N-methyl-5-(3,4-dihydroxycyclopent-1-yl)pentanamide | 1295634-10-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-methyl-5-(3,4-dihydroxycyclopent-1-yl)pentanamide
• CAS: 1295634-10-4
• 化学式: C₁₁H₂₁NO₃
• 分子量: 215.293
• InChiKey: ZXYIPBUQGBKWFM-ILWJIGKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.42
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  69.56
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-环戊烯-1,1-二甲酸二乙酯 在 N-甲基吗啉 、 盐酸 、 N-氯代丁二酰亚胺 、 四氧化锇 、 lithium aluminium tetrahydride 、 2,2,6,6-四甲基哌啶氧化物 、 10% Pd(OH)2 on carbon 、 氢气 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 N-甲基吗啉氧化物 、 lithium chloride 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 丙酮 、 甲苯 、 乙腈 、 mineral oil 为溶剂， 反应 76.0h， 生成 N-methyl-5-(3,4-dihydroxycyclopent-1-yl)pentanamide
  参考文献：
  名称：

  Synthesis and innate immunosuppressive effect of 1,2-cyclopentanediol derivatives

  摘要：

  Innate immunity is the front line of self-defense against infectious microorganisms. In mammals, innate immunity interacts with adaptive immunity and plays a key role in regulating the immune response. Therefore, innate immunity is a good pharmaceutical target for the development of immune regulators. After searching for natural substances that regulate innate immunity using an ex vivo Drosophila culture system, we identified a cyclopentanediol-type compound 1 as an immunosuppressor. In this study, we synthesized and evaluated 1 and its derivatives. Several methylamide- or phenylamide-containing derivatives showed effects that were 20-25 times more potent than those of 1. (c) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.01.049

文献信息

• Synthesis and innate immunosuppressive effect of 1,2-cyclopentanediol derivatives
  作者：Haruhisa Kikuchi、Kaori Okazaki、Mizuki Sekiya、Yasuyuki Uryu、Kazunori Ueda、Yasuhiro Katou、Shoichiro Kurata、Yoshiteru Oshima

  DOI：10.1016/j.ejmech.2011.01.049

  日期：2011.4

  Innate immunity is the front line of self-defense against infectious microorganisms. In mammals, innate immunity interacts with adaptive immunity and plays a key role in regulating the immune response. Therefore, innate immunity is a good pharmaceutical target for the development of immune regulators. After searching for natural substances that regulate innate immunity using an ex vivo Drosophila culture system, we identified a cyclopentanediol-type compound 1 as an immunosuppressor. In this study, we synthesized and evaluated 1 and its derivatives. Several methylamide- or phenylamide-containing derivatives showed effects that were 20-25 times more potent than those of 1. (c) 2011 Elsevier Masson SAS. All rights reserved.