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Synthesis of Spiro[indole-3,5'-isoxazoles] with Anticancer Activity via a Formal [4 + 1]-Spirocyclization of Nitroalkenes to Indoles.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 Jun 07; Vol. 84 (11), pp. 7123-7137. Date of Electronic Publication: 2019 May 22. - Publication Year :
- 2019
-
Abstract
- An acid-assisted [4 + 1]-cycloaddition of indoles with nitrostyrenes affords 4' H-spiro[indole-3,5'-isoxazoles] in a diastereomerically pure form. Several of these spirocyclic molecules exhibit promising anticancer activity by reducing viability and inducing differentiation of neuroblastoma cells.
- Subjects :
- Antineoplastic Agents chemical synthesis
Antineoplastic Agents chemistry
Cell Line, Tumor
Cell Proliferation drug effects
Cell Survival drug effects
Cyclization
Dose-Response Relationship, Drug
Drug Screening Assays, Antitumor
Humans
Indoles chemical synthesis
Indoles chemistry
Isoxazoles chemical synthesis
Isoxazoles chemistry
Molecular Structure
Spiro Compounds chemical synthesis
Spiro Compounds chemistry
Structure-Activity Relationship
Alkenes chemistry
Antineoplastic Agents pharmacology
Indoles pharmacology
Isoxazoles pharmacology
Nitro Compounds chemistry
Spiro Compounds pharmacology
Subjects
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 11
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31070030
- Full Text :
- https://doi.org/10.1021/acs.joc.9b00808