N-(3-phenyl-propyl)-glycine ethyl ester | 115882-27-4

• 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: N-(3-phenyl-propyl)-glycine ethyl ester
• 英文别名: N-(3-Phenyl-propyl)-glycin-aethylester；N-(γ-Phenyl-propyl)-glycin-aethylester；N-(3-phenyl-1-propyl)glycine ethyl ester；Ethyl 2-(3-phenylpropylamino)acetate
• CAS: 115882-27-4
• 化学式: C₁₃H₁₉NO₂
• mdl: MFCD12148693
• 分子量: 221.299
• InChiKey: FZQGLIFOFGFRCX-UHFFFAOYSA-N

物化性质

• 沸点：
  167-170 °C(Press: 11 Torr)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.461
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-phenyl-propyl)-glycine ethyl ester 在 sodium hydroxide 作用下， 生成 N-(3-phenylpropyl)glycine
  参考文献：
  名称：

  Discovery of Potent and Orally Bioavailable Macrocyclic Peptide–Peptoid Hybrid CXCR7 Modulators

  摘要：

  The chemokine receptor CXCR7 is an attractive target for a variety of diseases. While several small-molecule modulators of CXCR7 have been reported, peptidic macro cycles may provide advantages in terms of potency, selectivity, and reduced off-target activity. We produced a series of peptidic macrocycles that incorporate an N-linked peptoid functionality where the peptoid group enabled us to explore side-chain diversity well beyond that of natural amino acids. At the same time, theoretical calculations and experimental assays were used to track and reduce the polarity while closely monitoring the physicochemical properties. This strategy led to the discovery of macrocyclic peptide peptoid hybrids with high CXCR7 binding affinities (K-i < 100 nM) and measurable passive permeability (P-app > S X 10(-6) cm/s). Moreover, bioactive peptide 25 (K-i = 9 nM) achieved oral bioavailability of 18% in rats, which was commensurate with the observed plasma clearance values upon intravenous administration.

  DOI：

  10.1021/acs.jmedchem.7b01028
• 作为产物：
  描述：

  3-苯基-1-丙胺 、 溴乙酸乙酯 以 氯仿 为溶剂， 反应 2.0h， 生成 N-(3-phenyl-propyl)-glycine ethyl ester
  参考文献：
  名称：

  Discovery, synthesis and biochemical profiling of purine-2,6-dione derivatives as inhibitors of the human poly(A)-selective ribonuclease Caf1

  摘要：

  Eukaryotic mRNA contains a 3' poly(A) tail, which plays important roles in the regulation of mRNA stability and translation. Well-characterized enzymes involved in the shortening of the poly(A) tail include the multi-subunit Ccr4-Not deadenylase, which contains the Caf1 (Pop2) and Ccr4 catalytic components, and poly(A)-specific ribonuclease (PARN). Two Mg2+ ions present in the active sites of these ribonucleases are required for RNA cleavage. Here, we report the discovery, synthesis and biochemical profiling of purine-2,6-dione derivatives as (sub) micromolar inhibitors of Caf1. (C) 2015 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2015.07.095

文献信息

• Intramolecular Friedel−Crafts-Type Reactions Involving <i>N</i>-Acyliminium Ions Derived from Glycine Templates
  作者：Juan Domingo Sánchez、María Teresa Ramos、Carmen Avendaño

  DOI：10.1021/jo010166y

  日期：2001.8.1

  Enantiomerically pure 4-substituted 2-aralkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones (1b-m) in which the alkyl chain is (CH(2))(n), n = 1-3, behave as glycine templates giving by treatment with [hydroxy(tosyloxy)iodo]benzene in ethyl acetate cis-1-tosyloxy derivatives. When these compounds contain electron-rich aryl substituents with n = 2, they spontaneously cyclize through intramolecular

  对映体纯的4-取代的2-芳烷基-2,4-二氢-1H-吡嗪并[2,1-b]喹唑啉-3,6-二酮（1b-m），其中烷基链为（CH（2））（ n），n = 1-3，表现为甘氨酸模板，通过在乙酸乙酯的cis-1-tosyloxy衍生物中用[羟基（tosyloxy）碘]苯处理得到。当这些化合物包含n = 2的富电子芳基取代基时，它们通过分子内Friedel-Crafts型非对映选择性反应自发环化，生成五环或六环化合物。否则，它们通过溶剂分解得到顺式-1-烷氧基衍生物，如果n = 2、3，则可以在第二步中在酸中环化。所有这些反应必须通过类似于S（N）1机理的N-酰氨基发生。 。1-烷氧基-2-芳基甲基衍生物不愿环化，使反式-1-羟基化合物成为唯一的分离反应产物。
• Acyclic compounds promote release of growth hormone
  申请人：Merck & Co., Inc.

