Nitrene-transfer from azides to isocyanides: Unveiling its versatility as a promising building block for the synthesis of bioactive heterocycles

Sawant, Devesh M.; Joshi, Gaurav; Ansari, Arshad J.

doi:10.1016/j.isci.2024.109311

iScience

2024

DOI: 10.1016/j.isci.2024.109311

|View full text |Cite

Nitrene-transfer from azides to isocyanides: Unveiling its versatility as a promising building block for the synthesis of bioactive heterocycles

Devesh M. Sawant,

Gaurav Joshi,

Arshad J. Ansari

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...

Citation Types

Supporting

Mentioning

Contrasting

Year Published

2024

Publication Types

Select...

Article2

Relationship

Self Cite0

Independent2

Authors

Journals

Cited by 2 publications

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

Unveiling the Phosphine-Mediated N-Transfer from Azide to Isocyanide en Route to Carbodiimides and 4-Imino-1,3,2-diazaphosphetidines

Pastor,

Lopez-Leonardo,

Cutillas-Font

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

Intramolecular reactions between isocyano and iminophosphorane functions yield species containing an embedded 1,3,2diazaphosphetidine ring, as result of the [2 + 2] cycloaddition of the primary reactive product, the cyclic carbodiimide, with a second unit of reactant. DFT studies reveal a first rate-determining step entailing a [2 + 1] cycloaddition involving the isocyanide carbon atom and the P�N double bond, with the further intervention of a dipolar precursor of the intermediate carbodiimide. The 1,3,2-diazaphosphetidine ring of the final products is shown to be hydrolytically and thermally labile.

show abstract

Unveiling the Phosphine-Mediated N-Transfer from Azide to Isocyanide en Route to Carbodiimides and 4-Imino-1,3,2-diazaphosphetidines

Pastor,

Lopez-Leonardo,

Cutillas-Font

et al. 2024

Org. Lett.

View full text Add to dashboard Cite

show abstract

Design and Development of Novel Hybrids Based on Pyrrolo[2,1‐f][1,2,4]Triazine and 1‐(Methylpiperidin‐4‐yl) Aniline–Based Analogs: Exploring the Utility as Anticancer Agents via MERTK Inhibition

Sathe,

Jaiswal,

Kumar

et al. 2024

Chem Biol Drug Des

View full text Add to dashboard Cite

Mer‐tyrosine kinase (MERTK), a member of the AXL, TYRO3, and MERTK (TAM) family, is one of the promising targets for cancer treatment. It plays a key role in cancer cell survival and proliferation and regulates immune responses in cancer. The study aimed to rationally design and develop molecules considering the pharmacophoric requirements of MERTK using a multi‐synthetic approach followed by the hybridization of individual pharmacophores. A hybrid drug design approach was employed by hybridization of pyrrolo[2,1‐f][1,2,4]triazine and 1‐(methylpiperidin‐4‐yl)aniline pharmacophoric systems to develop novel leads (1K1–1K5). The molecules were synthesized via a multi‐step synthetic approach. The synthesized molecules were assessed for their pharmacological potential via cell viability, drug metabolism and pharmacokinetics (DMPK), and MERTK inhibition studies corroborated by in silico studies. IK5 was found to have an IC50 value of 0.36 μM towards A549, followed by 0.42 μM and 0.80 μM against MCF‐7 and MDA‐MB‐231 cells, respectively. Further, the molecules were also analyzed for their microsomal stability and were found to be stable with better intrinsic clearance profiles. The molecules thus pave a strategy for developing novel MERTK inhibitors and their advance in vitro and in vivo assessment in the future.

show abstract

scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.

Contact Info

customersupport@researchsolutions.com

10624 S. Eastern Ave., Ste. A-614

Henderson, NV 89052, USA

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Blog Terms and Conditions API Terms Privacy Policy Contact Cookie Preferences Do Not Sell or Share My Personal Information

Made with 💙 for researchers

Part of the Research Solutions Family.

Nitrene-transfer from azides to isocyanides: Unveiling its versatility as a promising building block for the synthesis of bioactive heterocycles

Cited by 2 publications

References 55 publications

Unveiling the Phosphine-Mediated N-Transfer from Azide to Isocyanide en Route to Carbodiimides and 4-Imino-1,3,2-diazaphosphetidines

Unveiling the Phosphine-Mediated N-Transfer from Azide to Isocyanide en Route to Carbodiimides and 4-Imino-1,3,2-diazaphosphetidines

Design and Development of Novel Hybrids Based on Pyrrolo[2,1‐f][1,2,4]Triazine and 1‐(Methylpiperidin‐4‐yl) Aniline–Based Analogs: Exploring the Utility as Anticancer Agents via MERTK Inhibition

Contact Info

Product

Resources

About