methyl N2-[(benzyloxy)carbonyl]-N6-((4-[(2-tert-butyl-6-methoxyquinolin-8-yl)amino]pentyl)-carbamoyl)-D-lysinate | 1375013-47-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl N2-[(benzyloxy)carbonyl]-N6-((4-[(2-tert-butyl-6-methoxyquinolin-8-yl)amino]pentyl)-carbamoyl)-D-lysinate
• CAS: 1375013-47-0
• 化学式: C₃₅H₄₉N₅O₆
• 分子量: 635.804
• InChiKey: YFUHYSXFGAUETP-ITCMONMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 重原子数：
  46.0
• 可旋转键数：
  16.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  139.91
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl N2-[(benzyloxy)carbonyl]-N6-((4-[(2-tert-butyl-6-methoxyquinolin-8-yl)amino]pentyl)-carbamoyl)-D-lysinate 在 palladium 10% on activated carbon 、 氢气 、 溶剂黄146 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 9.0h， 以81%的产率得到N6-((4-[(2-tert-butyl-6-methoxyquinolin-8-yl)amino]pentyl)carbamoyl)-D-lysine dihydrochloride
  参考文献：
  名称：

  Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: Synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities

  摘要：

  Three new series of 8-aminoquinolines with modifications in the side-chain by conjugation with amino acids, dipeptides and pseudodipeptides have been synthesized. The synthesized compounds were tested for in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, in vitro cytotoxicity in mammalian kidney cells (Vero), in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity and in vitro inhibition of beta-haematin formation. The promising compounds were also evaluated for in vivo blood-schizontocidal antimalarial activity against Plasmodium berghei infected mice. The analogues 55 and 101 produced highest antimalarial activities, in vitro. Analogues 52 and 59 exhibited promising antileishmanial and broad spectrum of antifungal activities, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.019
• 作为产物：
  描述：

  N,N'-羰基二咪唑 、 methyl (2R)-6-amino-2-(phenylmethoxycarbonylamino)hexanoate 、 N8-(4-amino-1-methylpentyl)-2-tert-butyl-6-methoxy-8-quinolinamine 以 二氯甲烷 为溶剂， 反应 8.0h， 以35%的产率得到methyl N2-[(benzyloxy)carbonyl]-N6-((4-[(2-tert-butyl-6-methoxyquinolin-8-yl)amino]pentyl)-carbamoyl)-D-lysinate
  参考文献：
  名称：

  Amino acid, dipeptide and pseudodipeptide conjugates of ring-substituted 8-aminoquinolines: Synthesis and evaluation of anti-infective, β-haematin inhibition and cytotoxic activities

  摘要：

  Three new series of 8-aminoquinolines with modifications in the side-chain by conjugation with amino acids, dipeptides and pseudodipeptides have been synthesized. The synthesized compounds were tested for in vitro antimalarial activity against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum strains, in vitro cytotoxicity in mammalian kidney cells (Vero), in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity and in vitro inhibition of beta-haematin formation. The promising compounds were also evaluated for in vivo blood-schizontocidal antimalarial activity against Plasmodium berghei infected mice. The analogues 55 and 101 produced highest antimalarial activities, in vitro. Analogues 52 and 59 exhibited promising antileishmanial and broad spectrum of antifungal activities, respectively. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.019