2-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)ethanol | 1021004-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并二恶烷
• 英文名称: 2-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)ethanol
• 英文别名: 2-(2,3-Dihydro-1,4-benzodioxin-6-ylamino)ethanol
• CAS: 1021004-79-4
• 化学式: C₁₀H₁₃NO₃
• 分子量: 195.218
• InChiKey: CZSICMULSXNZPL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  50.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-羟乙酰乙酸内酯 、 2-(2,3-dihydro-benzo[1,4]dioxin-6-ylamino)ethanol 、 3,4-二氯苯甲醛 在 L-脯氨酸 作用下， 以 乙醇 为溶剂， 以70%的产率得到6-(2-hydroxyethyl)-10-(3,4-dichlorophenyl)-2,3,7,10-tetrahydro-[1,4]dioxino[2,3-g]furo[3,4-b]quinolin-9(6H)-one
  参考文献：
  名称：

  氮杂鬼臼毒素通过破坏微管蛋白和单甘油导致淋巴瘤和肾癌消退

  摘要：

  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。

  DOI：

  10.1021/acsmedchemlett.1c00673
• 作为产物：
  描述：

  6-氨基-1,4-苯并二氧杂环 在 吡啶 、 乙醇 、 potassium hydroxide 作用下， 以 二氯甲烷 为溶剂， 生成 2-(2,3-dihydro-benzo[1,4]dioxin-6-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％。
• US5980584A
  申请人：——

  公开号：US5980584A

  公开（公告）日：1999-11-09