Methanamine, N-[(1-methyl-1H-indol-3-yl)methylene]- | 56971-86-9

• 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: Methanamine, N-[(1-methyl-1H-indol-3-yl)methylene]-
• 英文别名: N-methyl-1-(1-methylindol-3-yl)methanimine
• CAS: 56971-86-9
• 化学式: C₁₁H₁₂N₂
• 分子量: 172.23
• InChiKey: WHYNWJDVGJGKTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  Methanamine, N-[(1-methyl-1H-indol-3-yl)methylene]- 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 1-methyl-3-(methylaminomethyl)-1H-indole
  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
• 作为产物：
  描述：

  1-甲基吲哚-3-甲醛 、 甲胺 以 甲醇 为溶剂， 反应 3.0h， 生成 Methanamine, N-[(1-methyl-1H-indol-3-yl)methylene]-
  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

• Synthesis of novel trans-4-(phthalimidomethyl)- and 4-(imidazol-1-ylmethyl)-3-indolyl-tetrahydroisoquinolinones as possible aromatase inhibitors
  作者：Nikola T. Burdzhiev、Todor I. Baramov、Elena R. Stanoeva、Stanislav G. Yanev、Tsveta D. Stoyanova、Diana H. Dimitrova、Kristina A. Kostadinova

  DOI：10.1007/s11696-018-00677-7

  日期：2019.5

  The reaction of homophthalic anhydride with 1H-indol-3-carbaldimines was used for the preparation of trans- and cis-2-alkyl-3-indolyl-1-oxotetrahydroisoquinolin-4-carboxylic acids 3a–d. The stereochemistry of the reaction was investigated by means of 1H NMR spectroscopy. The carboxylic group of trans-3a–d was transformed stereoselectively via 4-hydroxymethyltetrahydroisoquinolin-1-ones into 4-(pht

  高邻苯二甲酸酐的用1个反应ħ吲哚-3- carbaldimines用于制备反式-和顺-2-烷基-3-吲哚基-1- oxotetrahydroisoquinolin -4-羧酸3a-d中。通过1 H NMR光谱研究反应的立体化学。的羧酸基团的反式-图3a-d是通过4- hydroxymethyltetrahydroisoquinolin -1-酮立体选择性地转化为4-（邻苯二甲酰） -衍生物反式- 6A，6B和4-（咪唑基甲基） -衍生物反式- 8B-d 。化合物反式- 6A，6B和图8b-d中为antiaromatase活性进行测试，和初步结果表明，phthalimidomethylisoquinolinone反式- 6b中在50μM浓度用40％降低芳香酶的活性。
• 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.