Novel spiroindoline quinazolinedione derivatives as anticancer agents and potential FLT3 kinase inhibitors

Divar, Masoumeh; Edraki, Najmeh; Damghani, Tahereh; Moosavi, Fatemeh; Mohabbati, Maryam; Alipour, Alireza; Pirhadi, Somayeh; Saso, Luciano; Khabnadideh, Soghra; Firuzi, Omidreza

doi:10.1016/j.bmc.2023.117367

Cited by 3 publications

(1 citation statement)

References 48 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, by taking advantage of their rigidity and three-dimensional structure, chemists have developed spiro compounds as effective ligand and catalyst motifs for asymmetric synthesis. Among various spiroheterocyclic scaffolds, spiroindoline constitutes the essential structural backbone of numerous pharmaceuticals and natural alkaloids . Some representative examples in this context are listed in Figure .…”

mentioning

confidence: 99%

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp²)–H and C(sp³)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Wang,

Sun,

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

Presented herein is a novel synthesis of pharmaceutically privileged spiroindoline derivatives via cascade reactions of N-methyl-N-nitrosoanilines with diazo homophthalimides. A group of mechanistic studies disclosed that the formation of product involves an unusual reaction mode of N-methyl-N-nitrosoaniline featuring an initial C(sp 2 )−H bond activation/alkylation followed by a C(sp 3 )−H bond activation/spiroannulation. To our knowledge, this is the first example in which N-methyl-N-nitrosoaniline acts as a C3N1 synthon to accomplish formal [4+1] spiroannulation with the participation of the N-methyl unit rather than the previously reported C2N1 synthon to undergo formal [3+2] annulation without the participation of the N-methyl unit. In general, this newly developed synthetic protocol features simple and readily accessible starting materials, valuable products, unique reaction mechanism, high efficiency and atom-economy, excellent compatibility with diverse functional groups, and ready scalability.

show abstract

mentioning

confidence: 99%

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp²)–H and C(sp³)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Wang,

Sun,

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

show abstract

Design, synthesis and antitumor activity of 2-substituted quinazoline-4-amine derivatives

Wang,

Yu,

Huang

et al. 2024

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

Design, Synthesis and Antitumor Activity of 2-Substituted Quinazoline-4-Amine Derivatives

Wang,

Yu,

Huang

et al. 2024

Preprint

View full text Add to dashboard Cite

Novel spiroindoline quinazolinedione derivatives as anticancer agents and potential FLT3 kinase inhibitors

Cited by 3 publications

References 48 publications

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp²)–H and C(sp³)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp²)–H and C(sp³)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Design, synthesis and antitumor activity of 2-substituted quinazoline-4-amine derivatives

Design, Synthesis and Antitumor Activity of 2-Substituted Quinazoline-4-Amine Derivatives

Contact Info

Product

Resources

About

Novel spiroindoline quinazolinedione derivatives as anticancer agents and potential FLT3 kinase inhibitors

Cited by 3 publications

References 48 publications

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp2)–H and C(sp3)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp2)–H and C(sp3)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Design, synthesis and antitumor activity of 2-substituted quinazoline-4-amine derivatives

Design, Synthesis and Antitumor Activity of 2-Substituted Quinazoline-4-Amine Derivatives

Contact Info

Product

Resources

About

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp²)–H and C(sp³)–H Bond Functionalization of N-Methyl-N-nitrosoanilines

Expeditious Synthesis of Spiroindoline Derivatives via Tandem C(sp²)–H and C(sp³)–H Bond Functionalization of N-Methyl-N-nitrosoanilines