3-[[1,1-dioxo-4-[(1R)-1-phenylpropyl]imino-1,2,5-thiadiazol-3-yl]amino]-2-hydroxy-N,N-dimethylbenzamide | 681510-51-0

• 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-[[1,1-dioxo-4-[(1R)-1-phenylpropyl]imino-1,2,5-thiadiazol-3-yl]amino]-2-hydroxy-N,N-dimethylbenzamide
• CAS: 681510-51-0
• 化学式: C₂₀H₂₃N₅O₄S
• 分子量: 429.5
• InChiKey: ZMNXZNXBUAETLC-OAHLLOKOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  132
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[(4-Ethoxy-1,1-dioxido-1,2,5-thiadiazol-3-yl)amino]-2-hydroxy-N,N-dimethylbenzamide 、 (R)-(+)-1-苯丙胺 在 N,N-二异丙基乙胺 作用下， 反应 12.0h， 以80%的产率得到3-[[1,1-dioxo-4-[(1R)-1-phenylpropyl]imino-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

文献信息

• Thiadiazoledioxides and thiadiazoleoxides as CXC- and CC-chemokine receptor ligands
  申请人：Taveras G. Arthur

  公开号：US20070264230A1

  公开（公告）日：2007-11-15

  Disclosed are novel compounds of the formula: and the pharmaceutically acceptable salts and solvates thereof. Examples of groups comprising Substituent A include heteroaryl, aryl, heterocycloalkyl, cycloalkyl, aryl, alkynyl, alkenyl, aminoalkyl, alkyl or amino. Examples of groups comprising Substituent B include aryl and heteroaryl. Also disclosed is a method of treating a chemokine mediated diseases, such as, cancer, angiogenisis, angiogenic ocular diseases, pulmonary diseases, multiple sclerosis, rheumatoid arthritis, osteoarthritis, stroke and cardiac reperfusion injury, acute pain, acute and chronic inflammatory pain, and neuropathic pain using a compound of formula IA.

  揭示了具有以下结构的新化合物：以及其药物可接受的盐和溶剂化物。包括取代基A的基团的例子包括杂环芳基，芳基，杂环烷基，环烷基，炔基，烯基，氨基烷基，烷基或氨基。包括取代基B的基团的例子包括芳基和杂环芳基。此外，还揭示了使用式IA的化合物治疗趋化因子介导的疾病的方法，例如，癌症，血管生成，血管生成性眼部疾病，肺部疾病，多发性硬化症，类风湿性关节炎，骨关节炎，中风和心脏再灌注损伤，急性疼痛，急性和慢性炎症性疼痛以及神经病理性疼痛。
• THIADIAZOLEDIOXIDES AND THIADIAZOLEOXIDES AS CXC- AND CC-CHEMOKINE RECEPTOR LIGANDS
  申请人：Schering Corporation

  公开号：EP1551818B1

  公开（公告）日：2009-02-04
• US7691856B2
  申请人：——

  公开号：US7691856B2

  公开（公告）日：2010-04-06
• 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.