4-乙酰氨基吲哚 | 15040-81-0

• 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
• 中文名称: 4-乙酰氨基吲哚
• 英文名称: N-(1H-indol-4-yl)acetamide
• 英文别名: 4-acetamidoindole；N-indol-4-yl-acetamide；4-Acetamido-indol
• CAS: 15040-81-0
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD02673629
• 分子量: 174.202
• InChiKey: KFOSTPNYFKCANZ-UHFFFAOYSA-N

物化性质

• 沸点：
  461.2±18.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-benzyl-2-chloro-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-4-amine 、 4-乙酰氨基吲哚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 1,4-二氧六环 为溶剂， 反应 12.0h， 以72%的产率得到 N-(1-(4-(benzylamino)-7,8-dihydro-5H-pyrano[4,3-d]pyrimidin-2-yl)-1H-indol-4-yl)acetamide
  参考文献：
  名称：

  Discovery of a new class of valosine containing protein (VCP/P97) inhibitors for the treatment of non-small cell lung cancer

  摘要：

  Valosine containing protein (VCP/p97) is a member of the AAA ATPase family involved in several essential cellular functions and plays an important role in the ubiquitin-mediated degradation of misfolded proteins. P97 has a significant role in maintaining the cellular protein homeostasis for tumor cell growth and survival and has been found overexpressed in many tumor types. No new molecule entities based on p97 target were approved in clinic. Herein, a series of novel pyrimidine structures as p97 inhibitors were designed and synthesized. After enzymatic evaluations, structure-activity relationships (SAR) were discussed in detailed. Among the screened compounds, derivative 35 showed excellent enzymatic inhibitory activity (IC50, 36 nM). The cellular inhibition results showed that compound 35 had good antiproliferative activity against the non-small cell lung cancer A549 cells (IC50, 1.61 mu M). Liver microsome stability showed that the half-life of compound 35 in human liver microsome was 42.3 min, which was more stable than the control CB-5083 (25.8 min). The in vivo pharmacokinetic results showed that the elimination phase half-lives of compound 35 were 4.57 h for ig and 3.64 h for iv, respectively and the oral bioavailability was only 4.5%. These results indicated that compound 35 could be effective for intravenous treatment of non-small cell lung cancer.

  DOI：

  10.1016/j.bmc.2018.12.036
• 作为产物：
  描述：

  2,6-二硝基甲苯 在 titanium(III) chloride 作用下， 以 吡啶 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.12h， 生成 4-乙酰氨基吲哚
  参考文献：
  名称：

  The chemistry of indoles. XIII. Syntheses of substituted indoles carrying an amino, nitro, methoxycarbonyl, or benzyloxy group at the 4-position and their 1-hydroxy derivatives.

  摘要：

  通过6-取代的反式-β-二甲氨基-2-硝基苯乙烯在控制条件下分别与三氯化钛(III)水溶液或氯化铵水溶液中的锌进行还原反应，制备了在4位带有硝基、甲氧羰基或苄氧基的各种1-羟基吲哚。4-取代的1-羟基吲哚的稳定性按以下顺序递减：4-硝基->4-甲氧羰基->4-苄氧基-1-羟基吲哚。这一结果清楚地表明，4-位上的吸电子基团可以稳定1-羟基吲哚结构。还发现，4-羟基-和4-苄氧基-吲哚可通过6-苄氧基-2-硝基苯基乙醛的还原反应方便地获得。同时，还描述了一种从肉桂啉制备4-或7-氨基吲哚的独特途径。

  DOI：

  10.1248/cpb.29.726

文献信息

• COMPOUND USED AS AUTOPHAGY REGULATOR, AND PREPARATION METHOD THEREFOR AND USES THEREOF
  申请人：WIGEN BIOMEDICINE TECHNOLOGY (SHANGHAI) CO., LTD.

  公开号：US20200190066A1

  公开（公告）日：2020-06-18

  It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

  该内容涉及作为自噬调节剂的化合物及其制备和使用方法，具体提供了一类具有通用公式(I)的化合物，或其药用可接受盐，这是一种自噬调节剂，特别是哺乳动物ATG8同源物调节剂。
• [EN] GLYCINE B ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCINE B
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2010139483A1

  公开（公告）日：2010-12-09

  The invention relates to pyrazolopyrimidine derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  该发明涉及吡唑吡咪啉衍生物及其药用可接受的盐。该发明进一步涉及一种制备这种化合物的方法。该发明的化合物是甘氨酸B拮抗剂，因此可用于控制和预防各种疾病，包括神经系统疾病。
• Bicyclic piperazine compound and use thereof
  申请人：Fukatsu Kohji

  公开号：US20070072865A1

  公开（公告）日：2007-03-29

  The present invention provides a compound represented by the formula: wherein R 1 is an acyl group, R 2 is a hydrocarbon group which may be substituted or the like, R 3 is a hydrocarbon group which may be substituted or the like, R 4 is a hydrocarbon group which may be substituted or the like, n is from 0 to 4, and X is an oxygen atom, a sulfur atom or the like, or a salt thereof. The invention also provides a compound which has a TGR23 antagonist activity and thus is useful for prevention and treatment of cancer.

  本发明提供一种化合物，其化学式为：其中，R1是酰基，R2是烃基，可以被取代或类似物，R3是烃基，可以被取代或类似物，R4是烃基，可以被取代或类似物，n为0至4，X为氧原子、硫原子或类似物或其盐。本发明还提供一种具有TGR23拮抗活性的化合物，因此可用于预防和治疗癌症。
• Compound used as autophagy regulator, and preparation method therefor and uses thereof
  申请人：WIGEN BIOMEDICINE TECHNOLOGY (SHANGHAI) CO., LTD.

  公开号：US11319303B2

  公开（公告）日：2022-05-03

  It is related to compounds used as autophagy modulators and a method for preparing and using the same, specifically providing a compound of general formula (I), or pharmaceutically acceptable salts thereof, which is a type of autophagy modulators, particularly mammalian ATG8 homologues modulators.

  本发明涉及用作自噬调节剂的化合物及其制备和使用方法，具体提供一种通式（I）化合物或其药学上可接受的盐，该化合物是一种自噬调节剂，尤其是哺乳动物ATG8同源物调节剂。
• US7795267B2
  申请人：——

  公开号：US7795267B2

  公开（公告）日：2010-09-14