2-methyl-3-(methylaminomethyl)indole | 335032-50-3

• 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: 2-methyl-3-(methylaminomethyl)indole
• 英文别名: N-Methyl-N-[(2-methyl-1H-indol-3-yl)methyl]amine；N-methyl-1-(2-methyl-1H-indol-3-yl)methanamine
• CAS: 335032-50-3
• 化学式: C₁₁H₁₄N₂
• mdl: MFCD08056294
• 分子量: 174.246
• InChiKey: QSEWWKLGOWVVGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.272
• 拓扑面积：
  27.8
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(methylaminomethyl)indole 以65%的产率得到(E)-N-methyl-N-(2-methyl-1H-indol-3-ylmethyl)-3-(7-oxo-5,6,7,8-tetrahydro-1,8-naphthyridin-3-yl)acrylamide
  参考文献：
  名称：

  Methods of agonizing and antagonizing FabK

  摘要：

  本发明提供了使用FabK多肽的激动剂和拮抗剂的方法，特别是用于调节细菌代谢或治疗细菌感染。

  公开号：

  US20040053814A1
• 作为产物：
  描述：

  2-甲基吲哚-3-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 9.0h， 生成 2-methyl-3-(methylaminomethyl)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

文献信息

• Methods of agonizing and antagonizing FabK
  申请人：——

  公开号：US20040053814A1

  公开（公告）日：2004-03-18

  The invention provides methods for using agonists and antagonists of FabK polypeptides, particularly to modulate the metabolism of bacteria or to treat bacterial infection.

  本发明提供了使用FabK多肽的激动剂和拮抗剂的方法，特别是用于调节细菌代谢或治疗细菌感染。
• [EN] FAB I INHIBITORS<br/>[FR] INHIBITEURS DE FAB I
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2001027103A1

  公开（公告）日：2001-04-19

  Compounds of formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections. In said formula, (A) is (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l), (m), (n), (o) or (p); (I) wherein R1 is H or C¿1-4?alkyl; R?2¿ is H, C¿1-4?alkyl or C3-6cycloalkyl; R?3¿ is (q), (r), (s), (t), (u), (v) or (w); R4 is H or C¿1-4?alkyl; (x) indicates that one of the two designated bonds is a double bond and the other is a single bond; R?5¿ is CH¿2? when the bond to which it is attached is a double bond; or R?5¿ is H or C¿1-4?alkyl when the bond to which it is attached is a single bond; R?6¿ is H or C¿1-4?alkyl; R?7¿ is H, C¿1-6?alkyl or -C0-6alkyl-Ar; Y is H, C1-4alkyl, N(R')2, NHC(O)R', NHCH2C(O)R' or NHC(O)CH=CHR'; each X independently is H, C1-4alkyl, CH2OH, OR', SR', CN, N(R')2, CH2N(R')2, NO2, CF3, CO2R', CON(R')2, COR', NR'C(O)R', F, Cl, Br, I or -S(O)rCF3; W is S or O, Q is H or C1-4alkyl; M is CH2 or O; L is CH2 or C(O); E is O or NR'; each R' independently is H, C1-6alkyl or -C0-6alkyl-Ar; and r is 0, 1 or 2; or a pharmaceutically acceptable salt thereof.

  公开了式（I）的化合物，它们是Fab I抑制剂，可用于治疗细菌感染。在所述式中，（A）是（a），（b），（c），（d），（e），（f），（g），（h），（i），（j），（k），（l），（m），（n），（o）或（p）;（I），其中R1为H或C1-4烷基; R?2¿为H，C1-4烷基或C3-6环烷基; R?3¿为（q），（r），（s），（t），（u），（v）或（w）; R4为H或C1-4烷基;（x）表示两个指定键中的一个是双键，另一个是单键;当其所连接的键是双键时，R?5¿为CH2;当其所连接的键是单键时，R?5¿为H或C1-4烷基; R?6¿为H或C1-4烷基; R?7¿为H，C1-6烷基或-C0-6烷基-Ar; Y为H，C1-4烷基，N（R'）2，NHC（O）R'，NHCH2C（O）R'或NHC（O）CH = CHR';每个X独立地为H，C1-4烷基，CH2OH，OR'，SR'，CN，N（R'）2，CH2N（R'）2，NO2，CF3，CO2R'，CON（R'）2，COR'，NR'C（O）R'，F，Cl，Br，I或-S（O）rCF3; W为S或O，Q为H或C1-4烷基; M为CH2或O; L为CH2或C（O）; E为O或NR';每个R'独立地为H，C1-6烷基或-C0-6烷基-Ar; r为0、1或2;或其药学上可接受的盐。
• FAB I inhibitors
  申请人：Miller H. William

  公开号：US20050250810A1

  公开（公告）日：2005-11-10

  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：Burgess J. Walter

  公开号：US20060116394A1

  公开（公告）日：2006-06-01

  Compounds are disclosed which are Fab I inhibitors and are useful in the treatment bacterial infections.

  本发明揭示了一种Fab I抑制剂，可用于治疗细菌感染。
• Compositions comprising multiple bioactive agents, and methods of using the same
  申请人：Berman M. Judd

  公开号：US20060142265A1

  公开（公告）日：2006-06-29

  In part, the present invention is directed to compositions comprising a FabI inhibitor and at least one other bioactive agent. In another part, the present invention is directed to antibacterial compositions comprising a compound of formulas I-III and at least one other antibacterial agent.

  本发明的一部分涉及含有FabI抑制剂和至少一种其他生物活性剂的组合物。另一部分，本发明涉及含有I-III式化合物和至少一种其他抗菌剂的抗菌组合物。