Synthesis of novel indole‐oxadiazole molecular hybrids by a regioselective C‐3 sulfenylation of indole with 1,3,4‐oxadiazole‐2‐thiols using iodine‐dimethyl sulfoxide and their anticancer properties

Dutta, Koushik; Majumdar, Ananda Guha; Kushwah, Nisha; Wadawale, Amey; Patro, Birija Sankar; Ghosh, Sunil K.

doi:10.1002/jhet.4549

Cited by 6 publications

(5 citation statements)

References 58 publications

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“…Many kinds of research have been focused to discover hybrid chemical agents with antimitotic activities [ 86 ], including indole-heterocycles hybrids derivatives with promising anticancer activities [ 87 , 88 ]. Pyrazole-oxindole derivatives were also developed and evaluated on tubulin polymerization, and different kinds of cancer cell lines such as HeLa, A549, and MCF7, St.25, St.26, and St.27 ( Figure 7 ), exhibited anti-tubulin activities with IC 50 values in the range 5.90–9.20 μM [ 89 ].…”

Section: Indole Analoguesmentioning

confidence: 99%

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Hawash

2022

Biomolecules

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Cancer accounts for numerous deaths each year, and it is one of the most common causes of death worldwide, despite many breakthroughs in the discovery of novel anticancer candidates. Each new year the FDA approves the use of new drugs for cancer treatments. In the last years, the biological targets of anticancer agents have started to be clearer and one of these main targets is tubulin protein; this protein plays an essential role in cell division, as well as in intracellular transportation. The inhibition of microtubule formation by targeting tubulin protein induces cell death by apoptosis. In the last years, numerous novel structures were designed and synthesized to target tubulin, and this can be achieved by inhibiting the polymerization or depolymerization of the microtubules. In this review article, recent novel compounds that have antiproliferation activities against a panel of cancer cell lines that target tubulin are explored in detail. This review article emphasizes the recent developments of tubulin inhibitors, with insights into their antiproliferative and anti-tubulin activities. A full literature review shows that tubulin inhibitors are associated with properties in the inhibition of cancer cell line viability, inducing apoptosis, and good binding interaction with the colchicine binding site of tubulin. Furthermore, some drugs, such as cabazitaxel and fosbretabulin, have been approved by FDA in the last three years as tubulin inhibitors. The design and development of efficient tubulin inhibitors is progressively becoming a credible solution in treating many species of cancers.

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Section: Indole Analoguesmentioning

confidence: 99%

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Hawash

2022

Biomolecules

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“…[136][137][138][139][140][141][142][143][144][145][146][147][148][149][150] Dutta and group studied the importantnce of the presence of the thioether linkage in these hybrids, which can be prepared using an iodine-catalyzed synthetic route (Scheme 12). [151] They have accomplished the transformation using indole and oxadiazolethiols as the precursors. The use of 10 mol% of iodine as catalyst and 2 equivalents of DMSO as an oxidant produced the desired product.…”

Section: Csp 2 à S Bond Formationmentioning

confidence: 99%

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

Reetu,

Kalita,

Dash

et al. 2024

ChemistrySelect

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Organic synthesis involves the production of important chemical structures using scalable and cost‐effective methods that are also environmentally friendly. In this review, a detailed analysis of the use of iodine and DMSO in various synthetic routes for the preparation of valuable targets are presented. These methods reduce the acceptance on expensive additives and reagents, and offer a more sustainable solution for the synthesis of these important chemical scaffolds.

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“…Further studies revealed that the incorporation of isobenzofuran or thioether between indole and 1,3,4-oxadiazole moieties could not improve the activity. [77,78]…”

Section: Indole/isatin-azole 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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Synthesis of novel indole‐oxadiazole molecular hybrids by a regioselective C‐3 sulfenylation of indole with 1,3,4‐oxadiazole‐2‐thiols using iodine‐dimethyl sulfoxide and their anticancer properties

Cited by 6 publications

References 58 publications

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Recent Advances of Tubulin Inhibitors Targeting the Colchicine Binding Site for Cancer Therapy

Iodine and DMSO as Surrogate of Hazardous Metal and Non‐Metal Reagents in Organic Synthesis

The anti‐breast cancer potential of indole/isatin hybrids

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