Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis of Palmarumycin CP17 and Its Methoxy Analogues
2.2. Antifungal Activity of Spirobisnaphthalene Palmarumycin CP17 and Its Methoxy Analogues
3. Materials and Methods
3.1. General Information
3.2. Synthesis of Spirobisnaphthalene Palmarumycin CP17 and Their Methoxy Analogues
5,8-Dimethoxytetralone (1)
5,8-Dimethoxytetralone methyl enol ether (2)
5,8-Dimethoxy-1,2,3,4-tetrahydrospiro[naphtha-ene-1,2′-naphtho-[1,8-de][1,3]dioxine (3)
5,8-Dimethoxy-2,3-dihydrospiro[naphthalene-1,2′-naphtho[1,8-de][1,3]dioxine-4-one (5)
5-Hydroxy-8-methoxy-2,3-dihydrospiro[naphthalene-1,2′-naphtho-[1,8-de][1,3]dioxine-4-one (6b)
8-Hydroxynaphthalen-1-yl-4,5,8-trihydroxynaphthalene ether (7)
8-((8-Hydroxynaphthalen-1-yl)oxy)naphthalene-1,4,5-triol (8)
5,8-Dihydroxy-1,2,3,4-tetrahydrospiro[naphthalene-1,2′-naphtho-[1,8-de][1,3]dioxine (9a) and 5-Hydroxy-8-methoxy-1,2,3,4-tetrahydrospiro[naphthalene-1,2′-naphtho-[1,8-de][1,3]dioxine (9b)
5,8-Diacetoxy-1,2,3,4-tetrahydrospiro[naphthalene-1,2’-naphtho-[1,8-de][1,3]dioxine (10a)
5-Acetoxy-8-methoxy-1,2,3,4-tetrahydrospiro[naphthalene-1,2′-naphtho-[1,8-de][1,3]dioxine (10b)
5,8-Diacetoxy-2,3-dihydrospiro[naphthalene-1,2′-naphtho[1,8-de][1,3]dioxine-4-one (11a) and 5-Acetoxy-8-methoxy-2,3-dihydrospiro[naphthalene-1,2′-naphtho[1,8-de][1,3]dioxine-4-one (11b)
5,8-Dihydroxy-2,3-dihydrospiro[naphthalene-1,2′-naphtho[1,8-de][1,3]dioxine-4-one (Palmarumycin CP17, 6a) and 5-Hydroxy-8-methoxy-2,3-di-hydrospiro[naphthalene-1,2′-naphtho[1,8-de][1,3]-dioxine-4-one (6b)
7-Methoxytetralone (13) and 6,7-Dimethoxytetralone (14)
6-Methoxy-3,4-dihydro-2H-spironaphthalene-1,2′-naphtho[1,8-de][1,3]dioxine (15), 7-Methoxy-3,4-dihydro-2H-spironaphthalene-1,2′-naphtho[1,8-de][1,3]dioxine (16) and 6,7-Dimethoxy-3,4-dihydro-2H-spironaphthaene-1,2′-naphtho[1,8-de][1,3]dioxine (17)
6-Methoxy-2,3-dihydrospiro[naphthalene-1,2′-naphtho[1,8-de][1,3]dioxine-4-one (18), 7-Methoxy-2,3-dihydrospiro[naphthalene-1,2′-naphtho-[1,8-de][1,3]dioxine-4-one (19) and 6,7-Dimethoxy-2,3-di-hydrospiro[naphthalene-1,2′-naphtho-[1,8-de][1,3]dioxine-4-one (20)
8-Hydroxynaphthalen-1-yl-4-hydroxy-6-methoxynaphthalene ether (21), 8-Hydroxynaphthalen-1-yl-4-hydroxy-7-methoxynaphthalene ether (22) and 8-Hydroxy-naphthalen-1-yl-4,7-dimethoxynaphthalene ether (23)
3.3. Bioassay of Spirobisnaphthalene Palmarumycin CP17 and Its Methoxy Analogues
4. Conclusions
Supplementary Materials
Acknowledgments
Author Contributions
Conflicts of Interest
References
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Compd. | R.S | P.P | B.C | F.O | P.A | F.G | C.A |
---|---|---|---|---|---|---|---|
3 | 44.5 | 33.6 | 50.5 | 10.3 | 21.7 | 18.6 | 49.7 |
5 | 54.5 | 73.7 | 61.2 | 13.0 | 33.3 | 18.6 | 49.7 |
8 | 48.9 | 43.5 | 60.5 | 16.0 | 38.3 | 23.0 | 51.4 |
9a | 52.1 | 57.0 | 68.4 | 16.3 | 23.0 | 13.9 | 44.7 |
9b | 51.1 | 75.0 | 57.9 | 14.0 | 29.8 | 11.6 | 54.8 |
10a | 55.3 | 63.5 | 69.0 | 21.7 | 36.7 | 18.6 | 58.0 |
10b | 42.3 | 50.6 | 67.2 | 14.9 | 26.5 | 18.6 | 53.1 |
11b | 71.3 | 0 | 67.1 | 10.0 | 2.7 | 23.0 | 59.0 |
6a | 48.9 | 43.5 | 60.5 | 16.0 | 38.3 | 23.0 | 51.4 |
6b | 52.4 | 64.7 | 60.5 | 21.3 | 39.0 | 41.9 | 50.6 |
Compd. | Fungi | Regression Eq. | EC50 (µg/mL) | Correlation efficient (R2) |
---|---|---|---|---|
5 | P. piricola | Y = −1.278 + 1.282X | 9.34 | 0.9604 |
9b | P. piricola | Y = −3.014 + 2.760X | 12.35 | 0.9525 |
11b | R. solani | Y = −2.076 + 1.980X | 11.18 | 0.9645 |
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Wang, R.; Liu, G.; Yang, M.; Wang, M.; Zhou, L. Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues. Molecules 2016, 21, 600. https://doi.org/10.3390/molecules21050600
Wang R, Liu G, Yang M, Wang M, Zhou L. Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues. Molecules. 2016; 21(5):600. https://doi.org/10.3390/molecules21050600
Chicago/Turabian StyleWang, Ruina, Guoyue Liu, Mingyan Yang, Mingan Wang, and Ligang Zhou. 2016. "Total Synthesis and Antifungal Activity of Palmarumycin CP17 and Its Methoxy Analogues" Molecules 21, no. 5: 600. https://doi.org/10.3390/molecules21050600