Synthesis of Ginkgolic Acid Analogues and Evaluation of Their Molluscicidal Activity
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of the compounds
2.2. Assay for molluscicidal activity
3. Experimental
3.1. General
3.2. Synthesis
3.2.1. Ethyl 6-methylsalicylate (1)
3.2.2. Ethyl O-acetyl-6-methylsalicylate (2)
3.2.3. Ethyl O-acetyl-6-bromomethylsalicylate (3)
3.2.4. 3-Acetoxy-2-ethoxycarbonylbenzyltriphenylphosphonium bromide (4)
3.2.5. General procedure for preparation of ethyl O-acetyl-6-(1-alkenyl)salicylates 5a–5g
3.2.6. Separation of Z and E isomers 6a–6g and 7a–7g of ethyl O-acetyl-6-(1-alkenyl)salicylates
3.2.7. General procedure for preparation of 6-(1-alkenyl)salicylic acids
3.2.8. (Z)-6-(1-Pentenyl)salicylic acid (8a)
3.2.9. (E)-6-(1-Pentenyl)salicylic acid (9a)
3.2.10. (Z)-6-(1-Heptenyl)salicylic acid (8b)
3.2.11. (E)-6-(1-Heptenyl)salicylic acid (9b)
3.2.12. (Z)-6-(1-Nonenyl)salicylic acid (8c)
3.2.13. (E)-6-(1-Nonenyl)salicylic acid (9c)
3.2.14. (Z)-6-(1-Undecenyl)salicylic acid (8d)
3.2.15. (E)-6-(1-Undecenyl)salicylic acid (9d)
3.2.16. (Z)-6-(1-Dodecenyl)salicylic acid (8e)
3.2.17. (E)-6-(1-Dodecenyl)salicylic acid (9e)
3.2.18. (Z)-6-(1-Tridecenyl)salicylic acid (8f)
3.2.19. (E)-6-(1-Tridecenyl)salicylic acid (9f)
3.2.20. (Z)-6-Phenylethenyl salicylic acid (8g)
3.2.21. (E)-6-Phenylethenyl salicylic acid (9g)
3.3. Molluscicidal activity tests
4. Conclusions
Conflict of Interest
Acknowledgments
References
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Sample Availability: Contact the authors. |
Compound | LD10 (C.L.)a | LD50 (C.L.)a | LD90 (C.L.)a | |||
8 (Z) | 9 (E) | 8 (Z) | 9 (E) | 8 (Z) | 9 (E) | |
a | 27.2 (9.3–44.1) | 14.6 (7.6–57.8) | 107.2 (32.4–133.8) | 56.1 (16.7–122.6) | 786.6 (322.6–1213.8) | 115.9 (35.1–643.1) |
b | 33.6 (7.5–75.6) | 22 (6.9–35.3) | 73.1 (48.4–130.4) | 54.2 (21.4–132.2) | 243.6 (134.9–1215) | 214.5 (78.3–462.8) |
c | 12.5 (4.8–19.6) | 6.5 (0.8–9.1) | 50.9 (6.5–68.7) | 27.5 (14.8–87.1) | 98.2 (25.5–150.6) | 74.3 (34.2–95.0) |
d | 18.4 (1.7–27.7) | 10.9 (1.6–17.3) | 43.7 (22.9–89.2) | 23.6 (10.5–26.9) | 135.7 (14.2–199.3) | 68.3 (63.4–801.6) |
e | 11.1 (3.0–17.0) | 7.7 (0.3–15.0) | 56.9 (24.9–63.6) | 31.4 (21.1–80.3) | 362.9 (83.4–595.5) | 88.7 (46.7–121.1) |
f | 13.3 (0.3–26.6) | 5.5 (1.5–6.2) | 47.2 (31.4–57.7) | 22.4 (4.3–25.3) | 338.7 (82.2–364.6) | 50.9 (23.3–62.8) |
g | 14.6 (3.3–25.9) | 11.4 (3.6–18.8) | 64.4 (40.1–127.7) | 37.2 (23.9–57.0) | 283.9 (138.6–2001) | 122.0 (74.6–366.6) |
GA C13:0 * | 1.6 (0.8–8.6) | 29.2 (4.2–60.8) | 64.6 (37.7–180.2) | |||
Niclosamide | 0.7 (0.3–0.9) | 1.5 (1.1–2.1) | 3.4 (2.3–7.9) |
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Zhang, P.; Pan, J.; Duan, W.; Li, X.; Zhang, Y.; Zhou, Y.; Jiang, Q.; Mao, Z.; Yu, P. Synthesis of Ginkgolic Acid Analogues and Evaluation of Their Molluscicidal Activity. Molecules 2011, 16, 4059-4069. https://doi.org/10.3390/molecules16054059
Zhang P, Pan J, Duan W, Li X, Zhang Y, Zhou Y, Jiang Q, Mao Z, Yu P. Synthesis of Ginkgolic Acid Analogues and Evaluation of Their Molluscicidal Activity. Molecules. 2011; 16(5):4059-4069. https://doi.org/10.3390/molecules16054059
Chicago/Turabian StyleZhang, Peng, Jiahu Pan, Wanxing Duan, Xuedong Li, Yao Zhang, Yibiao Zhou, Qingwu Jiang, Zuohua Mao, and Peizhong Yu. 2011. "Synthesis of Ginkgolic Acid Analogues and Evaluation of Their Molluscicidal Activity" Molecules 16, no. 5: 4059-4069. https://doi.org/10.3390/molecules16054059