1-methoxy-3-aminomethylene-2-oxindole dithiocarbamate | 637777-91-4

• 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-aminomethylene-2-oxindole dithiocarbamate
• 英文别名: methyl N-[(Z)-(1-methoxy-2-oxoindol-3-ylidene)methyl]carbamodithioate
• CAS: 637777-91-4
• 化学式: C₁₂H₁₂N₂O₂S₂
• 分子量: 280.371
• InChiKey: IYAVFZFWJZTQSY-CLFYSBASSA-N

物化性质

• 熔点：
  140-141 °C(Solvent: Acetone ; Hexane)
• 沸点：
  392.2±52.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-methoxy-3-aminomethylene-2-oxindole dithiocarbamate 在 sodium cyanoborohydride 作用下， 以 溶剂黄146 为溶剂， 反应 18.0h， 以63%的产率得到S-methyl 1-methoxy-3-aminomethyl-2-oxindole dithiocarbamate
  参考文献：
  名称：

  十字花科植物抗毒素Wasalexin A和B在植物病原性真菌Leptosphaeria maculans中的代谢。

  摘要：

  Wasalexins A和B是十字花科植物抗毒素，由两种基本不同的植物物种产生，加拿大的大草原上盛产一种野生物种，而日本则广泛种植一种调味品植物。有趣的是，两种植物都对经济上重要的真菌植物病原体黑腿真菌[Leptosphaeria maculans（Desm。）Ces。等，无性，Phoma lingam（Tode ex Fr.）Desm。]。研究了黄腐乳杆菌，对菜籽油有高毒力的菌株（BJ 125）和对芥末有毒力的较不常见的菌株（Laird 2 / Mayfair 2）中芥菜毒素A和B的转化。已经确定，两种真菌分离物均能够通过在异蜡毒素A的情况下还原或通过水解然后在异蜡毒素B的情况下还原而有效地代谢和分解毒素，从而有效地代谢和解毒。并非自然发生的，还发现其在黄斑狼疮的培养物中减少了。使用光谱方法阐明了新的代谢产物的结构，并通过合成进行了确认。生物测定法表明，芥子毒素的生物转化是一种解毒过程，

  DOI：

  10.1039/b609367a
• 作为产物：
  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

文献信息

• 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.
• Metabolism of the crucifer phytoalexins wasalexin A and B in the plant pathogenic fungus Leptosphaeria maculans
  作者：M. Soledade C. Pedras、Mojm?r Such?

  DOI：10.1039/b609367a

  日期：——

  Wasalexins A and B are crucifer phytoalexins produced by two substantially different plant species, a wild species abundant in the Canadian prairies and a condiment plant widely cultivated in Japan. Interestingly, both plant species are resistant to an economically important fungal plant pathogen, the blackleg fungus [Leptosphaeria maculans (Desm.) Ces. et de Not., asexual stage Phoma lingam (Tode

  Wasalexins A和B是十字花科植物抗毒素，由两种基本不同的植物物种产生，加拿大的大草原上盛产一种野生物种，而日本则广泛种植一种调味品植物。有趣的是，两种植物都对经济上重要的真菌植物病原体黑腿真菌[Leptosphaeria maculans（Desm。）Ces。等，无性，Phoma lingam（Tode ex Fr.）Desm。]。研究了黄腐乳杆菌，对菜籽油有高毒力的菌株（BJ 125）和对芥末有毒力的较不常见的菌株（Laird 2 / Mayfair 2）中芥菜毒素A和B的转化。已经确定，两种真菌分离物均能够通过在异蜡毒素A的情况下还原或通过水解然后在异蜡毒素B的情况下还原而有效地代谢和分解毒素，从而有效地代谢和解毒。并非自然发生的，还发现其在黄斑狼疮的培养物中减少了。使用光谱方法阐明了新的代谢产物的结构，并通过合成进行了确认。生物测定法表明，芥子毒素的生物转化是一种解毒过程，