5-丁基-2-(4-甲氧基苯基)-1H-吲哚-3-甲醛 | 588671-28-7

• 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
• 中文名称: 5-丁基-2-(4-甲氧基苯基)-1H-吲哚-3-甲醛
• 英文名称: 5-butyl-2-(4-methoxyphenyl)-1H-indole-3-carbaldehyde
• 英文别名: 1H-Indole-3-carboxaldehyde, 5-butyl-2-(4-methoxyphenyl)-
• CAS: 588671-28-7
• 化学式: C₂₀H₂₁NO₂
• 分子量: 307.392
• InChiKey: QTKSFCOYXUARHC-UHFFFAOYSA-N

物化性质

• 熔点：
  210 °C(Solv: methanol (67-56-1))
• 沸点：
  522.6±50.0 °C(Predicted)
• 密度：
  1.144±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  42.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-丁基-2-(4-甲氧基苯基)-1H-吲哚-3-甲醛 在 盐酸羟胺 、 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 3.0h， 以67%的产率得到5-n-butyl-3-[(hydroxyimino)methyl]-2-(4-methoxyphenyl)indole
  参考文献：
  名称：

  Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

  摘要：

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.030
• 作为产物：
  描述：

  5-butyl-2-(4-methoxyphenyl)-1H-indole 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 3.0h， 以44%的产率得到5-丁基-2-(4-甲氧基苯基)-1H-吲哚-3-甲醛
  参考文献：
  名称：

  Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

  摘要：

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.05.030

文献信息

• 3-Indolylmethylen-Derivate mit cytostatischer Wirkung
  申请人：Universitaet Regensburg

  公开号：EP1746087A1

  公开（公告）日：2007-01-24

  Die Erfindung betrifft 3-Indolylmethylen-Derivate mit der allgemeinen Formel II mit cytostatischer Wirkung, sowie ein Verfahren zur Herstellung der 3-Indolylmethylen-Derivate, deren Verwendung zur Herstellung von Arzneimitteln sowie 3-Indolylmethylen-Derivate enthaltende pharmazeutische Zusammensetzungen.

  本发明涉及具有通式 II 并具有细胞抑制活性的 3-吲哚亚甲基衍生物，以及制备 3-吲哚亚甲基衍生物的工艺、其在制备含有 3-吲哚亚甲基衍生物的药物和药物组合物中的用途。
• Aroyl hydrazones of 2-phenylindole-3-carbaldehydes as novel antimitotic agents
  作者：Susanne Vogel、Doris Kaufmann、Michaela Pojarová、Christine Müller、Tobias Pfaller、Sybille Kühne、Patrick J. Bednarski、Erwin von Angerer

  DOI：10.1016/j.bmc.2008.04.071

  日期：2008.6

  Cell cycle arrest of malignant cells is an important option for cancer treatment. In this study, we modified the structure of antimitotic 2-phenylindole-3-carbaldehydes by condensation with hydrazides of various benzoic and pyridine carboxylic acids. The resulting hydrazones inhibited the growth of MDA-MB 231 and MCF-7 breast cancer cells with IC50 values of 20-30 nM for the most potent derivatives. These 2-phenylindole derivatives also exerted an inhibitory effect on the growth of both proliferating and resting U-373 MG glioblastoma cells. Though the hydrazones exhibited similar structure-activity relationships as the aldehydes, they did not inhibit tubulin polymerization as the aldehydes but were capable of blocking the cell cycle in G(2)/M phase. The cell cycle arrest was accompanied by apoptosis as demonstrated by the activation of caspase-3. Since these 2-phenylindole-based hydrazones display no structural similarity with other antitumor drugs they are interesting candidates for further development. (c) 2008 Elsevier Ltd. All rights reserved.
• [(2-Phenylindol-3-yl)methylene]propanedinitriles inhibit the growth of breast cancer cells by cell cycle arrest in G2/M phase and apoptosis
  作者：Michaela Pojarová、Doris Kaufmann、Robert Gastpar、Tsuyuki Nishino、Przemyslaw Reszka、Patrick J. Bednarski、Erwin von Angerer

  DOI：10.1016/j.bmc.2007.07.046

  日期：2007.12

  Cell cycle arrest of malignant cells is an important option for cancer treatment. In this study, we modified the structure of antimitotic 2-phenylindole-3-carbaldehydes by condensation with malononitrile. The resulting methylene propanedinitriles inhibited the growth of MDA-MB 231 and MCF-7 breast cancer cells with IC50 values below 100 nM. Though they exhibited similar structure-activity relationships as the aldehydes, they did not inhibit tubulin polymerization but were capable of blocking the cell cycle in G(2)/M phase. The cell cycle arrest was accompanied by apoptosis as demonstrated by the activation of caspases 3 and 9. Since the new 2-phenylindole derivatives also inhibited the growth of transplanted MXT mouse mammary tumors, they are interesting candidates for further development. (C) 2007 Elsevier Ltd. All rights reserved.
• [DE] 3-INDOLYLMETHYLEN-DERIVATE MIT CYTOSTATISCHER WIRKUNG<br/>[EN] 3-INDOLYLMETHYLENE DERIVATIVES WITH CYTOSTATIC ACTION<br/>[FR] DERIVES DE 3-INDOLYL-METHYLENE A EFFET CYTOSTATIQUE
  申请人：UNIV REGENSBURG

  公开号：WO2007010044A1

  公开（公告）日：2007-01-25

  [EN] The invention relates to 3-indolylmethylene derivatives having the general formula I with cytostatic action, and to a process for preparing the 3-indolylmethylene derivatives, to their use for producing medicaments, and to pharmaceutical compositions comprising 3-indolylmethylene derivatives.
  [FR] L'invention concerne des dérivés de 3-indolyl-méthylène de formule générale (I) à effet cytostatique, un procédé de production desdits dérivés de 3-indolyl-méthylène, leur utilisation dans la production de médicaments ainsi que des compositions pharmaceutiques contenant des dérivés de 3-indolyl-méthylène.
  [DE] Die Erfindung betrifft 3-Indolylmethylen-Derivate mit der allgemeinen Formel I mit cytostatischer Wirkung, sowie ein Verfahren zur Herstellung der 3-Indolylmethylen-Derivate, deren Verwendung zur Herstellung von Arzneimitteln sowie 3-Indolylmethylen-Derivate enthaltende pharmazeutische Zusammensetzungen.
• Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells
  作者：Doris Kaufmann、Michaela Pojarová、Susanne Vogel、Renate Liebl、Robert Gastpar、Dietmar Gross、Tsuyuki Nishino、Tobias Pfaller、Erwin von Angerer

  DOI：10.1016/j.bmc.2007.05.030

  日期：2007.8

  Small molecules such as indoles are attractive as inhibitors of tubulin polymerization. Thus a number of 2-phenylindole-3-carbaldehydes with lipophilic substituents in both aromatic rings was synthesized and evaluated for antitumor activity in MDA-MB 231 and MCF-7 breast cancer cells. Some 5-alkylindole derivatives with a 4-methoxy group in the 2-phenyl ring strongly inhibit the growth of breast cancer cells with IC50 values of 5-20 nM. Their action can be rationalized by the cell cycle arrest in G(2)/M phase due to the inhibition of tubulin polymerization. (c) 2007 Elsevier Ltd. All rights reserved.