3-[(4-Ethoxy-1,1-dioxido-1,2,5-thiadiazol-3-yl)amino]-2-hydroxy-N,N-dimethylbenzamide | 1007404-14-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-[(4-Ethoxy-1,1-dioxido-1,2,5-thiadiazol-3-yl)amino]-2-hydroxy-N,N-dimethylbenzamide
• 英文别名: 3-[(4-ethoxy-1,1-dioxo-1,2,5-thiadiazol-3-yl)amino]-2-hydroxy-N,N-dimethylbenzamide
• CAS: 1007404-14-9
• 化学式: C₁₃H₁₆N₄O₅S
• 分子量: 340.36
• InChiKey: OHLMSSPBMZQBAL-UHFFFAOYSA-N

物化性质

• 沸点：
  510.0±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  129
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (1R)-1-(5-chloro-2-furyl)-2,2-dimethylpropan-1-amine 、 3-[(4-Ethoxy-1,1-dioxido-1,2,5-thiadiazol-3-yl)amino]-2-hydroxy-N,N-dimethylbenzamide 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 3-[[4-[(1R)-1-(5-chlorofuran-2-yl)-2,2-dimethylpropyl]imino-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]-2-hydroxy-N,N-dimethylbenzamide
  参考文献：
  名称：

  3,4-Diamino-2,5-thiadiazole-1-oxides as potent CXCR2/CXCR1 antagonists

  摘要：

  A series of novel and potent 3,4-diamino-2,5-thiadiazole-1-oxides were prepared and found to show excellent binding affinities for CXCR2 and CXCR1 receptors and excellent inhibitory activity of Gro-alpha and IL-8 mediated in vitro hPMN MPO release of CXCR2 and CXCR1 expressing cell lines. On the other hand, a closely related 3,4-diamino-2,5-thiadiazole-dioxide did not show functional activity despite its excellent binding affinities for CXCR2 and CXCR1 in membrane binding assays. A detailed SAR has been discussed in these two closely related structures. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.094
• 作为产物：
  描述：

  3-氨基-2-羟基-N,N-二甲基苯甲酰胺 、 3,4-二乙氧基-1,2,5-噻二唑-1,1-二氧化物 在 N,N-二异丙基乙胺 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以90%的产率得到3-[(4-Ethoxy-1,1-dioxido-1,2,5-thiadiazol-3-yl)amino]-2-hydroxy-N,N-dimethylbenzamide
  参考文献：
  名称：

  3,4-Diamino-2,5-thiadiazole-1-oxides as potent CXCR2/CXCR1 antagonists

  摘要：

  A series of novel and potent 3,4-diamino-2,5-thiadiazole-1-oxides were prepared and found to show excellent binding affinities for CXCR2 and CXCR1 receptors and excellent inhibitory activity of Gro-alpha and IL-8 mediated in vitro hPMN MPO release of CXCR2 and CXCR1 expressing cell lines. On the other hand, a closely related 3,4-diamino-2,5-thiadiazole-dioxide did not show functional activity despite its excellent binding affinities for CXCR2 and CXCR1 in membrane binding assays. A detailed SAR has been discussed in these two closely related structures. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.10.094