(4Z,7Z,10Z,13Z,16Z,19Z)-N-benzyldocosa-4,7,10,13,16,19-hexaenamide

• 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: (4Z,7Z,10Z,13Z,16Z,19Z)-N-benzyldocosa-4,7,10,13,16,19-hexaenamide
• 化学式: C₂₉H₃₉NO
• 分子量: 417.635
• InChiKey: QGOQGFAWRREGIL-KUBAVDMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  31
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二十二碳六烯酸 、 苄胺 在 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 12.5h， 以96%的产率得到(4Z,7Z,10Z,13Z,16Z,19Z)-N-benzyldocosa-4,7,10,13,16,19-hexaenamide
  参考文献：
  名称：

  合成脂肪酸酰胺的便捷方案

  摘要：

  已经从哺乳动物和植物来源报道了几类生物存在的脂肪酸酰胺。许多与哺乳动物来源的脂肪酸结合的酰胺表现出对个体受体的特异性激活。它们作为药理学工具或作为开发新疗法的先导化合物的潜力引起了人们极大的兴趣。因此，需要在不影响敏感功能的几何形状或位置的情况下，通过实用、高产和可扩展的协议来获取此类酰胺。满足所有这些要求的方案包括用羰基二咪唑 (CDI) 活化相应的酸，然后与所需的胺或其盐酸盐反应。已经以通常高产率制备了五十多种化合物。

  DOI：

  10.1055/s-0037-1611939

文献信息

• [EN] DERIVATIVES OF DOCOSAHEXAENOYLETHANOLAMIDE AND USES THEREOF<br/>[FR] DÉRIVÉS DE DOCOSAHEXAÉNOYLÉTHANOLAMIDE ET SES UTILISATIONS
  申请人：US HEALTH

  公开号：WO2013158302A1

  公开（公告）日：2013-10-24

  The invention provides derivatives of DEA which have increased potency and hydrolysis resistance as compared to DEA, and compositions thereof, as well as methods of using these derivatives to promote neurogenesis, neurite growth and/or length, and/or promote synaptogenesis.

  本发明提供了与DEA相比具有更高效能和更强水解抗性的DEA衍生物及其组成物，以及使用这些衍生物促进神经发生、神经突起生长和/或长度，以及/或促进突触形成的方法。
• DERIVATIVES OF DOCOSAHEXAENOYLETHANOLAMIDE AND USES THEREOF
  申请人：The United States of America, as Represented by The Secretary, Department of Health and Human Services

  公开号：EP2847178B1

  公开（公告）日：2017-01-04
• US9422308B2
  申请人：——

  公开号：US9422308B2

  公开（公告）日：2016-08-23
• A Docosahexaenoic Acid Derivative (N-Benzyl Docosahexaenamide) as a Potential Therapeutic Candidate for Treatment of Ovarian Injury in the Mouse Model
  作者：Lirong Guo、Qing Gao、Jieqiong Zhu、Xiaobao Jin、Hui Yin、Tao Liu

  DOI：10.3390/molecules27092754

  日期：——

  Commonly used clinical chemotherapy drugs, such as cyclophosphamide (CTX), may cause injury to the ovaries. Hormone therapies can reduce the ovarian injury risk; however, they do not achieve the desired effect and have obvious side effects. Therefore, it is necessary to find a potential therapeutic candidate for ovarian injury after chemotherapy. N-Benzyl docosahexaenamide (NB-DHA) is a docosahexaenoic acid derivative. It was recently identified as the specific macamide with a high degree of unsaturation in maca (Lepidium meyenii). In this study, the purified NB-DHA was administered intragastrically to the mice with CTX-induced ovarian injury at three dose levels. Blood and tissue samples were collected to assess the regulation of NB-DHA on ovarian function. The results indicated that NB-DHA was effective in improving the disorder of estrous cycle, and the CTX+NB-H group can be recovered to normal levels. NB-DHA also significantly increased the number of primordial follicles, especially in the CTX+NB-M and CTX+NB-H groups. Follicle-stimulating hormone and luteinizing hormone levels in all treatment groups and estradiol levels in the CTX+NB-H group returned to normal. mRNA expression of ovarian development-related genes was positive regulated. The proportion of granulosa cell apoptosis decreased significantly, especially in the CTX+NB-H group. The expression of anti-Müllerian hormone and follicle-stimulating hormone receptor significantly increased in ovarian tissues after NB-DHA treatment. NB-DHA may be a promising agent for treating ovarian injury.