6-fluoro-1-(4-chlorobenzyl)-indole-3-carboxaldehyde | 1294445-70-7

• 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
• 英文名称: 6-fluoro-1-(4-chlorobenzyl)-indole-3-carboxaldehyde
• 英文别名: 1-[(4-chlorophenyl)methyl]-6-fluoro-1H-indole-3-carboxaldehyde；1-[(4-Chlorophenyl)methyl]-6-fluoroindole-3-carbaldehyde
• CAS: 1294445-70-7
• 化学式: C₁₆H₁₁ClFNO
• 分子量: 287.721
• InChiKey: ZDJBYYMQCLSVEI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1H-吲哚-3-羧酸肼 、 6-fluoro-1-(4-chlorobenzyl)-indole-3-carboxaldehyde 在 碘苯二乙酸 、 溶剂黄146 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 3.5h， 生成 2-[1-[(4-chlorophenyl)methyl]-6-fluoroindol-3-yl]-5-(1H-indol-3-yl)-1,3,4-oxadiazole
  参考文献：
  名称：

  新型双-（吲哚基）-1,3,4-恶二唑类化合物作为强效细胞毒剂的简便合成

  摘要：

  效力的秘诀：通过碘代苯二乙酸酯促进的氧化环化反应，由相应的酰肼-hydr酮制备了一系列新的双（吲哚基）-1,3,4-恶二唑。对一组人类癌细胞系的评估显示，某些衍生物具有强大的细胞毒性，并且对不同类型的癌症具有可调节的选择性。

  DOI：

  10.1002/cmdc.201200363
• 作为产物：
  描述：

  6-氟吲哚 在 sodium hydride 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 6-fluoro-1-(4-chlorobenzyl)-indole-3-carboxaldehyde
  参考文献：
  名称：

  新型双-（吲哚基）-1,3,4-恶二唑类化合物作为强效细胞毒剂的简便合成

  摘要：

  效力的秘诀：通过碘代苯二乙酸酯促进的氧化环化反应，由相应的酰肼-hydr酮制备了一系列新的双（吲哚基）-1,3,4-恶二唑。对一组人类癌细胞系的评估显示，某些衍生物具有强大的细胞毒性，并且对不同类型的癌症具有可调节的选择性。

  DOI：

  10.1002/cmdc.201200363

文献信息

• Analogues and Derivatives of Oncrasin-1, a Novel Inhibitor of the C-Terminal Domain of RNA Polymerase II and Their Antitumor Activities
  作者：Shuhong Wu、Li Wang、Wei Guo、Xiaoying Liu、Jinsong Liu、Xiaoli Wei、Bingliang Fang

  DOI：10.1021/jm101417n

  日期：2011.4.28

  To optimize the antitumor activity of oncrasin-1, a small molecule RNA polymerase II inhibitor, We evaluated 69 oncrasin-1 analogues for their cytotoxic activity against normal human epithelial cells and K-Ras mutant tumor cells. About 40 of those compounds were as potent as or more potent than oncrasin-1 in tumor cells and had a minimal cytotoxic effect on normal cells. Structure activity relationship analysis revealed that most of the active compounds contained either a hydroxymethyl group or an aldehyde group as a substitute at the 3-position of the indole. Both electron-donating and electron-withdrawing groups in the benzene ring were well tolerated. The hydroxymethyl compounds ranged from equipotent with to 100 times as potent as the corresponding aldehyde compounds. We tested three active analogues' effect on RNA, polymerase phosphorylation and found that they all inhibited phosphorylation of the C-terminal domain of RNA polymerase suggesting that the active compounds might act through the same mechanisms as oncrasin-1.
• A Facile Synthesis of Novel Bis-(indolyl)-1,3,4-oxadiazoles as Potent Cytotoxic Agents
  作者：Dalip Kumar、V. Arun、N. Maruthi Kumar、Glen Acosta、Brett Noel、Kavita Shah

  DOI：10.1002/cmdc.201200363

  日期：2012.11

  A recipe for potency: A novel series of bis(indolyl)‐1,3,4‐oxadiazoles was prepared from the corresponding hydrazide‐hydrazones via iodobenzene diacetate‐promoted oxidative cyclization. Evaluation against a panel of human cancer cell lines revealed that some derivatives possess potent cytotoxicity with tunable selectivity for different cancer types.

  效力的秘诀：通过碘代苯二乙酸酯促进的氧化环化反应，由相应的酰肼-hydr酮制备了一系列新的双（吲哚基）-1,3,4-恶二唑。对一组人类癌细胞系的评估显示，某些衍生物具有强大的细胞毒性，并且对不同类型的癌症具有可调节的选择性。
• Novel bis(indolyl)hydrazide–hydrazones as potent cytotoxic agents
  作者：Dalip Kumar、N. Maruthi Kumar、Soumitra Ghosh、Kavita Shah

  DOI：10.1016/j.bmcl.2011.11.031

  日期：2012.1

  A series of bis(indolyl) hydrazide-hydrazones 5a-n were synthesized and evaluated for their cytotoxicity against selected human cancer cell lines. The reaction of indole-3-carboxaldehyde 2 with indole-3-carbohydrazide 4 in presence of catalytic amount of acetic acid afforded 5a-n in good yields. Among the synthesized bis(indolyl) hydrazide-hydrazones, the compound 5b with N-(p-chlorobenzyl) and bromo substituents was found to be the most potent against multiple cancer cell lines (IC(50) = 1.0 mu M, MDA-MB-231). The compound 5k exhibited selective cytotoxicity against breast cancer cell line MCF7 (IC(50) = 3.1 mu M). (C) 2011 Elsevier Ltd. All rights reserved.