1-(2,5-二甲氧基-4-i-丙基硫代苯基)-2-氨基丙烷盐酸盐 | 123643-26-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(2,5-二甲氧基-4-i-丙基硫代苯基)-2-氨基丙烷盐酸盐
• 英文名称: 4-isopropylthio-2,5-dimethoxyamphetamine
• 英文别名: 2,5-Dimethoxy-4-iso-propylthioamphetamine；1-(2,5-dimethoxy-4-propan-2-ylsulfanylphenyl)propan-2-amine
• CAS: 123643-26-5
• 化学式: C₁₄H₂₃NO₂S
• 分子量: 269.408
• InChiKey: BCWCXWKCQMBFBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  379.5±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  69.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,5-dimethoxy-4-i-propylthiobenzaldehyde 在 lithium aluminium tetrahydride 、 ammonium acetate 作用下， 以 四氢呋喃 为溶剂， 反应 36.0h， 生成 1-(2,5-二甲氧基-4-i-丙基硫代苯基)-2-氨基丙烷盐酸盐
  参考文献：
  名称：

  Sulfur-Substituted α-Alkyl Phenethylamines as Selective and Reversible MAO-A Inhibitors:  Biological Activities, CoMFA Analysis, and Active Site Modeling

  摘要：

  A series of phenethylamine derivatives with various ring substituents and with or without N-methyl and/or C-alpha methyl or ethyl groups was synthesized and assayed for their ability reversibly to inhibit monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B). Several compounds. showed potent and selective MAO-A inhibitory activity (IC50 in the submicromolar range) but none showed appreciable activity toward MAO-B. A three-dimensional quantitative structure-activity relationship study for MAO-A inhibition was performed on the series using comparative molecular field analysis (CoMFA). The resulting model gave a cross-validated q(2) of 0.72 and showed that in this series of compounds steric properties of the substituents were more important than electrostatic effects. Molecular modeling based on the recently published crystal structure of inhibitor-bound MAO-A provided detailed evidence for specific interactions of the ligands with the enzyme, supported by previous references and consistent with results from the CoMFA. On the basis of these results, structural determinants for selectivity of substituted amphetamines for MAO-A are discussed.

  DOI：

  10.1021/jm0493109

文献信息

• [EN] COMPOSITIONS COMPRISING TRYPSIN-CLEAVABLE AMPHETAMINE PRODRUGS AND INHIBITORS THEREOF<br/>[FR] COMPOSITIONS COMPRENANT DES PROMÉDICAMENTS DE TYPE AMPHÉTAMINE CLIVABLES PAR TRYPSINE ET LEURS INHIBITEURS
  申请人：PHARMACOFORE INC

  公开号：WO2011133347A1

  公开（公告）日：2011-10-27

  Pharmaceutical compositions and their methods of use are provided, where the pharmaceutical compositions comprise an amphetamine prodrug that provides enzymatically-controlled release of amphetamine or an amphetamine analog. The composition can further comprise an enzyme inhibitor that interacts with the enzyme(s) that mediates the enzymatically-controlled release of amphetamine or the amphetamine analog from the amphetamine prodrug so as to attenuate enzymatic cleavage of the amphetamine prodrug.

  提供药物组合物及其使用方法，其中药物组合物包括一种苯丙胺前药，可提供苯丙胺或苯丙胺类似物的酶控释放。该组合物还可以包括一个酶抑制剂，与介导苯丙胺前药中的苯丙胺或苯丙胺类似物的酶相互作用，以减弱苯丙胺前药的酶解裂。
• COMPOSITIONS FOR REDUCING RISK OF ADVERSE EVENTS CAUSED BY DRUG-DRUG INTERACTIONS
  申请人：JENKINS Thomas E.

  公开号：US20120232066A1

  公开（公告）日：2012-09-13

  The present disclosure provides a composition comprising a GABA A agonist and a GI enzyme inhibitor. The present disclosure also provides a composition comprising (a) a GI enzyme inhibitor and (b) a first drug that interacts with a second drug to produce an adverse effect when the second drug is co-ingested as a GI enzyme-cleavable prodrug with the first drug. Such an interaction can be additive or synergistic.

  本公开提供一种包含GABAA激动剂和GI酶抑制剂的组合物。本公开还提供一种包含（a）GI酶抑制剂和（b）第一药物的组合物，当第二药物以GI酶可切割的前药形式与第一药物共同摄入时，第一药物与第二药物相互作用产生不良效应。这种相互作用可以是加成的或协同的。
• [EN] COMPOSITIONS COMPRISING ENZYME-CLEAVABLE AMPHETAMINE PRODRUGS AND INHIBITORS THEREOF<br/>[FR] COMPOSITIONS COMPRENANT DES PROMÉDICAMENTS DE TYPE AMPHÉTAMINE CLIVABLES PAR ENZYME ET LEURS INHIBITEURS
  申请人：PHARMACOFORE INC

  公开号：WO2011133348A1

  公开（公告）日：2011-10-27

  Pharmaceutical compositions and their methods of use are provided, where the pharmaceutical compositions comprise an amphetamine prodrug that provides enzymatically-controlled release of amphetamine or an amphetamine analog. The composition can further comprise an enzyme inhibitor that interacts with the enzyme(s) that mediates the enzymatically-controlled release of amphetamine or the amphetamine analog from the amphetamine prodrug so as to attenuate enzymatic cleavage of the amphetamine prodrug.

  提供了药物组合物及其使用方法，其中药物组合物包括一种苯丙胺前药，该前药提供苯丙胺或苯丙胺类似物的酶控释放。该组合物还可以包括一种酶抑制剂，与介导苯丙胺前药中的苯丙胺或苯丙胺类似物的酶相互作用，以减轻苯丙胺前药的酶催化裂解。
• Compositions Comprising Enzyme-Cleavable Amphetamine Prodrugs and Inhibitors Thereof
  申请人：Jenkins Thomas E.

  公开号：US20130059914A1

  公开（公告）日：2013-03-07

  Pharmaceutical compositions and their methods of use are provided, where the pharmaceutical compositions comprise an amphetamine prodrug that provides enzymatically-controlled release of amphetamine or an amphetamine analog. The composition can further comprise an enzyme inhibitor that interacts with the enzyme(s) that mediates the enzymatically-controlled release of amphetamine or the amphetamine analog from the amphetamine prodrug so as to attenuate enzymatic cleavage of the amphetamine prodrug.

  提供了药物组合物及其使用方法，其中药物组合物包括一种苯丙胺前药，该前药提供酶控释放苯丙胺或苯丙胺类似物。该组合物还可以包括一种酶抑制剂，与介导苯丙胺前药中苯丙胺或苯丙胺类似物的酶相互作用，以减弱苯丙胺前药的酶解。
• Deuterium free, stable isotope labeled 2-phenylethylamine hallucinogens and/or stimulants, methods fo their preparation and their use
  申请人：Chiron AS

  公开号：EP2551675A1

  公开（公告）日：2013-01-30

  Deuterium free, stable isotope labeled hallucinogens and/or stimulants containing a 2-phenylethylamine-based structural unit and containing at least three stable isotopes selected from the group consisting of 13C, 15N and 18O as free bases and as their salts; method of their preparation and their use in the chemical analysis, in particular forensic chemical analysis, and in metabolic studies.

  不含氘的稳定同位素标记致幻剂和/或兴奋剂，含有一个以 2-苯基乙胺为基础的结构单元，并含有至少三个从 13C、15N 和 18O 组成的组中选出的稳定同位素作为游离碱及其盐；其制备方法及其在化学分析（特别是法医化学分析）和新陈代谢研究中的用途。