3,5-diacetylphenyl isocyanate | 169764-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-diacetylphenyl isocyanate
• 英文别名: 1-(3-acetyl-5-isocyanatophenyl)ethanone
• CAS: 169764-78-7
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: CBRZCPFSYADNNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,5-diacetylphenyl isocyanate 在 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-(3,5-Diacetyl-phenyl)-3-{3-[(2S,4R)-4-(4-fluoro-benzyl)-piperidin-2-yl]-propyl}-urea
  参考文献：
  名称：

  2,4-Disubstituted piperidines as selective CC chemokine receptor 3 (CCR3) antagonists: Synthesis and selectivity

  摘要：

  Linear unselective CCR3 antagonist leads with IC50 values in the 200 nM range were converted into low nM binding compounds selective at CCR3 by moving the piperidine nitrogen substituent to the carbon at the 2-position of the ring. Substitution of the piperidine nitrogen with simple alkyl and acyl groups was found to improve the selectivity of this new compound class. In particular, N-{3-[(2S, 4R)-1-(propyl)-4-(4-fluorobenzyl)piperidinyl]propyl}-N'-(3-acetylphenyl)urea exhibited single digit nanomolar IC50 values for CCR3 with > 100-fold selectivity against an extensive counter screen panel. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.08.012
• 作为产物：
  描述：

  三光气 、 3,5-diacetyl aniline 以 甲苯 为溶剂， 生成 3,5-diacetylphenyl isocyanate
  参考文献：
  名称：

  Guanylhydrazones and their use to treat inflammatory conditions

  摘要：

  这项发明涉及新的方法和组合物，可用于预防和改善消瘦症，即与癌症和其他慢性疾病相关的营养状况不佳和身体消耗的临床综合征。更具体地，该发明涉及芳香基胍基脲（更确切地称为胍基脲）组合物及其用于抑制巨噬细胞对精氨酸的摄取和/或其转化为尿素。这些组合物和方法还可用于预防细胞产生一氧化氮（NO），从而预防需要相同的人体内的NO介导的炎症和其他反应。在另一实施例中，这些化合物可用于抑制精氨酸依赖性肿瘤和感染中的精氨酸摄取。

  公开号：

  US05750573A1

文献信息

• Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency
  作者：George V. De Lucca、Ui Tae Kim、Brian J. Vargo、John V. Duncia、Joseph B. Santella、Daniel S. Gardner、Changsheng Zheng、Ann Liauw、Zhang Wang、George Emmett、Dean A. Wacker、Patricia K. Welch、Maryanne Covington、Nicole C. Stowell、Eric A. Wadman、Anuk M. Das、Paul Davies、Swamy Yeleswaram、Danielle M. Graden、Kimberly A. Solomon、Robert C. Newton、George L. Trainor、Carl P. Decicco、Soo. S. Ko

  DOI：10.1021/jm049530m

  日期：2005.3.1

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.
• Guanylhydrazones for treating inflammatory conditions
  申请人：Cytokine PharmaSciences, Inc.

  公开号：EP1160240B1

  公开（公告）日：2006-11-22
• US06180676B2
  申请人：——

  公开号：——

  公开（公告）日：——
• GUANYLHYDRAZONES FOR TREATING INFLAMMATORY CONDITIONS
  申请人：THE PICOWER INSTITUTE FOR MEDICAL RESEARCH

  公开号：EP0746312B1

  公开（公告）日：2002-09-25
• EP0746312A4
  申请人：——

  公开号：EP0746312A4

  公开（公告）日：1999-05-26