(1E, 4E)-1-(phenylamino)-1-(methylthio)-5-(3,4,5-trimethoxyphenyl)-penta-1,4-dien-3-one | 1443533-78-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (1E, 4E)-1-(phenylamino)-1-(methylthio)-5-(3,4,5-trimethoxyphenyl)-penta-1,4-dien-3-one
• 英文别名: (1E,4E)-1-anilino-1-methylsulfanyl-5-(3,4,5-trimethoxyphenyl)penta-1,4-dien-3-one
• CAS: 1443533-78-5
• 化学式: C₂₁H₂₃NO₄S
• 分子量: 385.484
• InChiKey: ANTJMCLNSKHFEM-KCIHDACCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4,4-bis(methylthio)but-3-en-2-one 在 potassium hydroxide 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 30.0h， 生成 (1E, 4E)-1-(phenylamino)-1-(methylthio)-5-(3,4,5-trimethoxyphenyl)-penta-1,4-dien-3-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a novel series of aryl S,N-ketene acetals as antileishmanial agents

  摘要：

  A series of aryl S,N-ketene acetals 7(a-f) was synthesized and evaluated for their in vitro and in vivo antileishmanial activity against Leishmania donovani. All the 6 compounds exhibited significant in vitro activity against intracellular amastigotes of L. donovani with IC50 values ranging from 1.2 to 3.5 mu M and were found promising as compared with reference drugs, sodium stibogluconate (SSG) and paromomycin. On the basis of good selectivity indices (SI), they were further tested for their in vivo potential against L. donovani/hamster model. Two compounds 7a and 7b showed significant inhibition of parasite multiplication, 72% and 83%, respectively. These compounds were comparable with SSG and superior to paromomycin. Preliminary in vitro metabolic investigations were also performed to assess the metabolic stability and in vitro hepatic intrinsic clearance (Cl-int) of compound 7b in hamster liver microsomes. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.025

文献信息

• Synthesis and biological evaluation of a novel series of aryl S,N-ketene acetals as antileishmanial agents
  作者：S.N. Suryawanshi、Santosh Kumar、Avinash Tiwari、Rahul Shivahare、Yashpal Singh Chhonker、Susmita Pandey、Nishi Shakya、Rabi Sankar Bhatta、Suman Gupta

  DOI：10.1016/j.bmcl.2013.04.025

  日期：2013.7

  A series of aryl S,N-ketene acetals 7(a-f) was synthesized and evaluated for their in vitro and in vivo antileishmanial activity against Leishmania donovani. All the 6 compounds exhibited significant in vitro activity against intracellular amastigotes of L. donovani with IC50 values ranging from 1.2 to 3.5 mu M and were found promising as compared with reference drugs, sodium stibogluconate (SSG) and paromomycin. On the basis of good selectivity indices (SI), they were further tested for their in vivo potential against L. donovani/hamster model. Two compounds 7a and 7b showed significant inhibition of parasite multiplication, 72% and 83%, respectively. These compounds were comparable with SSG and superior to paromomycin. Preliminary in vitro metabolic investigations were also performed to assess the metabolic stability and in vitro hepatic intrinsic clearance (Cl-int) of compound 7b in hamster liver microsomes. (c) 2013 Elsevier Ltd. All rights reserved.