(S)-methyl 3-(4-hydroxyphenyl)-2-(phenylacetamido)propanoate

• 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-(phenylacetamido)propanoate
• 英文别名: methyl (2S)-3-(4-hydroxyphenyl)-2-[(2-phenylacetyl)amino]propanoate
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: VNVRBDDZSYIUJK-INIZCTEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L-酪氨酸甲酯盐酸盐 、 苯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88.1%的产率得到(S)-methyl 3-(4-hydroxyphenyl)-2-(phenylacetamido)propanoate
  参考文献：
  名称：

  NOVEL COMPOUND ACCELERATING SECRETION OF HUMAN-DERIVED ANTI-MICROBIAL PEPTIDE, METHOD FOR PREPARING SAME, AND COMPOSITION HAVING SAME AS ACTIVE INGREDIENT

  摘要：

  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。

  公开号：

  US20130190397A1

文献信息

• Oxidative Amide Synthesis and N-Terminal α-Amino Group Ligation of Peptides in Aqueous Medium
  作者：Wing-Kei Chan、Chi-Ming Ho、Man-Kin Wong、Chi-Ming Che

  DOI：10.1021/ja064479s

  日期：2006.11.1

  A new method for oxidative synthesis of amides from alkynes and amines in high yields (up to 96%) using [Mn(2,6-Cl2TPP)Cl] 1 as a catalyst and Oxone/H2O2 as an oxidant in aqueous medium has been developed. This method could be used for N-terminal α-amino group ligation of unprotected peptides with aryl, aliphatic, and internal alkynes under mild conditions.

  开发了一种使用 [Mn(2,6-Cl2TPP)Cl] 1 作为催化剂和 Oxone/H2O2 作为氧化剂在水性介质中以高收率（高达 96%）从炔烃和胺氧化合成酰胺的新方法. 该方法可用于在温和条件下将未受保护的肽与芳基、脂肪族和内部炔烃的 N 端 α-氨基连接。
• [EN] ANTICANCER AGENTS BASED ON AMINO ACID DERIVATIVES<br/>[FR] AGENTS ANTICANCÉREUX À BASE DE DÉRIVÉS D'ACIDES AMINÉS
  申请人：3R VALO S E C

  公开号：WO2011011865A1

  公开（公告）日：2011-02-03

  The present invention provides compounds of formula (I): in which T is L or -A-NH-C(O)-L-; L is -(CH2)n- or -(CH2)p-Z-; A is -(CH2)m- or an alkyl component of a naturally occurring amino acid; R is -CO2R1, -CH2OH, -C(O)NH(hydroxyphenyl) or C(S)NH(hydroxyphenyl); R1 is H or is C1-C12 alkyl; X is -OH, OSO2R2, -Cl, -Br, or -I; R2 is C1-C12 alkyl or -CF3; Z is phenyl or naphthyl; m is an integer having a value of 1 to 20; n is an integer having a value of 1 to 20; and p is an integer having a value of 1 to 20 or an enantiomer, diastereoisomer, racemic mixture, pharmaceutically acceptable salt, solvate or prodrug thereof. These compounds can be useful as anticancer agents.

  本发明提供了以下式（I）的化合物：其中T是L或-A-NH-C（O）-L-；L是-(CH2)n-或-( )p-Z-；A是-( )m-或天然氨基酸的烷基成分；R是-CO2R1，- OH，-C（O）NH（羟基苯基）或C（S）NH（羟基苯基）；R1是H或是C1-C12烷基；X是-OH，OSO2R2，-Cl，-Br或-I；R2是C1-C12烷基或-CF3；Z是苯基或萘基；m是具有值1至20的整数；n是具有值1至20的整数；p是具有值1至20的整数或其对映体，非对映异构体，混合物，药用可接受的盐，溶剂化合物或前药。这些化合物可以用作抗癌剂。
• 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。
• 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.
• PHENYL-CONTAINING N-ACYL AMINE AND AMINOACID DERIVATIVES, METHODS FOR THE PRODUCTION THEREOF, A PHARMACEUTICAL COMPOSITION AND THE USE THEREOF
  申请人：Obschestvo S Ogranichennoi Otvetstennostiyu "Pharmenterprises"

  公开号：EP1876169B1

  公开（公告）日：2015-12-30