• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

23-羟基白桦酸 C-28 酯衍生物的合成及抗肿瘤活性研究。

Synthesis and biological activity of 23-hydroxybetulinic acid C-28 ester derivatives as antitumor agent candidates.

机构信息

School of Pharmacy, Yantai University, Yantai 264005, Shandong, China.

出版信息

Molecules. 2012 Jul 25;17(8):8832-41. doi: 10.3390/molecules17088832.

DOI:10.3390/molecules17088832
PMID:22832884
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6268522/
Abstract

23-Hydroxybetulinic acid (1) served as the precursor for the synthesis of C-28 ester derivatives. The target compounds were evaluated in vitro for their antitumor activities against five cell lines (A549, BEL-7402, SF-763, B16 and HL-60). Among the obtained compounds, 6i had the most potent antitumor activity, with the IC(50 values of 8.35 µM in HL-60 cells and showed similar antitumor activity as cyclophosphamide in H22 liver tumor and as 5-fluorouracil in B16 melanoma in vivo.

摘要

23-羟基白桦酸（1）可用作合成 C-28 酯衍生物的前体。目标化合物在体外对五种细胞系（A549、BEL-7402、SF-763、B16 和 HL-60）的抗肿瘤活性进行了评价。在所得到的化合物中，6i 具有最强的抗肿瘤活性，在 HL-60 细胞中的 IC（50 值为 8.35µM，并在体内显示出与环磷酰胺在 H22 肝癌和 5-氟尿嘧啶在 B16 黑色素瘤中相似的抗肿瘤活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8423/6268522/f1d2ad3eb34d/molecules-17-08832-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8423/6268522/d3e6d2017b51/molecules-17-08832-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8423/6268522/f1d2ad3eb34d/molecules-17-08832-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8423/6268522/d3e6d2017b51/molecules-17-08832-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8423/6268522/f1d2ad3eb34d/molecules-17-08832-sch001.jpg

相似文献

1
Synthesis and biological activity of 23-hydroxybetulinic acid C-28 ester derivatives as antitumor agent candidates.23-羟基白桦酸 C-28 酯衍生物的合成及抗肿瘤活性研究。
Molecules. 2012 Jul 25;17(8):8832-41. doi: 10.3390/molecules17088832.
2
Synthesis and biological activity of 28-amide derivatives of 23-hydroxy betulinic Acid as antitumor agent candidates.23-羟基白桦酸 28-酰胺衍生物的合成及抗肿瘤活性研究。
Med Chem. 2013 Nov;9(7):920-5. doi: 10.2174/1573406411309070005.
3
Synthesis and antitumor activity of novel 3-oxo-23-hydroxybetulinic acid derivatives.新型3-氧代-23-羟基桦木酸衍生物的合成及其抗肿瘤活性
Eur J Med Chem. 2014 Nov 24;87:159-67. doi: 10.1016/j.ejmech.2014.09.058. Epub 2014 Sep 18.
4
Synthesis and Biological Evaluation of Oxygen-containing Heterocyclic Ring-fused 23-Hydroxybetulinic Acid Derivatives as Antitumor Agents.含氧化杂环稠合的23-羟基桦木酸衍生物作为抗肿瘤剂的合成及生物学评价
Chem Biol Drug Des. 2015 Oct;86(4):424-31. doi: 10.1111/cbdd.12543. Epub 2015 Mar 6.
5
Synthesis, in vitro and in vivo antitumor activity of pyrazole-fused 23-hydroxybetulinic acid derivatives.吡唑稠合的23-羟基桦木酸衍生物的合成、体外和体内抗肿瘤活性
Bioorg Med Chem Lett. 2015 Feb 1;25(3):728-32. doi: 10.1016/j.bmcl.2014.11.058. Epub 2014 Nov 27.
6
[Synthesis and antitumor activity of 20-O-linked camptothecin ester derivatives].20-O-连接的喜树碱酯衍生物的合成及其抗肿瘤活性
Yao Xue Xue Bao. 2004 Aug;39(8):591-7.
7
Synthesis and biological evaluation of novel 1-O- and 14-O-derivatives of oridonin as potential anticancer drug candidates.冬凌草甲素新型1-O-和14-O-衍生物作为潜在抗癌候选药物的合成与生物学评价
Bioorg Med Chem Lett. 2008 Aug 15;18(16):4741-4. doi: 10.1016/j.bmcl.2008.06.097. Epub 2008 Jul 3.
8
Synthesis and antiproliferative evaluation of 23-hydroxybetulinic acid derivatives.23-羟基白桦酸衍生物的合成及抗增殖活性评价。
Eur J Med Chem. 2011 Jun;46(6):2490-502. doi: 10.1016/j.ejmech.2011.03.038. Epub 2011 Mar 25.
9
Synthesis and cytotoxic activity of 17-carboxylic acid modified 23-hydroxy betulinic acid ester derivatives.17-羧酸修饰的23-羟基桦木酸酯衍生物的合成及其细胞毒性活性
Bioorg Med Chem Lett. 2007 Mar 1;17(5):1475-8. doi: 10.1016/j.bmcl.2006.09.096. Epub 2006 Oct 4.
10
Design, synthesis and antitumor activity of triterpenoid pyrazine derivatives from 23-hydroxybetulinic acid.从 23-羟基白桦酸中设计、合成和抗肿瘤活性的三萜类吡嗪衍生物。
Eur J Med Chem. 2015 Jun 5;97:235-44. doi: 10.1016/j.ejmech.2015.04.057. Epub 2015 Apr 29.

