3-acetyl-2,2-dimethyl-5-(5-methoxy-2-nitrophenyl)-2,3-dihydro-1,3,4-thiadiazole | 1370029-90-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-acetyl-2,2-dimethyl-5-(5-methoxy-2-nitrophenyl)-2,3-dihydro-1,3,4-thiadiazole
• 英文别名: 1-[5-(5-Methoxy-2-nitrophenyl)-2,2-dimethyl-1,3,4-thiadiazol-3-yl]ethanone
• CAS: 1370029-90-5
• 化学式: C₁₃H₁₅N₃O₄S
• 分子量: 309.346
• InChiKey: LPAZSDDAYYTMOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-acetyl-2,2-dimethyl-5-(5-methoxy-2-nitrophenyl)-2,3-dihydro-1,3,4-thiadiazole 在 乙醇 、 tin(ll) chloride 、 碳酸氢钠 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以95%的产率得到3-acetyl-5-(2-amino-5-methoxyphenyl)-2,2-dimethyl-2,3-dihydro-1,3,4-thiadiazole
  参考文献：
  名称：

  1,3,4-Thiadiazole derivatives as selective inhibitors of iNOS versus nNOS: Synthesis and structure-activity dependence

  摘要：

  The synthesis of new compounds with a 1,3,4-thiadiazole structure, and their in vitro biological evaluation as inhibitors of both neuronal and inducible Nitric Oxide Synthase (nNOS and iNOS) is described. These compounds have been designed by an isosteric modification of a series of 4,5-dihydro-1H-pyrazole derivatives, previously described as the nNOS inhibitors. The insertion of the S atom in the heterocyclic ring induces a selective inhibition of the iNOS isoform. Some of these compounds show as iNOS inhibition percentage near of 100% at a concentration of 50 mu M, and the IC50 values measured for the more potent compounds are in a range of 20-40 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.047
• 作为产物：
  描述：

  5-甲氧基-2-硝基苯甲酸 在 劳森试剂 、 硫酸 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 对二甲苯 为溶剂， 反应 38.0h， 生成 3-acetyl-2,2-dimethyl-5-(5-methoxy-2-nitrophenyl)-2,3-dihydro-1,3,4-thiadiazole
  参考文献：
  名称：

  1,3,4-Thiadiazole derivatives as selective inhibitors of iNOS versus nNOS: Synthesis and structure-activity dependence

  摘要：

  The synthesis of new compounds with a 1,3,4-thiadiazole structure, and their in vitro biological evaluation as inhibitors of both neuronal and inducible Nitric Oxide Synthase (nNOS and iNOS) is described. These compounds have been designed by an isosteric modification of a series of 4,5-dihydro-1H-pyrazole derivatives, previously described as the nNOS inhibitors. The insertion of the S atom in the heterocyclic ring induces a selective inhibition of the iNOS isoform. Some of these compounds show as iNOS inhibition percentage near of 100% at a concentration of 50 mu M, and the IC50 values measured for the more potent compounds are in a range of 20-40 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.047

文献信息

• 1,3,4-Thiadiazole derivatives as selective inhibitors of iNOS versus nNOS: Synthesis and structure-activity dependence
  作者：Luisa C. López-Cara、M. Dora Carrión、Antonio Entrena、Miguel A. Gallo、Antonio Espinosa、Ana López、Germaine Escames、Darío Acuña-Castroviejo、M. Encarnación Camacho

  DOI：10.1016/j.ejmech.2012.01.047

  日期：2012.4

  The synthesis of new compounds with a 1,3,4-thiadiazole structure, and their in vitro biological evaluation as inhibitors of both neuronal and inducible Nitric Oxide Synthase (nNOS and iNOS) is described. These compounds have been designed by an isosteric modification of a series of 4,5-dihydro-1H-pyrazole derivatives, previously described as the nNOS inhibitors. The insertion of the S atom in the heterocyclic ring induces a selective inhibition of the iNOS isoform. Some of these compounds show as iNOS inhibition percentage near of 100% at a concentration of 50 mu M, and the IC50 values measured for the more potent compounds are in a range of 20-40 mu M. (C) 2012 Elsevier Masson SAS. All rights reserved.