bastadin 6 | 79067-74-6

• 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: bastadin 6
• 英文别名: 5,16,21,32,33,36-Hexabromo-4,20-dihydroxy-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.214,17.13,7.119,23]octatriaconta-1(32),3,5,7(38),14,16,19,21,23(35),30,33,36-dodecaene-11,26-dione；5,16,21,32,33,36-hexabromo-4,20-dihydroxy-12,25-bis(hydroxyimino)-2,18-dioxa-10,27-diazapentacyclo[28.2.2.214,17.13,7.119,23]octatriaconta-1(32),3,5,7(38),14,16,19,21,23(35),30,33,36-dodecaene-11,26-dione
• CAS: 79067-74-6
• 化学式: C₃₄H₂₆Br₆N₄O₈
• 分子量: 1098.03
• InChiKey: WSOCBHDTRCSWRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.2
• 重原子数：
  52
• 可旋转键数：
  0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  bastadin 6 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 以99%的产率得到
  参考文献：
  名称：

  Bastadin 6 的构效关系研究，一种来自海洋海绵的抗血管生成溴化酪氨酸衍生代谢物

  摘要：

  对 bastadin 6 (1) 进行了构效关系 (SAR) 研究，bastadin 6 (1) 是一种来自印度尼西亚海绵的溴化酪氨酸衍生代谢物，具有强大的抗血管生成活性。肟修饰类似物和溴修饰类似物的合成及其生物学评价表明，bastadin 6 (1) 中的肟部分和溴原子都发挥重要作用，显示出对人脐静脉的有效和选择性抗增殖活性内皮细胞 (HUVEC)。

  DOI：

  10.1002/ardp.200700231
• 作为产物：
  描述：

  N-Boc-3,5-dibromo-4-hydroxyphenethylamine 在 chromium dichloride 、 sodium hydroxide 、 双氧水 、 1-羟基苯并三唑 、 sodium hydrogensulfite 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 、 soybean peroxidase 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 33.58h， 生成 bastadin 6
  参考文献：
  名称：

  Total Synthesis of Bastadins 2, 3, and 6

  摘要：

  A chemoenzymatic strategy has been developed for the synthesis of bastadins 2, 3, and 6. The requisite dimeric dityrosine and isodityrosine building blocks were successfully prepared by oxidative C-C and C-O phenolic coupling of mono- and dihalogenated derivatives of tyrosine and tyramine using horseradish and soybean peroxidases. By carefully controlling the experimental parameters, the requisite synthons may now be prepared in synthetically useful yields without the exhaustive protection and deprotection of the sensitive functional groups.

  DOI：

  10.1021/jo9721204

文献信息

• Efficient total synthesis of bastadin 6, an anti-angiogenic brominated tyrosine-derived metabolite from marine sponge
  作者：Naoyuki Kotoku、Hiroaki Tsujita、Atsushi Hiramatsu、Chinatsu Mori、Noriko Koizumi、Motomasa Kobayashi

  DOI：10.1016/j.tet.2005.05.038

  日期：2005.7

  An efficient total synthesis of bastadin 6 (1), a cyclic tetramer of brominated tyrosine derivatives from the marine sponge, Ianthella basta, with selective anti-angiogenic activity, was accomplished. We developed a novel Ce(IV)-mediated oxidative coupling reaction of 2,6-dibromophenols to give the diaryl ether derivatives, the characteristic segment of 1. Condensation of two segments and subsequent

  有效地全合成了bastadin 6（1），这是一种来自海洋海绵Ianthella basta的溴化酪氨酸衍生物的环状四聚体，具有选择性的抗血管生成活性。我们开发了一种新型的Ce（IV）介导的2,6-二溴苯酚的氧化偶联反应，得到特征部分为1的二芳基醚衍生物。两个片段的缩合和随后的分子内大环化在九个步骤中得到了basastin 6（1），总产率为26％。
• Isolation of bastadin-6-O-sulfate and expedient purifications of bastadins-4, -5 and -6 from extracts of Ianthella basta
  作者：Christopher J. Gartshore、Mariam N. Salib、August A. Renshaw、Tadeusz F. Molinski

  DOI：10.1016/j.fitote.2017.12.003

  日期：2018.4

  Bastadin-6-34-O-sulfate ester (8) was isolated from methanol extracts of lanthella basta. The structure of 8 was characterized by analysis of MS and NMR data, and conversion through acid hydrolysis, to the parent compound, bastadin-6, which was identical by HPLC, MS and NMR with an authentic sample. An improved procedure for procurement of pure samples of bastadins-4 (4), -5 (5) and -6 (6) is described.
• Structure-Activity Relationships Study of Bastadin 6, an Anti-Angiogenic Brominated-Tyrosine Derived Metabolite from Marine Sponge
  作者：Naoyuki Kotoku、Atsushi Hiramatsu、Hiroaki Tsujita、Yoichi Hirakawa、Mami Sanagawa、Shunji Aoki、Motomasa Kobayashi

  DOI：10.1002/ardp.200700231

  日期：2008.9

  A structure‐activity relationship (SAR) study of bastadin 6 (1), a brominated tyrosine‐derived metabolite from Indonesian marine sponge having a potent anti‐angiogenic activity, was executed. The syntheses and their biological evaluation of the oxime‐modified analogues and bromine‐modified analogues revealed that both the oxime moieties and bromine atoms in bastadin 6 (1) play an important role to

  对 bastadin 6 (1) 进行了构效关系 (SAR) 研究，bastadin 6 (1) 是一种来自印度尼西亚海绵的溴化酪氨酸衍生代谢物，具有强大的抗血管生成活性。肟修饰类似物和溴修饰类似物的合成及其生物学评价表明，bastadin 6 (1) 中的肟部分和溴原子都发挥重要作用，显示出对人脐静脉的有效和选择性抗增殖活性内皮细胞 (HUVEC)。
• Total Synthesis of Bastadins 2, 3, and 6
  作者：Zhi-wei Guo、Koji Machiya、Grzegorz M. Salamonczyk、Charles J. Sih

  DOI：10.1021/jo9721204

  日期：1998.6.1

  A chemoenzymatic strategy has been developed for the synthesis of bastadins 2, 3, and 6. The requisite dimeric dityrosine and isodityrosine building blocks were successfully prepared by oxidative C-C and C-O phenolic coupling of mono- and dihalogenated derivatives of tyrosine and tyramine using horseradish and soybean peroxidases. By carefully controlling the experimental parameters, the requisite synthons may now be prepared in synthetically useful yields without the exhaustive protection and deprotection of the sensitive functional groups.