Studies on methyl xestopongoate analogues:design, synthesis and antitumor activities

SUN Dongyu; GONG Jingxu; LI Xuwen; HAN Guanying; GUO Yuewei

doi:10.11665/j.issn.1000-5048.20180405

Journal of China Pharmaceutical University > 2018 > 49(4): 413-421. > DOI: 10.11665/j.issn.1000-5048.20180405

SUN Dongyu, GONG Jingxu, LI Xuwen, HAN Guanying, GUO Yuewei. Studies on methyl xestopongoate analogues:design, synthesis and antitumor activities[J]. Journal of China Pharmaceutical University, 2018, 49(4): 413-421. DOI: 10.11665/j.issn.1000-5048.20180405

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Studies on methyl xestopongoate analogues:design, synthesis and antitumor activities

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Abstract

Abstract

Fifty-two methyl xestospongoate analogues were designed, synthesized and evaluated for the antiproliferative activity. Starting from alkynyl methyl ester and diyne, methyl xestospongoate analogues 4 ( a - m )- 7( a - m )were synthesized by Cadiot-Chodkiewitz coupling and Sonogashira coupling reactions. Their structures were identified by ¹H NMR, ¹³C NMR and HREI-MS. The cytotoxic inhibiton activities in vitro of some compounds were evaluated against human cancer cells A549 and P-388 by a CCK-8 method. Among them, compound 6k exhibited potent cell growth inhibitory activity against A549 and P-388 cancer cells, with IC₅₀ values of 9. 36 and 9. 62 μmol/L, respectively.

Keywords:
Methyl Xestospongoate,
polyacethlene,
analogues,
synthesis,
antitumor activity

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References (10)

References

[1]
Zhou ZF,Menna M,Cai YS,et al.Polyacetylenes of marine origin:chemistry and bioactivity[J].Chem Rev,2015,115(3):1543-1596.

[2]
Martin T,Martin VS.A short synthesis of trans-(+)-laurediol[J].Tetrahedron Lett,2000,41(14):2503-2505.

[3]
Hirsh S,Carmely S,Kashman Y.Brominated unsaturated acids from the marine sponge Xestospongia sp.[J].Tetrahedron,1987,43(14):3257-3261.

[4]
Taniguchi M,Uchio Y,Yasumoto K,et al.Brominated unsaturated fatty acids from marine sponge collected in Papua New Guinea[J].Chem Pharm Bull,2008,56(3):378-382.

[5]
Jiang W,Liu D,Deng ZW,et al.Brominated polyunsaturated lipids and their stereochemistry from the Chinese marine sponge Xestospongia testudinaria[J].Tetrahedron,2011,67(1):58-68.

[6]
Morinaka BI,Skepper CK,Molinski TF.Ene-yne tetrahydrofurans from the sponge Xestospongia muta.exploiting a weak CD effect for assignment of configuration[J].Org Lett,2007,9(10):1975-1978.

[7]
Bourguet ML,Rakotoarisoa MT,Martin MT,et al.Bioactive bromopolyacetylenes from the marine sponge Xestospongia testudinaria[J].Tetrahedron Lett,1992,33(2):225-226.

[8]
Liang LF,Wang T,Cai YS,et al.Brominated polyunsaturated lipids from the Chinese sponge Xestospongia testudinaria as a new class of pancreatic lipase inhibitors[J].E J Med Chem,2014,79(8):290-297.

[9]
Gong JX,He WF,Liu HL,et al.Synthesis and evaluation of pancreatic lipase inhibitory effects halogenated polyunsaturated lipids from marine natural products:methyl Xestospongoate and analogs[J].Helv Chim Acta,2016,99(1):78-82.

[10]
Gong JX,Wang HY,Yao LG,et al.First Total synthesis of the marine natural brominated polyunsaturated lipid Xestospongenyne as a potent pancreatic lipase inhibitory agent[J].Synlett,2015,27(3):391-394.

