N-(2-(diethylamino)ethyl)-2-methyl-7-[1,2-dihydro-5-nitro-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxamide | 1032266-53-7

• 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: N-(2-(diethylamino)ethyl)-2-methyl-7-[1,2-dihydro-5-nitro-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxamide
• 英文别名: (7Z)-N-[2-(diethylamino)ethyl]-2-methyl-7-(5-nitro-2-oxo-1H-indol-3-ylidene)-1,4,5,6-tetrahydroindole-3-carboxamide
• CAS: 1032266-53-7
• 化学式: C₂₄H₂₉N₅O₄
• 分子量: 451.525
• InChiKey: ZNFMAXYFBGIDKY-FXBPSFAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2-(diethylamino)ethyl)-2-methyl-7-[1,2-dihydro-5-nitro-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxamide 在 盐酸 、 铁粉 作用下， 以 水 为溶剂， 反应 40.0h， 生成 N-(2-(diethylamino)ethyl)-2-methyl-7-[5-amino-1,2-dihydro-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxamide
  参考文献：
  名称：

  3-Pyrrolo[b]Cyclohexylene-2-Dihydroindolinone Derivatives and Uses Thereof

  摘要：

  公式（I）的3-吡咯[ b ]环己烯-2-二氢吲哚酮衍生物或其药用盐及其用途。用于制备上述化合物的公式（II）的中间体。生物测定表明，上述化合物及其药用盐可以调节蛋白激酶（PKs）的活性，抑制酪氨酸激酶（PTKs）的活性，并抑制多种类型的肿瘤细胞。

  公开号：

  US20100160318A1
• 作为产物：
  描述：

  6-amino-5-oxohexanoic acid hydrochloride 在 吡啶 、 sodium dihydrogenphosphate 、 四磷十氧化物 、 四氯化钛 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 108.5h， 生成 N-(2-(diethylamino)ethyl)-2-methyl-7-[1,2-dihydro-5-nitro-2-oxo-3H-indol-(Z)-3-ylidene]-4,5,6,7-tetrahydro-1H-indole-3-carboxamide
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel 3-pyrrolo[b]cyclohexylene-2-dihydroindolinone derivatives as potent receptor tyrosine kinase inhibitors

  摘要：

  A novel series of 3-pyrrolo[b]cyclohexylene-2-dihydroindolinone derivatives targeting VEGFR-2, PDGFR-beta and c-Kit kinases were designed and synthesized. The molecular design was based on the SAR features of indolin-2-ones as kinase inhibitors. SAR study of the series allowed us to identify compounds possessing more potent inhibitory activities against the three kinases than sunitinb with IC50 values in the low nanomolar range in vitro. Additionally, some compounds also showed favorable antiproliferative activities against a panel of cancer cell lines (BXPC-3, T24, BGC, HEPG2 and HT29). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.037

文献信息

• 3-PYRROLO-CYCLOHEXYLENE-2-DIHYDRO-INDOLINONE DERIVATIVES AND USES THEREOF
  申请人：Jiangsu Simcere Pharmaceutical R&D Co., Ltd.

  公开号：EP2123649B1

  公开（公告）日：2012-02-29
• US8084621B2
  申请人：——

  公开号：US8084621B2

  公开（公告）日：2011-12-27
• Design, synthesis, and biological evaluation of novel 3-pyrrolo[b]cyclohexylene-2-dihydroindolinone derivatives as potent receptor tyrosine kinase inhibitors
  作者：Lei Ding、Feng Tang、Wei Huang、Qiu Jin、Han Shen、Ping Wei

  DOI：10.1016/j.bmcl.2013.08.037

  日期：2013.10

  A novel series of 3-pyrrolo[b]cyclohexylene-2-dihydroindolinone derivatives targeting VEGFR-2, PDGFR-beta and c-Kit kinases were designed and synthesized. The molecular design was based on the SAR features of indolin-2-ones as kinase inhibitors. SAR study of the series allowed us to identify compounds possessing more potent inhibitory activities against the three kinases than sunitinb with IC50 values in the low nanomolar range in vitro. Additionally, some compounds also showed favorable antiproliferative activities against a panel of cancer cell lines (BXPC-3, T24, BGC, HEPG2 and HT29). (C) 2013 Elsevier Ltd. All rights reserved.
• 3-Pyrrolo[b]Cyclohexylene-2-Dihydroindolinone Derivatives and Uses Thereof
  申请人：Tang Feng

  公开号：US20100160318A1

  公开（公告）日：2010-06-24

  3-pyrrolo[b]cyclohexylene-2-dihydro-indolinone derivatives of formula (I) or their pharmaceutically acceptable salts and uses thereof. The intermediates of formula (II) for preparing the above compounds. The bioassay shows that the above compounds and their pharmaceutically acceptable salts can modulate the activity of protein kinases (PKs), inhibit the activity of tyrosine kinases (PTKs) and inhibit many kinds of tumor cells as well as.

  公式（I）的3-吡咯[ b ]环己烯-2-二氢吲哚酮衍生物或其药用盐及其用途。用于制备上述化合物的公式（II）的中间体。生物测定表明，上述化合物及其药用盐可以调节蛋白激酶（PKs）的活性，抑制酪氨酸激酶（PTKs）的活性，并抑制多种类型的肿瘤细胞。