3-(2,5-dimethoxyphenyl)-N,N-dimethyl-3-oxo-1-propanamine hydrochloride | 63408-08-2

• 英文名称: 3-(2,5-dimethoxyphenyl)-N,N-dimethyl-3-oxo-1-propanamine hydrochloride
• 英文别名: 1-(2,5-dimethoxy-phenyl)-3-dimethylamino-propan-1-one; hydrochloride；1-(2,5-Dimethoxy-phenyl)-3-dimethylamino-propan-1-on; Hydrochlorid；1-(2,5-Dimethoxyphenyl)-3-(dimethylamino)propan-1-one;hydrochloride
• CAS: 63408-08-2
• 化学式: C₁₃H₁₉NO₃*ClH
• 分子量: 273.76
• InChiKey: VSTMLCCJOXLVCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.26
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2,5-dimethoxyphenyl)-N,N-dimethyl-3-oxo-1-propanamine hydrochloride 在 盐酸 、 水 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 50.0h， 生成 Ethyl 6-(2,5-dimethoxyphenyl)-2-formylpyridine-3-carboxylate
  参考文献：
  名称：

  Graef, Edgar; Troschuetz, Reinhard, Synthesis, 1999, # 7, p. 1216 - 1222

  摘要：

  DOI：

文献信息

• 2-(3-Aryl-3-oxopropen-1-yl)-9-<i>tert</i>-butyl-paullones: A New Antileishmanial Chemotype
  作者：Christina Reichwald、Orly Shimony、Ute Dunkel、Nina Sacerdoti-Sierra、Charles L. Jaffe、Conrad Kunick

  DOI：10.1021/jm7012166

  日期：2008.2.1

  A screening program directed to find new agents against Leishmania donovani, the parasite causing visceral leishmaniasis, revealed that paullones attenuate the proliferation of axenic amastigotes. Because these structures were not active in a test system involving infected macrophages, a structure optimization campaign was carried out. Concomitant introduction of an unsaturated side chain into the 2-position and a tert-butyl substituent into the 9-position of the parent scaffold led to compounds inhibiting also parasites dwelling in macrophages. By inclusion of the so elaborated scaffold into a chalcone substructure, the toxicity against uninfected host cells was significantly reduced. For the synthesis of this new compound class, a novel modification of the Heck-type palladium-catalyzed C,C-cross coupling strategy was used, employing a ketone Mannich base as precursor for the alkene reactant. The so-prepared compounds exhibited improved antileishmanial activity both on axenic amastigotes (GI(50) < 1 mu M) as well as on parasites in infected macrophages.