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Related Articles

[1]	Zhou ZF,Menna M,Cai YS,et al.Polyacetylenes of marine origin:chemistry and bioactivity[J].Chem Rev,2015,115(3):1543-1596.
[2]	Martin T,Martin VS.A short synthesis of trans-(+)-laurediol[J].Tetrahedron Lett,2000,41(14):2503-2505.
[3]	Hirsh S,Carmely S,Kashman Y.Brominated unsaturated acids from the marine sponge Xestospongia sp.[J].Tetrahedron,1987,43(14):3257-3261.
[4]	Taniguchi M,Uchio Y,Yasumoto K,et al.Brominated unsaturated fatty acids from marine sponge collected in Papua New Guinea[J].Chem Pharm Bull,2008,56(3):378-382.
[5]	Jiang W,Liu D,Deng ZW,et al.Brominated polyunsaturated lipids and their stereochemistry from the Chinese marine sponge Xestospongia testudinaria[J].Tetrahedron,2011,67(1):58-68.
[6]	Morinaka BI,Skepper CK,Molinski TF.Ene-yne tetrahydrofurans from the sponge Xestospongia muta.exploiting a weak CD effect for assignment of configuration[J].Org Lett,2007,9(10):1975-1978.
[7]	Bourguet ML,Rakotoarisoa MT,Martin MT,et al.Bioactive bromopolyacetylenes from the marine sponge Xestospongia testudinaria[J].Tetrahedron Lett,1992,33(2):225-226.
[8]	Liang LF,Wang T,Cai YS,et al.Brominated polyunsaturated lipids from the Chinese sponge Xestospongia testudinaria as a new class of pancreatic lipase inhibitors[J].E J Med Chem,2014,79(8):290-297.
[9]	Gong JX,He WF,Liu HL,et al.Synthesis and evaluation of pancreatic lipase inhibitory effects halogenated polyunsaturated lipids from marine natural products:methyl Xestospongoate and analogs[J].Helv Chim Acta,2016,99(1):78-82.
[10]	Gong JX,Wang HY,Yao LG,et al.First Total synthesis of the marine natural brominated polyunsaturated lipid Xestospongenyne as a potent pancreatic lipase inhibitory agent[J].Synlett,2015,27(3):391-394.

[1]	CHENG Xiaohong, JIANG Li, DONG Xingting, KANG Xiulin, LIU Lifang. Identification of chemical constituents in Fufang Shechuangzi Xiji（Lotion）by UPLC-Q-TOF-MS/MS[J]. Journal of China Pharmaceutical University, 2022, 53(4): 452-466. DOI: 10.11665/j.issn.1000-5048.20220408
[2]	WANG Jingyi, DONG Yangyang, QI Chulu, ZHANG Jiayao, ZHANG Minjie, WANG Hao. Chemical constituents of the stem bark of Bombax ceiba L.[J]. Journal of China Pharmaceutical University, 2016, 47(5): 570-574. DOI: 10.11665/j.issn.1000-5048.20160511
[3]	XU Yunhui, JIANG Xueyang, XU Jian, JIANG Renwang, ZHANG Jie, XIE Zijian, FENG Feng. Chemical constituents from Callicarpa kwangtungensis Chun[J]. Journal of China Pharmaceutical University, 2016, 47(3): 299-302. DOI: 10.11665/j.issn.1000-5048.20160309
[4]	MA Lin, ZHANG Rongfei, YU Shule, WU Zhengfeng, ZHAO Shouxun, Wang Lei, YE Wencai, ZHANG Jian, YIN Zhiqi. Chemical constituents of Fructus Gleditsiae Abnormalis[J]. Journal of China Pharmaceutical University, 2015, 46(2): 188-193. DOI: 10.11665/j.issn.1000-5048.20150209
[5]	LI Jiu-hui, CHEN Guang-ying, HAN Chang-ri, MO Zheng-rong, SONG Xiao-ping. Chemical constituents from the stems of Vatica mangachpoi Blanco[J]. Journal of China Pharmaceutical University, 2012, 43(1): 25-27.
[6]	QU Wei, ZHAO Ling, LIANG Jing-yu. Chemical constituents from Saururus chinensis(Lour.) Baill[J]. Journal of China Pharmaceutical University, 2011, 42(6): 507-509.
[7]	WANG Hang, FENG Fang, WANG Xue-qua. Chemical constituents of Zhizidahuang decoction detected by HPLC-PDA-ESI-MS/MS[J]. Journal of China Pharmaceutical University, 2009, 40(3): 232-237.
[8]	Chemical Constituents ofDendrobium fimbriatum Hook.([J]. Journal of China Pharmaceutical University, 2001, (3): 42-44.
[9]	Studies of Chemical Constituents of Ficus Carica L[J]. Journal of China Pharmaceutical University, 1996, (4): 13-15.
[10]	COMPARISON BETWEEN THE OIL CONSTITUENTS OF WILD AND OF CULTIVATED A TRACTYLODES LANCEA BY GC/MS[J]. Journal of China Pharmaceutical University, 1989, (5): 289-290.

Studies on methyl xestopongoate analogues:design, synthesis and antitumor activities

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