(3-((3-butyl-1,2,4-oxadiazol-5-yl)methyl)-7-methyl-1,1-dioxidobenzo[d]isothiazol-2(3H)-yl)(3-(trifluoromethyl)phenyl)methanone

• 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-((3-butyl-1,2,4-oxadiazol-5-yl)methyl)-7-methyl-1,1-dioxidobenzo[d]isothiazol-2(3H)-yl)(3-(trifluoromethyl)phenyl)methanone
• 英文别名: [3-[(3-butyl-1,2,4-oxadiazol-5-yl)methyl]-7-methyl-1,1-dioxo-3H-1,2-benzothiazol-2-yl]-[3-(trifluoromethyl)phenyl]methanone
• 化学式: C₂₃H₂₂F₃N₃O₄S
• 分子量: 493.507
• InChiKey: BOZOOQCBHOFXBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  34
• 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：
  102
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  邻,对甲苯磺酰胺 在 草酰氯 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 copper diacetate 、 potassium carbonate 、 三乙胺 、 N,N-二甲基甲酰胺 、 三氟乙酸 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 1.0h， 生成 (3-((3-butyl-1,2,4-oxadiazol-5-yl)methyl)-7-methyl-1,1-dioxidobenzo[d]isothiazol-2(3H)-yl)(3-(trifluoromethyl)phenyl)methanone
  参考文献：
  名称：

  Identification of benzofused five-membered sultams, potent dual NOD1/NOD2 antagonists in vitro and in vivo

  摘要：

  Nucleotide-binding oligomerization domain-containing proteins 1 and 2 play important roles in immune system activation. Recently, a shift has occurred due to the emerging knowledge that preventing nucleotide-binding oligomerization domains (NODs) signaling could facilitate the treatment of some cancers, which warrants the search for dual antagonists of NOD1 and NOD2. Herein, we undertook the synthesis and identification of a new class of derivatives of dual NOD1/NOD2 antagonists with novel benzofused five-membered sultams. Compound 14k was finally demonstrated to be the most potent molecule that inhibits both NOD1-and NOD2-stimulated NF-kappa B and MAPK signaling in vitro and in vivo. (C) 2020 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2020.112575

文献信息

• Identification of benzofused five-membered sultams, potent dual NOD1/NOD2 antagonists in vitro and in vivo
  作者：Yao Ma、Xueyuan Li、Yameng Pei、Jingjia Ye、Xiduan Wei、Jingshu Yang、Guangxu Si、Jingyuan Tian、Yi Dong、Gang Liu

  DOI：10.1016/j.ejmech.2020.112575

  日期：2020.10

  Nucleotide-binding oligomerization domain-containing proteins 1 and 2 play important roles in immune system activation. Recently, a shift has occurred due to the emerging knowledge that preventing nucleotide-binding oligomerization domains (NODs) signaling could facilitate the treatment of some cancers, which warrants the search for dual antagonists of NOD1 and NOD2. Herein, we undertook the synthesis and identification of a new class of derivatives of dual NOD1/NOD2 antagonists with novel benzofused five-membered sultams. Compound 14k was finally demonstrated to be the most potent molecule that inhibits both NOD1-and NOD2-stimulated NF-kappa B and MAPK signaling in vitro and in vivo. (C) 2020 Elsevier Masson SAS. All rights reserved.