riccardin D trimethyl ether | 117240-50-3

• 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: riccardin D trimethyl ether
• 英文别名: 3,16,24-trimethoxy-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene
• CAS: 117240-50-3
• 化学式: C₃₁H₃₀O₄
• 分子量: 466.577
• InChiKey: FJEJCLBBEHTIJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.06
• 重原子数：
  35.0
• 可旋转键数：
  3.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  36.92
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  riccardin D trimethyl ether 在 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 4-[(Dimethylamino)methyl]-14-oxapentacyclo[20.2.2.210,13.115,19.02,7]nonacosa-1(24),2(7),3,5,10(29),11,13(28),15,17,19(27),22,25-dodecaene-3,16,24-triol
  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：

  5-(1,3-dioxan-2-yl)-2-methoxyphenol 在 盐酸 、 sodium tetrahydroborate 、 2,2,6,6-四甲基-3,5-庚二酮 、 18-冠醚-6 、 四溴化碳 、 5%-palladium/activated carbon 、 水 、 氢气 、 sodium methylate 、 potassium carbonate 、 caesium carbonate 、 三乙胺 、 三苯基膦 、 copper(I) bromide 作用下， 以 四氢呋喃 、 N-甲基吡咯烷酮 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 20.0 ℃ 、300.01 kPa 条件下， 反应 108.0h， 生成 riccardin D trimethyl ether
  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

文献信息

• A Synthesis-Driven Structure Revision of ‘Plagiochin E’, a Highly Bioactive Bisbibenzyl
  作者：Andreas Speicher、Matthias Groh、Josef Zapp、Anu Schaumlöffel、Michael Knauer、Gerhard Bringmann

  DOI：10.1055/s-0029-1217510

  日期：2009.7

  from Marchantia polymorpha, a liverwort. The total synthesis of the proposed structure for plagiochin E and of two structurally and biosynthetically related bisbibenzyls and comparison of the NMR data of the synthetic compounds with those of the isolated bisbibenzyls necessitates a structure revision for plagiochin E. Exemplarily for this metabolite, the stereostructure was investigated, by racemate

  最近，一种名为 plagiochin E 的双苄基显示出显着的抗真菌和抗肿瘤活性，从地钱地衣中分离出来。plagiochin E 和两种结构和生物合成相关的双苄基的拟议结构的全合成以及合成化合物的 NMR 数据与分离的双苄基的 NMR 数据的比较需要对 plagiochin E 进行结构修正。 例如，对于这种代谢物，立体结构是通过对手性 Lux Cellulose-1 相的外消旋体拆分进行研究，使用 HPLC-CD 偶联和量子化学 CD 计算，清楚地将 P 构型分配给较快的对映体，将 M 构型分配给较慢的对映体。
• Syntheses of Macrocyclic Bis(bibenzyl) Compounds Derived from Perrottetin E
  作者：Andreas Speicher、Matthias Groh、Markus Hennrich、Anh-Minh Huynh

  DOI：10.1002/ejoc.201001023

  日期：2010.12

  Macrocyclic bis(bibenzyl) compounds are natural products from liverworts and are of growing interest due to recent reports on new isolated compounds and on their remarkable biological activities. We report here on a flexible and general approach to the total set of nine bis(bibenzyl) compounds of the riccardin and plagiochin type derived from perrottetin E. The structures were confirmed through their

  大环双（联苄）化合物是来自苔类植物的天然产物，由于最近关于新的分离化合物及其显着生物活性的报道，人们越来越感兴趣。我们在此报告了对源自 perrottetin E 的 riccardin 和 plagiochin 类型的九种双（联苄基）化合物的总集合的灵活和通用方法。 通过光谱数据确认了结构，并与分离产品的数据进行了仔细比较排除芳烃连接和替代模式中的任何错误。
• Fatty acids and cyclic bis(bibenzyls) from the New Zealand liverwort Monoclea forsteri
  作者：Masao Toyota、Fumihiro Nagashima、Yoshinori Asakawa

  DOI：10.1016/0031-9422(88)87032-8

  日期：1988.1

  Abstract Two novel fatty acids named monocleic and monocleolic acids and two new cyclic bis(bibenzyls) riccardins D and C were isolated from the New Zealand large thalloid liverwort Monoclea forsteri together with the previously known bis(bibenzyls) riccardin C and perrottetin E. The structures of the new fatty acids were established to be 10-keto-octadec-6-yn-8(E)-enoic acid and 10-hydroxy-octadec-6-yn-8(E)-enoic

  摘要 从新西兰大型类地草 Monoclea forsteri 中分离出两种新的单核酸和单核油酸以及两种新的环状双（联苄基）riccardin D 和 C，以及之前已知的双（联苄基）riccardin C 和 perrottetin E。新的脂肪酸被确定为 10-keto-octadec-6-yn-8(E)-enoic acid 和 10-hydroxy-octadec-6-yn-8(E)-enoic acid 通过化学和 1H 和13CNMR光谱数据。新的双（联苄）的结构也由广泛的 2D COZY NMR 和不同的 NOE 光谱确定。目前的物种在化学上与 Metzgeriales 和 Marchantiales 的成员不同。
• TOYOTA, MASAO;NAGASHIMA, FUMIHIRO;ASAKAWA, YOSHINORI, PHYTOCHEMISTRY, 27,(1988) N 8, C. 2603-2608
  作者：TOYOTA, MASAO、NAGASHIMA, FUMIHIRO、ASAKAWA, YOSHINORI

  DOI：——

  日期：——
• Chenopodene, marchantin P and riccardin G from the liverwort Marchantia chenopoda
  作者：Motoo Tori、Mamiko Aoki、Yoshinori Asakawa

  DOI：10.1016/s0031-9422(00)97015-8

  日期：1994.5

  Marchantia chenopoda collected in Venezuela has been studied and chenopodene, which has a new sesquiterpene skeleton, together with marchantin P and riccardin G, both of which are macrocyclic bis(bibenzyls), were isolated.