Azide-alkyne cycloaddition en route to ferrocenyl-methoxy-methyl-isatin-conjugates: Synthesis, anti-breast cancer activities and molecular docking studies

Rani, Anu; Singh, Gurjot; Kaur, Ramandeep; Palma, Gabriella; Perumal, Shanen; Kaur, Mandeep; Ebenezer, Oluwakemi; Awolade, Paul; Singh, Pushpinder; Kumar, Vipan

doi:10.1016/j.jorganchem.2019.121072

Cited by 10 publications

(8 citation statements)

References 23 publications

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“…(Reproduced from ref. [37] Copyright (2020), with permission from Elsevier) Scheme 4. Synthetic strategy for isatin (oxime)-ferrocene-1,2,3-triazole conjugates.…”

Section: Anti-microbial Activitymentioning

confidence: 99%

“…Antiproliferative drugs are utilized to impede the spread of malignant cells around normal cells or tissues. In a study by Rani et al ., [49] a novel series of conjugates of 1,2,3‐triazole‐linked ferrocenyl‐methoxy‐methyl‐isatin were designed and examined for anti‐proliferative activity against estrogen‐responsive and estrogen‐insensitive cell lines. Compound 44 exhibited low cytotoxicity and optimal activity with an octyl chain spacer and a ‐CH 3 group at the 5 th position, showing IC 50 values of 14.62 M for MCF‐7 and 79.63 M for MDA‐MB‐231 cells.…”

Section: Biological Assessment Of 123‐triazole Tethered Isatin Hybridsmentioning

confidence: 99%

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A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

Rohila,

Sebastian,

Ansari

et al. 2024

Chemistry & Biodiversity

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Heterocyclic compounds containing 1,2,3‐triazole and isatin as core structures have emerged as promising drug candidates due to their diverse biological activities such as anti‐cancer, antifungal, antimicrobial, antitumor, anti‐epileptic, antiviral, and more. The presence of 1,2,3‐triazoles and isatin heterocycles in these hybrids, both individually known for their medicinal significance, has increasingly piqued the interest of drug discovery researchers, as they seek to delve deeper into their extensive pharmacological potential for enhancing therapeutic efficacy. Moreover, these hybrid compounds are synthetically accessible using readily available materials. Therefore, there is a pressing need to provide a comprehensive overview of the existing knowledge in this field, offering valuable insights to readers and paving the way for the discovery of novel 1,2,3‐triazole‐linked isatin hybrids with therapeutic potential.

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“…(Reproduced from ref. [37] Copyright (2020), with permission from Elsevier) Scheme 4. Synthetic strategy for isatin (oxime)-ferrocene-1,2,3-triazole conjugates.…”

Section: Anti-microbial Activitymentioning

confidence: 99%

Section: Biological Assessment Of 123‐triazole Tethered Isatin Hybridsmentioning

confidence: 99%

A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

Rohila,

Sebastian,

Ansari

et al. 2024

Chemistry & Biodiversity

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“…Isatin‐ferrocene hybrid 85 (IC 50 : 35.92 and 20.13 µM) exhibited higher potency relative to tamoxifen (IC 50 : 50 and 75 µM) against MCF‐7 and MDA‐MB‐231 cell lines. [ 126 ] Consequently, these hybrids were worthy of further investigations.…”

Section: Miscellaneous Indole/isatin 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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“…Ferrocene-1,2,3-triazole-isatin hybrid 141 (IC 50 : 35.92 and 20.13 µM, MTT assay) was more potent than tamoxifen (IC 50 : 50 and 75 µM) against MCF-7 and MDA-MB-231 breast cancer cell lines. [181] The SAR revealed that the carbon spacer between 1,2,3-triazole and isatin as well as substituent at C-5 position of isatin moiety influenced the activity greatly, [181] and replacement of isatin moiety by pteridin-4(3H)-one or naphthalimide resulted in the loss of activity, [182,183] whereas replacement by 9H-pyrido [3,4-b]indole was tolerated as evidenced by that ferrocene-1,2,3-triazole-9H-pyrido [3,4-b]indole hybrids 142a,b (IC 50 : 3.7 and 6.8 µM, MTT assay) showed higher antiproliferative activity against MCF-7 breast cancer cells than harmine (IC 50 : 13.6 µM) and 5-fluorouracil (IC 50 : 23.9 µM). [184,185] In addition, 0.013-18.5 µM, MTT assay) exhibited considerable antiproliferative activity against MCF-7 breast cancer cells, and the SAR elucidated that electron-donating group especially methoxy group on the phenyl ring was favorable to the activity, and the number of methoxy groups was in positive correlation with the activity.…”

Section: Indole-pyridine/quinoline Hybridsmentioning

confidence: 99%

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

Song,

Zhang,

Zhang

et al. 2023

Archiv der Pharmazie

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Breast cancer, as one of the most common invasive malignancies and the leading cause of cancer‐related deaths in women globally, poses a significant challenge in the world health system. Substantial advances in diagnosis and treatment have significantly improved the survival rate of breast cancer patients, but the number of incidences and deaths of breast cancer are projected to increase by 40% and 50%, respectively, by 2040. Chemotherapy is one of the principal treatments for breast cancer therapy, but multidrug resistance and severe side effects remain the major obstacles to the success of treatment. Hence, there is a vital need to develop novel chemotherapeutic agents to combat this deadly disease. 1,2,3‐Triazole, which can be effectively constructed by click chemistry, not only can serve as a linker to connect different anti‐breast cancer pharmacophores but also is a valuable pharmacophore with anti‐breast cancer potential and favorable properties such as hydrogen bonding, moderate dipole moment, and enhanced water solubility. Particularly, 1,2,3‐triazole‐containing hybrids have demonstrated promising in vitro and in vivo anti‐breast cancer potential against both drug‐sensitive and drug‐resistant forms and possessed excellent selectivity by targeting different biological pathways associated with breast cancer, representing privileged scaffolds for the discovery of novel anti‐breast cancer candidates. This review concentrates on the latest advancements of 1,2,3‐triazole‐containing hybrids with anti‐breast cancer potential, including work published between 2020 and the present. The structure–activity relationships (SARs) and mechanisms of action are also reviewed to shed light on the development of more effective and multitargeted candidates.

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Azide-alkyne cycloaddition en route to ferrocenyl-methoxy-methyl-isatin-conjugates: Synthesis, anti-breast cancer activities and molecular docking studies

Cited by 10 publications

References 23 publications

A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

A Comprehensive Review of the Diverse Spectrum Activity of 1,2,3‐Triazole‐linked Isatin Hybrids

The anti‐breast cancer potential of indole/isatin hybrids

The anti‐breast cancer therapeutic potential of 1,2,3‐triazole‐containing hybrids

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