Target cum Flexibility: Synthesis of Indolo[1,2-b]isoquinoline Derivatives via Cobalt-Catalyzed [2+2+2] Cyclotrimerization

Swami, Anuradha; Ramana, Chepuri V.

doi:10.1055/s-0034-1379950

Cited by 12 publications

(2 citation statements)

References 4 publications

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“…The derivatives ubiquitously exist in natural products and synthetic biologically active molecules and have gained great attention due to their numerous biological activities. For example, indolo[1,2-b]isoquinoline derivatives ( Figure 1 A–C) have been reported as melatonin antagonists, estrogen receptor inhibitors, and tubulin polymerization inhibitors, respectively [ 27 , 28 ].…”

Section: Introductionmentioning

confidence: 99%

“…Molecules 2023, 28, x FOR PEER REVIEW 2 of 22 attention due to their numerous biological activities. For example, indolo [1,2-b]isoquinoline derivatives (Figure 1A-C) have been reported as melatonin antagonists, estrogen receptor inhibitors, and tubulin polymerization inhibitors, respectively [27,28]. Recently, our group designed and synthesized some potential α-glucosidase inhibitors, including two series of indole derivatives (Figure 1D,E) [29,30].…”

Section: Introductionmentioning

confidence: 99%

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Anti-α-Glucosidase, SAR Analysis, and Mechanism Investigation of Indolo[1,2-b]isoquinoline Derivatives

Liu

et al. 2023

Molecules

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To find potential α-glucosidase inhibitors, indolo[1,2-b]isoquinoline derivatives (1–20) were screened for their α-glucosidase inhibitory effects. All derivatives presented potential α-glucosidase inhibitory effects with IC50 values of 3.44 ± 0.36~41.24 ± 0.26 μM compared to the positive control acarbose (IC50 value: 640.57 ± 5.13 μM). In particular, compound 11 displayed the strongest anti-α-glucosidase activity, being ~186 times stronger than acarbose. Kinetic studies found that compounds 9, 11, 13, 18, and 19 were all reversible mix-type inhibitors. The 3D fluorescence spectra and CD spectra results revealed that the interaction between compounds 9, 11, 13, 18, and 19 and α-glucosidase changed the conformational changes of α-glucosidase. Molecular docking and molecular dynamics simulation results indicated the interaction between compounds and α-glucosidase. In addition, cell cytotoxicity and drug-like properties of compound 11 were also investigated.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Anti-α-Glucosidase, SAR Analysis, and Mechanism Investigation of Indolo[1,2-b]isoquinoline Derivatives

Liu

et al. 2023

Molecules

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Cobalt‐Catalyzed [2 + 2 + 2] Cycloaddition Reactions

Glasel,

Hapke

2023

Patai's Chemistry of Functional Groups

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Cobalt‐catalyzed [2 + 2 + 2] cycloaddition reactions are an important tool for the assembly of carbo‐ and hetero‐cyclic ring systems from simple precursor molecules such as alkynes, alkenes, nitriles, and other heterocumulenes such as isocyanates. Cyclopentadienyl (Cp)‐cobalt complexes are still one of the most important classes of catalysts, but in situ generated cobalt catalyst systems are becoming increasingly important for the assembly of achiral as well as chiral target molecules from a large variety of substrates. Substrates comprise simple terminal as well as internal alkynes, diynes, and higher oligoynes and also allow target‐oriented syntheses of unusually large as well as highly substituted molecules as well as natural product synthesis with a cyclotrimerization as the key step of the synthetic sequence. The utilization of olefins as cyclization partners allows the synthesis of products with lesser degree of unsaturation such as cyclohexadienes, cyclohexenes, and dihydropyridines, just to name a view examples. Chiral catalyst systems allow the enantioselective synthesis of biaryls and products with central chirality, and chiral starting materials allow the synthesis of diastereomeric helicenes in an efficient manner. Novel catalysts and reaction engineering allow reaction conditions such as conventional thermal or microwave heating, photochemically assisted cyclizations, and the use of plug‐flow reactors.

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cyclotrimerization

Bönnemann¹

2020

Catalysis From a to Z

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Target cum Flexibility: Synthesis of Indolo[1,2-b]isoquinoline Derivatives via Cobalt-Catalyzed [2+2+2] Cyclotrimerization

Cited by 12 publications

References 4 publications

Anti-α-Glucosidase, SAR Analysis, and Mechanism Investigation of Indolo[1,2-b]isoquinoline Derivatives

Anti-α-Glucosidase, SAR Analysis, and Mechanism Investigation of Indolo[1,2-b]isoquinoline Derivatives

Cobalt‐Catalyzed [2 + 2 + 2] Cycloaddition Reactions

cyclotrimerization

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