2-(indan-5-ylamino)ethanol | 1020939-56-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-(indan-5-ylamino)ethanol
• 英文别名: 2-(2,3-dihydro-1H-inden-5-ylamino)ethanol
• CAS: 1020939-56-3
• 化学式: C₁₁H₁₅NO
• 分子量: 177.246
• InChiKey: WBPPPFLSTJURFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(Phenylmethylene)-2,4(3H,5H)-furandione 、 2-(indan-5-ylamino)ethanol 以 乙醇 为溶剂， 生成 4-(2-hydroxyethyl)-10-phenyl-3,4,6,7,8,10-hexahydro-1H-cyclopenta[g]furo[3,4-b]quinoline-1-one
  参考文献：
  名称：

  胶束装配中的陷获切换了潜在的治疗性发光体氮杂鬼臼毒素的准分子群体。

  摘要：

  Azapodophyllotoxin是一类新型的抗肿瘤药物，具有出色的治疗活性，了解其在仿生微环境中的理化性质可能在其细胞间定位，功效和递送方面具有重要意义。目前的工作概括了一个环境问题的天才，4-（2-羟乙基）-10-苯基-3,4,6,7,8,10-六氢-1H-环戊[g]呋喃[3,4] -b]喹啉-1-一（HPFQ），来自抗癌药物Azapodophyllotoxin，在阳离子CTAB，阴离子SDS和中性Triton X-100的不同电荷模型仿生胶束微环境中，采用紫外线可见吸收，稳定荧光，时间分辨荧光和荧光各向异性研究。作为一种独特的现象，HPFQ抗癌剂在极性不同的溶剂中表现出丰富的荧光，这归因于局部激发，电荷转移和受激准分子发射的混合作用。在两种类型的表面活性剂联合体中，在生理和缺氧pH值下，胶束前和胶束后HPFQ的光物理发生了戏剧性的变化。在光激发下，抗癌HPFQ存在于单体-受体平衡物

  DOI：

  10.1016/j.saa.2019.117723
• 作为产物：
  描述：

  5-氨基茚旦 在 吡啶 、 乙醇 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 2-(indan-5-ylamino)ethanol
  参考文献：
  名称：

  Identification of the First Inhibitor of the GBP1:PIM1 Interaction. Implications for the Development of a New Class of Anticancer Agents against Paclitaxel Resistant Cancer Cells

  摘要：

  Class III beta-tubulin plays a prominent role in the development of drug resistance to paclitaxel by allowing the incorporation of the GBP1 GTPase into microtubules. Once in the cytoskeleton. GBP1 binds to prosurvival kinases such as PIM1 and initiates a signaling pathway that induces resistance to paclitaxel. Therefore, the inhibition of the GBP1:PIM1 interaction could potentially revert resistance to paclitaxel. A panel of 44 4-azapodophyllotoxin. derivatives was screened in the NCI-60 cell panel. The result is that 31 are active and the comparative analysis demonstrated specific activity in paclitax el-resistant cells, Using surface plasmon resonance, we were able to prove that NSC756093 is a potent in vitro inhibitor of the GBP1:PIM1 interaction and that this property is maintained in vivo in ovarian cancer cells resistant to paclitaxel. Through bioinformatics, molecular modeling and mutagenesis studies, we identified the putative NSC756093 binding site at the interface between the helical and the LG domain of GBP1. According to our results by binding to this site the NSC756093 compound is able to stabilize a conformation of GBP1 not suitable for binding to PIM1.

  DOI：

  10.1021/jm5009902

文献信息

• Synthesis of novel functionalized 4-aza-2,3-didehydropodophyllotoxin derivatives with potential antitumor activity
  作者：Ajay Kumar、Antonio E. Alegria

  DOI：10.1002/jhet.467

  日期：2010.11

  Novel arylamino alcohols were synthesized and these alcohols were used to prepare 12 novel N-(2-hydroxy-ethyl)-2,3-didehydroazapodophyllotoxins, in one step, by simple reflux in ethanol. Isolated yields in the range of 50-70% were obtained.

