(S)-methyl 4-methyl-2-(2-phenylacetamido)pentanoate | 65414-68-8

• 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 4-methyl-2-(2-phenylacetamido)pentanoate
• 英文别名: N-phenylacetyl-L-leucine methyl ester；N-Phenylacetyl-L-leucin-methylester；methyl (2S)-4-methyl-2-[(2-phenylacetyl)amino]pentanoate
• CAS: 65414-68-8
• 化学式: C₁₅H₂₁NO₃
• 分子量: 263.337
• InChiKey: YPPQVRQQTPJCDS-ZDUSSCGKSA-N

物化性质

• 沸点：
  410.4±28.0 °C(Predicted)
• 密度：
  1.061±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  (S)-methyl 4-methyl-2-(2-phenylacetamido)pentanoate 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 (2S)-N-hydroxy-4-methyl-2-[(2-phenylacetyl)amino]pentanamide
  参考文献：
  名称：

  Development of Synthetic Aminopeptidase N/CD13 Inhibitors to Overcome Cancer Metastasis and Angiogenesis

  摘要：

  Cancer metastasis is a major barrier to its treatment and an important cause of patient death. Antimetastatic agents hold promise for patients with advanced metastatic tumors. Aminopeptidase N/CD13 (APN) is being pursued by many as an important target against cancer metastasis and angiogenesis, but there are few reports on the in vivo evaluation of synthetic APN inhibitors. Herein, a series of compounds targeting APN were synthesized and evaluated for their antimetastasis and antiangiogenesis potency both in vitro and in vivo. Excitingly, compounds 4m, 4t, and 4cc, with the most potent APN inhibitory activities, displayed significant antimetastasis and antiangiogenesis effects in vitro and in vivo, suggesting that those synthetic APN inhibitors have the potential to overcome cancer metastasis and angiogenesis.

  DOI：

  10.1021/ml3000758
• 作为产物：
  描述：

  苯甲醛 在 哌啶 、 sodium tetrahydroborate 、 氧气 、 potassium carbonate 作用下， 以 乙醇 、 乙腈 为溶剂， -30.0~20.0 ℃ 、101.33 kPa 条件下， 反应 11.33h， 生成 (S)-methyl 4-methyl-2-(2-phenylacetamido)pentanoate
  参考文献：
  名称：

  使用O2立体要求α-取代的丙二腈与胺进行氧化酰胺化反应。

  摘要：

  简单地使用分子氧和碳酸盐碱即可实现易于获得的1,1-二氰基烷烃与手性或非手性胺之间的高效酰胺化方法。该氧化方案可以高度化学选择性，实用和快速的方式应用于空间和电子挑战性底物。环丙基和硫醚底物的使用可支持α-过氧丙二腈物种的自由基形成，后者可以环化成二恶英，后者可以单价氧化丙二腈α-碳二酮以提供能够与胺亲核试剂反应的活化的酰基氰化物。

  DOI：

  10.1002/anie.201603399

文献信息

• 一种用于酰胺合成的催化剂及其制备与应用
  申请人：兰州大学

  公开号：CN114874227A

  公开（公告）日：2022-08-09

  本发明公开了一种用于酰胺合成的催化剂及其制备与应用，所述催化剂为硫代或硒代的吡喃并双嘧啶类化合物，其结构简单新颖，催化效率高，原子经济性好；本发明催化剂可以用于酰胺化合物的合成，具体为：在羧酸组分、胺组分、催化剂以及三苯基膦或二苯基膦氧中加入有机溶剂，在光照或室温或加热条件下搅拌，直至三苯基膦或二苯基膦氧消耗完全，分离纯化得到酰胺化合物。该酰胺化合物合成方法简单易纯化，催化反应无须额外的除水或惰性气体保护等操作，在常温、加热及光照等条件下都能直接催化羧酸转变为相应的酰胺，且光照条件下反应时间短，产率高，副产物单一，N、O选择性好，能直接用于酰胺或多肽的固相合成，具有广阔的工业化应用前景。
• Lipophilic Permeability Efficiency Reconciles the Opposing Roles of Lipophilicity in Membrane Permeability and Aqueous Solubility
  作者：Matthew R. Naylor、Andrew M. Ly、Mason J. Handford、Daniel P. Ramos、Cameron R. Pye、Akihiro Furukawa、Victoria G. Klein、Ryan P. Noland、Quinn Edmondson、Alexandra C. Turmon、William M. Hewitt、Joshua Schwochert、Chad E. Townsend、Colin N. Kelly、Maria-Jesus Blanco、R. Scott Lokey

  DOI：10.1021/acs.jmedchem.8b01259

  日期：2018.12.27

  As drug discovery moves increasingly toward previously "undruggable" targets such as protein-protein interactions, lead compounds are becoming larger and more lipophilic. Although increasing lipophilicity can improve membrane permeability, it can also incur serious liabilities, including poor water solubility, increased toxicity, and faster metabolic clearance. Here we introduce a new efficiency metric, especially relevant to "beyond rule of 5" molecules, that captures, in a simple, unitless value, these opposing effects of lipophilicity on molecular properties. Lipophilic permeability efficiency (LPE) is defined as log D-dec/w(7.4) - m(lipo)cLogP + b(scaffold), where log D-dec/w(7.4) is the experimental decadiene-water distribution coefficient (pH 7.4), cLogP is the calculated octanol-water partition coefficient, and m(lipo) and b(scaffold) are scaling factors to standardize LPE values across different cLogP metrics and scaffolds. Using a variety of peptidic and nonpeptidic macrocycle drugs, we show that LPE provides a functional assessment of the efficiency with which a compound achieves passive membrane permeability at a given lipophilicity.
• Cornforth, Chemistry of Penicillin
  作者：Cornforth

  DOI：——

  日期：——