  公开号：US05663171A1

  公开（公告）日：1997-09-02

  The present invention is directed to certain compounds of the general structural formula: ##STR1## wherein R.sub.1, R.sub.1a, R.sub.2a, R.sub.3, R.sub.3a, R.sub.4, R.sub.5, R.sub.6, A, W, and n are as defined herein. These compounds promote the release of growth hormone in humans and animals. This property can be utilized to promote the growth of food animals to render the production of edible meat products more efficient, and in humans, to treat physiological or medical conditions characterized by a deficiency in growth hormone secretion, such as short stature in growth hormone deficient children, and to treat medical conditions which are improved by the anabolic effects of growth hormone. Growth hormone releasing compositions containing such compounds as the active ingredient thereof are also disclosed.

  本发明涉及一些具有通用结构式的化合物：##STR1## 其中R.sub.1，R.sub.1a，R.sub.2a，R.sub.3，R.sub.3a，R.sub.4，R.sub.5，R.sub.6，A，W和n的定义如本文所述。这些化合物促进人类和动物的生长激素释放。这种特性可用于促进食用动物的生长，使可食用肉制品的生产更加高效，并且在人类中，可用于治疗生长激素分泌不足所表现出的生理或医学状况，例如生长激素缺乏的儿童的矮小症，以及治疗通过生长激素的合成作用得到改善的医学状况。还公开了含有这些化合物作为活性成分的生长激素释放组合物。
• SERINE DERIVATIVE
  申请人：YAMANOUCHI PHARMACEUTICAL CO. LTD.

  公开号：EP0696586A1

  公开（公告）日：1996-02-14

  A serine derivative represented by general formula (I) or a pharmaceutically acceptable salt thereof, having an anti-PCP(phencyclidine) activity and being useful as a psychotropic, wherein X represents sulfur or oxygen; Y represents nitrogen or CH; R¹ and R² represent each independently hydrogen, lower alkyl or an amino-protecting group, or R¹ and R² may be combined together to form 4- to 9-membered nitrogenous cycloalkyl; R³ represents hydrogen, carboxy, protected carboxy, aralkyl, or lower alkyl which may be hydroxylated; R⁴ represents hydrogen or hydroxy; R⁵ represents hydrogen or lower alkyl; A represents lower alkylene; B represents (1) an (un)saturated 4-to 10-membered nitrogenous cycloalkyl group which may be substituted by lower alkyl or aralkyl, or (2) a bicyclic nitrogenous hydrocarbon ring group comprising a 4- to 8-membered nitrogenous cycloalkyl group and a benzene ring fused together; and ... represents a single or a double bond.

  一种由通式(I)代表的丝氨酸衍生物或其药学上可接受的盐，具有抗五氯苯环利定(PCP)活性并可用作精神药物，其中X代表硫或氧；Y代表氮或CH；R¹和R²各自独立地代表氢、低级烷基或氨基保护基团，或R¹和R²可结合在一起形成4-9元含氮环烷基；R³ 代表氢、羧基、保护羧基、芳烷基或可羟基化的低级烷基； R⁴ 代表氢或羟基； R⁵ 代表氢或低级烷基； A 代表低级亚烷基；B 代表(1)可被低级烷基或芳烷基取代的(非)饱和 4 至 10 元含氮环烷基，或 (2)由 4 至 8 元含氮环烷基和苯环熔合而成的双环含氮烃环基；以及.代表单键或双键。
• Discovery, synthesis and biochemical profiling of purine-2,6-dione derivatives as inhibitors of the human poly(A)-selective ribonuclease Caf1
  作者：Gopal P. Jadhav、Ishwinder Kaur、Maryati Maryati、Blessing Airhihen、Peter M. Fischer、G. Sebastiaan Winkler

  DOI：10.1016/j.bmcl.2015.07.095

  日期：2015.10

  Eukaryotic mRNA contains a 3' poly(A) tail, which plays important roles in the regulation of mRNA stability and translation. Well-characterized enzymes involved in the shortening of the poly(A) tail include the multi-subunit Ccr4-Not deadenylase, which contains the Caf1 (Pop2) and Ccr4 catalytic components, and poly(A)-specific ribonuclease (PARN). Two Mg2+ ions present in the active sites of these ribonucleases are required for RNA cleavage. Here, we report the discovery, synthesis and biochemical profiling of purine-2,6-dione derivatives as (sub) micromolar inhibitors of Caf1. (C) 2015 The Authors. Published by Elsevier Ltd.
• v. Braun; Blessing; Cahn, Chemische Berichte, 1924, vol. 57, p. 910
  作者：v. Braun、Blessing、Cahn

  DOI：——

  日期：——