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

Citation:

PDF (1136 KB)

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

More Information

Graphical Abstract

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

FullText(HTML)

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.

Related Articles

Related Articles

[1] ZHU Song, JIANG Jing, LIU Yang, ZOU Wenyu, HU Pengwei, LU Yuting, SONG Min, HANG Taijun. Structural identification of the related substances of lorazepam tablets by LC-MS[J]. Journal of China Pharmaceutical University, 2021, 52(5): 555-565. DOI: 10.11665/j.issn.1000-5048.20210507

[2] LIANG Fangmei, NI Yueling, WANG Lu, HANG Taijun, SONG Min. Structural identification of the related substances of fusidic acid by LC-MS[J]. Journal of China Pharmaceutical University, 2018, 49(3): 322-332. DOI: 10.11665/j.issn.1000-5048.20180311

[3] YIN Xiaoya, WANG Cheng, MING Guojun, HANG Taijun. Identification of the related substances in pioglitazone hydrochloride by hyphenated LC-MS techniques[J]. Journal of China Pharmaceutical University, 2017, 48(6): 701-710. DOI: 10.11665/j.issn.1000-5048.20170611

[4] FANG Daqing, LIU Fang, ZHANG Sijia, CAI Chaoqun, LIU Minzhuo, LIU Jinghan, YANG Chunhua, WANG Hao. One new diterpenoid alkaloid from Aconitum carmichaeli[J]. Journal of China Pharmaceutical University, 2017, 48(5): 568-571. DOI: 10.11665/j.issn.1000-5048.20170510

[5] CHEN Wenhua, ZOU Limin, ZHANG Fei, ZHANG Liandi, LIAO Mingyi, DING Li. Identification of the related substances in bendamustine hydrochloride[J]. Journal of China Pharmaceutical University, 2015, 46(3): 333-338. DOI: 10.11665/j.issn.1000-5048.20150312

[6] ZHOU Yongmei, SHI Xianming, MA Lei, ZHANG Sifang. Isolation and identification of Withaphysalins from Physalis minima[J]. Journal of China Pharmaceutical University, 2015, 46(1): 62-65. DOI: 10.11665/j.issn.1000-5048.20150107

[7] RAO Ya-kun, DING Li, YU Yong. Structural identification of two major impurities in sodium levofolinate[J]. Journal of China Pharmaceutical University, 2012, 43(4): 350-354.

[8] WANG Ying, YIN Hong-ping, CHEN Tao, WANG Min. Preliminary structural identification and protection on renal cell injury of acidic polysaccharide from Cordyceps sinensis[J]. Journal of China Pharmaceutical University, 2009, 40(6): 559-564.

[9] Isolation and Identification of Two Taxane DiterpenoidCompounds[J]. Journal of China Pharmaceutical University, 2001, (3): 32-34.

[10] Studies on 1H NMR of Naturally Occurring Taxane Diterpenoids and Revising Suggestions on Some Structures[J]. Journal of China Pharmaceutical University, 1998, (4): 19-22+25.

Cited By

Catalog

Get Citation

PDF

XML

Article views (1227) PDF downloads (1234) Cited by()

Turn off MathJax
Article Contents

Abstract

References

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]	ZHU Song, JIANG Jing, LIU Yang, ZOU Wenyu, HU Pengwei, LU Yuting, SONG Min, HANG Taijun. Structural identification of the related substances of lorazepam tablets by LC-MS[J]. Journal of China Pharmaceutical University, 2021, 52(5): 555-565. DOI: 10.11665/j.issn.1000-5048.20210507
[2]	LIANG Fangmei, NI Yueling, WANG Lu, HANG Taijun, SONG Min. Structural identification of the related substances of fusidic acid by LC-MS[J]. Journal of China Pharmaceutical University, 2018, 49(3): 322-332. DOI: 10.11665/j.issn.1000-5048.20180311
[3]	YIN Xiaoya, WANG Cheng, MING Guojun, HANG Taijun. Identification of the related substances in pioglitazone hydrochloride by hyphenated LC-MS techniques[J]. Journal of China Pharmaceutical University, 2017, 48(6): 701-710. DOI: 10.11665/j.issn.1000-5048.20170611
[4]	FANG Daqing, LIU Fang, ZHANG Sijia, CAI Chaoqun, LIU Minzhuo, LIU Jinghan, YANG Chunhua, WANG Hao. One new diterpenoid alkaloid from Aconitum carmichaeli[J]. Journal of China Pharmaceutical University, 2017, 48(5): 568-571. DOI: 10.11665/j.issn.1000-5048.20170510
[5]	CHEN Wenhua, ZOU Limin, ZHANG Fei, ZHANG Liandi, LIAO Mingyi, DING Li. Identification of the related substances in bendamustine hydrochloride[J]. Journal of China Pharmaceutical University, 2015, 46(3): 333-338. DOI: 10.11665/j.issn.1000-5048.20150312
[6]	ZHOU Yongmei, SHI Xianming, MA Lei, ZHANG Sifang. Isolation and identification of Withaphysalins from Physalis minima[J]. Journal of China Pharmaceutical University, 2015, 46(1): 62-65. DOI: 10.11665/j.issn.1000-5048.20150107
[7]	RAO Ya-kun, DING Li, YU Yong. Structural identification of two major impurities in sodium levofolinate[J]. Journal of China Pharmaceutical University, 2012, 43(4): 350-354.
[8]	WANG Ying, YIN Hong-ping, CHEN Tao, WANG Min. Preliminary structural identification and protection on renal cell injury of acidic polysaccharide from Cordyceps sinensis[J]. Journal of China Pharmaceutical University, 2009, 40(6): 559-564.
[9]	Isolation and Identification of Two Taxane DiterpenoidCompounds[J]. Journal of China Pharmaceutical University, 2001, (3): 32-34.
[10]	Studies on 1H NMR of Naturally Occurring Taxane Diterpenoids and Revising Suggestions on Some Structures[J]. Journal of China Pharmaceutical University, 1998, (4): 19-22+25.

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

Abstract

References

Related Articles

Catalog

Export File

Citation

Format

Content