One-pot access to 11-methyl-6H-indolo[2,3-b]quinolines via iodine-mediated annulation of indoles with 2-vinylanilines and evaluation of their biological activities

Yan, Jinglan; Fang, Zeguo; Su, Jianglong; He, Qun; Al-Maharik, Nawaf; Zhang, Qian; Wei, Yanhong; Li, Dong

doi:10.1039/d3qo01319g

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Six-membered Ring Formation With One-heteroatom1

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2024

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“…Wei, Li, and colleagues 60 devised an easy one-pot method to produce a wide range of 11-methyl-6 H -indolo[2,3- b ]quinolines 16 ( Scheme 10 ). This was achieved using an I 2 -mediated annulation process involving indoles 14 and 2-vinylanilines 15.…”

Section: Six-membered Ring Formation With One-heteroatommentioning

confidence: 99%

I₂/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

Singhal,

Choudhary,

Malik

et al. 2024

RSC Adv.

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Section: Six-membered Ring Formation With One-heteroatommentioning

confidence: 99%

I₂/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

Singhal,

Choudhary,

Malik

et al. 2024

RSC Adv.

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Indoloquinoline Alkaloids as Antimalarials: Advances, Challenges, and Opportunities

Parvatkar,

Diagne,

Zhao

et al. 2024

ChemMedChem

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Malaria infections affect almost half of the world's population, with over 200 million cases reported annually. Cryptolepis sanguinolenta, a plant native to West Africa, has long been used across various regions of Africa for malaria treatment. Chemical analysis has revealed that the plant is abundant in indoloquinolines, which have been shown to possess antimalarial properties. Cryptolepine, neocryptolepine, and isocryptolepine are well‐studied indoloquinoline alkaloids known for their potent antimalarial activity. However, their structural rigidity and associated cellular toxicity are major drawbacks for preclinical development. This review focuses on the potential of indoloquinoline alkaloids (cryptolepine, neocryptolepine, and isocryptolepine) as scaffolds in drug discovery. The article delves into their antimalarial effects in vitro and in vivo, as well as their proposed mechanisms of action and structure‐activity relationship studies. Several studies aim to improve these leads by reducing cytotoxicity while preserving or enhancing antimalarial activity and gaining insights into their mechanisms of action. These investigations highlight the potential of indoloquinolines as a scaffold for developing new antimalarial drugs.

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One-pot access to 11-methyl-6H-indolo[2,3-b]quinolines via iodine-mediated annulation of indoles with 2-vinylanilines and evaluation of their biological activities

Abstract: A simple, straightforward and efficient method for the synthesis of a series of 11-methyl-6H-indolo[2,3-b]quinolines bearing different substituents on the indole and quinoline rings is described.

Cited by 2 publications

References 59 publications

I₂/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

I₂/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

Indoloquinoline Alkaloids as Antimalarials: Advances, Challenges, and Opportunities

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One-pot access to 11-methyl-6H-indolo[2,3-b]quinolines via iodine-mediated annulation of indoles with 2-vinylanilines and evaluation of their biological activities

Abstract: A simple, straightforward and efficient method for the synthesis of a series of 11-methyl-6H-indolo[2,3-b]quinolines bearing different substituents on the indole and quinoline rings is described.

Cited by 2 publications

References 59 publications

I2/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

I2/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

Indoloquinoline Alkaloids as Antimalarials: Advances, Challenges, and Opportunities

Contact Info

Product

Resources

About

I₂/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis

I₂/DMSO-mediated oxidative C–C and C–heteroatom bond formation: a sustainable approach to chemical synthesis