1-(3,4,5-trimethoxyphenoxy)-3-<4-(2-nitrophenyl)piperazinyl>propan-2-ol | 74760-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-(3,4,5-trimethoxyphenoxy)-3-<4-(2-nitrophenyl)piperazinyl>propan-2-ol
• 英文别名: 1-[4-(2-nitro-phenyl)-piperazin-1-yl]-3-(3,4,5-trimethoxy-phenoxy)-propan-2-ol；(+/-)-1-[3-(3,4,5-trimethoxyphenoxy)-2-hydroxy-propyl]-4-(2-nitro-phenyl)-piperazine；1-[4-(2-nitrophenyl)piperazin-1-yl]-3-(3,4,5-trimethoxyphenoxy)propan-2-ol
• CAS: 74760-12-6
• 化学式: C₂₂H₂₉N₃O₇
• 分子量: 447.488
• InChiKey: LKKKLBXDQBYTFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-(3,4,5-trimethoxyphenoxy)-3-<4-(2-nitrophenyl)piperazinyl>propan-2-ol 生成 1-(3,4,5-trimethoxyphenoxy)-3-<4-(2-aminophenyl)piperazinyl>propan-2-ol monohydrochloride
  参考文献：
  名称：

  ENGEL, JURGEN;FLEISHHAUER, ILONA;JAKOVLEV, VLADIMIR;KLEEMANN, AXEL;KUTSCH+, J. MEP. CHEM., 33,(1990) N1, C. 2976-2981

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,5-三甲氧基苯酚 在 sodium hydroxide 作用下， 以 异丙醇 为溶剂， 反应 6.0h， 生成 1-(3,4,5-trimethoxyphenoxy)-3-<4-(2-nitrophenyl)piperazinyl>propan-2-ol
  参考文献：
  名称：

  Chemistry and pharmacology of the non-benzodiazepine anxiolytic enciprazine and related compounds

  摘要：

  In the course of studies on tranquilizers, new non-benzodiazepine-like compounds were synthesized. These are 1-(3,4,5-trimethoxyphenoxy)-3-[4-(2-methoxyphenyl)piperazinyl]prop an-2-ol (INN: enciprazine) and derivatives thereof which were screened pharmacologically in order to evaluate their central nervous system activity. Compounds with marked antiaggressive and anxiolytic properties but without dependence potential could be detected. Enciprazine was selected for clinical investigations.

  DOI：

  10.1021/jm00173a012

文献信息

• 1-[3-(3,4,5-Trimethoxyphenoxy)-2-hydroxy-propyl]-4-
  申请人：Degussa Aktiengesellschaft

  公开号：US04335126A1

  公开（公告）日：1982-06-15

  There are prepared compounds corresponding to the general formula ##STR1## in which R.sup.1 is a hydrogen atom, a C.sub.2 to C.sub.6 -alkanoyl group, a C.sub.3 to C.sub.6 -alkenoyl group, a C.sub.3 to C.sub.6 -cycloalkyl carbonyl group, a benzoyl group, an alkoxybenzoyl group, a nicotinoyl group, a thienyl carbonyl group, a furyl carbonyl group, a phenylacetyl group or a C.sub.1 to C.sub.4 -alkoxyphenyl acetyl group and R.sup.2 represents a phenyl, naphthyl or pyridyl group or such group substituted by the groups R.sup.3 and R.sup.4, the groups R.sup.3 and R.sup.4, which may be the same or different, each representing hydrogen, hydroxyl, fluorine, chlorine, bromine, a nitro group, a trifluoromethyl group, a C.sub.1 to C.sub.6 -alkyl group, a C.sub.1 to C.sub.6 -alkoxy group, a C.sub.1 to C.sub.6 -alkyl thio group, a C.sub.1 to C.sub.6 -alkyl sulphonyl group, a C.sub.2 to C.sub.6 -alkanoyl group, an amino group, an acylamino group or an acyloxy group in which the acyl is of the type defined in respect to R.sup.1, and their salts. The compounds are pharmacodynamically active.

  根据一般的公式##STR1##，存在相应的制备化合物，其中R.sup.1是一个氢原子，一个C.sub.2至C.sub.6的烷酰基团，一个C.sub.3至C.sub.6的烯酰基团，一个C.sub.3至C.sub.6的环烷基甲酰基团，一个苯甲酰基团，一个烷氧基苯甲酰基团，一个尼康酰基团，一个噻吩甲酰基团，一个呋喃甲酰基团，一个苯乙酰基团或一个C.sub.1至C.sub.4的烷氧基苯乙酰基团，而R.sup.2代表一个苯基，萘基或吡啶基团或由R.sup.3和R.sup.4组成的这类基团，R.sup.3和R.sup.4可以相同或不同，每个代表氢，羟基，氟，氯，溴，硝基，三氟甲基，C.sub.1至C.sub.6的烷基，C.sub.1至C.sub.6的烷氧基，C.sub.1至C.sub.6的烷基硫基，C.sub.1至C.sub.6的烷基亚磺酰基，C.sub.2至C.sub.6的烷酰基，氨基，酰氨基或酰氧基，其中酰基是R.sup.1定义的类型，以及它们的盐。这些化合物具有药理动力学活性。
• ENGEL, JURGEN;FLEISHHAUER, ILONA;JAKOVLEV, VLADIMIR;KLEEMANN, AXEL;KUTSCH+, J. MEP. CHEM., 33,(1990) N1, C. 2976-2981
  作者：ENGEL, JURGEN、FLEISHHAUER, ILONA、JAKOVLEV, VLADIMIR、KLEEMANN, AXEL、KUTSCH+

  DOI：——

  日期：——
• US4335126A
  申请人：——

  公开号：US4335126A

  公开（公告）日：1982-06-15
• Chemistry and pharmacology of the non-benzodiazepine anxiolytic enciprazine and related compounds
  作者：Juergen Engel、Ilona Fleischhauer、Vladimir Jakovlev、Axel Kleemann、Bernhard Kutscher、Bernd Nickel、Horst Rauer、Ulrich Werner、Istvan Szelenyi

  DOI：10.1021/jm00173a012

  日期：1990.11

  In the course of studies on tranquilizers, new non-benzodiazepine-like compounds were synthesized. These are 1-(3,4,5-trimethoxyphenoxy)-3-[4-(2-methoxyphenyl)piperazinyl]prop an-2-ol (INN: enciprazine) and derivatives thereof which were screened pharmacologically in order to evaluate their central nervous system activity. Compounds with marked antiaggressive and anxiolytic properties but without dependence potential could be detected. Enciprazine was selected for clinical investigations.