2-(1-(diethyl amino)ethyl)naphtha[2,3-b]furan-4,9-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 2-(1-(diethyl amino)ethyl)naphtha[2,3-b]furan-4,9-dione
• 英文别名: 2-[1-(Diethylamino)ethyl]benzo[f][1]benzofuran-4,9-dione；2-[1-(diethylamino)ethyl]benzo[f][1]benzofuran-4,9-dione
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: OLBGJNGIKRGEBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-乙酰基呋喃并-1,4-萘醌 在 sodium tetrahydroborate 、 氯化亚砜 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 10.0h， 生成 2-(1-(diethyl amino)ethyl)naphtha[2,3-b]furan-4,9-dione
  参考文献：
  名称：

  BBI608衍生物及其制备与用途

  摘要：

  本发明属于医药技术领域，涉及一类BBI608衍生物及其在抗肿瘤药物中的应用。所述衍生物及其药学上可接受的盐的结构如下：其中X、R1、R2、R3如权利要求书和说明书所述。本发明所述的衍生物及其药学上可接受的盐可用于制备抗肿瘤的药物，尤其是制备治疗胃癌(包括胃食管连接癌)和胰腺癌的药物。HepG2细胞活性研究中发现大部分化合物的细胞抑制活性明显优于抗癌药物BBI608。

  公开号：

  CN107973788B

文献信息

• BBI608衍生物及其制备与用途
  申请人：沈阳药科大学

  公开号：CN107973788B

  公开（公告）日：2021-07-09

  本发明属于医药技术领域，涉及一类BBI608衍生物及其在抗肿瘤药物中的应用。所述衍生物及其药学上可接受的盐的结构如下：其中X、R1、R2、R3如权利要求书和说明书所述。本发明所述的衍生物及其药学上可接受的盐可用于制备抗肿瘤的药物，尤其是制备治疗胃癌(包括胃食管连接癌)和胰腺癌的药物。HepG2细胞活性研究中发现大部分化合物的细胞抑制活性明显优于抗癌药物BBI608。
• Design, synthesis and activity of BBI608 derivatives targeting on stem cells
  作者：Qifan Zhou、Chen Peng、Fangyu Du、Linbo Zhou、Yajie Shi、Yang Du、Dongdong Liu、Wenjiao Sun、Meixia Zhang、Guoliang Chen

  DOI：10.1016/j.ejmech.2018.03.054

  日期：2018.5

  STAT3 plays a vital role in maintaining the self-renewal of tumor stem cells. BBI608, a small molecule identified by its ability to inhibit gene transcription driven by STAT3 and cancer stemness properties, can inhibit stemness gene expression and kill stemness-high cancer cells isolated from a variety of cancer types. In order to improve the pharmacokinetic properties of BBI608 and the antitumor activity, a series of BBI608 derivatives were designed and synthesized here. Most of these compounds were more potent than BBI608 on HepG2 cells, compound LD-8 had the most potent inhibitory activity among them and was 5.4-fold more potent than BBI608 (IC50 = 11.2 mu M), but had considerable activity on normal liver cells L-02. Compounds LD-17 (IC50 = 3.5 mu M) and LD-19 (10(50) = 2.9 mu M) were found to possess significant inhibitory activities and good selectivity. The results showed that compound LD-19 was worthy to investigate further as a lead compound according to its potent inhibitory activity, ideal ClogP value and better water solubility. (C) 2018 Elsevier Masson SAS. All rights reserved.