(S)-methyl 3-(4-hydroxyphenyl)-2-(palmitamido)propanoate | 214706-38-4

• 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: (S)-methyl 3-(4-hydroxyphenyl)-2-(palmitamido)propanoate
• 英文别名: methyl (2S)-2-(hexadecanoylamino)-3-(4-hydroxyphenyl)propanoate
• CAS: 214706-38-4
• 化学式: C₂₆H₄₃NO₄
• 分子量: 433.632
• InChiKey: SMNMQSKECJFRIF-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  31
• 可旋转键数：
  19
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-methyl 3-(4-hydroxyphenyl)-2-(palmitamido)propanoate 在 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成 N-palmitoyl-L-tyrosine
  参考文献：
  名称：

  从两亲性肽中寻找受生物启发的水凝胶：用于稳定释放抗癌药的纳米粒子稳定剂的模板†

  摘要：

  由于其在生物医学领域中的多样化应用，在过去的几十年中，有效的刺激响应水凝胶的发展迅速扩展。根据这种漂移，我们旨在调节一系列具有通式Me-（CH 2）14 -CO-NH-CH（X）-COOH的两亲肽类似物，其中X = CH 2 Ph在水凝胶仪I中（L -Phe）和II（D -Phe）且X = CH 2 Ph（OH）在水凝剂III（L-Tyr），无论其在C端中心的配置如何，在室温下都具有极好的固定水的能力，最小水凝胶I-III的胶凝浓度为0.04％/ 0.05％/ 0.02％w / v。。为了验证该阈值浓度差异，我们进行了计算分析，证明了水凝胶化剂I和III的侧链与两亲物和芳香环的亚甲基单元保持高度平面的能力，从而通过范德华力和pi促进了良好的对应关系。 –pi堆叠。因此，水凝剂I和III在比水凝剂II优越的有序组织中自组装。此外，光谱和显微镜实验表明，水凝胶化剂在超分子水平上表现出β-折叠构

  DOI：

  10.1039/c9nj01763a
• 作为产物：
  描述：

  2-氨基-3-(4-苯基甲氧基苯基)丙酸甲酯 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 (S)-methyl 3-(4-hydroxyphenyl)-2-(palmitamido)propanoate
  参考文献：
  名称：

  Initial structure–activity relationships of lysophosphatidic acid receptor antagonists: discovery of a high-affinity LPA1/LPA3 receptor antagonist

  摘要：

  A recently reported dual LPA(1)/LPA(3) receptor antagonist (VPC12249, 1) has been modified herein so as to optimize potency and selectivity at LPA receptors. Compounds containing variation in the acyl lipid chain and linker region have been synthesized and screened for activity at individual LPA receptors. LPA(1)-selective (14b) and LPA(3)-selective (10g,m) compounds of modest potency have been discovered. Additionally, 2-pyridyl derivative 10t exhibits a K-i value of 18 nM at the LPA(1) receptor and is significantly more potent than 1 at the LPA(3) receptor. This paper describes the synthetic methods, biological evaluation, and structure-activity relationships (SARs) of LPA receptor antagonists. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.076

文献信息

• Multi-stimuli responsive self-healing metallo-hydrogels: tuning of the gel recovery property
  作者：Shibaji Basak、Jayanta Nanda、Arindam Banerjee

  DOI：10.1039/c3cc48896a

  日期：——

  Self-healable, multi-stimuli responsive metallo-hydrogels based on a series of tyrosine containing amphiphiles have been discovered. Formation of these metallo-gels is highly selective to Ni²⁺ ions. Moreover, the self-healing property can be modulated by varying the chain length of the corresponding gelator amphiphiles.

  基于一系列含酪氨酸的两性分子发现了可自修复、多刺激响应的金属水凝胶。这些金属凝胶的形成对Ni²⁺离子高度选择性。此外，自愈合性能可以通过改变相应凝胶体两性分子的链长来调节。
• NOVEL COMPOUND ACCELERATING SECRETION OF HUMAN-DERIVED ANTI-MICROBIAL PEPTIDE, METHOD FOR PREPARING SAME, AND COMPOSITION HAVING SAME AS ACTIVE INGREDIENT
  申请人：Neopharm Co., Ltd.

  公开号：US20130190397A1

  公开（公告）日：2013-07-25

  Disclosed is a compound having an acceleration effect on the secretion of human β-defensin, LL-37, which is a human-derived anti-microbial peptide, a method for preparing same, and a composition for accelerating the secretion of anti-microbial peptide having same as an active ingredient, and the compound and the composition using same of the present invention enhance the anti-microbial effect and the immunity control effect that the anti-microbial peptide has in the body by accelerating the secretion of the anti-microbial peptide in the body.

