N-Phenylacetyl alanine methyl ester | 41109-05-1

• 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-Phenylacetyl alanine methyl ester
• 英文别名: N-phenylacetylalanine methyl ester；N-phenylacetyl-DL-alanine methyl ester；N-Phenylacetyl-DL-alanin-methylester；methyl 3-chloro-N-phenylacetylalaninate；N-Phenylacetyl-D.L.-alaninmethylester；Methyl 2-[(2-phenylacetyl)amino]propanoate
• CAS: 41109-05-1；127043-26-9；64562-94-3
• 化学式: C₁₂H₁₅NO₃
• mdl: MFCD00085498
• 分子量: 221.256
• InChiKey: DLCNTEDUKYKOIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-Phenylacetyl alanine methyl ester 在 一水合肼 作用下， 以 甲醇 为溶剂， 生成 N-(1-hydrazinyl-1-oxopropan-2-yl)-2-phenylacetamide
  参考文献：
  名称：

  Synthesis and antitumor evaluation of some 1,3,4-oxadiazole-2(3H)-thione and 1,2,4-triazole-5(1H)-thione derivatives

  摘要：

  A series of 1,3,4-oxadiazole-2-thione and 1,2,4-triazole-5-thione derivatives have been successfully synthesized and studied for their antitumor activity. These compounds were prepared from carboxylic acids and chiral aminoacid esters. The prepared compounds were evaluated for their cytotoxicity against cancer in vitro using hydroxyurea (HU) as positive control. A fair number of compounds were found to have significant antitumor activity. To study the molecular basis of interaction and affinity of binding of the target molecules, all the compounds were docked into the ATPase domain of TP-II and tubulin using Schrodinger.

  DOI：

  10.1007/s00044-010-9544-6
• 作为产物：
  描述：

  N-(Phenylacetyl)dehydroalanine methyl ester 在 Co catalyst 氢气 作用下， 生成 N-Phenylacetyl alanine methyl ester
  参考文献：
  名称：

  不对称反应。九。双(二甲基乙醛肟)钴(II)碱配合物催化加氢烯烃类化合物

  摘要：

  对21种烯烃化合物与双(二甲基乙醛肟)钴(II)-吡啶络合物催化加氢的研究表明，所有具有吸电子和弱给电子取代基的(注：图略)型烯烃化合物都是可还原的. 在（备注：图略）型烯烃化合物的情况下，烷基配合物的分离和进一步加氢，以及α-苯基丙烯酮的氘化反应支持α-烷基配合物是加氢中间体的观点。得出的结论是，吸电子效应加速了第一步（烷基配合物的形成）和第二步（烷基部分的还原裂解），而空间压缩阻止了第一步并加速了第二步。讨论了反应机理。

  DOI：

  10.1246/bcsj.47.463

文献信息

• METHOD FOR THE PRODUCTION OF RAMIPRIL
  申请人：BERK Holger

  公开号：US20090017509A1

  公开（公告）日：2009-01-15

  An improved method for preparing ramipril is disclosed, and also an intermediate for use in the method.

  揭示了一种改进的制备雷米普利的方法，以及用于该方法的中间体。
• Nonpeptidic Oxazole-Based Prolyl Oligopeptidase Ligands with Disease-Modifying Effects on α-Synuclein Mouse Models of Parkinson’s Disease
  作者：Tommi P. Kilpeläinen、Henri T. Pätsi、Reinis Svarcbahs、Ulrika H. Julku、Tony S. Eteläinen、Hengjing Cui、Samuli Auno、Nina Sipari、Susanna Norrbacka、Teppo O. Leino、Maria Jäntti、Timo T. Myöhänen、Erik A. A. Wallén

  DOI：10.1021/acs.jmedchem.3c00235

  日期：2023.6.8

  reducing α-synuclein (αSyn) dimerization and enhancing protein phosphatase 2A activity in a concentration–response manner, as well as reducing reactive oxygen species production. From the best performing oxazoles, HUP-55 was selected for in vivo studies. Its brain penetration was evaluated, and it was tested in αSyn virus vector-based and αSyn transgenic mouse models of Parkinson’s disease, where it

  脯氨酰寡肽酶（PREP）是人体内广泛分布的丝氨酸蛋白酶，可裂解含脯氨酸的肽；然而，最近的研究表明，它对神经退行性病变致病过程的影响源自直接的蛋白质-蛋白质相互作用（PPI），而不是来自其对某些神经肽水平的调节。我们发现了新型非肽类恶唑类 PREP 抑制剂，它偏离了 PREP 抑制剂已知的构效关系。这些新化合物是 PREP 的 PPI 的有效调节剂，以浓度响应方式减少 α-突触核蛋白 (αSyn) 二聚化并增强蛋白磷酸酶 2A 活性，并减少活性氧的产生。从性能最好的恶唑中，选择HUP-55进行体内研究学习。我们评估了它的大脑渗透性，并在基于 αSyn 病毒载体和帕金森病 αSyn 转基因小鼠模型中进行了测试，它恢复了运动障碍并降低了纹状体和黑质中寡聚 αSyn 的水平。
• [EN] PREP BINDING LIGANDS<br/>[FR] LIGANDS DE LIAISON DE PREP
  申请人：UNIV HELSINKI

  公开号：WO2023209191A1

  公开（公告）日：2023-11-02

  The invention concerns a novel class of Prolyl oligopeptidase binding ligands, a pharmaceutical composition comprising same, the use of said ligands as medicaments, particularly, but not exclusively to promote autophagy and/or treat a disease involving a reduction in PPA2 activity or PP2A dysfunction.

  本发明涉及一类新型的脯氨酰寡肽酶结合配体、包含该配体的药物组合物、所述配体作为药物的用途，特别是但不限于促进自噬和/或治疗涉及 PPA2 活性降低或 PP2A 功能障碍的疾病。
• Barton, Patrick; Laws, Andrew P.; Page, Michael I., Journal of the Chemical Society. Perkin transactions II, 1994, # 9, p. 2021 - 2030
  作者：Barton, Patrick、Laws, Andrew P.、Page, Michael I.

  DOI：——

  日期：——
• Anodic oxidation of N-acyl and N-alkoxycarbonyl dipeptide esters as a key step for the formation of chiral heterocyclic synthetic building blocks
  作者：Apostolos Papadopoulos、Burhansha Lewall、Eberhard Steckhan、Klaus-Dieter Ginzel、Falk Knoch、Martin Nieger

  DOI：10.1016/s0040-4020(01)87046-0

  日期：1991.1

  The anodic oxidation of N-protected dipeptide esters using chloride as a redox catalyst can be performed regioselectively at the C-terminal amino acid. With methanol as solvent, glycine as the C-terminal, and L-valine or L-proline as N-terminal amino acid methoxylation at the glycine residue takes place. Deprotection of this product leads to the (3S,6RS)-6-methoxy-2,5-piperazinedione(3) which can be applied as a chiral cationic glycine equivalent. The exchange of the methoxy group by C-nucleophiles takes place with high trans-diastereoselectivity under steric control by the substituent in 3-position. With branched amino acids at the C-terminus of the dipeptide ester the anodic oxidation in acetonitrile/methanol (95:5) as solvent with tetraethylammonium chloride as supporting electrolyte and redox catalyst leads to methyl imidazolidin-4-one-2-carboxylates. The cyclization takes place via the intermediate formation of the N-acylimino ester of the C-terminal amino acid.