N-(5-(diethylamino)pentan-2-yl)-2-methylquinolin-4-amine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-(5-(diethylamino)pentan-2-yl)-2-methylquinolin-4-amine
• 英文别名: N⁴,N⁴-diethyl-1-methyl-N¹-(2-methyl-[4]quinolyl)-butanediyldiamine；N⁴,N⁴-Diaethyl-1-methyl-N¹-(2-methyl-[4]chinolyl)-butandiyldiamin；1-N,1-N-diethyl-4-N-(2-methylquinolin-4-yl)pentane-1,4-diamine
• 化学式: C₁₉H₂₉N₃
• 分子量: 299.459
• InChiKey: IZNZCUVAAPISHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  28.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吲哚甲醛 、 N-(5-(diethylamino)pentan-2-yl)-2-methylquinolin-4-amine 在 哌啶 作用下， 以 乙腈 为溶剂， 以20%的产率得到2-((E)-2-(1H-indol-3-yl)vinyl)-N-(5-(diethylamino)pentan-2-yl)quinolin-4-amine
  参考文献：
  名称：

  Novel Conjugated Quinoline–Indoles Compromise Plasmodium falciparum Mitochondrial Function and Show Promising Antimalarial Activity

  摘要：

  A novel class of antimalarial compounds, based on an indol-3-yl linked to the 2-position of a 4-aminoquinoline moiety, shows promising activity against the malaria parasite, Plasmodium falciparum. Compounds with a quaternary nitrogen on the quinoline show improved activity against the chloroquine-resistant K1 strain. Nonquaternerized 4-amino-quinolines retain significant potency but are relatively less active against the K1 strain. Alkylation of the 4-amino group preferentially improves the activity against the chloroquine-sensitive 3D7 strain. The quinoline-indoles show only weak activity as inhibitors of beta-hematin formation, and their activities are only weakly antagonized by a hemoglobinase inhibitor. The compounds appear to dissipate mitochondrial potential as an early event in their antimalarial action and therefore may exert their activity by compromising Plasmodium mitochondrial function. Interestingly, we observed a structural relationship between our compounds and the anticancer and anthelminthic compound, pyrvinium pamoate, which has also been proposed to exert its action via compromising mitochondrial function.

  DOI：

  10.1021/jm400656s
• 作为产物：
  描述：

  邻氨基苯甲醇 在 potassium phosphate 、 palladium diacetate 、 C₁₂H₈BrMnN₂O₅ 、 双(2-二苯基磷苯基)醚 、 lithium chloride 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 43.0h， 生成 N-(5-(diethylamino)pentan-2-yl)-2-methylquinolin-4-amine
  参考文献：
  名称：

  了解环境和有氧条件下可见光引发的锰催化合成喹啉和萘啶

  摘要：

  多环芳烃N-杂环是天然产物和活性药物成分中一些最常见的结构单元。已经做出重大努力来开发催化方案，包括那些在高温下使用无受体脱氢策略的方案，以生产多环芳烃N-杂环，如喹啉和萘啶。然而，由可见光驱动的光引发催化提供了一种更温和且通常更具选择性的方案作为热反应的替代方案。在这里，我们展示了使用光催化剂 [Mn(L 1 H)(CO) 3 Br] (L 1 ) 从邻氨基苄醇和酮催化合成喹啉和萘啶H = 7-hydroxy-2-methyl-1,8-naphthyridine- N -oxide)，在 1,8-naphthyridine- N上带有一个酚单元-氧化物支架，在环境和有氧条件下，可见光照明。我们描述了在适度反应条件下超过 30 个示例的广泛的、官能团耐受的底物范围。在 KOH 存在的情况下，使用环境空气作为氧化剂，将各种含有供电子和缺电子基团的 2-氨基苯甲醇和 (2-氨基吡啶-3-基)

  DOI：

  10.1021/acscatal.2c05086

文献信息

• Rubzow; Arendaruk, Zhurnal Obshchei Khimii, 1949, vol. 19, p. 1689,1690; engl. Ausg. S. a 121, a 122
  作者：Rubzow、Arendaruk

  DOI：——

  日期：——
• Katayanagi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1946, vol. 66, p. Ausg. B, S. 159, 162
  作者：Katayanagi

  DOI：——

  日期：——
• Novel Conjugated Quinoline–Indoles Compromise Plasmodium falciparum Mitochondrial Function and Show Promising Antimalarial Activity
  作者：Silvia C. Teguh、Nectarios Klonis、Sandra Duffy、Leonardo Lucantoni、Vicky M. Avery、Craig A. Hutton、Jonathan B. Baell、Leann Tilley

  DOI：10.1021/jm400656s

  日期：2013.8.8

  A novel class of antimalarial compounds, based on an indol-3-yl linked to the 2-position of a 4-aminoquinoline moiety, shows promising activity against the malaria parasite, Plasmodium falciparum. Compounds with a quaternary nitrogen on the quinoline show improved activity against the chloroquine-resistant K1 strain. Nonquaternerized 4-amino-quinolines retain significant potency but are relatively less active against the K1 strain. Alkylation of the 4-amino group preferentially improves the activity against the chloroquine-sensitive 3D7 strain. The quinoline-indoles show only weak activity as inhibitors of beta-hematin formation, and their activities are only weakly antagonized by a hemoglobinase inhibitor. The compounds appear to dissipate mitochondrial potential as an early event in their antimalarial action and therefore may exert their activity by compromising Plasmodium mitochondrial function. Interestingly, we observed a structural relationship between our compounds and the anticancer and anthelminthic compound, pyrvinium pamoate, which has also been proposed to exert its action via compromising mitochondrial function.
• Understanding the Visible-Light-Initiated Manganese-Catalyzed Synthesis of Quinolines and Naphthyridines under Ambient and Aerobic Conditions
  作者：Kamaless Patra、Arindom Bhattacherya、Chenfei Li、Jitendra K. Bera、Han Sen Soo

  DOI：10.1021/acscatal.2c05086

  日期：2022.12.16

  scope of >30 examples under modest reaction conditions. A variety of 2-aminobenzyl alcohols containing electron-donating and electron-deficient groups and (2-aminopyridin-3-yl)methanol are converted to the corresponding quinolines and naphthyridines using ambient air as an oxidant in the presence of KOH. We synthesized a wide range of derivatives, including some of the bioactive antimalarial drug chloroquine

  多环芳烃N-杂环是天然产物和活性药物成分中一些最常见的结构单元。已经做出重大努力来开发催化方案，包括那些在高温下使用无受体脱氢策略的方案，以生产多环芳烃N-杂环，如喹啉和萘啶。然而，由可见光驱动的光引发催化提供了一种更温和且通常更具选择性的方案作为热反应的替代方案。在这里，我们展示了使用光催化剂 [Mn(L 1 H)(CO) 3 Br] (L 1 ) 从邻氨基苄醇和酮催化合成喹啉和萘啶H = 7-hydroxy-2-methyl-1,8-naphthyridine- N -oxide)，在 1,8-naphthyridine- N上带有一个酚单元-氧化物支架，在环境和有氧条件下，可见光照明。我们描述了在适度反应条件下超过 30 个示例的广泛的、官能团耐受的底物范围。在 KOH 存在的情况下，使用环境空气作为氧化剂，将各种含有供电子和缺电子基团的 2-氨基苯甲醇和 (2-氨基吡啶-3-基)