Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. In Vitro Assay of Antiproliferative Activity
2.3. Theoretical Calculation and Analysis
3. Experimental Section
3.1. General Information
3.2. Preparation of Catalyst
3.3. Synthesis of 7-isopropyl-1,1-dimethyl-1,2,3,4-tetrahydronaphthalene (2)
3.4. Synthesis of 6-isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one (3)
3.5. Synthesis of 2-bromo-6-isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one (4)
3.6. Synthesis of 2-(5-amino-1H-1,2,4-triazol-3-ylthio)-6-isopropyl-4,4-dimethyl-3,4-dihydronaphthalen-1 (2H)-one (5)
3.7. General Procedure for the Synthesis of the Target Compounds (6a–6q)
3.8. In Vitro Antiproliferative Evaluation
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 2–5 and 6a–6q are available from the authors. |
Comp. | R | Comp. | R | Comp. | R |
---|---|---|---|---|---|
6a | 2′,4′,6′-Me | 6g | 2′,3′,4′′,5′,6′-F | 6m | 4′-Me |
6b | 2′,5′-Me | 6h | 3′-NO2-4′-Cl | 6n | 2′-Cl |
6c | 2′-NO2 | 6i | H | 6o | 4′-Br |
6d | 3′-Br | 6j | 4′-Cl | 6p | 2′,4′-F |
6e | 4′-CF3 | 6k | 3′-NO2 | 6q | 4′-CN |
6f | 4′-OMe | 6l | 4′-NO2 |
Compound | IC50 (µM) | ||||
---|---|---|---|---|---|
A549 | HT-29 | T-24 | MCF-7 | HepG2 | |
6a (R = 2′,4′,6′-Me) | >100 | >100 | 72.46±2.02 | >100 | >100 |
6b (R = 2′,5′-Me) | 48.73 ± 3.43 | 41.52 ± 1.45 | >100 | >100 | >100 |
6c (R = 2′-NO2) | 29.73 ± 3.07 | 37.27 ± 1.67 | >100 | >100 | >100 |
6d (R = 3′-Br) | 30.21 ± 0.02 | 25.86 ± 2.59 | 45.51 ± 0.95 | >100 | 44.31 ± 1.29 |
6e (R = 4′-CF3) | 82.36 ± 3.49 | >100 | >100 | >100 | >100 |
6f (R = 4′-OMe) | 84.61 ± 3.90 | 25.35 ± 3.30 | >100 | >100 | >100 |
6g (R = 2′,3′,4 ′,5′,6′-F) | 13.28 ± 1.55 | 23.49 ± 3.48 | 17.09 ± 0.02 | 4.42 ± 0.93 | 15.51 ± 2.39 |
6h (R = 3′-NO2-4′-Cl) | 9.89 ± 1.77 | 22.22 ± 2.42 | 26.91 ± 1.19 | 28.86 ± 1.73 | 21.43 ± 2.36 |
6i–6q and 2–5 | >100 | >100 | >100 | >100 | >100 |
5-FU | >100 | >100 | 42.81 ± 0.59 | 52.54 ± 0.67 | 20.71 ± 0.52 |
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Zhu, X.-P.; Lin, G.-S.; Duan, W.-G.; Li, Q.-M.; Li, F.-Y.; Lu, S.-Z. Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety. Molecules 2020, 25, 986. https://doi.org/10.3390/molecules25040986
Zhu X-P, Lin G-S, Duan W-G, Li Q-M, Li F-Y, Lu S-Z. Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety. Molecules. 2020; 25(4):986. https://doi.org/10.3390/molecules25040986
Chicago/Turabian StyleZhu, Xia-Ping, Gui-Shan Lin, Wen-Gui Duan, Qing-Min Li, Fang-Yao Li, and Shun-Zhong Lu. 2020. "Synthesis and Antiproliferative Evaluation of Novel Longifolene-Derived Tetralone Derivatives Bearing 1,2,4-Triazole Moiety" Molecules 25, no. 4: 986. https://doi.org/10.3390/molecules25040986