  本发明揭示了一种具有促进人类β-防御素LL-37分泌的加速效果的化合物，该化合物是一种源自人体的抗微生物肽，提供了制备该化合物的方法以及以其为活性成分的促进抗微生物肽分泌的组合物。本发明的化合物和组合物通过加速体内抗微生物肽的分泌，增强了抗微生物肽在人体内具有的抗微生物效果和免疫控制效果。
• Synthesis, physicochemical, and biological activities of novel N-acyl tyrosine monomeric and Gemini surfactants in single and SDS/CTAB-mixed micellar system
  作者：Nausheen Joondan、Sabina Jhaumeer-Laulloo、Prakashanand Caumul、Matthew Akerman

  DOI：10.1002/poc.3675

  日期：2017.10

  Mixed micellar behavior of the N‐acyl Gemini surfactant with conventional cationic (CTAB) and anionic (SDS) surfactants in aqueous solution was studied. The negative value of the interaction parameter β12 observed for the N‐acyl Gemini in binary mixture with CTAB surfactant indicated a synergistic interaction within the mixed micellar system. However, the binary mixture with SDS displayed antagonistic

  合成了一系列具有不同链长（C 10 -C 18）和不饱和度的单链N-酰基酪氨酸表面活性剂，以及链长为C 12的N-酰基双子酪氨酸表面活性剂，结构为使用光谱分析确认。评估了链长和不饱和度对N-酰基酪氨酸表面活性剂的理化和抗菌性能的影响。C 12该衍生物在单链表面活性剂中显示出最佳的抗菌活性，并且油酰衍生物中双键的存在增强了其饱和类似物的抗菌活性。N-酰基双子叶表面活性剂在该系列中表现出最高的抗菌活性，并且比其单链类似物还显示出更大的胶束形成能力。研究了N-酰基双子叶表面活性剂与常规阳离子（CTAB）和阴离子（SDS）表面​​活性剂在水溶液中的混合胶束行为。相互作用参数的负值β 12在与CTAB表面活性剂的二元混合物中观察到的N-酰基双子座表明混合胶束体系内有协同作用。但是，具有SDS的二元混合物表现出拮抗作用。N-酰基双子叶表面活性剂与CTAB的二元混合物比SDS混合物具有更好的抗菌活性和发
• Compound accelerating secretion of human-derived anti-microbial peptide, method for preparing same, and composition having same as active ingredient
  申请人：Neopharm Co., Ltd.

  公开号：US08809390B2

  公开（公告）日：2014-08-19

  Disclosed is a compound having an acceleration effect on the secretion of human β-defensin, LL-37, which is a human-derived anti-microbial peptide, a method for preparing same, and a composition for accelerating the secretion of anti-microbial peptide having same as an active ingredient, and the compound and the composition using same of the present invention enhance the anti-microbial effect and the immunity control effect that the anti-microbial peptide has in the body by accelerating the secretion of the anti-microbial peptide in the body.

  本发明揭示了一种化合物，其对人类β-防御素LL-37的分泌具有加速作用，LL-37是一种人源抗微生物肽，还揭示了一种制备该化合物的方法以及一种以该化合物为活性成分的加速抗微生物肽分泌的组合物。本发明的化合物和组合物通过加速体内抗微生物肽的分泌，增强了抗微生物肽在体内的抗微生物和免疫调节作用。
• Synthesis and structure–activity relationships of tyrosine-based inhibitors of autotaxin (ATX)
  作者：James E. East、Andrew J. Kennedy、Jose L. Tomsig、Alexandra R. De Leon、Kevin R. Lynch、Timothy L. Macdonald

  DOI：10.1016/j.bmcl.2010.09.030

  日期：2010.12

  Autotaxin (ATX) is a secreted soluble enzyme that generates lysophosphatidic acid (LPA) through its lysophospholipase D activity. Because of LPA's role in neoplastic diseases, ATX is an attractive therapeutic target due to its involvement in LPA biosynthesis. Here we describe the SAR of ATX inhibitor, VPC8a202, and apply this SAR knowledge towards developing a high potency inhibitor. We found that electron density in the pyridine region greatly influences activity of our inhibitors at ATX. (C) 2010 Elsevier Ltd. All rights reserved.