2-hydroxy-N,N-dimethyl-3-[[4-[(1R)-1-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)propyl]imino-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]benzamide | 1007404-16-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 2-hydroxy-N,N-dimethyl-3-[[4-[(1R)-1-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)propyl]imino-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]benzamide
• CAS: 1007404-16-1
• 化学式: C₂₃H₂₈N₆O₅S
• 分子量: 500.579
• InChiKey: MTPPDQAZXQWYES-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  144
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (1R)-1-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)propan-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 2-hydroxy-N,N-dimethyl-3-[[4-[(1R)-1-(4-methyl-2,3-dihydro-1,4-benzoxazin-7-yl)propyl]imino-1,1-dioxo-1,2,5-thiadiazol-3-yl]amino]benzamide
  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

文献信息

• 3,4-Diamino-2,5-thiadiazole-1-oxides as potent CXCR2/CXCR1 antagonists
  作者：Purakkattle Biju、Arthur Taveras、Younong Yu、Junying Zheng、Jianhua Chao、Diane Rindgen、James Jakway、R. William Hipkin、James Fossetta、Xuedong Fan、Jay Fine、Hongchen Qiu、J. Robert Merritt、John J. Baldwin

  DOI：10.1016/j.bmcl.2007.10.094

  日期：2008.1

  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.