1-[(2-fluorophenyl)methyl]-5-methoxyindole-3-carbaldehyde | 1226223-66-0

• 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: 1-[(2-fluorophenyl)methyl]-5-methoxyindole-3-carbaldehyde
• CAS: 1226223-66-0
• 化学式: C₁₇H₁₄FNO₂
• 分子量: 283.302
• InChiKey: JVFRVPMMFWDFCR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.23
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  丙二酸 、 1-[(2-fluorophenyl)methyl]-5-methoxyindole-3-carbaldehyde 在 哌啶 、 吡啶 、 盐酸 作用下， 以 水 为溶剂， 反应 12.0h， 以56.2%的产率得到(E)-3-(1-(2-fluorobenzyl)-5-methoxy-1H-indol-3-yl)acrylic acid
  参考文献：
  名称：

  Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes

  摘要：

  Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-alpha. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 mu M and a binding affinity for ap2 with the apparent K-i values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.006
• 作为产物：
  描述：

  5-甲氧基吲哚 在 potassium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 2.83h， 生成 1-[(2-fluorophenyl)methyl]-5-methoxyindole-3-carbaldehyde
  参考文献：
  名称：

  Design, synthesis and biological evaluation of thiazole- and indole-based derivatives for the treatment of type II diabetes

  摘要：

  Present studies have shown that the lipid carrier has a significant role in several aspects of metabolic syndrome in A-FABP/ap2-deficient mice, including type 2 diabetes and atherosclerosis. 38 Thiazole- and indole-based derivatives were synthesized and investigated for their inhibitory effects on the production of LPS-stimulated TNF-alpha. Among them, 12b exhibited an excellent inhibitory efficiency compared to BMS309403 (95% vs. 85%) at the concentration of 10 mu M and a binding affinity for ap2 with the apparent K-i values 33 nM. Oral administration of 12b at a dosage of 50 mg/kg effectively reduced the levels of plasma blood glucose, triglycerides, insulin, total cholesterol and alanine aminotransferase in high-fat/diet-induced obesity model. The results highlighted that 12b was a potent anti-diabetic agent. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.006

文献信息

• Synthesis and biological evaluation of novel podophyllotoxin analogs as antitumor agents
  作者：Zhong-Heng Zhang、Li-Ming Zhang、Gang Luo、Shi Zhang、Hong Chen、Jing Zhou

  DOI：10.1080/10286020.2014.913578

  日期：2014.5.4

  A series of 4β N-indole-substituted podophyllotoxin derivatives were synthesized. Nine target compounds were evaluated against human cancer cell lines (HeLa, K562, and K562/A02) using MTT assay including three imine derivatives 8, 9, and 10in vitro. The result showed that the three compounds had higher antitumor activity than their reduced forms. Among them, compounds 8, 9, 11, and 16 were superior

  一系列4β的ñ -吲哚取代的鬼臼毒素衍生物的合成。九个目标化合物对人癌症细胞系评价（HeLa细胞，K562，K562和/ A02），使用MTT测定法包括三名亚胺衍生物8，9，和10体外。结果显示这三种化合物具有比其还原形式更高的抗肿瘤活性。其中，化合物8，9，11，和16均优于阳性对照VP-16。