(5-甲氧基-1H-吲哚-3-基)-乙酸 肼 | 57000-48-3

• 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
• 中文名称: (5-甲氧基-1H-吲哚-3-基)-乙酸 肼
• 中文别名: (5-甲氧基-1H-吲哚-3-基)-乙酸肼
• 英文名称: 2-(5-methoxy-1H-indol-3-yl)acetohydrazide
• CAS: 57000-48-3
• 化学式: C₁₁H₁₃N₃O₂
• mdl: MFCD01074508
• 分子量: 219.243
• InChiKey: AVJDUEZEDGKGIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  80.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5-甲氧基-1H-吲哚-3-基)-乙酸 肼 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.25h， 生成 3-((5-methoxy-1H-indol-3-yl)methyl)-4-methyl-1H-1,2,4-triazol-5(4H)-one
  参考文献：
  名称：

  Novel N-Acetyl Bioisosteres of Melatonin: Melatonergic Receptor Pharmacology, Physicochemical Studies, and Phenotypic Assessment of Their Neurogenic Potential

  摘要：

  Herein we present a new family of melatonin-based compounds, in which the acetamido group of melatonin has been bioisosterically replaced by a series of reversed amides and azoles, such as oxazole, 1,2,4-oxadiazole; and 1,8,4, oxadiazole, as well as other related five-membered heterocycles, namely, 1,3,4-oxadiazol(thio)ones, 1,3,4-triazol(thio)ones, and an 1,3,4-thiadiazole. New compounds were fully characterized at melatonin receptors (MT1R and MT2R), and results were rationalized by superimposition studies of their structures to the bioactive conformation of melatonin. We also found that several of these melatonin-based compounds promoted differentiation of rat neural stem cells to a neuronal phenotype in vitro, in some cases to a higher extent than melatonin. This unique profile constitutes the starting point for further pharmacological studies to assess the mechanistic pathways and the relevance of neurogenesis induced by melatonin-related structures.

  DOI：

  10.1021/acs.jmedchem.5b00245
• 作为产物：
  描述：

  2-(5-甲氧基-1H-吲哚-3-基)乙酸乙酯 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 0.75h， 以98%的产率得到(5-甲氧基-1H-吲哚-3-基)-乙酸 肼
  参考文献：
  名称：

  Novel N-Acetyl Bioisosteres of Melatonin: Melatonergic Receptor Pharmacology, Physicochemical Studies, and Phenotypic Assessment of Their Neurogenic Potential

  摘要：

  Herein we present a new family of melatonin-based compounds, in which the acetamido group of melatonin has been bioisosterically replaced by a series of reversed amides and azoles, such as oxazole, 1,2,4-oxadiazole; and 1,8,4, oxadiazole, as well as other related five-membered heterocycles, namely, 1,3,4-oxadiazol(thio)ones, 1,3,4-triazol(thio)ones, and an 1,3,4-thiadiazole. New compounds were fully characterized at melatonin receptors (MT1R and MT2R), and results were rationalized by superimposition studies of their structures to the bioactive conformation of melatonin. We also found that several of these melatonin-based compounds promoted differentiation of rat neural stem cells to a neuronal phenotype in vitro, in some cases to a higher extent than melatonin. This unique profile constitutes the starting point for further pharmacological studies to assess the mechanistic pathways and the relevance of neurogenesis induced by melatonin-related structures.

  DOI：

  10.1021/acs.jmedchem.5b00245

文献信息

• Substituted imidazo [1,5-a] [1,2,4] triazolo [4,3-d] [1,4] benzodiazepine derivatives
  申请人：——

  公开号：US20020103371A1

  公开（公告）日：2002-08-01

  The present invention is a compound of formula 1 The compound and derivatives or pharmaceutically acceptable salts thereof of the invention have a good affinity and selectivity to the GABA A &agr;5 receptor and are useful for the treatment of diseases related to this receptor.

  本发明是一种化合物，化学式为1。该发明的化合物及其衍生物或药学上可接受的盐具有良好的亲和力和选择性，对GABA A &agr;5受体具有作用，并可用于治疗与该受体相关的疾病。
• PIOTROWSKA H.; SERAFIN B.; WEJROCH-MATACZ K., POL. J. PHARMACOL. PHARM., 1975, 27, NO 3, 297-303
  作者：PIOTROWSKA H.、 SERAFIN B.、 WEJROCH-MATACZ K.

  DOI：——

  日期：——
• BENZODIAZEPINE DERIVATIVES AS GABA A RECEPTOR MODULATORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1337535A2

  公开（公告）日：2003-08-27
• US6743789B2
  申请人：——

  公开号：US6743789B2

  公开（公告）日：2004-06-01
• [EN] BENZODIAZEPINE DERIVATIVES AS GABA A RECEPTOR MODULATORS<br/>[FR] DERIVES DE BENZODIAZEPINE COMME MODULATEURS DE RECEPTEUR GABA A
  申请人：HOFFMANN LA ROCHE

  公开号：WO2002040487A2

  公开（公告）日：2002-05-23

  The present invention relates to compounds of formula (I), wherein R1 is hydrogen, halogen, lower alkyl, lower alkoxy, hydroxy, cyano, trifluoromethyl, trifluoromethoxy or lower alkylthio; R2 is -C(O)O-lower alkyl, isoxazol, 1,2,4-oxadiazol-3-yl or 1,2,4-oxadiazol-5-yl, which rings may be substituted by lower alkyl, trifluoromethyl or cycloalkyl; R3 is hydrogen, lower alkyl, -(CH¿2?)n-cycloalkyl, -(CH2)n-halogen, -(CH2)n-pyridin-4-yl, or -(CH2)n-phenyl, wherein the phenyl ring may be substituted by one or two substituents selected from the group consisting of lower alkoxy, halogen, -SO2CH3, phenyl, OCF3, nitro, CF3, -NR2, or is -(CH2)n-indolyl, optionally substituted by lower alkyl or lower alkoxy, or is pyrrolidinyl-5-oxo, -C(O)-NR2, -(CH2)n-OH, -(CH2)n-NR2 or -(CH2)n-benzo[1,3]dioxole; R is hydrogen or lower alkyl; and n is 0, 1, 2 or 3; and to their pharmaceutically acceptable acid addition salts. These compounds have a good affinity to the GABA A α5 receptor and they are therefore useful for the treatment of diseases, related to this receptor.