  合成了新颖的芳基氨基醇，并将这些醇用于一步简单地在乙醇中回流制备12种新颖的N-（2-羟基-乙基）-2,3-二氢氢化氮杂鬼臼毒素。获得的分离产率为50-70％。
• Azapodophyllotoxin Causes Lymphoma and Kidney Cancer Regression by Disrupting Tubulin and Monoglycerols
  作者：Arvin M. Gouw、Vineet Kumar、Angel Resendez、Fidelia B. Alvina、Natalie S. Liu、Katherine Margulis、Ling Tong、Richard N. Zare、Sanjay V. Malhotra、Dean W. Felsher

  DOI：10.1021/acsmedchemlett.1c00673

  日期：2022.4.14

  the NSC750212 mode of action in vivo. On the basis of the structure of AZP and its mode of action, AZP disrupts tubulin polymerization. Through desorption electrospray ionization mass spectrometry imaging, NSC750212 was found to inhibit lipid metabolism. NSC750212 suppresses monoglycerol metabolism depleting lipids and thereby inhibits tumor growth. The dual mode of tubulin polymerization disruption and

  天然化合物筛选确定了几种抗癌化合物，其中氮杂草毒素 (AZP) 被发现是最有效的。AZP 导致小鼠和人类淋巴瘤和肾细胞癌 (RCC) 肿瘤衍生细胞系的活力降低。合成并筛选了新型 AZP 衍生物，鉴定化合物 NSC750212 在体外和体内均能抑制淋巴瘤和 RCC 的生长。纳米免疫测定用于评估 NSC750212 的体内作用模式。根据 AZP 的结构及其作用方式，AZP 会破坏微管蛋白聚合。通过解吸电喷雾电离质谱成像，发现 NSC750212 抑制脂质代谢。NSC750212 抑制单甘油代谢消耗脂质，从而抑制肿瘤生长。
• Identification of the First Inhibitor of the GBP1:PIM1 Interaction. Implications for the Development of a New Class of Anticancer Agents against Paclitaxel Resistant Cancer Cells
  作者：Mirko Andreoli、Marco Persico、Ajay Kumar、Nausicaa Orteca、Vineet Kumar、Antonella Pepe、Sakkarapalayam Mahalingam、Antonio E. Alegria、Lella Petrella、Laima Sevciunaite、Alessia Camperchioli、Marisa Mariani、Antonio Di Dato、Ettore Novellino、Giovanni Scambia、Sanjay V. Malhotra、Cristiano Ferlini、Caterina Fattorusso

  DOI：10.1021/jm5009902

  日期：2014.10.9

  Class III beta-tubulin plays a prominent role in the development of drug resistance to paclitaxel by allowing the incorporation of the GBP1 GTPase into microtubules. Once in the cytoskeleton. GBP1 binds to prosurvival kinases such as PIM1 and initiates a signaling pathway that induces resistance to paclitaxel. Therefore, the inhibition of the GBP1:PIM1 interaction could potentially revert resistance to paclitaxel. A panel of 44 4-azapodophyllotoxin. derivatives was screened in the NCI-60 cell panel. The result is that 31 are active and the comparative analysis demonstrated specific activity in paclitax el-resistant cells, Using surface plasmon resonance, we were able to prove that NSC756093 is a potent in vitro inhibitor of the GBP1:PIM1 interaction and that this property is maintained in vivo in ovarian cancer cells resistant to paclitaxel. Through bioinformatics, molecular modeling and mutagenesis studies, we identified the putative NSC756093 binding site at the interface between the helical and the LG domain of GBP1. According to our results by binding to this site the NSC756093 compound is able to stabilize a conformation of GBP1 not suitable for binding to PIM1.
• Entrapment in micellar assemblies switches the excimer population of potential therapeutic luminophore azapodophyllotoxin
  作者：Soham Mukherjee、Smruti Gupta、Kapil Ganorkar、Ajay Kumar、Sujit Kumar Ghosh

  DOI：10.1016/j.saa.2019.117723

  日期：2020.3

  pre-micellar and post-micellar at physiological and anoxic pH. On photo-excitation, anti-cancer HPFQ exists in monomer-excimer equilibrium with varying ratios in different polarity regions. The marked enhancement in fluorescence intensity of HPFQ in post-micellar region of the surfactant under study probably arises due to regeneration of the monomer from its excimer. This reoccurrence reduces the possibility

  Azapodophyllotoxin是一类新型的抗肿瘤药物，具有出色的治疗活性，了解其在仿生微环境中的理化性质可能在其细胞间定位，功效和递送方面具有重要意义。目前的工作概括了一个环境问题的天才，4-（2-羟乙基）-10-苯基-3,4,6,7,8,10-六氢-1H-环戊[g]呋喃[3,4] -b]喹啉-1-一（HPFQ），来自抗癌药物Azapodophyllotoxin，在阳离子CTAB，阴离子SDS和中性Triton X-100的不同电荷模型仿生胶束微环境中，采用紫外线可见吸收，稳定荧光，时间分辨荧光和荧光各向异性研究。作为一种独特的现象，HPFQ抗癌剂在极性不同的溶剂中表现出丰富的荧光，这归因于局部激发，电荷转移和受激准分子发射的混合作用。在两种类型的表面活性剂联合体中，在生理和缺氧pH值下，胶束前和胶束后HPFQ的光物理发生了戏剧性的变化。在光激发下，抗癌HPFQ存在于单体-受体平衡物