N-phenylacetylproline | 2752-38-7

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 脯氨酸类衍生物
• 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-phenylacetylproline
• 英文别名: N²-Phenylacetyl-L-asparagin；1-Phenylacetyl-pyrrolidine-2-carboxylic acid；1-(2-phenylacetyl)pyrrolidine-2-carboxylic acid
• CAS: 2752-38-7
• 化学式: C₁₃H₁₅NO₃
• mdl: MFCD00451541
• 分子量: 233.267
• InChiKey: UBQCWSGRNIOFFC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  N-phenylacetylproline 在 氯化亚砜 、 potassium carbonate 作用下， 以 甲醇 、 水 为溶剂， 生成 1-Phenylacetyl-pyrrolidine-2-carboxylic acid methyl ester
  参考文献：
  名称：

  1-Phenyl-2-aminoethanol derivatives

  摘要：

  该发明涉及以下化合物的公式：- R.sup.1.CH(OH).CH.sub.2 NH.CR.sup.2 R.sup.3.A.sup.1. NH.CO.CHR.sup.4.A.sup.2.NR.sup.5. Q I，其中R.sup.1是3,4-双[(3-8C)癸酰氧基]-苯基，3,5-双[(3-8C)癸酰氧基]苯基，3-[(3-8C)癸酰氧基]甲基-4-[(3-8C)癸酰氧基]苯基，4-[(3-8C)癸酰氧基]苯基，2-氯苯基或3,5-二氯-4-氨基苯基；R.sup.2和R.sup.3独立地是氢或(1-4C)烷基；A.sup.1是(1-4C)烷基；A.sup.2是直链键或(1-4C)烷基；R.sup.4是氢，(1-6C)烷基，苯基-(1-4C)烷基或卤代苯基-(1-4C)烷基；而R.sup.5是(1-6C)烷基；或者R.sup.4和R.sup.5共同形成(2-5C)烷基；Q是(3-12C)癸酰基，[(3-6C)癸氧基]羰基，苯乙酰基，苯氧乙酰基，苯甲酰基或苄氧羰基，其中苯环上可能选择携带卤素，(1-4C)烷基，(1-4C)癸氧基和三氟甲基等取代基；以及其药学上可接受的酸盐；制备它们的方法；以及其药物组合物。公式I的化合物是局部抗炎剂。代表性化合物是1-[3,4-双(季戊酰氧基)苯基]-2-{2-[(N-苯乙酰基-丙基)氨基]-1,1-二甲基-乙基氨基}乙醇。

  公开号：

  US04323575A1
• 作为产物：
  描述：

  苯乙酰氯 、 DL-脯氨酸 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 N-phenylacetylproline
  参考文献：
  名称：

  Penicillin G acylase-mediated kinetic resolution of racemic 1-( N -acylamino)alkylphosphonic and 1-( N -acylamino)alkylphosphinic acids and their esters

  摘要：

  Extensive studies on the penicillin G acylase-mediated kinetic resolution of N-acylated 1-aminoalkylphosphonic and 1-aminoalkylphosphinic acids as well as their esters were carried out to recognise the relationships between the substrate structure, reaction conditions, and the enzymatic hydrolytic deacylation efficiency and stereoselectivity. Reactivity of 1-(N-acylamino)alkylphosphonic and 1-(N-acylamino)allcylphosphinic acids and their esters in the penicillin G acylase-mediated hydrolytic deacylation reaction depends strongly on the kind of their N-acyl group, with high preference to the hydrolytic splitting of the N-phenylacetyl moiety. The initial hydrolysis rates of 1-(N-phenylacetylamino)alkylphosphonic acid dimethyl esters 2 are mostly distinctly lower in comparison with the corresponding free acids 3 and rapidly decrease with the increasing steric effect of the substituent at the alpha-position. In contrary to the substituents at the alpha-carbon, bulky substituents at the phosphorus hinder the enzymatic hydrolysis to a much lesser degree. The penicillin G acylase-mediated stereospecific hydrolysis of N-acyl group of both racemic 1-(N-acylamino)alkylphosphonic acids 3 and their dimethyl esters 2 proved to be, in most cases, a highly effective method for the kinetic resolution of these compounds: High enzyme enantioselectivity E-values exceeding 100, or synthetically useful E-values exceeding 20 (in two cases) were obtained for the N-acylated phosphonic acid analogues of alanine, phenylalanine, valine, leucine, and asparagine, as well as for their dimethyl esters, with the exception of the dimethyl ester of phosphonic analogue of valine 2e, that E-value was low (E=1.2). Also for the N-acylated H-phosphinic acid analogues of alanine, as well as phenylphosphinic acid analogue of alanine, high enzyme enantioselectivity values exceeding 100 were obtained. In contrary, E-values for both diastereomers of ethyl ester of phenylphosphinic analogue of alanine 2k were low (E=7 and 13). For the all accomplished assignments penicillin G acylase exhibited stereochemical preference for the (R)-substrate. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2016.05.011

