(E)-4-(5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanamido)-5-phenylpent-2-enoic acid | 1424360-77-9

• 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: (E)-4-(5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanamido)-5-phenylpent-2-enoic acid
• 英文别名: (E,4S)-4-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-(phenylmethoxycarbonylamino)pentanoyl]amino]-5-phenylpent-2-enoic acid
• CAS: 1424360-77-9
• 化学式: C₂₉H₃₇N₃O₇
• 分子量: 539.629
• InChiKey: JORXMTUBCAUQMJ-RKEDLRMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  39
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  143
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-4-(5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanamido)-5-phenylpent-2-enoic acid 在 4-二甲氨基吡啶 、 三乙酰氧基硼氢化钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 52.0h， 生成 (E)-[4-(1-benzyl-3-methylcarbamoylallylcarbamoyl)-4-isopropylaminobutylamino]acetic acid benzyl ester
  参考文献：
  名称：

  Anti-malarial activity of new N-acetyl-l-leucyl-l-leucyl-l-norleucinal (ALLN) derivatives against Plasmodium falciparum

  摘要：

  Malaria is the most common of the parasitic diseases in tropical and subtropical regions. Adverse side effects of anti-malarial drugs have precluded them as a potential clinical drug. In this study, novel derivatives of N-acetyl-L-leucyl-L-leucyl-L-norleucinal (ALLN) based on a variety of dipeptidyl alpha,beta-unsaturated amides containing lysine as a part were synthesized and evaluated. Lower toxicity was achieved by reducing or eliminating the tendency of forming chemically reactive and toxic intermediates and metabolites. The synthesized compounds were evaluated for anti-malarial efficacy against Plasmodium falciparum and cytotoxicity in human epitheloid carcinoma cervix (HeLa cells) by estimating the therapeutic index (TI). N-Methyl amide with N'-Boc protection among them exhibited strong anti-malarial activity and N-methyl amide with N'-m-methylbenzyl amide showed excellent anti-malarial activity with much lower toxicity than the ALLN. Therefore, the two chemicals, as well as the underlying design rationale, could be useful in the discovery and development of new anti-malarial drugs. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.100
• 作为产物：
  描述：

  ethyl (2E,4S)-4-[(tert-butoxycarbonyl)amino]-5-phenylpent-2-enoate 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 76.0h， 生成 (E)-4-(5-(((benzyloxy)carbonyl)amino)-2-((tert-butoxycarbonyl)amino)pentanamido)-5-phenylpent-2-enoic acid
  参考文献：
  名称：

  ALLN (N-acetyl-L-Leucyl-Lleucyl-L-norleucinal) 유도체 화합물을 유효성분으로 함유하는 말라리아 감염 질환의 예방 또는 치료용 조성물

  摘要：

  本发明涉及含有ALLN衍生物化合物作为有效成分的抗疟疾组合物，该化合物可用作预防和治疗疟疾感染疾病的药学组合物，其中该化合物包含ALLN（N-乙酰-L-亮氨酸-L-亮氨酸-L-正亮醛）衍生物化合物作为有效成分。

  公开号：

  KR101491624B1