3-(3,4-dichlorobenzylidene)-6-methoxy-oxindole | 114727-46-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(3,4-dichlorobenzylidene)-6-methoxy-oxindole
• 英文别名: 3-[(3,4-dichlorophenyl)methylidene]-6-methoxy-1H-indol-2-one
• CAS: 114727-46-7
• 化学式: C₁₆H₁₁Cl₂NO₂
• 分子量: 320.175
• InChiKey: FZJBOSJAIXLMEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorobenzylidene)-6-methoxy-oxindole 在 palladium on activated charcoal 氢气 、 sodium hydride 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 3.75h， 生成 2-[3-[(3,4-dichlorophenyl)methyl]-6-methoxy-2-oxo-3H-indol-1-yl]acetic acid
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of substituted 2(1H)-benzimidazolone- and oxindole-1-acetic acids

  摘要：

  Potent in vitro inhibition of the enzyme aldose reductase (AR) was observed with several members of a series of 3-alkylated 2(1H)-benzimidazolone-1-acetic acids, as well as with analogs from a structurally-related series of oxindole-1-acetic acids with 3-alkyl or 3-alkylidene substituents. Intrinsic activity against AR was, in general, greatest in compounds from the second series, especially with analogs which contain alkylidene side chains, with typical IC50 values of less-than-or-equal-to 1 muM. However, in a streptozotocin-diabetic rat model, the best compounds from either series failed to prevent sorbitol accumulation in lens or sciatic nerve to the degree observed with AR inhibitors such as ponalrestat or zopolrestat.

  DOI：

  10.1016/0223-5234(92)90112-e
• 作为产物：
  描述：

  6-甲氧基-2-氧化吲哚 、 3,4-二氯苯甲醛 在 四氢吡咯 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以85%的产率得到3-(3,4-dichlorobenzylidene)-6-methoxy-oxindole
  参考文献：
  名称：

  Synthesis and aldose reductase inhibitory activity of substituted 2(1H)-benzimidazolone- and oxindole-1-acetic acids

  摘要：

  Potent in vitro inhibition of the enzyme aldose reductase (AR) was observed with several members of a series of 3-alkylated 2(1H)-benzimidazolone-1-acetic acids, as well as with analogs from a structurally-related series of oxindole-1-acetic acids with 3-alkyl or 3-alkylidene substituents. Intrinsic activity against AR was, in general, greatest in compounds from the second series, especially with analogs which contain alkylidene side chains, with typical IC50 values of less-than-or-equal-to 1 muM. However, in a streptozotocin-diabetic rat model, the best compounds from either series failed to prevent sorbitol accumulation in lens or sciatic nerve to the degree observed with AR inhibitors such as ponalrestat or zopolrestat.

  DOI：

  10.1016/0223-5234(92)90112-e

文献信息

• Synthesis and aldose reductase inhibitory activity of substituted 2(1H)-benzimidazolone- and oxindole-1-acetic acids
  作者：HR Howard、R Sarges、TW Siegel、TA Beyer

  DOI：10.1016/0223-5234(92)90112-e

  日期：1992.11

  Potent in vitro inhibition of the enzyme aldose reductase (AR) was observed with several members of a series of 3-alkylated 2(1H)-benzimidazolone-1-acetic acids, as well as with analogs from a structurally-related series of oxindole-1-acetic acids with 3-alkyl or 3-alkylidene substituents. Intrinsic activity against AR was, in general, greatest in compounds from the second series, especially with analogs which contain alkylidene side chains, with typical IC50 values of less-than-or-equal-to 1 muM. However, in a streptozotocin-diabetic rat model, the best compounds from either series failed to prevent sorbitol accumulation in lens or sciatic nerve to the degree observed with AR inhibitors such as ponalrestat or zopolrestat.