Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction
Abstract
:1. Introduction
2. Results and Discussion
3. Experimental Section
3.1. General
3.2. General Experimental Procedures for the Synthesis of Compounds 3–5
3.3. Characterization Data of Compounds 3–5
3.4. Cytotoxicity Assay
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References and Notes
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Sample Availability: Samples of the compounds 3–5 are available from the authors. |
Entry a | Solvent | T (°C) | Time (h) | Yield b (%) | Dr c |
---|---|---|---|---|---|
1 | toluene | 80 | 5 | 67 | 10:1 |
2 | DCE | reflux | 5 | 61 | 15:1 |
3 | EtOAc | reflux | 5 | 48 | 12:1 |
4 | EtOH | reflux | 5 | 83 | 18:1 |
5 | THF | reflux | 5 | 71 | 16:1 |
6 | H2O | 80 | 5 | 39 | 11:1 |
7 | CH3CN | reflux | 5 | 82 | 19:1 |
8 | EtOH | 40 | 48 | 52 | 17:1 |
9 d | EtOH | reflux | 3 | 89 | 20:1 |
10 e | EtOH | reflux | 5 | 57 | 16:1 |
11 f | EtOH | reflux | 3 | 72 | 19:1 |
Compound | 3le | 3fa | 3la | 3ia | 3fd | 4da | 5ia | 5ba | 5oa | 5pa | Cisplatin |
---|---|---|---|---|---|---|---|---|---|---|---|
K562 IC50 (μM) | 43.5 | 51.3 | 33.8 | 77.8 | 62.3 | 38.5 | 49.4 | 79.0 | 22.3 | 27.6 | 21.3 |
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Lin, B.; Zhou, G.; Gong, Y.; Wei, Q.-D.; Tian, M.-Y.; Liu, X.-L.; Feng, T.-T.; Zhou, Y.; Yuan, W.-C. Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction. Molecules 2017, 22, 645. https://doi.org/10.3390/molecules22040645
Lin B, Zhou G, Gong Y, Wei Q-D, Tian M-Y, Liu X-L, Feng T-T, Zhou Y, Yuan W-C. Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction. Molecules. 2017; 22(4):645. https://doi.org/10.3390/molecules22040645
Chicago/Turabian StyleLin, Bing, Gen Zhou, Yi Gong, Qi-Di Wei, Min-Yi Tian, Xiong-Li Liu, Ting-Ting Feng, Ying Zhou, and Wei-Cheng Yuan. 2017. "Molecular Hybridization-Guided One-Pot Multicomponent Synthesis of Turmerone Motif-Fused 3,3′-Pyrrolidinyl-dispirooxindoles via a 1,3-Dipolar Cycloaddition Reaction" Molecules 22, no. 4: 645. https://doi.org/10.3390/molecules22040645