[1-(1,2-Dimethyl-1H-indol-3-yl)-meth-(E)-ylidene]-methyl-amine | 119491-03-1

• 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: [1-(1,2-Dimethyl-1H-indol-3-yl)-meth-(E)-ylidene]-methyl-amine
• 英文别名: 1,2-Dimethyl-3-(methyliminomethyl)-1H-indole；1-(1,2-dimethylindol-3-yl)-N-methylmethanimine
• CAS: 119491-03-1
• 化学式: C₁₂H₁₄N₂
• 分子量: 186.257
• InChiKey: SVPBCSMQZGRMEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  [1-(1,2-Dimethyl-1H-indol-3-yl)-meth-(E)-ylidene]-methyl-amine 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 0.5h， 生成 1,2-dimethyl-3-(methylaminomethyl)-1H-indole
  参考文献：
  名称：

  Methyl-triflate-mediated dearylmethylation of N-(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature

  摘要：

  在无金属条件下，在水介质中通过亲电脱芳香化/重芳香化实现了N-(芳甲基)羧酰胺的去芳甲基化。

  DOI：

  10.1039/c9gc00176j
• 作为产物：
  描述：

  1,2-二甲基吲哚 在 三氯氧磷 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 [1-(1,2-Dimethyl-1H-indol-3-yl)-meth-(E)-ylidene]-methyl-amine
  参考文献：
  名称：

  Indole Naphthyridinones as Inhibitors of Bacterial Enoyl-ACP Reductases FabI and FabK

  摘要：

  Bacterial enoyl-ACP reductase (FabI) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis and is an attractive target for the development of novel antibacterial agents. Previously we reported the development of FabI inhibitor 4 with narrow spectrum antimicrobial activity and in vivo efficacy against Staphylococcus aureus via intraperitoneal. (ip) administration. Through iterative medicinal chemistry aided by X-ray crystal structure analysis, a new series of inhibitors has been developed with greatly increased potency against FabI-containing organisms. Several of these new inhibitors have potent antibacterial activity against multidrug resistant strains of S. aureus, and compound 30 demonstrates exceptional oral (po) in vivo efficacy in a S. aureus infection model in rats. While optimizing FabI inhibitory activity, compounds 29 and 30 were identified as having low micromolar FabK inhibitory activity, thereby increasing the antimicrobial spectrum of these compounds to include the FabK-containing pathogens Streptococcus pneumoniae and Enterococcus faecalis. The results described herein support the hypothesis that bacterial enoyl-ACP reductases are valid targets for antibacterial agents.

  DOI：

  10.1021/jm0204035

文献信息

• Fab I Inhibitors
  申请人：Miller William H.

  公开号：US20080125423A1

  公开（公告）日：2008-05-29

  Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

  公式（I）的化合物被揭示为Fab I抑制剂，可用于治疗细菌感染。
• FAB I INHIBITORS
  申请人：Miller William H.

  公开号：US20090275572A1

  公开（公告）日：2009-11-05

  Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

  公式（I）的化合物被揭示为Fab I抑制剂，并且在治疗细菌感染方面是有用的。
• Fab I inhibitors
  申请人：Affinium Pharmaceuticals, Inc.

  公开号：US07524843B2

  公开（公告）日：2009-04-28

  Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

  公式（I）的化合物被披露为Fab I抑制剂，并且在治疗细菌感染方面是有用的。
• FAB I inhibitors
  申请人：Affinium Pharmaceuticals, Inc.

  公开号：US08173646B2

  公开（公告）日：2012-05-08

  Compounds of the Formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

  公开了化学式（I）的化合物，它们是Fab I抑制剂，可用于治疗细菌感染。
• Indole Naphthyridinones as Inhibitors of Bacterial Enoyl-ACP Reductases FabI and FabK
  作者：Mark A. Seefeld、William H. Miller、Kenneth A. Newlander、Walter J. Burgess、Walter E. DeWolf、Patricia A. Elkins、Martha S. Head、Dalia R. Jakas、Cheryl A. Janson、Paul M. Keller、Peter J. Manley、Terrance D. Moore、David J. Payne、Stewart Pearson、Brian J. Polizzi、Xiayang Qiu、Stephen F. Rittenhouse、Irene N. Uzinskas、Nicola G. Wallis、William F. Huffman

  DOI：10.1021/jm0204035

  日期：2003.4.1

  Bacterial enoyl-ACP reductase (FabI) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis and is an attractive target for the development of novel antibacterial agents. Previously we reported the development of FabI inhibitor 4 with narrow spectrum antimicrobial activity and in vivo efficacy against Staphylococcus aureus via intraperitoneal. (ip) administration. Through iterative medicinal chemistry aided by X-ray crystal structure analysis, a new series of inhibitors has been developed with greatly increased potency against FabI-containing organisms. Several of these new inhibitors have potent antibacterial activity against multidrug resistant strains of S. aureus, and compound 30 demonstrates exceptional oral (po) in vivo efficacy in a S. aureus infection model in rats. While optimizing FabI inhibitory activity, compounds 29 and 30 were identified as having low micromolar FabK inhibitory activity, thereby increasing the antimicrobial spectrum of these compounds to include the FabK-containing pathogens Streptococcus pneumoniae and Enterococcus faecalis. The results described herein support the hypothesis that bacterial enoyl-ACP reductases are valid targets for antibacterial agents.