4-bromo-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide

• 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: 4-bromo-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide
• 英文别名: 4-bromo-N-[2-(5-methoxy-1H-indol-3-yl)ethyl]benzamide
• 化学式: C₁₈H₁₇BrN₂O₂
• mdl: MFCD01481690
• 分子量: 373.249
• InChiKey: URPYXNUUQKBSLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-bromo-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide 在 aluminium hydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 生成 N-(4-bromobenzyl)-5-methoxytryptamine
  参考文献：
  名称：

  Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines

  摘要：

  The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K-i < 1 nM) and with >100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.

  DOI：

  10.1021/jm00039a004
• 作为产物：
  描述：

  5-甲氧基色胺 、 4-溴苯甲酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以74%的产率得到4-bromo-N-(2-(5-methoxy-1H-indol-3-yl)ethyl)benzamide
  参考文献：
  名称：

  Effect of N-Amide Substitution on Antioxidative Activities of Melatonin Derivatives

  摘要：

  五种N-酰胺取代褪黑激素（MLT）衍生物被合成并评估其抗氧化活性，化合物9-12显示出比MLT更高的电子自旋共振（ESR）响应。4-溴苯甲酰和萘甲酰衍生物（10和11）在芬顿反应中表现出比MLT更强的羟自由基抑制作用。在MLT核心结构上N1位置的取代（乙酰基（8）、苯甲酰基（9）、4-溴苯甲酰基（10）和萘甲酰基（11））以及N2位置的4-溴苯甲酰基（12）减少了衍生物在铁还原抗氧化能力（FRAP）测定中的还原能力。化合物8-11在2,2'-叠氮基（3-乙基苯并噻唑啉-6-磺酸）二钠盐（ABTS）测定中也表现出比它们的母体化合物更低的抗氧化能力；而化合物12的自由基清除活性与MLT类似。所有芳基衍生物（9-12）对过氧自由基的熄灭能力比MLT高出约三倍，特别是苯甲酰化衍生物（9和10）在氧自由基吸收能力（ORAC）测定中表现出最高的能力。

  DOI：

  10.3390/scipharm88010003

文献信息

• Influence of Amine Substituents on 5-HT2A versus 5-HT2C Binding of Phenylalkyl- and Indolylalkylamines
  作者：Richard A. Glennon、Malgorzata Dukat、Mohamed El-Bermawy、Ho Law、Joseph De Los Angeles、Milt Teitler、Allison King、Katharine Herrick-Davis

  DOI：10.1021/jm00039a004

  日期：1994.6

  The effect of 15 different amine substituents on 5-HT2A and 5-HT2C serotonin receptor binding was investigated for two series of compounds (i.e., phenylalkylamine and indolylalkylamine derivatives). In general, amine substitution decreases receptor affinity; however, N-(4-bromobenzyl) substitution results in compounds that bind at 5-HT2A receptors with high affinity (K-i < 1 nM) and with >100-fold selectivity. Although parallel structural modifications in the two series result in parallel shifts in 5-HT2C binding, these same modifications alter 5-HT2A binding in a less consistent manner.
• Effect of N-Amide Substitution on Antioxidative Activities of Melatonin Derivatives
  作者：Panyada Panyatip、Nutjaree Pratheepawanit Johns、Aroonsri Priprem、Kouichi Nakagawa、Ploenthip Puthongking

  DOI：10.3390/scipharm88010003

  日期：——

  Five N-amide substituted melatonin (MLT) derivatives were synthesized and evaluated for antioxidative activities, and compounds 9–12 showed higher electron spin resonance (ESR) response than MLT. 4-Bromobenzoyl and naphthoyl derivatives (10 and 11) presented stronger hydroxyl radical inhibitory effect than MLT in Fenton reaction. The substitution at the N1-position on the MLT core structure with acetyl (8), benzoyl (9), 4-bromobenzoyl (10), and naphthoyl (11) and N2-substitution with 4-bromobenzoyl (12) decreased the reducing power of the derivatives in ferric reducing antioxidant power (FRAP) assay. Compounds 8–11 also presented lower antioxidant capacity than their parent compound in 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) disodium salt (ABTS) assay; whereas, compound 12 presented radical scavenging activity similarly to MLT. All aryl derivatives (9–12) showed higher ability to quench peroxyl radicals than MLT about three times, especially the benzoylated derivatives (9 and 10) that presented the highest ability in oxygen radical absorbance capacity (ORAC) assay.

  五种N-酰胺取代褪黑激素（MLT）衍生物被合成并评估其抗氧化活性，化合物9-12显示出比MLT更高的电子自旋共振（ESR）响应。4-溴苯甲酰和萘甲酰衍生物（10和11）在芬顿反应中表现出比MLT更强的羟自由基抑制作用。在MLT核心结构上N1位置的取代（乙酰基（8）、苯甲酰基（9）、4-溴苯甲酰基（10）和萘甲酰基（11））以及N2位置的4-溴苯甲酰基（12）减少了衍生物在铁还原抗氧化能力（FRAP）测定中的还原能力。化合物8-11在2,2'-叠氮基（3-乙基苯并噻唑啉-6-磺酸）二钠盐（ABTS）测定中也表现出比它们的母体化合物更低的抗氧化能力；而化合物12的自由基清除活性与MLT类似。所有芳基衍生物（9-12）对过氧自由基的熄灭能力比MLT高出约三倍，特别是苯甲酰化衍生物（9和10）在氧自由基吸收能力（ORAC）测定中表现出最高的能力。