isobrassinin | 881853-68-5

• 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: isobrassinin
• 英文别名: Carbamodithioic acid, (1H-indol-2-ylmethyl)-, methyl ester；methyl N-(1H-indol-2-ylmethyl)carbamodithioate
• CAS: 881853-68-5
• 化学式: C₁₁H₁₂N₂S₂
• 分子量: 236.362
• InChiKey: XXVHTDZCNVORLP-UHFFFAOYSA-N

物化性质

• 熔点：
  82-84 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  436.9±47.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  isobrassinin 在 phenyltrimethylammonium tribromide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以76%的产率得到3-Methylsulfanyl-1,9-dihydro-4-thia-2,9-diaza-fluorene
  参考文献：
  名称：

  Isobrassinin and its analogues: Novel types of antiproliferative agents

  摘要：

  Isobrassinin (2-(S-methyidithiocarbamoylaminomethyl)indole (7a), a regioisomer of the cruciferous phytoalexin brassinin (1), exerted marked antiproliferative effects on the HeLa, A431 and MCF7 cell lines (> 78.6% inhibition at 30 mu M). For structure-activity relationships, further analogues were synthesized. The highest cytotoxic effect was displayed by 2-phenylimino-1,3-thiazino[5.6-b]indole (10) (10 mu M, 76.8%-HeLa and 46.3% -MCF7). The effect of the natural phytoalexin brassinin was also determined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.016
• 作为产物：
  描述：

  1H-吲哚-2-羧酰胺 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 5.0h， 生成 isobrassinin
  参考文献：
  名称：

  Isobrassinin and its analogues: Novel types of antiproliferative agents

  摘要：

  Isobrassinin (2-(S-methyidithiocarbamoylaminomethyl)indole (7a), a regioisomer of the cruciferous phytoalexin brassinin (1), exerted marked antiproliferative effects on the HeLa, A431 and MCF7 cell lines (> 78.6% inhibition at 30 mu M). For structure-activity relationships, further analogues were synthesized. The highest cytotoxic effect was displayed by 2-phenylimino-1,3-thiazino[5.6-b]indole (10) (10 mu M, 76.8%-HeLa and 46.3% -MCF7). The effect of the natural phytoalexin brassinin was also determined. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.016

文献信息

• Unprecedented chemical structure and biomimetic synthesis of erucalexin, a phytoalexin from the wild crucifer Erucastrum gallicum
  作者：M. Soledade C. Pedras、Mojmir Suchy、Pearson W. K. Ahiahonu

  DOI：10.1039/b515331j

  日期：——

  total synthesis and antifungal activity of erucalexin, a novel phytoalexin produced by the wild crucifer dog mustard are described. Erucalexin is a structurally unique plant alkaloid, representing the first example of a spiro[2H-indole-2,5'(4'H)-thiazol]-3-one, likely derived from a C-3-C-2 carbon migration in a 3-substituted indolyl nucleus.

  描述了芥蓝素的分离，结构测定，总合成和抗真菌活性。芥蓝素是野生十字花科狗芥菜产生的一种新型植物抗毒素。芥蓝素是一种结构独特的植物生物碱，代表螺[2H-吲哚-2,5'（4'H）-噻唑] -3-one的第一个实例，可能源自C-3-C-2碳迁移在3-取代的吲哚基核中。
• Metabolism and Metabolites of Dithiocarbamates in the Plant Pathogenic Fungus Leptosphaeria maculans
  作者：M. Soledade C. Pedras、Vijay K. Sarma-Mamillapalle

  DOI：10.1021/jf302038a

  日期：2012.8.15

  Synthetic compounds containing a dithiocarbamate group are known to have a variety of biological effects and applications including antifungal, herbicidal, and insecticidal application. Leptosphaeria maculans is a fungal pathogen of crucifers able to detoxify efficiently the only plant natural product containing a dithiocarbamate group, the phytoalexin brassinin. To evaluate the effects of dithiocarbamates on L. maculans, a number of structurally diverse S-methyl dithiocarbamates containing indolyl, biphenyl, and benzimidazolyl moieties were synthesized, and their antifungal activities and metabolism by L. maculans were investigated. All dithiocarbamates were transformed by L. maculans through hydrolysis to the corresponding amines, which were less antifungal than the parent compounds. Two dithiocarbonates were shown to be much less antifungal than the corresponding dithiocarbamates. Results of this investigation indicate that S-methyl dithiocarbamates are not useful inhibitors of L. maculans and that their rates of transformation by L. maculans did not correlate with the antifungal activity of the particular compound.
• METHOD FOR INHIBITING BRASSININ OXIDASE
  申请人：Pedras M. Soledade C.

  公开号：US20100317703A1

  公开（公告）日：2010-12-16

  The present disclosure relates to a method for inhibiting brassinin oxidase comprising treating a pathogen that is producing BO with an effective amount of selected Paldoxin compounds.
• Isobrassinin and its analogues: Novel types of antiproliferative agents
  作者：Péter Csomós、István Zupkó、Borbála Réthy、Lajos Fodor、George Falkay、Gábor Bernáth

  DOI：10.1016/j.bmcl.2006.09.016

  日期：2006.12

  Isobrassinin (2-(S-methyidithiocarbamoylaminomethyl)indole (7a), a regioisomer of the cruciferous phytoalexin brassinin (1), exerted marked antiproliferative effects on the HeLa, A431 and MCF7 cell lines (> 78.6% inhibition at 30 mu M). For structure-activity relationships, further analogues were synthesized. The highest cytotoxic effect was displayed by 2-phenylimino-1,3-thiazino[5.6-b]indole (10) (10 mu M, 76.8%-HeLa and 46.3% -MCF7). The effect of the natural phytoalexin brassinin was also determined. (c) 2006 Elsevier Ltd. All rights reserved.