N1,N10-bis(dihydrocaffeoyl)spermidine | 132194-39-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N1,N10-bis(dihydrocaffeoyl)spermidine
• 英文别名: N1,N8-bis(dihydrocaffeoyl)spermidine；N1,N10-dihydrocaffeoyl spermidine；3-(3,4-dihydroxyphenyl)-N-[3-({4-[3-(3,4-dihydroxyphenyl)propanamido]butyl}amino)propyl]propanamide；3-(3,4-dihydroxyphenyl)-N-[4-[3-[3-(3,4-dihydroxyphenyl)propanoylamino]propylamino]butyl]propanamide
• CAS: 132194-39-9
• 化学式: C₂₅H₃₅N₃O₆
• 分子量: 473.569
• InChiKey: RNEHQZRKZJSYOL-UHFFFAOYSA-N

物化性质

• 沸点：
  848.9±65.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  151
• 氢给体数：
  7
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  亚精胺 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 硫代水杨酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 生成 N1,N10-bis(dihydrocaffeoyl)spermidine
  参考文献：
  名称：

  Optimising inhibitors of Trypanothione reductase using solid-phase chemistry

  摘要：

  A series of inhibitors of the enzyme trypanothione reductase has been identified using directed solid-phase chemistry. The compounds were based on a series of polyamine scaffolds and used the natural product kukoamine A as the lead structure. A compound with a K-i of 76 nM was identified, although somewhat surprisingly the compound appeared to be noncompetitive in nature. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00471-6

文献信息

• Simple syntheses of N-alkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A
  作者：Stratos Vassis、George Karigiannis、George Balayiannis、Maria Militsopoulou、Petros Mamos、George W Francis、Dionissios Papaioannou

  DOI：10.1016/s0040-4039(00)02308-x

  日期：2001.2

  trimethylsilyl γ-aminobutyrate and of N-trityl-γ-aminobutyric acid with methyl β-alaninate, respectively, followed by LiAlH4 reduction, produced N-monoalkylated spermidine fragments and analogues of the spermine alkaloid kukoamine A. The applicability of this methodology on the solid phase was also demonstrated.

  通过琥珀酰亚胺基N-三苯甲基-β-丙氨酸酯与三甲基甲硅烷基γ-氨基丁酸酯的偶合可容易地将琥珀酰胺化N-三苯甲基-β-丙氨酰基-γ-氨基丁酸酯和N-三苯甲基-γ-氨基丁酰基-β-丙氨酸酰化各种胺用N-三苯甲基-γ-氨基丁酸和β-丙氨酸甲酯分别还原，然后用LiAlH 4还原，生成N-单烷基化亚精胺片段和精胺生物碱kukoamine A的类似物。该方法在固相上的适用性也是演示。
• A Convenient Synthesis of Bis-(dihydro)caffeoylspermidines
  作者：Lili He、Jian Sun、Pengjuan Zhou、Jingwen Ji、Lijuan Zhai、Dong Tang、Jinbo Ji、Haikang Yang、Zafar Iqbal、Zhixiang Yang

  DOI：10.2174/0115701786265776230929180406

  日期：2024.4

  bisdihydrocaffeoylspermidine using cheaper and commercially available starting materials in 97% and 86% overall yields, respectively. The synthetic scheme can be upgraded to the commercial-scale synthesis of these compounds.

  咖啡酰亚精胺是许多植物物种中天然存在的有价值的生物碱。这些生物碱是传统药物中使用的许多植物提取物的药理学重要成分。双咖啡酰亚精胺和双二氢咖啡酰亚精胺具有抗氧化、抗炎和酶抑制特性，使其成为更安全的治疗剂的宝贵天然来源。然而，这些化合物在自然界中的可用性有限引起了合成化学家的关注。因此，我们使用更便宜且市售的起始原料合成了双咖啡酰亚精胺和双二氢咖啡酰亚精胺，总产率分别为 97% 和 86%。该合成方案可以升级为这些化合物的商业规模合成。
• US9012687B2
  申请人：——

  公开号：US9012687B2

  公开（公告）日：2015-04-21
• Optimising inhibitors of Trypanothione reductase using solid-phase chemistry
  作者：Bordin Chitkul、Mark Bradley

  DOI：10.1016/s0960-894x(00)00471-6

  日期：2000.10

  A series of inhibitors of the enzyme trypanothione reductase has been identified using directed solid-phase chemistry. The compounds were based on a series of polyamine scaffolds and used the natural product kukoamine A as the lead structure. A compound with a K-i of 76 nM was identified, although somewhat surprisingly the compound appeared to be noncompetitive in nature. (C) 2000 Elsevier Science Ltd. All rights reserved.