N-{[5-fluoro-1-((E)-3,7-dimethylocta-2,6-dienyl)-1H-indol-3-yl]methyl}-N-(methyl)propan-1-amine | 1263047-95-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-{[5-fluoro-1-((E)-3,7-dimethylocta-2,6-dienyl)-1H-indol-3-yl]methyl}-N-(methyl)propan-1-amine
• 英文别名: (E)-N-((1-(3,7-dimethylocta-2,6-dienyl)-5-fluoro-1H-indol-3-yl)methyl)-N-methylpropan-1-amine；N-[[1-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-fluoro-indol-3-yl]methyl]-N-methyl-propan-1-amine；N-[[1-[(2E)-3,7-dimethylocta-2,6-dienyl]-5-fluoroindol-3-yl]methyl]-N-methylpropan-1-amine
• CAS: 1263047-95-5
• 化学式: C₂₃H₃₃FN₂
• 分子量: 356.527
• InChiKey: AXFWLLSQFWRRMW-XDHOZWIPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  8.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  香叶基溴 在 sodium hydride 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 24.0h， 生成 N-{[5-fluoro-1-((E)-3,7-dimethylocta-2,6-dienyl)-1H-indol-3-yl]methyl}-N-(methyl)propan-1-amine
  参考文献：
  名称：

  Amphiphilic Indole Derivatives as Antimycobacterial Agents: Structure–Activity Relationships and Membrane Targeting Properties

  摘要：

  Antibacterials that disrupt cell membrane function have the potential to eradicate "persister" organisms and delay the emergence of resistance. Here we report the antimycobacterial activities of 4-fluoro and 6-methoxyindoles bearing a cationic amphiphilic motif represented by a lipophilic n-octyl side chain at position 1 and a positively charged azepanyl or 1,4-dioxa-8-azaspiro[4.5]decane moiety at position 3. These analogues exhibited balanced profiles of potency (Mycobacterium bovis BCG, M tuberculosis H37Rv), selective activity, solubility, and metabolic stability. Bacteriological mechanism of action investigations on a representative analogue revealed cell membrane permeabilization and depolarization in M bovis BCG. These membrane-related changes preceded cell death indicating that the loss in membrane integrity was not an epiphenomenon. Bactericidal activity was observed against both growing and nongrowing mycobacterial cultures. The analogue also upregulated cell envelope stress inducible promoters piniBAC and pclgR, implicating the involvement of envelope-related targets in its mode of action.

  DOI：

  10.1021/acs.jmedchem.6b01530

文献信息

• SMALL MOLECULE INHIBITORS OF ISOPRENYLCYSTEINE CARBOXYL METHYLTRANSFERASE WITH POTENTIAL ANTICANCER ACTIVITY
  申请人：Leow Jo Lene

  公开号：US20120197014A1

  公开（公告）日：2012-08-02

  The present invention generally relates to inhibitors of isoprenylcysteine carboxyl methyltransferase (Icmt), in particularly to compounds that inhibit Icmt activity and pharmaceutical compositions thereof. The invention also relates to methods of disease treatment using the same.

  本发明通常涉及异戊二烯基半胱氨酸羧甲基转移酶（Icmt）的抑制剂，特别是抑制Icmt活性的化合物及其药物组合物。本发明还涉及使用这些抑制剂进行疾病治疗的方法。
• Block copolymer composition, a process for its preparation and a hot melt adhesive comprising said composition
  申请人：SHELL INTERNATIONALE RESEARCH MAATSCHAPPIJ B.V.

  公开号：EP0636654A1

  公开（公告）日：1995-02-01

  Block copolymer composition, comprising: (a) 100 parts weight of a linear styrene/isoprene/styrene triblock copolymer, said copolymer having a styrene content in the range of from 10 to 50% by weight based on the total weight of block copolymer, and apparent total molecular weight in the range of from 5,000 to 300,000, said block copolymer composition having free poly(styrene) content of at most 6% and being obtainable by anionic sequential polymerization of styrene and isoprene in a solvent comprising of cyclopentane and/or cyclohexane, optionally in combination with second initiation to provide triblock copolymer being mixed with a predetermined amount of <+ 40 wt% of diblock copolymer; termination of the living block copolymer(s) with a proton donating terminating agent; and recovery of the final block copolymer(s) from the solvent solution by hot water and/or steam coagulation dewatering and/or drying and/or mixing in a predetermined well adjusted amount of similar block containing diblock copolymer, the final block copolymer composition having a solution viscosity in toluene (25 wt%) at 25 °C in the range of from 0.1 to 3 (b) 0.1 to 5 parts by weight of a stabilizer set comprising: I one or more specific UV stabilizer, and one or more phosphite antioxidants, and adhesive hot melt compositions containing said composition.

  嵌段共聚物组合物，包括 (a) 100 重量份的线性苯乙烯/异戊二烯/苯乙烯三嵌段共聚物，以嵌段共聚物总重量计 算，苯乙烯含量在 10%至 50%（重量百分比）之间，表观总分子量在 5,000 至 300,000 之间、所述嵌段共聚物组合物的游离聚苯乙烯含量不超过 6%，可通过苯乙烯和异戊二烯在环戊烷和/或环己烷组成的溶剂中进行阴离子序聚合反应获得，也可选择与第二引发结合，以提供与预定量 <+ 40 wt% 的二嵌段共聚物混合的三嵌段共聚物；用质子捐赠型终止剂终止活嵌段共聚物；通过热水和/或蒸汽凝固脱水和/或干燥和/或与预定量的含有二嵌段共聚物的类似嵌段充分混合，从溶剂溶液中回收最终嵌段共聚物，最终嵌段共聚物组合物在 25 °C 时在甲苯（25 wt%）中的溶液粘度范围为 0.1 至 3 (b) 0.1 至 5 重量份的稳定剂组，包括 I 一种或多种特定紫外线稳定剂和一种或多种亚磷酸酯抗氧化剂，以及含有所述组合物的粘合剂热熔胶组合物。
• US8742100B2
  申请人：——

  公开号：US8742100B2

  公开（公告）日：2014-06-03
• Amphiphilic Indole Derivatives as Antimycobacterial Agents: Structure–Activity Relationships and Membrane Targeting Properties
  作者：Tianming Yang、Wilfried Moreira、Samuel Agyei Nyantakyi、Huan Chen、Dinah binte Aziz、Mei-Lin Go、Thomas Dick

  DOI：10.1021/acs.jmedchem.6b01530

  日期：2017.4.13

  Antibacterials that disrupt cell membrane function have the potential to eradicate "persister" organisms and delay the emergence of resistance. Here we report the antimycobacterial activities of 4-fluoro and 6-methoxyindoles bearing a cationic amphiphilic motif represented by a lipophilic n-octyl side chain at position 1 and a positively charged azepanyl or 1,4-dioxa-8-azaspiro[4.5]decane moiety at position 3. These analogues exhibited balanced profiles of potency (Mycobacterium bovis BCG, M tuberculosis H37Rv), selective activity, solubility, and metabolic stability. Bacteriological mechanism of action investigations on a representative analogue revealed cell membrane permeabilization and depolarization in M bovis BCG. These membrane-related changes preceded cell death indicating that the loss in membrane integrity was not an epiphenomenon. Bactericidal activity was observed against both growing and nongrowing mycobacterial cultures. The analogue also upregulated cell envelope stress inducible promoters piniBAC and pclgR, implicating the involvement of envelope-related targets in its mode of action.