(+)-norbalasubramide | 1431767-88-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (+)-norbalasubramide
• 英文别名: (S,R)-(+)-norbalasubramide；(5S,6R)-5-hydroxy-6-phenyl-1,2,3,5,6,7-hexahydro-4H-azocino[5,4-b]indol-4-one；(5S,6R)-5-hydroxy-6-phenyl-1,2,3,5,6,7-hexahydroazocino[5,4-b]indol-4-one
• CAS: 1431767-88-2
• 化学式: C₁₉H₁₈N₂O₂
• 分子量: 306.364
• InChiKey: BNHSSLGGGYRMIX-AEFFLSMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  65.1
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(2-溴乙基)吲哚 在 4-二甲氨基吡啶 、 sodium dihydrogenphosphate dihydrate 、 四丁基氟化铵 、 氨 、 lithium 、 copper(II) bis(trifluoromethanesulfonate) 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 22.75h， 生成 (+)-norbalasubramide
  参考文献：
  名称：

  The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide

  摘要：

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.

  DOI：

  10.1055/s-0032-1316893

文献信息

• Asymmetric synthesis and biological activities of natural product (+)-balasubramide and its derivatives
  作者：Jun Li、Jianzu Li、Yuan Xu、Yunjie Wang、Luyong Zhang、Li Ding、Yining Xuan、Tao Pang、Hansen Lin

  DOI：10.1080/14786419.2015.1071363

  日期：2016.4.2

  The natural product (+)-balasubramide (3j) and its derivatives (3a–3i) were synthesized using a two-step asymmetric synthesis, and the biological activities of 3a–3j were determined in vitro. Methyl (2S,3R)-(+)-3-phenyloxirane-2-carboxylate (1h), the asymmetric synthesis of which was described in a previous paper, was selected as the starting material. Compounds 3a–3j were evaluated for their neuroprotective

  通过两步不对称合成合成了天然产物（+）-巴拉舒酰胺（3j）及其衍生物（3a-3i），并在体外测定了3a-3j的生物活性。选择（2S，3R）-（+）-3-苯基环氧乙烷-2-羧酸甲酯（1h），它的不对称合成在先前的文章中进行了描述，被选为起始原料。化合物3a–3j对它们的神经保护，抗氧化和抗神经炎症作用进行了评估。（+）-Balasubramide及其在6-苯环中具有不同负电性基团的衍生物几乎不产生神经保护和抗氧化作用，但在BV-2小胶质细胞中诱导了强效的抗神经炎作用（3g例外）。化合物3c在其6-苯环中具有三氟甲基的化合物，是一种特别有效的抗神经炎药。这些结果证明（+）-巴拉舒布酰胺的6-苯基环的电负性是其对神经炎症抑制作用的重要决定因素。更多的负电性取代基可产生更强的抗神经炎作用。而且，细胞毒性测定表明所测试的化合物没有明显的作用。
• Balasubramide衍生物的应用及制备方法
  申请人：广东药学院

  公开号：CN105343061B

  公开（公告）日：2018-03-20

  本发明公开了Balasubramide衍生物的应用及制备方法。本发明所述Balasubramide衍生物的结构式如式（Ⅰ）所示，所述Balasubramide衍生物具有优异的抗神经细胞炎症活性，而且均没有细胞毒性。本发明同时设计科学合理的合成线路，简单高效，获得最高80%的产率，ee值为97%以上。（Ⅰ）。
• Synthesis of the indoloazocine derivatives from a chiral indol amide-stabilized sulfur ylide
  作者：Maira Juárez-Calderón、David M. Aparicio、Dino Gnecco、Jorge R. Juárez、Laura Orea、Angel Mendoza、Fernando Sartillo-Piscil、Esther del Olmo、Joel L. Terán

  DOI：10.1016/j.tetlet.2013.03.068

  日期：2013.5

  We present here a synthetic route for the access to a series of diverse indoloazocine derivatives through selective epoxidation of chiral sulfonium salt 4, which reacts with diverse aromatic and aliphatic aldehydes to give trans-glycidic amides, followed by an intramolecular electrophilic aromatic substitution promoted by Cu(OTf)(2) giving the desired heterocyclic compound in a high chemical yield. Using this strategy, the total synthesis of (S,R)-(+)-norbalasubramide was achieved. (c) 2013 Elsevier Ltd. All rights reserved.
• The Use of Sodium Chlorite in the Direct Synthesis of Glycidic Amides: Enantiopure Synthesis of Both Enantiomers of Norbalasubramide
  作者：Leticia Quintero、Fernando Sartillo-Piscil、Lilia Fuentes、Mireya Hernández-Juarez、Joel Terán

  DOI：10.1055/s-0032-1316893

  日期：——

  Recently, the first direct method for preparing 2,3-epoxyamides (glycidic amides) was disclosed. Now in this letter, the enantiopure synthesis of both enantiomers of norbalasubramide featuring this synthetic method is reported. To this end, chiral N-allyltryptamine 12 was prepared and transformed into an inseparable mixture of diastereomeric epoxyamides 13a/13b, which were submitted to intramolecular cyclization with Cu(OTf)(2) to afford a separable mixture of eight-membered ring lactams 14a and 14b. Finally, after removal of the protective group and the chiral auxiliary an enantiopure synthesis of the title compounds was completed.