文献信息

• Methods and compounds for inhibiting mrp1
  申请人：——

  公开号：US20030100576A1

  公开（公告）日：2003-05-29

  The present invention further relates to a method of inhibiting MRP1 in a mammal which comprises administering to a mammal in need thereof an effective amount of a compound of formula (I).

  本发明还涉及一种抑制哺乳动物中MRP1的方法，包括向需要的哺乳动物施用化合物(I)的有效量。
• Hepatitis C Virus Inhibitors
  申请人：Belema Makonen

  公开号：US20100080772A1

  公开（公告）日：2010-04-01

  The present disclosure relates to compounds, compositions and methods for the treatment of hepatitis C virus (HCV) infection. Also disclosed are pharmaceutical compositions containing such compounds and methods for using these compounds in the treatment of HCV infection.

  本公开涉及化合物、组合物和治疗丙型肝炎病毒（HCV）感染的方法。还公开了含有这些化合物的药物组合物以及使用这些化合物治疗HCV感染的方法。
• N-(5-MEMBERED AROMATIC RING)-AMIDO ANTI-VIRAL COMPOUNDS
  申请人：Schmitz Ulrich Franz

  公开号：US20070265265A1

  公开（公告）日：2007-11-15

  Disclosed are compounds having Formula (I) and the compositions and methods thereof for treating or preventing a viral infection mediated at least in part by a virus in the Flaviviridae family of viruses, wherein A, R 2 , m, R, V, W, T, Z, R 1 , Y, and p are disclosed herein.

  揭示了具有Formula (I)的化合物，以及用于治疗或预防由Flaviviridae病毒家族中的病毒至少部分介导的病毒感染的组合物和方法，其中A、R2、m、R、V、W、T、Z、R1、Y和p在此处被揭示。
• [EN] INHIBITORS OF HEPATITIS C VIRUS REPLICATION<br/>[FR] INHIBITEURS DE LA RÉPLICATION DU VIRUS DE L'HÉPATITE C
  申请人：MERCK SHARP & DOHME

  公开号：WO2010111483A1

  公开（公告）日：2010-09-30

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种公式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。
• INHIBITORS OF HEPATITIS C VIRUS REPLICATION
  申请人：Merck Sharp & Dohme Corp.

  公开号：US20190127365A1

  公开（公告）日：2019-05-02

  The present invention relates to compounds of formula (I) that are useful as hepatitis C virus (HCV) NS5A inhibitors, the synthesis of such compounds, and the use of such compounds for inhibiting HCV NS5A activity, for treating or preventing HCV infections and for inhibiting HCV viral replication and/or viral production in a cell-based system.

  本发明涉及一种具有式（I）的化合物，该化合物可用作丙型肝炎病毒（HCV）NS5A抑制剂，以及该类化合物的合成，以及利用该类化合物抑制HCV NS5A活性，用于治疗或预防HCV感染，以及在基于细胞的系统中抑制HCV病毒复制和/或病毒产生。