Design, synthesis and biological evaluation of a novel library of antimitotic C2-aroyl/arylimino tryptamine derivatives that are also potent inhibitors of indoleamine-2, 3-dioxygenase (IDO)

Chauhan, Jyoti; Dasgupta, Moumita; Luthra, Tania; Awasthi, Akanksha; Tripathy, Sayantan; Banerjee, Anindyajit; Paul, Santanu; Nag, Debasish; Chakrabarti, Saikat; Chakrabarti, Gopal; Sen, Subhabrata

doi:10.1016/j.ejps.2018.08.033

Cited by 6 publications

(3 citation statements)

References 39 publications

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“…Tetrahydro-β-carbolines were also evaluated for the photochemical cleavage to deliver 2-carbonyl tryptamines, which were previously prepared by oxidation with DDQ, NBS, or iodide . As shown in Scheme , the tetrahydro-β-carbolines with various protecting groups, such as CO 2 Me, Ac, Ms, and SO 2 Ph on the N2 position, were ideal substrates for the oxidative cleavage and afforded the corresponding products in good yields ( 22 – 25 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of C2-Carbonyl Indoles via Visible Light-Induced Oxidative Cleavage of an Aminomethylene Group

et al. 2022

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A strategy for photochemical oxidative cleavage of the aminomethylene group at the C2 position of indole was developed to synthesize C2-carbonyl indoles. The reaction was initiated by the photochemical oxidation of N1, followed by a water-assisted concerted H-shift by abstracting hydrogen from aminomethylene. Bromopyridine was discovered to play dual roles as an oxidant for the regeneration of photocatalysts and as an accelerant for the single-electron transfer process.

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Section: Resultsmentioning

confidence: 99%

Synthesis of C2-Carbonyl Indoles via Visible Light-Induced Oxidative Cleavage of an Aminomethylene Group

et al. 2022

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“…Recently, tryptamine derivatives 51a and 51b were identified as tubulin−IDO bifunctional inhibitors based on a C 2 -aroyl/ arylimino indoles hybrid 109 (Figure 11B). Compounds 51a and 51b showed potent tubulin polymerization inhibition (IC 50 is around 5 μM) and inhibited the cellular IDO activity in A549 and MCF-7 cancer cells (Figure 10B).…”

Section: Dual Inhibitors Of Tubulin and Othermentioning

confidence: 99%

Recent Progress on Tubulin Inhibitors with Dual Targeting Capabilities for Cancer Therapy

et al. 2021

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Microtubules play a crucial role in multiple cellular functions including mitosis, cell signaling, and organelle trafficking, which makes the microtubule an important target for cancer therapy. Despite the great successes of microtubule-targeting agents in the clinic, the development of drug resistance and dose-limiting toxicity restrict their clinical efficacy. In recent years, multitarget therapy has been considered an effective strategy to achieve higher therapeutic efficacy, in particular dual-target drugs. In terms of the synergetic effect of tubulin and other antitumor agents such as receptor tyrosine kinases inhibitors, histone deacetylases inhibitors, DNA-damaging agents, and topoisomerase inhibitors in combination therapy, designing dual-target tubulin inhibitors is regarded as a promising approach to overcome these limitations and improve therapeutic efficacy. In this Perspective, we discussed rational target combinations, design strategies, structure−activity relationships, and future directions of dual-target tubulin inhibitors.

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“…1 Among them, 2-aroyl benzofurans and indoles have attracted increasing attention in recent decades due to their important activities as promising drug candidates. 2 For example, rugchalcone A–B ( 1 and 2 ) showed promising anti-inflammatory activity. 2-Aroylindoles 3 and 4 are potent tubulin-inhibitory antimitotic agents (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-acyl benzofurans and indoles based on nucleophile-intercepted Meyer–Schuster rearrangement of o-hydroxyphenyl and o-aminophenyl propargylic alcohols

Li,

Jiang,

et al. 2024

Org. Chem. Front.

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Design, synthesis and biological evaluation of a novel library of antimitotic C2-aroyl/arylimino tryptamine derivatives that are also potent inhibitors of indoleamine-2, 3-dioxygenase (IDO)

Cited by 6 publications

References 39 publications

Synthesis of C2-Carbonyl Indoles via Visible Light-Induced Oxidative Cleavage of an Aminomethylene Group

Synthesis of C2-Carbonyl Indoles via Visible Light-Induced Oxidative Cleavage of an Aminomethylene Group

Recent Progress on Tubulin Inhibitors with Dual Targeting Capabilities for Cancer Therapy

Synthesis of 2-acyl benzofurans and indoles based on nucleophile-intercepted Meyer–Schuster rearrangement of o-hydroxyphenyl and o-aminophenyl propargylic alcohols

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