(+)-serinolamide B | 1452323-25-9

• 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: (+)-serinolamide B
• 英文别名: Serinolamide B；(E)-N-[(2R)-1-hydroxy-3-methoxypropan-2-yl]octadec-4-enamide
• CAS: 1452323-25-9
• 化学式: C₂₂H₄₃NO₃
• 分子量: 369.588
• InChiKey: IAONXYMLFOCVGA-UFBKIKKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-serinolamide B 在 Jones reagent 作用下， 以 丙酮 为溶剂， 反应 1.0h， 以68%的产率得到
  参考文献：
  名称：

  作用于大麻素受体的海洋蓝藻脂肪酸酰胺

  摘要：

  引人注目的 cAMP：来自海洋蓝藻的某些脂肪酸酰胺可以模拟内源性大麻素。Serinolamide B，一种从 Guamanian 样本中鉴定出的新类似物，以及malyngamide B，一种大型蓝藻代谢物的代表性成员，可以通过大麻素受体减少毛喉素诱导的 cAMP 积累。

  DOI：

  10.1002/cbic.201200502
• 作为产物：
  描述：

  octadec-4-yn-1-ol 在 吡啶 、 lithium aluminium tetrahydride 、 重铬酸吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 (+)-serinolamide B
  参考文献：
  名称：

  Concise synthesis of (+)-serinolamide A

  摘要：

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.09.084

文献信息

• Synthesis and Evaluation of Serinolamide Derivatives as Sphingosine-1-Phosphate-1 (S1P1) Receptor Agonists
  作者：Sun Jun Park、Jushin Kim、Jaehwan Kim、Yoowon Kim、Elijah Hwejin Lee、Hyeon Jeong Kim、Siwon Kim、Byungeun Kim、Rium Kim、Ji Won Choi、Jong-Hyun Park、Ki Duk Park

  DOI：10.3390/molecules27092818

  日期：——

  Sphingosine-1-phosphate-1 (S1P1) receptor agonists are well-known drugs for treating multiple sclerosis (MS) caused by autoreactive lymphocytes that attack the myelin sheath. Therefore, an effective therapeutic strategy is to reduce the lymphocytes in the blood by inducing S1P1 receptor internalization. We synthesized serinolamide A, a natural product of the sea, and performed S1P1 receptor internalization assay to evaluate functionally antagonistic S1P1 receptor agonist activity. In order to synthesize derivatives with better efficacy than serinolamide A and B, new derivatives were synthesized by introducing the phenyl ring moiety of fingolimod. Among them, compounds 19 and 21 had superior S1P1 agonistic effects to serinolamide. We also confirmed that compound 19 effectively inhibited lymphocyte outflow in peripheral lymphocyte count (PLC) assay.

  Sphingosine-1-phosphate-1 (S1P1) 受体激动剂是治疗由自身免疫淋巴细胞攻击髓鞘引起的多发性硬化症（MS）的常用药物。因此，一种有效的治疗策略是通过诱导 S1P1 受体内化来减少血液中的淋巴细胞。我们合成了海洋天然产物丝氨酰胺A，并进行了 S1P1 受体内化试验，评估其功能上的拮抗 S1P1 受体激动剂活性。为了合成比丝氨酰胺A和B更有效的衍生物，我们通过引入芬格莫德的苯环基团，合成了新的衍生物。其中，化合物19和21具有比丝氨酰胺更优异的S1P1激动作用。我们还确认，化合物19有效地抑制了外周淋巴细胞计数（PLC）试验中的淋巴细胞外流。
• Organocatalytic Approach to the Enantioselective Total Synthesis of (+)-Serinolamides A and B and (+)-Lacosamide
  作者：Suresh B. Waghmode、Amardeep R. Jadhao

  DOI：10.1055/a-2222-3822

  日期：2024.5

  A short and highly efficient enantioselective synthesis of (+)-serinolamide A, B and (+)-lacosamide from 3-methoxypropanal using l-proline-catalyzed α-amination, Grubbs metathesis, and acid-amine coupling as key steps is reported.

  使用 3-甲氧基丙醛，短时高效对映选择性合成 (+)-丝氨醇酰胺 A、B 和 (+)-拉科酰胺我据报道，脯氨酸催化的α-氨基化、格拉布斯复分解和酸-胺偶联是关键步骤。
• Concise synthesis of (+)-serinolamide A
  作者：Ya-Ru Gao、Shi-Huan Guo、Zhuan-Xiang Zhang、Shuai Mao、Yan-Lei Zhang、Yong-Qiang Wang

  DOI：10.1016/j.tetlet.2013.09.084

  日期：2013.11

  Serinolamide A, isolated from a species of marine cyanobacteria, exhibits a moderate agonist effect and selectivity for the CB1 cannabinoid receptor, which is unusual for marine natural products. Herein, we reported a highly efficient enantiospecific first total synthesis of (+)-serinolamide A from L-serine in nine steps with 30% overall yield. The synthesis method provides a facile, practicable, and economical approach for the preparation of other similar endocanabinoid lipids. (C) 2013 Elsevier Ltd. All rights reserved.
• Marine Cyanobacterial Fatty Acid Amides Acting on Cannabinoid Receptors
  作者：Rana Montaser、Valerie J. Paul、Hendrik Luesch

  DOI：10.1002/cbic.201200502

  日期：2012.12.21

  Striking cAMP: Certain fatty acid amides from marine cyanobacteria can mimic the endocannabinoids. Serinolamide B, a new analogue identified from a Guamanian sample, and malyngamide B, a representative member of a large class of cyanobacterial metabolites, can decrease forskolin‐induced cAMP accumulation through the cannabinoid receptors.

  引人注目的 cAMP：来自海洋蓝藻的某些脂肪酸酰胺可以模拟内源性大麻素。Serinolamide B，一种从 Guamanian 样本中鉴定出的新类似物，以及malyngamide B，一种大型蓝藻代谢物的代表性成员，可以通过大麻素受体减少毛喉素诱导的 cAMP 积累。