ethyl 5,11-dihydroindolo[3,2-b]carbazole-6-carboxylate | 229020-86-4

• 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: ethyl 5,11-dihydroindolo[3,2-b]carbazole-6-carboxylate
• 英文别名: indolo[3,2-b]carbazole-6-carboxylic acid ethyl ester；ethyl indolo[3,2-b]carbazole-6-carboxylate；ethyl 5,11-dihydroindolo[3,2-b]carbazole-12-carboxylate
• CAS: 229020-86-4
• 化学式: C₂₁H₁₆N₂O₂
• 分子量: 328.37
• InChiKey: BOPARTZFXUIWDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  57.9
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  ethyl 5,11-dihydroindolo[3,2-b]carbazole-6-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以93%的产率得到indolo[3,2-b]carbazole-6-carboxylic acid
  参考文献：
  名称：

  Ah受体配体6-甲酰吲哚[3,2-b]咔唑代谢物的合成

  摘要：

  描述了芳烃受体高亲和力配体 6-甲酰基吲哚并 [3,2-b] 咔唑的五种单羟基化和二羟基化代谢物的合成。代谢物的结构是...

  DOI：

  10.1002/ejoc.200400087
• 作为产物：
  描述：

  [2-(1H-indol-3-ylmethyl)-1H-indol-3-yl]-oxo-acetic acid ethyl ester 在 甲烷磺酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以92%的产率得到ethyl 5,11-dihydroindolo[3,2-b]carbazole-6-carboxylate
  参考文献：
  名称：

  Ah受体配体6-甲酰吲哚[3,2-b]咔唑代谢物的合成

  摘要：

  描述了芳烃受体高亲和力配体 6-甲酰基吲哚并 [3,2-b] 咔唑的五种单羟基化和二羟基化代谢物的合成。代谢物的结构是...

  DOI：

  10.1002/ejoc.200400087

文献信息

• SYNTHESIS OF DIINDOLYLMETHANES AND INDOLO[3,2-B]CARBAZOLES, COMPOUNDS FORMED THEREBY, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：Wisconsin Alumni Research Foundation

  公开号：US20160039754A1

  公开（公告）日：2016-02-11

  Described is a method to make diindolylmethanes and indolyl/pyrrolylmethanes, The method includes the steps of contacting an ether comprising an arylpropargyl moiety and an amine-protected, substituted or unsubstituted aniline moiety with a substituted or unsubstituted indol or a substituted or unsubstituted pyrrole, in the presence of a metal-containing catalyst, for a time and at a temperature to cause an annulation/arylation cascade reaction that yields a diindolylmethane or a indolyl/pyrrolylmethane. The resulting compounds are effective to modulate activity of arylhydrocarbon receptors, to inhibit activity of PCSK9, and to stimulate secretion of glucagon-like peptide 1 in mammals.

  描述了一种制备二吲哚基甲烷和吲哚基/吡咯基甲烷的方法。该方法包括以下步骤：在金属催化剂的存在下，使包含芳基炔丙基部分和胺保护的、取代的或未取代的苯胺部分的醚与取代的或未取代的吲哚或取代的或未取代的吡咯接触，接触一段时间和温度，以引发环化/芳基化级联反应，从而产生二吲哚基甲烷或吲哚基/吡咯基甲烷。所得化合物能有效调节芳基烃受体的活性，抑制PCSK9的活性，并刺激哺乳动物胰高血糖素样肽1的分泌。
• Synthesis and biological evaluation of FICZ analogues as agonists of aryl hydrocarbon receptor
  作者：Hao Wu、Binkai Liu、Ka Yang、Gabrielle N. Winston-McPherson、Eric D. Leisten、Chad M. Vezina、William A. Ricke、Richard E. Peterson、Weiping Tang

  DOI：10.1016/j.bmcl.2020.126959

  日期：2020.3

  The aryl hydrocarbon receptor (AhR) is a ligand activated transcription factor involved in multiple biological processes including immune cell differentiation, intestinal function and inflammation. Based on the scaffold of naturally occurring AhR ligand 6-formylindolo (3,2-b) carbazole (FICZ, 2), a series of analogues has been designed, synthesized and evaluated by cell-based assays. The structure-activity

  芳烃受体（AhR）是一种配体激活的转录因子，参与多种生物过程，包括免疫细胞分化、肠道功能和炎症。基于天然存在的 AhR 配体 6-甲酰基吲哚 (3,2-b) 咔唑 (FICZ, 2) 的支架，一系列类似物已被设计、合成并通过基于细胞的测定进行评估。构效关系研究成功发现了具有极强活性的化合物11e。
• Syntheses of 6-substituted indolo[3,2-b]carbazoles, including 6-formylindolo[3,2-b]carbazole, an extremely efficient ligand for the TCDD (Ah) receptor
  作者：Joakim Tholander、Jan Bergman

