5-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dichlorophenyl)-1,2,4-oxadiazol-3-amine | 1269775-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 5-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dichlorophenyl)-1,2,4-oxadiazol-3-amine
• 英文别名: 5-(1,3-benzodioxol-5-yl)-N-(3,4-dichlorophenyl)-1,2,4-oxadiazol-3-amine
• CAS: 1269775-39-4
• 化学式: C₁₅H₉Cl₂N₃O₃
• 分子量: 350.161
• InChiKey: LBHMEWRYOZNMST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  69.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(benzo[d][1,3]dioxole-6-carbonyl)-3-(3,4-dichlorophenyl)guanidine 在 sodium hypochlorite 、 水 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以16 mg的产率得到5-(benzo[d][1,3]dioxol-5-yl)-N-(3,4-dichlorophenyl)-1,2,4-oxadiazol-3-amine
  参考文献：
  名称：

  Discovery, Optimization, and Pharmacological Characterization of Novel Heteroaroylphenylureas Antagonists of C−C Chemokine Ligand 2 Function

  摘要：

  Through the application of TRAP (target-related affinity profiling), we identified a novel class of heteroaroylphenylureas that inhibit human CCL2-induced chemotaxis of monocytes/macrophages both in vitro and in vivo. This inhibition was concentration-dependent and selective with regard to other chemokines. The compounds, however, did not antagonize the binding of I-125-labeled CCL2 to the CCR2 receptor nor did they block CCR2-mediated signal transduction responses such as calcium mobilization. Optimization of early leads for potency and pharmacokinetic parameters resulted in the identification of 17, a potent inhibitor of chemotaxis (IC50 = 80 nM) with excellent oral bioavailability in rats (F = 60%). Compound 17 reduced swelling and joint destruction in two rat models of rheumatoid arthritis and delayed disease onset and produced near complete resolution of symptoms in a mouse model of multiple sclerosis.

  DOI：

  10.1021/jm1012903