(+)-serinolamide A | 1342300-14-4

• 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: (+)-serinolamide A
• 英文别名: Serinolamide A；(E)-N-[(2R)-1-hydroxy-3-methoxypropan-2-yl]-N-methyloctadec-4-enamide
• CAS: 1342300-14-4
• 化学式: C₂₃H₄₅NO₃
• 分子量: 383.615
• InChiKey: CJAVPRNATZCNLN-NBRGKURFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  27
• 可旋转键数：
  19
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+)-serinolamide A 、 (-)-(R)-α-methoxy-α-(9-anthryl)acetic acid 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 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以2.2 mg的产率得到[(2S)-3-methoxy-2-[methyl-[(E)-octadec-4-enoyl]amino]propyl] (2R)-2-anthracen-9-yl-2-methoxyacetate
  参考文献：
  名称：

  Cannabinomimetic Lipid from a Marine Cyanobacterium

  摘要：

  NMR-guided fractionation of two independent collections of the marine cyanobacteria Lyngbya majuscula obtained from Papua New Guinea and Oscillatoria sp. collected in Panama led to the isolation of the new lipids serinolamide A (3) and propenediester (4). Their structures were determined by NMR and MS data analysis. Serinolamide A (3) exhibited a moderate agonist effect and selectivity for the CB, cannabinoid receptor (K(i) = 1.3 mu M, >5-fold) and represents the newest addition to the known cannabinomimetic natural products of marine origin.

  DOI：

  10.1021/np200610t
• 作为产物：
  描述：

  1-十五碳烯 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 (+)-serinolamide A
  参考文献：
  名称：

  （+）-丝氨酰胺A † ‡的对映选择性全合成

  摘要：

  描述了一种由外消旋的丁二烯单环氧化物作为起始原料制备（+）-丝氨酰胺A 1的短而高效的对映选择性合成方法。该合成利用钯催化的Trost的动态动力学不对称转化（DYKAT）和交叉复分解（CM）作为关键步骤。

  DOI：

  10.1039/c5ra06609c

文献信息

• Enantioselective total synthesis of (+)-serinolamide A
  作者：Suraksha Gahalawat、Satyendra Kumar Pandey

  DOI：10.1039/c5ra06609c

  日期：——

  A short and highly efficient enantioselective synthetic approach to (+)-serinolamide A 1 from racemic butadiene monoepoxide as a starting material is described. The synthesis utilizes the palladium catalyzed Trost's Dynamic Kinetic Asymmetric Transformation (DYKAT) and cross-metathesis (CM) as key steps.

  描述了一种由外消旋的丁二烯单环氧化物作为起始原料制备（+）-丝氨酰胺A 1的短而高效的对映选择性合成方法。该合成利用钯催化的Trost的动态动力学不对称转化（DYKAT）和交叉复分解（CM）作为关键步骤。
• 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。
• 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.
• Cannabinomimetic Lipid from a Marine Cyanobacterium
  作者：Marcelino Gutiérrez、Alban R. Pereira、Hosana M. Debonsi、Alessia Ligresti、Vincenzo Di Marzo、William H. Gerwick

  DOI：10.1021/np200610t

  日期：2011.10.28

  NMR-guided fractionation of two independent collections of the marine cyanobacteria Lyngbya majuscula obtained from Papua New Guinea and Oscillatoria sp. collected in Panama led to the isolation of the new lipids serinolamide A (3) and propenediester (4). Their structures were determined by NMR and MS data analysis. Serinolamide A (3) exhibited a moderate agonist effect and selectivity for the CB, cannabinoid receptor (K(i) = 1.3 mu M, >5-fold) and represents the newest addition to the known cannabinomimetic natural products of marine origin.
• 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。