, 4‐thiadiazole framework is explored in the present report for potential anti‐breast cancer action.…”

Section: Introductionmentioning

confidence: 96%

“…Several heterocyclic frameworks containing indole and thiadiazole motifs exhibit notable anti-breast cancer efficacy, as shown in Figure 2. [32][33][34][35][36][37] Considering the remarkable anti-breast cancer efficacy of indole and thiadiazole derivatives, a new class of indole-linked 1, 3, 4-thiadiazole framework is explored in the present report for potential anti-breast cancer action.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Indole‐Linked Thiadiazoles and their Anticancer Action against Triple‐Negative Breast Cancer

Gavadia,

Rasgania,

Sahu

et al. 2024

Chemistry & Biodiversity

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With a lack of targeted therapy and significantly high metastasis, heterogeneity, and relapse rates, Triple‐Negative Breast Cancer (TNBC) offers substantial treatment challenges and demands more chemotherapeutic interventions. In the present study, indole‐endowed thiadiazole derivatives have been synthesized and screened for antiproliferative potency against the triple‐negative breast cancer MDA‐MB‐231 cell line. Compound 4h, possessing chlorophenyl moiety, displays the best anticancer potency (IC50: 0.43 μM) in the cell viability assay. The title compounds demonstrate substantial docking competency against the EGFR receptor (PDB ID: 3POZ), validating their in‐vitro ant proliferative action. With a high docking score (‐9.9 to ‐8.7 kcal/mol), the indole hybrids display significant binding propensity comparable to the co‐crystallized ligand TAK‐285 and occupy a similar strategic position in the active domain of the designated receptor. The quantum and electronic properties of the integrated templates are evaluated through DFT, and optimal values of the deduced global reactivity indices, such as energy gap, electronegativity, ionization potential, chemical potential, electrophilicity, etc., suggest their apt biochemical reactivity. The indole hybrids show near‐appropriate pharmacokinetic efficacy and bioavailability in the in‐silico studies, indicating their candidacy for potential drug usage. Promising in‐vitro anticancer action and binding interfaces project indole conjugates as potential leads in addressing the TNBC dilemma.

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“…[27,28] Different indole ring substitutions in compounds can enhance their ability to inhibit the proliferation of cancer cells. [29][30][31][32][33] Based on a literature analysis, in this review we have summarized and highlighted the indole derivatives as CBS inhibitors (discovered after 2018). We have also discussed the structure-activity relationship (SAR) of indole derivatives as CBS inhibitors.…”

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confidence: 99%

Indole derivatives targeting colchicine binding site as potential anticancer agents

Goel

Jaiswal

Jain

2023

Archiv der Pharmazie

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Microtubules are appealing as intracellular targets for anticancer activity due to their importance in cell division. Three important binding sites are present on the tubulin protein: taxane, vinca, and colchicine binding sites (CBS). Many USFDA‐approved drugs such as paclitaxel, ixabepilone, vinblastine, and combretastatin act by altering the dynamics of the microtubules. Additionally, a large number of compounds have been synthesized by medicinal chemists around the globe that target different tubulin binding sites. Although CBS inhibitors have proved their cytotoxic potential, no CBS‐targeting drug had been able to reach the market. Several studies have reported design, synthesis, and biological evaluation of indole derivatives as potential anticancer agents. These compounds have been shown to inhibit cancer cell proliferation, induce apoptosis, and disrupt microtubule formation. Moreover, the binding affinity of these compounds to the CBS has been demonstrated using molecular docking studies and competitive binding assays. The present work has reviewed indole derivatives as potential colchicine‐binding site inhibitors. The structure–activity relationship studies have revealed the crucial pharmacophoric features required for the potent and selective binding of indole derivatives to the CBS. The development of these compounds with improved efficacy and reduced toxicity could potentially lead to the development of novel and effective cancer therapies.

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Synthesis and Anticancer Evaluation of Novel Indole Based Arylsulfonylhydrazides against Human Breast Cancer Cells

Cited by 26 publications

References 42 publications

The anti‐breast cancer potential of indole/isatin hybrids

The anti‐breast cancer potential of indole/isatin hybrids

Synthesis of Indole‐Linked Thiadiazoles and their Anticancer Action against Triple‐Negative Breast Cancer

Indole derivatives targeting colchicine binding site as potential anticancer agents

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