N-α-Naphthylacetyl-L-alanine | 32667-83-7

• 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: N-α-Naphthylacetyl-L-alanine
• 英文别名: (2S)-2-[(2-naphthalen-1-ylacetyl)amino]propanoic acid
• CAS: 32667-83-7
• 化学式: C₁₅H₁₅NO₃
• mdl: MFCD08485082
• 分子量: 257.289
• InChiKey: FUEHQQBAKMAHCM-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-α-Naphthylacetyl-L-alanine 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 1.67h， 生成
  参考文献：
  名称：

  In aquo ppm level detection of acrylamide through S-to-N acyl transfer mediated activation of pro-sensors

  摘要：

  开发了水溶性丙烯酰化合物的前体传感器，包括丙烯酰胺（AM）。

  DOI：

  10.1039/c5cc02721g
• 作为产物：
  描述：

  methyl (2S)-2-[(2-naphthalen-1-ylacetyl)amino]propanoate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 6.0h， 生成 N-α-Naphthylacetyl-L-alanine
  参考文献：
  名称：

  通过简单去除或包含N-Boc-Protection即可进行有机凝胶-水凝胶转化

  摘要：

  由于从先进材料到生物医学的广泛应用，有机和水凝胶化剂的开发正在上升。然而，由共同的结构支架设计两种类型的胶凝剂是具有挑战性的，并且如果可以通过简单的方法实现它们之间的转化，则这将变得更加重要。本工作报道了由氨基酸/基于肽的两亲性前体在N端带有萘基，在C端带有伯胺的亲水性乙氧基单元的设计和合成方法。在碱性介质中，两亲物伯胺上的叔丁氧羰基（Boc）保护导致有效的有机胶凝剂（最小胶凝浓度（MGC）= 0.075–1.5％  w / v）。有趣的是，在酸性条件下，从乙氧基单元上除去Boc保护基，可以生成能够胶凝水的两亲物（MGC = 0.9–3.0％  w / v）。简单的保护和脱保护化学用于通过改变pH值来实现有机凝胶和水凝胶之间的转化。研究了不同脂肪族和芳香族氨基酸的组合，以发现它们对凝胶特性的累积影响。场发射扫描电子显微镜（FESEM）和透射电子显微镜（TEM）被用来研究热可逆凝胶的超分子形

  DOI：

  10.1002/chem.201101173

文献信息

• Bolaform homodiamides of N-protected alanines as efficient and versatile sono- and thermo-gelators offering phase-selectivity, optical-transparency and enzyme-assisted release
  作者：Amarendar Reddy M、Aashish Sharma、Qysar Maqbool、Aasheesh Srivastava

  DOI：10.1039/c3ra42047g

  日期：——

  We report a series of bolaform homodiamides of N-protected alanines that exhibit efficient thermo-reversible gelation of a broad variety of solvents. Gelation of these solvents upon bath-sonication was also achieved. Overall superior gelation profiles were exhibited by gelators in which the aromatic moiety was bonded to the N-terminus of the alanine by amide bonds (rather than by carbamate bonds). Rigidification of aggressive, hydrogen-bonding solvents such as small-chain alcohols and alcohol–water mixtures was also achieved by these amide-gelators. AFM of chirally-pure samples showed the presence of nanofibers exhibiting helicity. The contributions of inter-molecular hydrogen bonding as well as π-stacking to the self-assembly of these gelators were assessed by variable-temperature NMR and UV-vis studies. FTIR data indicated the extensive propensity of these gelators to form β-sheet-like assemblies. Phase-selective gelation, even in the presence of salts in the aqueous layer, could be achieved – both by thermal processing as well as by bath-sonication at room temperature. The ability to achieve phase-selective gelation by sonication at ambient conditions opens new avenues for spill-control applications. Entrapment of tetracycline and its papain-assisted release was demonstrated to exemplify the potential utility of these gels in drug-delivery applications.

  我们报告了一系列 N 保护丙氨酸的波拉形式同二元酰胺，它们在多种溶剂中表现出高效的热可逆凝胶化。这些溶剂在水浴溶解时也能凝胶化。芳香分子通过酰胺键（而不是氨基甲酸酯键）与丙氨酸的 N 端结合的凝胶剂总体上表现出较好的凝胶特性。这些酰胺凝胶剂还能使侵蚀性氢键溶剂（如小链醇和醇水混合物）刚性化。手性纯样品的原子力显微镜显示出纳米纤维的螺旋性。变温核磁共振和紫外可见光研究评估了分子间氢键和 π 堆积对这些凝胶剂自组装的贡献。傅立叶变换红外光谱数据表明，这些凝胶剂具有形成 β 片状组装体的广泛倾向。即使在水层中存在盐分的情况下，也能通过热处理和室温下的水浴溶解实现相选择性凝胶化。在环境条件下通过超声处理实现相选择凝胶化的能力为溢出控制应用开辟了新的途径。四环素的包埋及其木瓜蛋白酶辅助释放试验证明了这些凝胶在药物输送应用中的潜在效用。
• Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
  申请人：——

  公开号：US20040043977A1

  公开（公告）日：2004-03-04

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  本发明涉及一种抑制&bgr;-淀粉样肽释放和/或其合成的化合物，因此在治疗阿尔茨海默病方面具有用途。此外，还公开了包含抑制&bgr;-淀粉样肽释放和/或其合成的化合物的制药组合物，以及使用这种制药组合物预防和治疗阿尔茨海默病的方法。
• Cycloalkyl, lactam, lactone and related compounds, pharmaceutical compositions comprising same, and methods for inhibiting beta-amyloid peptide release and/or its synthesis by use of such compounds
  申请人：——

  公开号：US20040058900A1

  公开（公告）日：2004-03-25

  Disclosed are compounds which inhibit &bgr;-amyloid peptide release and/or its synthesis, and, accordingly, have utility in treating Alzheimer's disease. Also disclosed are pharmaceutical compositions comprising a compound which inhibits &bgr;-amyloid peptide release and/or its synthesis as well as methods for treating Alzheimer's disease both prophylactically and therapeutically with such pharmaceutical compositions.

  本发明涉及一种抑制β-淀粉样肽的释放和/或合成的化合物，因此在治疗阿尔茨海默病方面具有用途。本发明还涉及包含抑制β-淀粉样肽释放和/或合成的化合物的制药组合物，以及使用这种制药组合物预防和治疗阿尔茨海默病的方法。
• N-(ARYL/HETEROARYLACETYL) AMINO ACID ESTERS, PHARMACEUTICAL COMPOSITIONS COMPRISING SAME, AND METHODS FOR INHIBITING BETA-AMYLOID PEPTIDE RELEASE AND/OR ITS SYNTHESIS BY USE OF SUCH COMPOUNDS
  申请人：Elan Pharmaceuticals, Inc.

  公开号：EP0951464B1

  公开（公告）日：2005-05-11
• US6476263B1
  申请人：——

  公开号：US6476263B1

  公开（公告）日：2002-11-05