6-chloro-3-iminoindolin-2-one | 1261152-95-7

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 6-chloro-3-iminoindolin-2-one
• 英文别名: 6-chloro-3-imino-1H-indol-2-one
• CAS: 1261152-95-7
• 化学式: C₈H₅ClN₂O
• 分子量: 180.593
• InChiKey: WMJZIPHBFLQSNV-UHFFFAOYSA-N

物化性质

• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  53
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-chloro-3-iminoindolin-2-one 在 硫酸 、 水 、 sodium acetate 、 一水合肼 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 4.0h， 生成 (E)-6-chloro-3-[[4-(methylsulfonyl)phenyl]methylene]indolin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors

  摘要：

  Fourteen new 3-[4-(amino/methylsulfonyl) phenyl]methylene-indolin-2-one derivatives were synthesized. Six compounds displayed potent inhibitory activities against COX-1/2 and 5-LOX with IC(50) in the range of 0.10-9.87 mu M. Particularly, 10f exhibited well balanced inhibitory action on these enzymes (IC(50) = 0.10-0.56 mu M). More importantly, 10f and several other compounds had comparable or stronger anti-inflammatory and analgesic activities, but better gastric tolerability in vivo, as compared with darbufelone mesilate and tenidap sodium. Therefore, our findings may aid in the design of new and safe anti-inflammatory reagents for the intervention of painful inflammatory diseases, such as rheumatoid arthritis at clinic. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.056
• 作为产物：
  描述：

  Ν-(3-chlorophenyl)-2-hydroxyiminoacetamide 在 硫酸 作用下， 生成 6-chloro-3-iminoindolin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 3-[4-(amino/methylsulfonyl)phenyl]methylene-indolin-2-one derivatives as novel COX-1/2 and 5-LOX inhibitors

  摘要：

  Fourteen new 3-[4-(amino/methylsulfonyl) phenyl]methylene-indolin-2-one derivatives were synthesized. Six compounds displayed potent inhibitory activities against COX-1/2 and 5-LOX with IC(50) in the range of 0.10-9.87 mu M. Particularly, 10f exhibited well balanced inhibitory action on these enzymes (IC(50) = 0.10-0.56 mu M). More importantly, 10f and several other compounds had comparable or stronger anti-inflammatory and analgesic activities, but better gastric tolerability in vivo, as compared with darbufelone mesilate and tenidap sodium. Therefore, our findings may aid in the design of new and safe anti-inflammatory reagents for the intervention of painful inflammatory diseases, such as rheumatoid arthritis at clinic. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.10.056

文献信息

• Catalytic Enantioselective Decarboxylative Mannich-Type Reaction of <i>N</i>-Unprotected Isatin-Derived Ketimines
  作者：Masanao Sawa、Shotaro Miyazaki、Ryohei Yonesaki、Hiroyuki Morimoto、Takashi Ohshima

  DOI：10.1021/acs.orglett.8b02306

  日期：2018.9.7

  The first catalytic enantioselective decarboxylative Mannich-type reaction of N-unprotected ketimines is reported, directly providing N-unprotected 3-tetrasubstituted 3-aminooxindoles in high yield and ee without protection/deprotection steps. The utility of this reaction is demonstrated in the short step synthesis of (+)-AG-041R.

  报道了N-未保护的酮亚胺的第一个催化对映选择性脱羧曼尼希型反应，无需保护/去保护步骤即可直接以高收率和ee提供N-未保护的3-四取代的3-氨基羟吲哚。该反应的实用性在（+）-AG-041R的短步合成中得到证明。