(Z)-3-(1-(1H-pyrrol-2-yl)propylidene)-1-(3-(dimethylamino)propyl)-5-fluoroindolin-2-one hydrochloride | 1392330-56-1

• 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: (Z)-3-(1-(1H-pyrrol-2-yl)propylidene)-1-(3-(dimethylamino)propyl)-5-fluoroindolin-2-one hydrochloride
• 英文别名: (3Z)-1-[3-(dimethylamino)propyl]-5-fluoro-3-[1-(1H-pyrrol-2-yl)propylidene]indol-2-one;hydrochloride
• CAS: 1392330-56-1
• 化学式: C₂₀H₂₄FN₃O*ClH
• 分子量: 377.889
• InChiKey: KONTVVUBWQTDKI-HVENRQQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  39.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-丙酰吡咯 、 1-[3-(dimethylamino)propyl]-5-flouro-indolin-2-one 在 四氢吡咯 、 盐酸 作用下， 以 乙醇 、 乙醚 为溶剂， 反应 3.0h， 生成 (Z)-3-(1-(1H-pyrrol-2-yl)propylidene)-1-(3-(dimethylamino)propyl)-5-fluoroindolin-2-one hydrochloride
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of 1-(3-dimethylamino)propyl indolin-2-one derivatives

  摘要：

  A series of 1-(3-dimethylaminopropyl)indolin-2-one derivatives were designed and synthesized based on the structural features of TMP-20, LK-B030, and BX-517. These newly synthesized derivatives were evaluated for in vitro activity against five human cancer cell lines and three HUVECs. Results revealed that all of the target compounds 1a-h generally show potent activity against these cancer cell lines and higher selectivity on VEGF- and bFGF-stimulated HUVECs than HUVEC. In particular, 1f (IC(50)s: 1.10-1.47 mu M) is 1.8-6.0-fold more potent than sunitinib against MDA-MB-231, A549, HL-60 and K-562, and 1.6-2.8-fold more potent than LK-B030 against MDA-MB-231 and A549.

  DOI：

  10.1007/s00044-012-0170-3

文献信息

• Synthesis and in vitro antitumor activity of 1-(3-dimethylamino)propyl indolin-2-one derivatives
  作者：Kai Lv、Li-Li Wang、Xin-Bo Zhou、Ming-Liang Liu、Hong-Ying Liu、Zhi-Bing Zheng、Song Li

  DOI：10.1007/s00044-012-0170-3

  日期：2013.4

  A series of 1-(3-dimethylaminopropyl)indolin-2-one derivatives were designed and synthesized based on the structural features of TMP-20, LK-B030, and BX-517. These newly synthesized derivatives were evaluated for in vitro activity against five human cancer cell lines and three HUVECs. Results revealed that all of the target compounds 1a-h generally show potent activity against these cancer cell lines and higher selectivity on VEGF- and bFGF-stimulated HUVECs than HUVEC. In particular, 1f (IC(50)s: 1.10-1.47 mu M) is 1.8-6.0-fold more potent than sunitinib against MDA-MB-231, A549, HL-60 and K-562, and 1.6-2.8-fold more potent than LK-B030 against MDA-MB-231 and A549.