Late-stage <i>ortho</i>-C–H alkenylation of 2-arylindazoles in aqueous medium by Manganese(<scp>i</scp>)-catalysis

Das, Krishna Kanta; Ghosh, Asim Kumar; Hajra, Alakananda

doi:10.1039/d2ra03547b

Cited by 10 publications

(4 citation statements)

References 56 publications

(17 reference statements)

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“…Recently, Hajra and co-workers employed manganese catalysis for the C–H alkenylation of 2-arylindazoles 64 with alkynes 36/38 (Scheme 27). 158 The reaction was performed in water as reaction medium. Both terminal 36 and internal alkynes 38 were proved to be viable to give the desired alkene products 65 with high levels of E -stereoselectivity.…”

Section: Hydroarylation Of C–c Multiple Bondsmentioning

confidence: 99%

Manganese-catalyzed hydroarylation of multiple bonds

Maayuri

Gandeepan

2023

Org. Biomol. Chem.

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Section: Hydroarylation Of C–c Multiple Bondsmentioning

confidence: 99%

Manganese-catalyzed hydroarylation of multiple bonds

Maayuri

Gandeepan

2023

Org. Biomol. Chem.

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“…Compound 4 was synthesized in accordance with the literature [51]. Sodium valproate (6.64 g, 40 mmol), propargyl bromide (7.14 g, 60 mmol), and K 2 CO 3 (1.6 g, 12 mmol) were dissolved in 25 mL DMF and stirred at room temperature.…”

Section: The Synthetic Route Of Compoundmentioning

confidence: 99%

Synthesis and Antitumor Evaluation of Biotin-SN38-Valproic Acid Conjugates

Zhang

et al. 2023

Molecules

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Despite the strong anticancer activity of SN38 (7-ethyl-10-hydroxy-camptothecin), the severe side effects and loss of anticancer activity caused by the lack of selectivity to cancer cells and hydrolysis of ring E prevent its clinical application. To address the issue, herein a multifunctional SN38 derivative (compound 9) containing biotin (tumor-targeting group) and valproic acid (histone deacetylase inhibitor, HDACi) was synthesized via click chemistry and evaluated using MTT assay. The in vitro cytotoxicity study showed that compound 9 exhibited superior cytotoxicity than irinotecan against human cervical cancer HeLa cells, albeit it was inferior to SN38. More significantly, compound 9 significantly reduced toxicity in mouse embryonic fibroblast NIH3T3 cells, indicating that compound 9 had the capacity to enhance tumor targeting due to its cell selectivity. Further studies demonstrated that, compared with irinotecan, compound 9 induced similar apoptosis of cancer cells. Consequently, compound 9 can not only improve its tumor-targeting ability mediated by biotin but also exert potent anticancer activity through the effect of SN38 and valproic acid, indicating that the design concept is an effective strategy for the structural modification of SN38.

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“…The most recent report using Mn-16 as a precatalyst for the hydroarylation of alkynes was made by Hajra and co-workers . Among the most noteworthy contributions of this work are the incorporation of a new type of aryl compound, 2-arylindazoles, along with their excellent performance in aqueous medium (Figure ).…”

Section: Hydrofunctionalization Of Unsaturated C–c Bondsmentioning

confidence: 99%

“…The most recent report using Mn-16 as a precatalyst for the hydroarylation of alkynes was made by Hajra and co-workers. 79 Among the most noteworthy contributions of this work are the incorporation of a new type of aryl compound, 2-arylindazoles, along with their excellent performance in aqueous medium ( Figure 11 ). As was also observed in other catalytic systems of this nature, considerably lower yields were obtained with different Mn-based precursors, solvents (except for 1,4-dioxane), and bases.…”

Section: Hydrofunctionalization Of Unsaturated C–c Bondsmentioning

confidence: 99%

Homogeneous Manganese-Catalyzed Hydrofunctionalizations of Alkenes and Alkynes: Catalytic and Mechanistic Tendencies

Torres-Calis

Garcı́a

2022

ACS Omega

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In recent years, many manganese-based homogeneous catalytic precursors have been developed as powerful alternatives in organic synthesis. Among these, the hydrofunctionalizations of unsaturated C–C bonds correspond to outstanding ways to afford compounds with more versatile functional groups, which are commonly used as building blocks in the production of fine chemicals and feedstock for the industrial field. Herein, we present an account of the Mn-catalyzed homogeneous hydrofunctionalizations of alkenes and alkynes with the main objective of finding catalytic and mechanistic tendencies that could serve as a platform for the works to come.

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Late-stage ortho-C–H alkenylation of 2-arylindazoles in aqueous medium by Manganese(i)-catalysis

Abstract: Earth-abundant and water-tolerant manganese(i) catalyzed alkenylation of 2-arylindazole with alkyl and aryl alkynes through C–H bond activation is described with a unique level of E-selectivity.

Cited by 10 publications

References 56 publications

Manganese-catalyzed hydroarylation of multiple bonds

Manganese-catalyzed hydroarylation of multiple bonds

Synthesis and Antitumor Evaluation of Biotin-SN38-Valproic Acid Conjugates

Homogeneous Manganese-Catalyzed Hydrofunctionalizations of Alkenes and Alkynes: Catalytic and Mechanistic Tendencies

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