Newly synthesized 3-sulfenylindole derivatives from 4-hydroxydithiocoumarin using an oxidative cross dehydrogenative coupling reaction (OCDCR): potential lead molecules for antiproliferative activity

Mondal, Santa; Mahato, Karuna; Arora, Neha; Kankane, Dheerendra; Singh, Umed; Ali, Saghir; Khan, Aftab Hossain; Ghosh, Siddhartha Sankar; Khan, Abu T.

doi:10.1039/d0ob00054j

Cited by 9 publications

(4 citation statements)

References 37 publications

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“…[105] Indole-thioflavone hybrids 66a,b (IC 50 : 6.32 and 7.21 µM) possessed potent activity in fighting against MCF-7 cancer cells, with the SAR demonstrated that the introduction of substituents into C-5 position of indole moiety reduced the activity. [106] Mechanistically, these hybrids elevated ROS and caused cell damage leading to cell death. [108] Inducing apoptosis was the mechanism via which hybrid 69 suppressed cell proliferation.…”

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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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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“…Catalytic amount of molecular iodine was used along with TBHP in presence of 10 mol% CuBr 2 as an additive at room temperature (Scheme 68). [126] Utilising the concept of sulfonylation, Peddinti and Aegurla demonstrated an iodine/(TBHP)-mediated protocol for the construction of C(sp 2 )À SO 2 and C(sp 3 )À SO 2 bonds through a radical pathway and an ionic pathway, respectively. The denitrative sulfonylation (DNSF) of β-nitrostyrenes with arylsulfo + nylhydrazides proceeded via addition-elimination pathway.…”

Section: Cà S Bond Formation Reactionsmentioning

confidence: 99%

“…Catalytic amount of molecular iodine was used along with TBHP in presence of 10 mol% CuBr 2 as an additive at room temperature (Scheme 68). [126] …”

Section: Sulfenylation/sulfonylation Reactionsmentioning

confidence: 99%

I₂/TBHP Reagent System: A Modern Paradigm for Organic Transformations**

2022

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Molecular iodine in combination with TBHP offers an advanced concept for organic synthesis and catalysis by improving the selectivity and sustainability of organic transformations. It leads to the development of metal free greener protocols under ambient conditions either as a catalytic duo or as a reagent system in combination with an additive. The advent of this indispensable tool led to formation of complex organic architectures empowering novel reaction pathways through CÀ H functionalization, cyclization, cycloaddition, rearrangement, sulfonylation/sulfenylation and oxidation reactions in organic synthesis.

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“…Due to the nucleophilic nature of the ring, a range of electrophilic sulfur species are employed for the functionalization of C-3 and C-2 position. These conditions involve transition metals catalysts, [37] iodine, [38] strong bases, [39] and photocatalysts. [40] However few examples have been described using photo promoted cascades.…”

Section: Recent Developments On the Photocatalytic Synthesis Of Indoles Oxindoles And Indolinesmentioning

confidence: 99%

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

Correia

Santos

Pissinati

et al. 2021

The Chemical Record

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Over the last decade, visible‐light photocatalysis has proved to be a powerful tool for the construction of N‐heterocyclic frameworks, important constituents of natural products, insecticides, pharmacologically relevant therapeutic agents and catalysts. This account highlights recent developments and established methods towards the photocatalytic cascades for preparation of different classes of N‐heterocycles, giving emphasis on our contribution to the field.

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Newly synthesized 3-sulfenylindole derivatives from 4-hydroxydithiocoumarin using an oxidative cross dehydrogenative coupling reaction (OCDCR): potential lead molecules for antiproliferative activity

Abstract: Synthesis of 3-sulfenyl indole derivatives is achieved through oxidative cross-dehydrogenative coupling reaction. A few such newly synthesized compounds have also exhibited anti-proliferative activity via reactive oxygen species mediated cell damage.

Cited by 9 publications

References 37 publications

The anti‐breast cancer potential of indole/isatin hybrids

The anti‐breast cancer potential of indole/isatin hybrids

I₂/TBHP Reagent System: A Modern Paradigm for Organic Transformations**

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

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Newly synthesized 3-sulfenylindole derivatives from 4-hydroxydithiocoumarin using an oxidative cross dehydrogenative coupling reaction (OCDCR): potential lead molecules for antiproliferative activity

Abstract: Synthesis of 3-sulfenyl indole derivatives is achieved through oxidative cross-dehydrogenative coupling reaction. A few such newly synthesized compounds have also exhibited anti-proliferative activity via reactive oxygen species mediated cell damage.

Cited by 9 publications

References 37 publications

The anti‐breast cancer potential of indole/isatin hybrids

The anti‐breast cancer potential of indole/isatin hybrids

I2/TBHP Reagent System: A Modern Paradigm for Organic Transformations**

Recent Advances on Photoinduced Cascade Strategies for the Synthesis of N‐Heterocycles

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Product

Resources

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I₂/TBHP Reagent System: A Modern Paradigm for Organic Transformations**