  DOI：10.1016/s0040-4020(99)00268-9

  日期：1999.5

  number of 6-substituted indolo[3,2-b]carbazoles have been synthesized using 2,3-diindolylmethane 5 as a crucial precursor. Most notably, 6-formylindolo[3,2-b]carbazole 3 has been synthesized, and thereby a previously assigned structure has been confirmed. 6-Formylindolo[3,2-b]carbazole 3 is an extremely efficient ligand for the TCDD (Ah) receptor. A much improved synthesis of 2,3-diindolylmethane 5 has

  已经使用2，3-二吲哚基甲烷5作为关键的前体合成了许多6-取代的吲哚并[3，2- b ]咔唑。最值得注意的是，已经合成了6-甲酰基吲哚并[3，2- b ]咔唑3，从而证实了先前指定的结构。6-甲酰基吲哚并[3,2- b ]咔唑3是TCDD（Ah）受体的极为有效的配体。还已经开发出大大改善的2，3-二吲哚基甲烷5的合成。
• Concise Synthesis of 6-Formylindolo[3,2-<i>b</i>]carbazole (FICZ)
  作者：Daisuke Sekine、Shota Okeda、Seijiro Hosokawa

  DOI：10.1246/cl.140843

  日期：2014.12.5

  A concise synthesis of 6-formylindolo[3,2-b]carbazole (FICZ), a potent ligand of the aryl hydrocarbon receptor (AhR), has been established. The conjugate addition of the enolate derived from indoly...

  6-甲酰基吲哚并[3,2-b]咔唑（FICZ）是芳基烃受体（AhR）的一种有效配体，其简明合成已经建立。吲哚衍生物烯醇的共轭加成...
• Detection method and kit
  申请人：The European Union, represented by the European Commission

  公开号：EP3064946A1

  公开（公告）日：2016-09-07

  Uses of ethyl 5,11-dihydroindolo[3,2-b]carbazole-6-carboxylate as a fluorescent ligand probe, preferably in a binding assay for quantitative analysis in combination with a recombinant aryl hydrocarbon receptor (AhR) protein. A method for detection or quantitative analysis of suspected aryl hydrocarbon receptor (AhR) ligands in a sample, the method comprising the steps of: (a) providing a sample possibly containing at least one known or unknown AhR ligand; (b) mixing said sample with a composition comprising a recombinant AhR protein bound to ethyl 5,11-dihydroindolo[3,2-b]carbazole-6-carboxylate; and (c) determining the presence or the total amount of said at least one known or unknown AhR ligand in the sample by fluorescence spectroscopy. Use e.g. for screening of unknown compounds to determine their binding ability to AhR; for analyzing unknown chemical mixtures to assess the presence of ligands able to bind to AhR; for screening of Polycyclic Aromatic Hydrocarbon (PAHs) from water, food or sediment; for screening of PAHs or dioxin-like compounds in water, food or sediment; for testing for pollutant removal in water and waste water treatment plants; for testing for water reuse; for testing the presence of dioxin-like compounds in incinerator plants; or for testing of bodily fluids of humans or animals exposed to PAHs or dioxin-like compounds.

  5,11-二氢吲哚并[3,2-b]咔唑-6-羧酸乙酯作为荧光配体探针的用途，优选与重组芳基烃受体（AhR）蛋白结合进行定量分析的结合测定。一种检测或定量分析样品中可疑芳基烃受体（AhR）配体的方法，该方法包括以下步骤(a) 提供可能含有至少一种已知或未知 AhR 配体的样品；(b) 将所述样品与包含与 5,11-二氢吲哚并[3,2-b]咔唑-6-羧酸乙酯结合的重组 AhR 蛋白的组合物混合；以及 (c) 通过荧光光谱测定样品中所述至少一种已知或未知 AhR 配体的存在或总量。例如筛选未知化合物，确定其与 AhR 的结合能力；分析未知化学混合物，评估是否存在能够与 AhR 结合的配体；筛选水、食物或沉积物中的多环芳香烃（PAHs）；筛选水、食物或沉积物中的多环芳香烃或二恶英类化合物；用于检测水和废水处理厂的污染物去除情况；用于检测水的再利用情况；用于检测焚化炉中是否存在二恶英类化合物；或用于检测暴露于多环芳烃或二恶英类化合物的人类或动物的体液。