eudistomin Y₄ | 1007893-77-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: eudistomin Y₄
• 英文别名: (3-bromo-4-hydroxyphenyl)(6-bromo-9H-pyrido[3,4-b]indol-1-yl)methanone；eudistomin Y4；(3-bromo-4-hydroxyphenyl)-(6-bromo-9H-pyrido[3,4-b]indol-1-yl)methanone
• CAS: 1007893-77-7
• 化学式: C₁₈H₁₀Br₂N₂O₂
• 分子量: 446.098
• InChiKey: AEXFJGQPZSMAKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  eudistomin Y₄ 在 sodium tetrahydroborate 、 氯化铵 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以13.3 mg的产率得到eudistomin Y9
  参考文献：
  名称：

  Beta-carboline alkaloids derived from the ascidian Synoicum sp.

  摘要：

  Six beta-carboline alkaloids (1-6) of the eudistomin Y class were isolated from the Korean ascidian Synoicum sp. These compounds were chemically converted to a known compound, eudistomin Y-1 (7) and six new derivatives, designated eudistomins Y-8-Y-13 (8-13). Several of these natural and synthetic compounds exhibited moderate to significant antimicrobial activity, weak cytotoxic activity, and inhibitory activities toward sortase A, isocitrate lyase, and Na+/K+-ATPase. Structure-activity relationships were also deduced. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.002
• 作为产物：
  描述：

  5-溴吲哚-3-甲醛 在 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 ammonium acetate 、 三溴化硼 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 52.5h， 生成 eudistomin Y₄
  参考文献：
  名称：

  Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues

  摘要：

  优迪斯托明Y类化合物是一系列β-咔啉，最初从韩国南海附近的海鞘中分离出来。这些化合物含有溴取代基，这是海洋天然产物的典型特征之一。我们在此报道了七种新的基于β-咔啉的代谢物，即优迪斯托明Y1至Y7及其羟甲基化苯基衍生物的化学合成与生物学评价。利用溴取代色胺和溴取代苯基甘油醛作为关键中间体，通过酸催化的皮克特-斯彭格勒反应合成了优迪斯托明Y1至Y7及其衍生物，并通过1H和13C核磁共振及质谱进行了全面表征。生物学研究表明，所有化合物对乳腺癌细胞系MDA-231均显示出中等的生长抑制活性，IC50值在15至63μM之间，且羟甲基化苯基产品的抑制活性高于相应的天然产物优迪斯托明Y1至Y7。

  DOI：

  10.3390/md11051427

文献信息

• Tandem iodine-mediated oxidations of tetrahydro-β-carbolines: total synthesis of eudistomins Y1–Y7
  作者：Joseph D. Panarese、Stephen P. Waters

  DOI：10.1039/c3ob40661j

  日期：——

  An efficient iodine-mediated oxidation of tetrahydro-β-carbolines is described to yield aromatic β-carboline products with tandem C–H oxidation. The utility of the method was demonstrated in total syntheses of the alkaloids eudistomins Y1–Y7.

  报道了一种高效的碘介导的四氢-β-咔啉氧化反应，通过串联C-H氧化生成芳香β-咔啉类产物。该方法在生物碱合成中得到了应用，证明了其在尤迪斯通明素Y1至Y7的全合成中的实用性。
• A Cascade Coupling Strategy for One-Pot Total Synthesis of β-Carboline and Isoquinoline-Containing Natural Products and Derivatives
  作者：Yan-Ping Zhu、Mei-Cai Liu、Qun Cai、Feng-Cheng Jia、An-Xin Wu

  DOI：10.1002/chem.201301734

  日期：2013.7.29

  Multi‐birds with one stone: A cascade coupling strategy was developed for the synthesis of β‐carbolines. The method can direct the synthesis of β‐carboline and isoquinoline‐containing natural products with high yields. Moreover, this protocol can also be further applied towards the total synthesis of natural products fascaplysin and papaverin (see scheme).

