<2-14C> indole-3-aldehyde | 85619-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: <2-14C> indole-3-aldehyde
• 英文别名: [2-14C]-indole-3-carboxaldehyde；1H-indole-3-carbaldehyde
• CAS: 85619-53-0
• 化学式: C₉H₇NO
• 分子量: 147.15
• InChiKey: OLNJUISKUQQNIM-RHRFEJLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.98
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  32.86
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  <2-14C> indole-3-aldehyde 在 盐酸羟胺 、 sodium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 <2-14C> indole-3-aldehyde oxime
  参考文献：
  名称：

  十字花科植物的化学防御：褐芥菜和萝卜中植物抗毒素和吲哚-3-乙腈的诱导和代谢

  摘要：

  十字花科植物抗毒素芸苔素和环芸苔素以及相关化合物 indole-3-carboxaldehyde、glucobrassicin 和 indole-3-acetaldoxime 的代谢在芥菜和 B. rapa 的各种植物组织中进行了研究。用芸苔素进行的代谢研究表明，芥菜的茎通过 indole-3-carboxaldehyde 将放射性标记的芸苔素代谢为 indole-3-乙酸，这是一种类似于“黑腿病”真菌（Phoma lingam/Leptosphaeria maculans）的解毒途径。此外，已确定四氘化芸苔素被掺入芥菜和油菜中的植物抗毒素芸苔素中。另一方面，四氘代吲哚芥子油苷葡糖苷未掺入芸苔素中，尽管芸苔素和吲哚硫代葡萄糖苷的化学结构表明相互关联的生物发生。重要的是，四氘代吲哚-3-乙醛肟是植物抗毒素芸苔素、芸苔素和螺芸苔素的有效前体。在芥菜和芥菜组织中的诱导实验表明，indole-3-acetonitrile

  DOI：

  10.1016/s0031-9422(02)00026-2
• 作为产物：
  描述：

  [14C-2]indole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 0.75h， 生成 <2-14C> indole-3-aldehyde
  参考文献：
  名称：

  十字花科植物的化学防御：褐芥菜和萝卜中植物抗毒素和吲哚-3-乙腈的诱导和代谢

  摘要：

  十字花科植物抗毒素芸苔素和环芸苔素以及相关化合物 indole-3-carboxaldehyde、glucobrassicin 和 indole-3-acetaldoxime 的代谢在芥菜和 B. rapa 的各种植物组织中进行了研究。用芸苔素进行的代谢研究表明，芥菜的茎通过 indole-3-carboxaldehyde 将放射性标记的芸苔素代谢为 indole-3-乙酸，这是一种类似于“黑腿病”真菌（Phoma lingam/Leptosphaeria maculans）的解毒途径。此外，已确定四氘化芸苔素被掺入芥菜和油菜中的植物抗毒素芸苔素中。另一方面，四氘代吲哚芥子油苷葡糖苷未掺入芸苔素中，尽管芸苔素和吲哚硫代葡萄糖苷的化学结构表明相互关联的生物发生。重要的是，四氘代吲哚-3-乙醛肟是植物抗毒素芸苔素、芸苔素和螺芸苔素的有效前体。在芥菜和芥菜组织中的诱导实验表明，indole-3-acetonitrile

  DOI：

  10.1016/s0031-9422(02)00026-2

文献信息

• Fate of Indole-3-carbinol in Cultured Human Breast Tumor Cells
  作者：Richard E. Staub、Chunling Feng、Bruce Onisko、George S. Bailey、Gary L. Firestone、Leonard F. Bjeldanes

  DOI：10.1021/tx010056m

  日期：2002.2.1

  Indole-3-carbinol (I3C), a natural component of Brassica vegetables, is a promising cancer preventive agent that can reduce the incidence of tumors in reproductive organs when administered in the diet. Here we report on the metabolic fate of radiolabeled I3C in MCF-7 cells. I3C was surprisingly inert to metabolism by these cells with a half-life in medium of approximately 40 h. [H-3]I3C levels in media declined at a similar rate whether incubation was with cultured cells or in cell-free medium. Neither [H-3]I3C nor its modified products accumulated in MCF-7 cells and only low levels of intact I3C were detected in cellular fractions. In contrast, I3C represented over 30% of the radioactivity in media even after 72 h. In cytosolic fractions, the 3-(cystein-S-ylmethyl) and 3-(glutathion-S-ylmethyl) conjugates of [H-3]I3C were the primary conversion products identified after 16 h, representing similar to50% and similar to15% of the radioactivity in these fractions, respectively. The reaction of I3C with thiols appears to be nonenzymatic since the cysteine conjugate is produced when I3C is incubated in cell-free medium containing additional cysteine. Both cellular and extracellular proteins were nonspecifically modified with [3H]I3C. In medium, proteins are radiolabeled even in the absence of cells, indicating again that enzymatic activation was not required. I3C was also oxidized to indole-3-carboxaldehyde and indole-3-carboxylic acid in culture medium independent of cells. Unexpectedly, 3,3'-diindolylmethane (DIM), an I3C product with in vitro and in vivo biological activity, was detected in cellular fractions and appeared to accumulate in the nucleus, representing similar to40% of this fraction after 72 h treatment. These findings suggest that MCF-7 cells do not vigorously metabolize I3C and that the major route of reaction is with cellular thiols such as glutathione and proteins. The accumulation of DIM in the nucleus suggests that this product may have a role in the cellular biological activities of I3C.
• Schallenberg, Juergen; Meyer, Eckart, Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 1, p. 108 - 112
  作者：Schallenberg, Juergen、Meyer, Eckart

  DOI：——

  日期：——
• MORRISON, H.;MOHAMMAD, TAJ;SEVERNS, B., J. LABELL. COMPOUNDS AND RADIOPHARM., 27,(1989) N, C. 565-569
  作者：MORRISON, H.、MOHAMMAD, TAJ、SEVERNS, B.

  DOI：——

  日期：——
• SCHALLENBERG, J.;MEYER, E., Z. NATURFORSCH., 1983, 38, N 1, 108-112
  作者：SCHALLENBERG, J.、MEYER, E.

  DOI：——

  日期：——