1-methoxy-3-aminomethylidene-2-oxoindole | 253599-68-7

• 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: 1-methoxy-3-aminomethylidene-2-oxoindole
• 英文别名: (3Z)-3-(aminomethylidene)-1-methoxyindol-2-one
• CAS: 253599-68-7
• 化学式: C₁₀H₁₀N₂O₂
• 分子量: 190.202
• InChiKey: BJKZSDYFRNEROJ-VURMDHGXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.89
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.56
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-methoxy-3-aminomethylidene-2-oxoindole 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 1-methoxy-3-aminomethylene-2-oxindole dithiocarbamate
  参考文献：
  名称：

  Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity

  摘要：

  Phytoalexins are inducible chemical defenses produced by plants in response to diverse forms of stress, including microbial attack. Our search for phytoalexins from cruciferous plants resistant to economically important fungal diseases led us to examine stinkweed or pennycress (Thlaspi arvense), a potential source of disease resistance to blackleg. We have investigated phytoalexin production in leaves of T. arvense under abiotic (copper chloride) and biotic elicitation by Leptosphaeria maculans (Desm.) Ces. et de Not. [asexual stage Phoma lingam (Tode ex Fr.) Desm.], and report here two phytoalexins, wasalexin A and arvelexin (4-methoxyindolyl-3-acetonitrile), their syntheses and antifungal activity against isolates of P. lingam/L. maculans, as well as the isolation of isovitexin, a constitutive glycosyl flavonoid of stinkweed, having antioxidant properties but devoid of antifungal activity. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(03)00441-2
• 作为产物：
  描述：

  1-methoxy-3-chloromethylidene-2-oxoindole 在 ammonium hydroxide 作用下， 以94%的产率得到1-methoxy-3-aminomethylidene-2-oxoindole
  参考文献：
  名称：

  Wasalexins A和B，来自芥末的新植物抗毒素：分离，合成和抗真菌活性。

  摘要：

  芥蓝（Wasabia japonica，同种Eutrema wasabi）中两种植物抗毒素的化学结构测定，芥蓝对黑腿真菌[Leptosphaeria maculans（Desm。）Ces。等人，无性阶段Phoma lingam（Tode ex Fr.）Desm。]，以及它们的合成和对P. lingam和山葵假单胞菌的分离物的抗真菌活性已有报道。

  DOI：

  10.1016/s0960-894x(99)00523-5

文献信息

• Wasalexins A and B, new phytoalexins from wasabi: Isolation, synthesis, and antifungal activity
  作者：M. Soledade C. Pedras、John L. Sorensen、Francis I. Okanga、Irina L. Zaharia

  DOI：10.1016/s0960-894x(99)00523-5

  日期：1999.10

  Eutrema wasabi), a plant resistant to virulent isolates of the blackleg fungus [Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode ex Fr.) Desm.], as well as their synthesis and antifungal activity towards isolates of P. lingam and P. wasabiae is reported.

  芥蓝（Wasabia japonica，同种Eutrema wasabi）中两种植物抗毒素的化学结构测定，芥蓝对黑腿真菌[Leptosphaeria maculans（Desm。）Ces。等人，无性阶段Phoma lingam（Tode ex Fr.）Desm。]，以及它们的合成和对P. lingam和山葵假单胞菌的分离物的抗真菌活性已有报道。
• Phytoalexins from Thlaspi arvense, a wild crucifer resistant to virulent Leptosphaeria maculans: structures, syntheses and antifungal activity
  作者：M.S.C. Pedras、P.B. Chumala、M. Suchy

  DOI：10.1016/s0031-9422(03)00441-2

  日期：2003.11

  Phytoalexins are inducible chemical defenses produced by plants in response to diverse forms of stress, including microbial attack. Our search for phytoalexins from cruciferous plants resistant to economically important fungal diseases led us to examine stinkweed or pennycress (Thlaspi arvense), a potential source of disease resistance to blackleg. We have investigated phytoalexin production in leaves of T. arvense under abiotic (copper chloride) and biotic elicitation by Leptosphaeria maculans (Desm.) Ces. et de Not. [asexual stage Phoma lingam (Tode ex Fr.) Desm.], and report here two phytoalexins, wasalexin A and arvelexin (4-methoxyindolyl-3-acetonitrile), their syntheses and antifungal activity against isolates of P. lingam/L. maculans, as well as the isolation of isovitexin, a constitutive glycosyl flavonoid of stinkweed, having antioxidant properties but devoid of antifungal activity. (C) 2003 Elsevier Ltd. All rights reserved.