  一块石头的多鸟：开发了一种级联偶联策略来合成β-咔啉。该方法可以指导高产率合成含β-咔啉和异喹啉的天然产物。此外，该方案还可以进一步应用于天然产物fascaplysin和papaverin的全合成（参见方案）。
• Total Syntheses of Eudistomins Y₁-Y₇by an Efficient One-Pot Process of Tandem Benzylic Oxidation and Aromatization of 1-Benzyl-3,4-dihydro-β-Carbolines
  作者：Tien Ha Trieu、Jing Dong、Qiang Zhang、Bo Zheng、Tian-Zhuo Meng、Xia Lu、Xiao-Xin Shi

  DOI：10.1002/ejoc.201300080

  日期：2013.6

  The first total synthesis of eudistomin Y7 (7) and total syntheses of eudistomins Y1–Y6 (1–6) are described. An efficient room-temperature conversion of 1-benzyl-3,4-dihydro-β-carbolines (11) into 1-benzoyl-β-carbolines (14) by a one-pot process of tandem benzylic oxidation and aromatization as the key step of these total syntheses was also studied in detail.

  描述了eudistomin Y7 (7) 的首次全合成和eudistomin Y1–Y6 (1–6) 的全合成。1-苄基-3,4-二氢-β-咔啉（11）在室温下通过串联苄基氧化和芳构化的一锅法高效转化为1-苯甲酰基-β-咔啉（14）作为关键步骤还详细研究了这些全合成。
• Total synthesis of Eudistomins Y1–Y6
  作者：J. Phillip Kennedy、Micah L. Breininger、Craig W. Lindsley

  DOI：10.1016/j.tetlet.2009.09.180

  日期：2009.12

  The first total synthesis of Eudistomins Y-1-Y-6, brominated phenolic beta-carboline marine metabolites with a unique benzoyl moiety at C1, have been prepared in three steps, utilizing MAOS, in overall yields ranging from 6% to 25%. (C) 2009 Elsevier Ltd. All rights reserved.
• Total Synthesis and Biological Activity of Marine Alkaloid Eudistomins Y1–Y7 and Their Analogues
  作者：Huijuan Jin、Puyong Zhang、Krikor Bijian、Sumei Ren、Shengbiao Wan、Moulay Alaoui-Jamali、Tao Jiang

  DOI：10.3390/md11051427

  日期：——

  Eudistomin Y class compounds are a series of β-carbolines which was originally isolated from a marine turnicate or ascidian near the South Korea Sea. These compounds contain bromo-substituted groups, which is one of the typical characters of marine natural products. We report herein the chemical synthesis and biological evaluation of seven new β-carboline-based metabolites, Eudistomins Y1–Y7, and their hydroxyl-methylated phenyl derivatives. Using bromo-substituted tryptamines and bromo-substituted phenylglyoxals as the key intermediates, Eudistomins Y1–Y7 and their derivatives were synthesized via the acid-catalyzed Pictet-Spengler reaction and fully characterized by 1H- and 13C-NMR and mass spectroscopy. Biological studies revealed that all of the compounds showed moderate growth inhibitory activity against breast carcinoma cell line MDA-231 with IC50 of 15–63 μM and the inhibitory activities of hydroxyl-methylated phenyl products were higher than that of the corresponding natural products Eudistomins Y1–Y7.

  优迪斯托明Y类化合物是一系列β-咔啉，最初从韩国南海附近的海鞘中分离出来。这些化合物含有溴取代基，这是海洋天然产物的典型特征之一。我们在此报道了七种新的基于β-咔啉的代谢物，即优迪斯托明Y1至Y7及其羟甲基化苯基衍生物的化学合成与生物学评价。利用溴取代色胺和溴取代苯基甘油醛作为关键中间体，通过酸催化的皮克特-斯彭格勒反应合成了优迪斯托明Y1至Y7及其衍生物，并通过1H和13C核磁共振及质谱进行了全面表征。生物学研究表明，所有化合物对乳腺癌细胞系MDA-231均显示出中等的生长抑制活性，IC50值在15至63μM之间，且羟甲基化苯基产品的抑制活性高于相应的天然产物优迪斯托明Y1至Y7。