[14C-2]indole | 25713-20-6

• 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: [14C-2]indole
• 英文别名: [2-14C]-indole；<2-14C> indole；1H-[2-¹⁴C]indole；<2-¹⁴C>-Indol；1H-Indole-2-14C；1H-indole
• CAS: 25713-20-6
• 化学式: C₈H₇N
• 分子量: 119.139
• InChiKey: SIKJAQJRHWYJAI-ZQBYOMGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  9.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  15.79
• 氢给体数：
  1.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  [14C-2]indole 在 N-溴代丁二酰亚胺(NBS) 、 正丁基锂 、 四丁基氟化铵 、 水 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 正戊烷 为溶剂， 反应 13.25h， 生成 N^α-(2-mercaptoacetyl)-L-[2-¹⁴C]tryptophan
  参考文献：
  名称：

  基于手性池策略的[2-14C]吲哚合成（2-巯基乙酰基）-L-[2-14C]色氨酸作为选择性金属-β-内酰胺酶抑制剂

  摘要：

  金属-β-内酰胺酶使细菌对广泛的常用β-内酰胺抗生素产生抗药性。L-氨基酸的几种硫醇衍生物已显示出它们对金属-β-内酰胺酶 IMP-1 的抑制作用。在这项研究中，(2-巯基乙酰基)-L-色氨酸作为一种新型的金属-β-内酰胺酶抑制剂，在吲哚环的2-位上用碳-14标记，以[2-14 C]吲哚为关键基于手性池策略的合成中间体。以[ 14 C]碳酸钡为原料，整个合成分10步进行，总放射化学产率为3.6%。

  DOI：

  10.1002/jlcr.3485
• 作为产物：
  描述：

  N-[¹⁴C]formyl-o-toluidine 在 potassium tert-butylate 作用下， 反应 0.25h， 以0.44 g的产率得到[14C-2]indole
  参考文献：
  名称：

  基于手性池策略的[2-14C]吲哚合成（2-巯基乙酰基）-L-[2-14C]色氨酸作为选择性金属-β-内酰胺酶抑制剂

  摘要：

  金属-β-内酰胺酶使细菌对广泛的常用β-内酰胺抗生素产生抗药性。L-氨基酸的几种硫醇衍生物已显示出它们对金属-β-内酰胺酶 IMP-1 的抑制作用。在这项研究中，(2-巯基乙酰基)-L-色氨酸作为一种新型的金属-β-内酰胺酶抑制剂，在吲哚环的2-位上用碳-14标记，以[2-14 C]吲哚为关键基于手性池策略的合成中间体。以[ 14 C]碳酸钡为原料，整个合成分10步进行，总放射化学产率为3.6%。

  DOI：

  10.1002/jlcr.3485

文献信息

• Chemical defenses of crucifers: elicitation and metabolism of phytoalexins and indole-3-acetonitrile in brown mustard and turnip
  作者：M.Soledade C Pedras、Corwin M Nycholat、Sabine Montaut、Yiming Xu、Abdul Q Khan

  DOI：10.1016/s0031-9422(02)00026-2

  日期：2002.3

  to that followed by the "blackleg" fungus (Phoma lingam/Leptosphaeria maculans). In addition, it was established that tetradeuterated brassinin was incorporated into the phytoalexin brassilexin in B. juncea and B. rapa. On the other hand, the tetradeuterated indole glucosinolate glucobrassicin was not incorporated into brassinin, although the chemical structures of brassinins and indole glucosinolates

  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
• 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：——