marchantin C | 88418-47-7

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: marchantin C
• 英文别名: marchantin；2,15-dioxapentacyclo[22.2.2.13,7.110,14.016,21]triaconta-1(26),3,5,7(30),10(29),11,13,16(21),17,19,24,27-dodecaene-4,17-diol
• CAS: 88418-47-7
• 化学式: C₂₈H₂₄O₄
• 分子量: 424.496
• InChiKey: BLRFPCOIKKIKNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  marchantin C 在 manganese(IV) oxide 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以70%的产率得到15,18-Etheno-2,6:9,13-dimetheno-1,14-benzodioxacyclodocosin-12,24-diol, 22-bromo-7,8,19,20-tetrahydro-
  参考文献：
  名称：

  Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents

  摘要：

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.004
• 作为产物：
  描述：

  marchantin C dimethyl ether 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到marchantin C
  参考文献：
  名称：

  双双苄基衍生物通过延缓P -gp活性使耐长春新碱的KB / VCR细胞对化疗药物敏感

  摘要：

  已知P-糖蛋白（P -gp）通过充当外排泵主动将化疗药物转运出癌细胞来介导多药耐药性（MDR）。P -gp功能的抑制可能代表逆转MDR的策略之一。我们以前曾报道过，番石榴素C（MC）是一种来自地蒿的大环双联二苄基化合物，可作为抗有丝分裂剂发挥抗肿瘤活性。本研究旨在评估MC及其三种合成衍生物（MC1，MC2和MC3）对P的可能调节作用。-gp在抗VCR的KB / VCR单元中。细胞毒性试验的结果表明，在这四种化合物中，MC是KB和KB / VCR细胞中最有效的细胞增殖抑制剂，而三种MC衍生的化学物质在相同条件下几乎没有抗增殖活性。然而，在表达P -gp的MDR细胞中，对这些化合物增强VCR细胞毒性的效力的分析导致鉴定出MC2是逆转耐药性更有效的化学物质。进一步的研究表明，MC2能够降低罗丹明123的流出，进而增加KB / VCR细胞中罗丹明123和阿霉素的积累，表明MC2通过抑制P重新使细胞

  DOI：

  10.1016/j.bmc.2010.07.055

文献信息

• Design, synthesis and biological evaluation of novel macrocyclic bisbibenzyl analogues as tubulin polymerization inhibitors
  作者：Bin Sun、Lin Li、Qing-wen Hu、Fei Xie、Hong-bo Zheng、Huan-min Niu、Hui-qing Yuan、Hong-xiang Lou

  DOI：10.1016/j.ejmech.2016.06.007

  日期：2016.10

  analysis and a tubulin polymerization assay in HCC1482 cells. The binding mode of compound 88 to tubulin was also investigated utilizing a molecular docking study. In conclusion, the present study improves our understanding of the action of bisbibenzyl-based tubulin polymerization inhibitors and provides a new molecular scaffold for the further development of antitumor agents that target tubulin.

  设计，合成了一系列新颖的大环双联二苄基类似物，并对其体外抗增殖活性进行了评估。所有化合物均在包括多药耐药表型在内的五种人类癌细胞系中进行了测试。在这些新的分子，化合物88，92和94表现出优异的抗癌活性针对Hela细胞，K562，HCC1428，HT29，和PC-3 /文件的细胞系，具有平均IC 50值范围为2.23μM到3.86μM，和更有效的比亲本化合物马可汀C的效力要强于阳性对照阿霉素。此外，化合物88的作用机理通过在HCC1482细胞中的细胞周期分析和微管蛋白聚合测定法研究了TGF-β。还利用分子对接研究来研究化合物88与微管蛋白的结合模式。总之，本研究提高了我们对基于双联苄基微管蛋白聚合抑制剂作用的理解，并为靶向微管蛋白的抗肿瘤药物的进一步开发提供了新的分子支架。
• Synthesis of marchantin C, a novel microtubule inhibitor from liverworts
  作者：Andreas Speicher、Judith Holz

  DOI：10.1016/j.tetlet.2010.03.125

  日期：2010.6

  Recently, remarkable microtubule inhibitor and anti-tumor activities of the bisbibenzyl marchantin C—isolated from liverworts like Marchantia polymorpha since 1983—were found. In this Letter we describe the first and efficient total synthesis of this subtype of bisbibenzylic compounds with two biarylether connections. The structure was confirmed by the spectroscopic data which were analyzed carefully

  最近，人们发现了自1983年以来就从多形玛氏花之类的地草中分离出的双联苄基马氏素C，具有显着的微管抑制剂和抗肿瘤活性。在这封信中，我们描述了具有两个联芳基醚连接的双联二苄基化合物亚型的第一个有效的全合成方法。通过光谱数据证实了该结构，对光谱数据进行了仔细分析以排除芳烃连接和取代模式中的任何错误。
• Bisbibenzyl derivatives sensitize vincristine-resistant KB/VCR cells to chemotherapeutic agents by retarding P-gp activity
  作者：Guang-min Xi、Bin Sun、Hui-hui Jiang、Feng Kong、Hui-qing Yuan、Hong-xiang Lou

  DOI：10.1016/j.bmc.2010.07.055

  日期：2010.9

  transport chemotherapeutic agents out of carcinoma cells. Inhibition of P-gp function may represent one of the strategies to reverse MDR. We have previously reported that marchantin C (MC), a macrocyclic bisbibenzyl compound from liverworts, exerts anti-tumor activity as an antimitotic agent. This study was designed to evaluate the possible modulatory effect of MC and its three synthetic derivatives (MC1

  已知P-糖蛋白（P -gp）通过充当外排泵主动将化疗药物转运出癌细胞来介导多药耐药性（MDR）。P -gp功能的抑制可能代表逆转MDR的策略之一。我们以前曾报道过，番石榴素C（MC）是一种来自地蒿的大环双联二苄基化合物，可作为抗有丝分裂剂发挥抗肿瘤活性。本研究旨在评估MC及其三种合成衍生物（MC1，MC2和MC3）对P的可能调节作用。-gp在抗VCR的KB / VCR单元中。细胞毒性试验的结果表明，在这四种化合物中，MC是KB和KB / VCR细胞中最有效的细胞增殖抑制剂，而三种MC衍生的化学物质在相同条件下几乎没有抗增殖活性。然而，在表达P -gp的MDR细胞中，对这些化合物增强VCR细胞毒性的效力的分析导致鉴定出MC2是逆转耐药性更有效的化学物质。进一步的研究表明，MC2能够降低罗丹明123的流出，进而增加KB / VCR细胞中罗丹明123和阿霉素的积累，表明MC2通过抑制P重新使细胞
• Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents
  作者：Juan Jiang、Bin Sun、Yan-yan Wang、Min Cui、Li Zhang、Chang-zhi Cui、Yan-feng Wang、Xi-gong Liu、Hong-xiang Lou

  DOI：10.1016/j.bmc.2012.02.004

  日期：2012.4

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.