3-[(1-methyl-1H-benzimidazol-2-yl)oxy]benzaldehyde | 1429498-35-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(1-methyl-1H-benzimidazol-2-yl)oxy]benzaldehyde
• 英文别名: 3-(1-Methylbenzimidazol-2-yl)oxybenzaldehyde；3-(1-methylbenzimidazol-2-yl)oxybenzaldehyde
• CAS: 1429498-35-0
• 化学式: C₁₅H₁₂N₂O₂
• 分子量: 252.272
• InChiKey: SFUPXTQGWKGCTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(1-methyl-1H-benzimidazol-2-yl)oxy]benzaldehyde 、 丙二酸二乙酯 在 哌啶乙酸盐 作用下， 以 甲苯 为溶剂， 反应 14.0h， 以50%的产率得到2-[3-(1-methyl-1H-benzoimidazol-2-yloxy)-benzylidene]malonic acid diethyl ester
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461
• 作为产物：
  描述：

  2-溴苯并咪唑 在 吡啶 、 铜 、 potassium carbonate 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 26.0h， 生成 3-[(1-methyl-1H-benzimidazol-2-yl)oxy]benzaldehyde
  参考文献：
  名称：

  Design and Synthesis of Benzimidazole-Linked meta-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities

  摘要：

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2012.678461

文献信息

• ANTI-CANCER COMPOUND AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  申请人：Carry Jean-Christophe

  公开号：US20120220621A1

  公开（公告）日：2012-08-30

  The invention relates to a compound of formula (I), more specifically in the levorotatory form (1 a ) thereof, in particular the form having a rotatory power [α]D=−38.6+0.7 at a concentration of 0.698 mg/ml in methanol. The compound may be in the form of a base or an acid addition salt, in particular a pharmaceutically acceptable acid. The compound is a selective Aurora A and B kinase inhibitor and can be used as an anticancer drug.

  该发明涉及公式（I）的化合物，更具体地说是其左旋型（1a），特别是其旋光度为[α]D=−38.6+0.7（在甲醇中浓度为0.698mg/ml时），该化合物可以是碱性或酸性盐的形式，特别是药用可接受的酸性盐。该化合物是一种选择性的Aurora A和B激酶抑制剂，可用作抗癌药物。
• US9073917B2
  申请人：——

  公开号：US9073917B2

  公开（公告）日：2015-07-07
• US9221817B2
  申请人：——

  公开号：US9221817B2

  公开（公告）日：2015-12-29
• Design and Synthesis of Benzimidazole-Linked <i>meta</i>-Substituted Benzylidenes/Benzyls as Biologically Significant New Chemical Entities
  作者：Raman K. Verma、Rajiv Mall、Prithwish Ghosh、Vijay Kumar

  DOI：10.1080/00397911.2012.678461

  日期：2013.7.18

  meta-Linked thiazolidinedione (TZD) and diethyl malonate (DEM)based benzylidenes and methyl acetoacetate (MAA)based benzyl moieties linked to the 2-position of N-methyl benzimidazole were synthesized. TZD- and DEM-based compounds were synthesized by condensation of 2,4-thiazolidinedone and DEM respectively with the corresponding 3-substituted benzaldehyde, whereas MAA-based compounds were obtained by halogen displacement with the corresponding 3-substituted phenol. These new chemical entities were designed to provide a balanced agonism at the peroxisome proliferator activated receptor alpha/gamma (PPAR/) in the management of type 2 diabetes: a move from glitazones to selective PPAR modulators (SPPARMs). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.