引用本文的文献

1
Antibacterial activities of triterpenoidal compounds isolated from Calothamnus quadrifidus leaves.从 Calothamnus quadrifidus 叶中分离得到的三萜类化合物的抗菌活性。
BMC Complement Altern Med. 2019 May 9;19(1):102. doi: 10.1186/s12906-019-2512-x.
2
Recent Developments in the Functionalization of Betulinic Acid and Its Natural Analogues: A Route to New Bioactive Compounds.桦木酸及其天然类似物的功能化研究进展：新型生物活性化合物的合成途径。
Molecules. 2019 Jan 19;24(2):355. doi: 10.3390/molecules24020355.
3
Comparison of the crystal structures of methyl 4-bromo-2-(meth-oxy-meth-oxy)benzoate and 4-bromo-3-(meth-oxy-meth-oxy)benzoic acid.

本文引用的文献

1
New betulinic acid derivatives induce potent and selective antiproliferative activity through cell cycle arrest at the S phase and caspase dependent apoptosis in human cancer cells.新型白桦脂酸衍生物通过细胞周期阻滞在 S 期和 caspase 依赖性细胞凋亡诱导人癌细胞强烈且选择性的增殖抑制活性。
Biochimie. 2011 Jun;93(6):1065-75. doi: 10.1016/j.biochi.2011.02.014. Epub 2011 Mar 4.
2
Synthesis and cytotoxic activity of 17-carboxylic acid modified 23-hydroxy betulinic acid ester derivatives.17-羧酸修饰的23-羟基桦木酸酯衍生物的合成及其细胞毒性活性
Bioorg Med Chem Lett. 2007 Mar 1;17(5):1475-8. doi: 10.1016/j.bmcl.2006.09.096. Epub 2006 Oct 4.
3
4-溴-2-(甲氧基甲氧基)苯甲酸甲酯与4-溴-3-(甲氧基甲氧基)苯甲酸的晶体结构比较。
Acta Crystallogr E Crystallogr Commun. 2016 Mar 11;72(Pt 4):477-81. doi: 10.1107/S2056989016003777. eCollection 2016 Apr 1.
4
Ethyl trans-12-(pyridin-4-yl)-9,10-ethano-anthracene-11-carboxyl-ate.反式-12-(吡啶-4-基)-9,10-亚乙基蒽-11-羧酸乙酯
Acta Crystallogr Sect E Struct Rep Online. 2014 Apr 2;70(Pt 5):o512. doi: 10.1107/S1600536814006588. eCollection 2014 May 1.
5
4-Bromo-2-(dieth-oxy-meth-yl)phenyl benzoate.4-溴-2-(二乙氧基甲基)苯甲酸苯酯
Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 16;69(Pt 4):o553. doi: 10.1107/S1600536813006351. Print 2013 Apr 1.
6
Diethyl 2,6-dimethyl-4-[4-(3-phenyl-acrylo-yloxy)phen-yl]-1,4-dihydro-pyridine-3,5-dicarboxyl-ate hemihydrate.2,6-二甲基-4-[4-(3-苯基丙烯酰氧基)苯基]-1,4-二氢吡啶-3,5-二羧酸二乙酯半水合物
Acta Crystallogr Sect E Struct Rep Online. 2013 Mar 1;69(Pt 3):o389. doi: 10.1107/S1600536813004108. Epub 2013 Feb 16.
Sensitization for anticancer drug-induced apoptosis by betulinic Acid.
桦木酸对抗癌药物诱导凋亡的致敏作用。
Neoplasia. 2005 Feb;7(2):162-70. doi: 10.1593/neo.04442.
4
Betulinic acid and its derivatives: a review on their biological properties.桦木酸及其衍生物：生物学特性综述
Curr Med Chem. 2005;12(6):657-66. doi: 10.2174/0929867053202214.
5
Betulinic acid and its derivatives as anti-angiogenic agents.桦木酸及其衍生物作为抗血管生成剂。
Bioorg Med Chem Lett. 2004 May 3;14(9):2181-4. doi: 10.1016/j.bmcl.2004.02.044.
6
A review of natural and modified betulinic, ursolic and echinocystic acid derivatives as potential antitumor and anti-HIV agents.天然及修饰的桦木酸、熊果酸和刺囊酸衍生物作为潜在抗肿瘤和抗HIV药物的综述。
Mini Rev Med Chem. 2003 Sep;3(6):525-39. doi: 10.2174/1389557033487917.
7
23-Hydroxybetulinic acid-mediated apoptosis is accompanied by decreases in bcl-2 expression and telomerase activity in HL-60 Cells.
Life Sci. 2002 Nov 22;72(1):1-9. doi: 10.1016/s0024-3205(02)02176-8.
8
Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.桦木酸对肿瘤细胞系具有选择性细胞毒性，而对正常细胞则无此作用。
Cancer Lett. 2002 Jan 10;175(1):17-25. doi: 10.1016/s0304-3835(01)00718-2.
9
Triterpenoids from Pulsatilla chinensis.白头翁中的三萜类化合物。
Phytochemistry. 1996 Jun;42(3):799-802. doi: 10.1016/0031-9422(96)00043-x.
10
Discovery of betulinic acid as a selective inhibitor of human melanoma that functions by induction of apoptosis.桦木酸作为一种通过诱导凋亡发挥作用的人类黑色素瘤选择性抑制剂的发现。
Nat Med. 1995 Oct;1(10):1046-51. doi: 10.1038/nm1095-1046.