Category Ranking

98%

Total Visits

921

Avg Visit Duration

2 minutes

Citations

20

Article Abstract

The synthesis of polysubstituted spirocyclopropyl oxindoles using a series of rare-earth metal (REM) salts is reported. REMs, in particular Sc(OTf), allowed access to the target compounds by a multicomponent reaction with high diastereoselectivity (≤94:6:0:0). Density functional theory calculations on the model reaction are consistent with the observed selectivity and revealed that the special coordinating capabilities and the oxophilicity of the metal are key factors in inducing the formation of one main diastereoisomer.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10167684PMC
http://dx.doi.org/10.1021/acs.orglett.3c00772DOI Listing

Publication Analysis

Top Keywords

spirocyclopropyl oxindoles
8
rare-earth metal
8
highly diastereoselective
4
diastereoselective multicomponent
4
multicomponent synthesis
4
synthesis spirocyclopropyl
4
oxindoles enabled
4
enabled rare-earth
4
metal salts
4
salts synthesis
4

Similar Publications

Dual-targeting agents represent a promising approach in cancer treatment, offering several significant advantages over traditional single-target therapies or drug combinations. In this connection, herein a series of spirocyclopropyl oxindole-piperazine/morpholine based carboxamides were rationally designed, synthesized, and evaluated for their dual inhibition (tubulin polymerization and VEGFR-2 kinase) activity. Among the synthesized derivatives, compound 8u exhibited potent cytotoxicity against the HepG-2 cell line with an IC of 1.

View Article and Find Full Text PDF

A series of 1H-1,2,3-triazole-tethered spirocyclopropyl oxindole-isatin hybrids were synthesized using a copper-promoted click reaction and evaluated for their anti-proliferative activities against triple-negative breast cancer cell lines. The most potent compound in the series outperformed tamoxifen and 5-fluorouracil, with selectivity indices of 1.60 and 1.

View Article and Find Full Text PDF
Article Synopsis
  • A new method for creating spirocyclopropyl and spiropyrazoline oxindoles was developed, using 3-ylideneoxindoles and ethyl diazoacetate without any catalysts.
  • The study found that using ClCHCHCl as the solvent produced spirocyclopropyl oxindoles with moderate to excellent yields, while MeOH led to spiropyrazoline oxindoles with moderate to good yields.
  • This method is beneficial due to the easy-to-use materials, straightforward procedure, and potential for further transformations of the products.
View Article and Find Full Text PDF

Tumor progression depends on angiogenesis, which is stimulated by growth factors like VEGF, targeting VEGFR kinase with small molecules is an effective anti-angiogenic therapeutic approach. The rational modification of sunitinib (VEGFR-2 inhibitor) to spirocyclopropyloxindoline carboxamides have been performed and their in vitro cytotoxic profiling was evaluated. The molecular modelling studies enabled the screening of designed analogues and identifying the possible interactions within the type III allosteric inhibitor binding site of VEGFR-2.

View Article and Find Full Text PDF

We have demonstrated a Pd(0)-catalyzed Heck/C(sp)-H activation cascade for the synthesis of spirocyclopropyl oxindoles in high yields from easily accessible -bromoacrylamides. The formation of spirocyclopropyl oxindole is guided by an unconventional four-membered palladacycle through C(sp)-H activation. The reaction exhibits a wide range of substrate scope and operates efficiently with a mere 0.

View Article and Find Full Text PDF