ethyl N-benzoyl-L-phenylalanyl-L-alaninate | 140195-91-1

• 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: ethyl N-benzoyl-L-phenylalanyl-L-alaninate
• 英文别名: (S)-2-((S)-2-Benzoylamino-3-phenyl-propionylamino)-propionic acid ethyl ester；ethyl (2S)-2-[[(2S)-2-benzamido-3-phenylpropanoyl]amino]propanoate
• CAS: 140195-91-1
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: DWYWJLGUPOVHCY-YJBOKZPZSA-N

物化性质

• 沸点：
  620.6±55.0 °C(Predicted)
• 密度：
  1.165±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-benzoyl-L-phenylalanyl-L-alaninate 生成 N-(tert-butoxycarbonyl)-β,β-dimethyl-L-phenylalanine
  参考文献：
  名称：

  Pyruvamide Compounds as Inhibitors of Dust Mite Group 1 Peptidase Allergen and Their Use

  摘要：

  本发明一般涉及治疗化合物领域，更具体地涉及某些丙酮酰胺化合物的公式（X）（为方便起见，以下统称为“PVA化合物”），该化合物在某些情况下抑制尘螨1组蛋白酶过敏原（例如Der p 1、Der f 1、Eur m 1）。本发明还涉及包含这种化合物的药物组合物，以及在体外和体内使用这种化合物和组合物来抑制尘螨1组蛋白酶过敏原，并用于治疗由尘螨1组蛋白酶过敏原介导的疾病和疾病，通过抑制尘螨1组蛋白酶过敏原而得到缓解的疾病和疾病；哮喘；鼻炎；过敏性结膜炎；特应性皮炎；由尘螨引发的过敏症状；由尘螨1组蛋白酶过敏原引发的过敏症状；以及犬类特应性。

  公开号：

  US20120322722A1
• 作为产物：
  描述：

  Boc-Phe-Ala-OEt 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 生成 ethyl N-benzoyl-L-phenylalanyl-L-alaninate
  参考文献：
  名称：

  The Discovery of Potent, Selective, and Reversible Inhibitors of the House Dust Mite Peptidase Allergen Der p 1: An Innovative Approach to the Treatment of Allergic Asthma

  摘要：

  Blocking the bioactivity of allergens is conceptually attractive as a small-molecule therapy for allergic diseases but has not been attempted previously. Group 1 allergens of house dust mites (HDM) are meaningful targets in this quest because they are globally prevalent and clinically important triggers of allergic asthma. Group 1 HDM allergens are cysteine peptidases whose proteolytic activity triggers essential steps in the allergy cascade. Using the HDM allergen Der p 1 as an archetype for structure-based drug discovery, we have identified a series of novel, reversible inhibitors. Potency and selectivity were manipulated by optimizing drug interactions with enzyme binding pockets, while variation of terminal groups conferred the physicochemical and pharmacokinetic attributes required for inhaled delivery. Studies in animals challenged with the gamut of HDM allergens showed an attenuation of allergic responses by targeting just a single component, namely, Der p 1. Our findings suggest that these inhibitors may be used as novel therapies for allergic asthma.

  DOI：

  10.1021/jm501102h

文献信息

• A Fast Procedure for the Preparation of Amides/Peptides from Carboxylic Acids and Azides via Two Redox Reactions: Application to the Synthesis of Methionine Enkephalin
  作者：Sunil K. Ghosh、Rekha Verma、Usha Ghosh、Vasant R. Mamdapur

  DOI：10.1246/bcsj.69.1705

  日期：1996.6

  A one-pot self regulated approach for the synthesis of amides/peptides based on two reduction–oxidation (redox) reactions has been described. The primary and secondary amides/peptides are made by using azidotrimethylsilane and alkyl azides/α-azido acid derivatives respectively as the direct source of amine components. Benzeneselenol, generated in the reaction medium during carboxyl activation, has

  已经描述了基于两个还原-氧化（氧化还原）反应的用于合成酰胺/肽的一锅自调节方法。一级和二级酰胺/肽分别使用叠氮三甲基硅烷和烷基叠氮化物/α-叠氮酸衍生物作为胺组分的直接来源制备。已发现在羧基活化过程中在反应介质中产生的苯甲酚是用于将叠氮化物转化为伯胺的有效还原剂。该方法已应用于甲硫氨酸脑啡肽的合成。
• Pyruvamide compounds as inhibitors of dust mite group 1 peptidase allergen and their use
  申请人：Robinson Clive

  公开号：US08541363B2

  公开（公告）日：2013-09-24

  The present invention pertains generally to the field of therapeutic compounds and more specifically to certain pyruvamide compounds of the formula (X) (for convenience, collectively referred to herein as “PVA compounds”), which, inter alia, inhibit a dust mite Group 1 peptidase allergen (e.g., Der p 1, Der f 1, Eur m 1). The present invention also pertains to pharmaceutical compositions comprising such compounds, and the use of such compounds and compositions, both in vitro and in vivo, to inhibit a dust mite Group 1 peptidase allergen, and in the treatment of diseases and disorders that are mediated by a dust mite Group 1 peptidase allergen; that are ameliorated by the inhibition of a dust mite Group 1 peptidase allergen; asthma; rhinitis; allergic conjunctivitis; atopic dermatitis; an allergic condition which is triggered by dust mites; an allergic condition which is triggered by a dust mite Group 1 peptidase allergen; and canine atopy.

  本发明涉及治疗化合物领域，更具体地涉及某些式为（X）的丙酮酰胺化合物（为方便起见，在此统称为“PVA化合物”），它们可以抑制尘螨群1肽酶过敏原（例如Der p 1、Der f 1、Eur m 1）。本发明还涉及包含这些化合物的制药组合物，以及使用这些化合物和组合物在体内和体外抑制尘螨群1肽酶过敏原，并用于治疗由尘螨群1肽酶过敏原介导的疾病和障碍，这些疾病和障碍可以通过抑制尘螨群1肽酶过敏原得到改善，如哮喘、鼻炎、过敏性结膜炎、特应性皮炎、由尘螨引起的过敏症状、由尘螨群1肽酶过敏原引起的过敏症状和犬过敏症。
• One pot amide/ peptide synthesis via two redox reactions
  作者：Sunil K. Ghosh、Usha Singh、Vasant R. Mamdapur

  DOI：10.1016/s0040-4039(00)77720-3

  日期：1992.2

  A new and highly efficient one-pot self-regulated approach to amide/ peptide synthesis has been developed based on two redox reactions using azide as a latent amine component. For the first time, selenophenol, generated in situ has been found to be an effective reducing agent for the conversion of azides to amines.
• PYRUVAMIDE COMPOUNDS AS INHIBITORS OF DUST MITE GROUP 1 PEPTIDASE ALLERGEN
  申请人：St. George's Hospital Medical School

  公开号：EP2526116B1

  公开（公告）日：2015-05-13
• US8541363B2
  申请人：——

  公开号：US8541363B2

  公开（公告）日：2013-09-24