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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[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]	ZHAO Xiaomei, WANG Xin, JI Xia, Zhang Jing, ZHANG Hua, HU Guoqiang. Synthesis and antitumor activity of heteroatom-substituted azulenes derivatives of 1,2-benzothiazine[J]. Journal of China Pharmaceutical University, 2024, 55(5): 634-638. DOI: 10.11665/j.issn.1000-5048.2023120503
[2]	LI Mingtao, XU Dan, XUE Wenjun, YOU Qidong, SUN Liping. Design, synthesis and antitumor activities of oxazolo［5, 4-d］pyrimidine derivatives[J]. Journal of China Pharmaceutical University, 2017, 48(4): 425-431. DOI: 10.11665/j.issn.1000-5048.20170406
[3]	QIAO Yixue, MOU Yi, HUANG Zhangjian, AI Yong, KANG Fenghua, LAI Yisheng, ZHANG Yihua. Synthesis and antitumor activities of novel CDDO-Me analogues[J]. Journal of China Pharmaceutical University, 2015, 46(3): 289-293. DOI: 10.11665/j.issn.1000-5048.20150305
[4]	MAO Chunfang, XU Chenjun, WANG Xuemin, LI Xianghua, ZHANG Wei, WANG Xinyang, LING Yong. Design, synthesis and antitumor activity of farnesylthiosalicylamide derivatives[J]. Journal of China Pharmaceutical University, 2015, 46(2): 162-168. DOI: 10.11665/j.issn.1000-5048.20150204
[5]	HU Kun, ZHOU Anfei, JIANG Hefei, XU Yuanyuan, HUANG Qianhui, YANG Jie, CHEN Xin, REN Jie. Synthesis and antitumor activities of podophyllotoxin derivatives[J]. Journal of China Pharmaceutical University, 2014, 45(1): 33-38. DOI: 10.11665/j.issn.1000-5048.20140105
[6]	LIU Dexiu, PAN Huaying, SHI Hui, HUANG Xiaoying, LOU Hongxiang. Synthesis and antitumor activity of a novel bisbibenzyl derivative[J]. Journal of China Pharmaceutical University, 2013, 44(6): 515-519. DOI: 10.11665/j.issn.1000-5048.20130605
[7]	ZHANG Shi-bo, ZHANG Zhen-zhen, DING Ye, LAI Yi-sheng, MOU Yi, AI Yong, JI Hui, ZHANG Yi-hua. Synthesis and antitumor activity of NO-donating CDDO analogues[J]. Journal of China Pharmaceutical University, 2012, 43(4): 293-297.
[8]	HU Kun, XU Hua-jin, XIN Wen-qun, CHEN Xin, REN Jie. Synthesis and antitumor activity of nitrogen mustard derivatives of formononetin[J]. Journal of China Pharmaceutical University, 2012, 43(2): 113-119.
[9]	ZHA Xiao-ming, ZHANG Fei-ran, SHAN Jia-qi, CHEN Yan-ke, ZHANG Yi-hua, LIU Jun, SUN Hong-bin. Synthesis and in vitro antitumor activities of novel soladulcidine derivatives[J]. Journal of China Pharmaceutical University, 2010, 41(6): 493-498.
[10]	CHEN Li, MENG Fei, WANG Zhi-feng, ZHANG Yi-hua. Synthesis and antitumor activity of novel oleanolic acid-nitrate conjugates[J]. Journal of China Pharmaceutical University, 2010, 41(6): 487-492.

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

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