N-(4-hydroxyphenylacetyl)-L-phenylalanine | 911123-01-8

• 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: N-(4-hydroxyphenylacetyl)-L-phenylalanine
• 英文别名: (2S)-2-[[2-(4-hydroxyphenyl)acetyl]amino]-3-phenylpropanoic acid
• CAS: 911123-01-8
• 化学式: C₁₇H₁₇NO₄
• 分子量: 299.326
• InChiKey: XBRFTZWYYQDMJM-HNNXBMFYSA-N

物化性质

• 沸点：
  610.6±55.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-[(4-hydroxyphenyl)acetyl]-L-phenylalanine methyl ester 在 氢氧化钾 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 生成 N-(4-hydroxyphenylacetyl)-L-phenylalanine
  参考文献：
  名称：

  扩大生物催化的范围：固体支持底物上的氧化生物转化。

  摘要：

  氧化生物催化反应是在固相载体上进行的，从而扩展了可以在固相上进行的生物转化的全部内容。各种苯乙酸和苯甲酸类似物通过酶可裂解接头连接到可控孔玻璃珠上。过氧化物酶（大豆和氯）、酪氨酸酶和醇氧化酶/脱氢酶催化的反应产生了一系列产物，包括低聚酚、卤代芳烃、儿茶酚和芳醛。在使用α-胰凝乳蛋白酶选择性水解化学非不稳定酰胺键从珠子裂解后回收所得产物。用聚乙二醇 (PEG) 接头修饰的可控孔玻璃 (CPG) 比非 PEG 化的 CPG 或非溶胀聚合物树脂提供了显着更高的产品产率。

  DOI：

  10.1002/adsc.200800188

文献信息

• Alcaligenes faecalis penicillin G acylase-catalyzed enantioselective acylation of dl-phenylalanine and derivatives in aqueous medium
  作者：Xiangyu Gong、Erzheng Su、Pixiang Wang、Dongzhi Wei

  DOI：10.1016/j.tetlet.2011.08.056

  日期：2011.10

  A new strategy based on enantioselective acylation properties of relatively unknown penicillin G acylase from Alcaligenes faecalis has been developed for the production of pharmacologically interesting enantiomerically pure d-phenylalanine. In order to get high reaction rate and enantioselectivity, two key factors (pH and temperature) and eight different acyl donors were optimized, and the optimal

  已经开发了基于相对未知的粪便产青霉素的青霉素G酰基转移酶的对映选择性酰化性质的新策略，用于生产药理学上有趣的对映体纯的d-苯丙氨酸。为了获得高反应速率和对映选择性，对两个关键因素（pH和温度）和八个不同的酰基供体进行了优化，并使用苯乙酰胺作为酰基供体，在pH 10、35°C下进行了最佳的酰化反应。该对映选择性酰化方法还通过在对映纯中有效产生五种不同的对位取代的苯丙氨酸衍生物来说明。
• NOVEL MULTITARGET DRUG FOR TREATING DISEASES IN MAMMALS
  申请人："Pharmenterprises Eurasia" Limited Liability Company

  公开号：EP3632424A1

  公开（公告）日：2020-04-08

  The invention relates to the chemistry of organic compounds, pharmacology and medicine and concerns therapy for obesity, psoriasis, Crohn's disease, colitis, irritable bowel syndrome, diarrhea, nausea and vomiting, as well as a number of other diseases associated with the activity of cathepsin S, cannabinoid receptors type 1, tachykinin receptors type 1 and 2, prokineticin receptors type 1 and 2, bradykinin receptors type 1, melanocortin receptors MC4R, serotonin receptors 5-HT2B and NB-kB signaling pathway, by using benzyl (2S)-2-[2-(4-hydroxyphenyl)acetamido]-3-phenylpropanoate compound. The compound and pharmaceutically acceptable adducts, hydrates and solvates thereof are a cathepsin S inhibitor, cannabinoid receptor type 1 agonist, tachykinin receptor type 1 and 2 antagonist, prokineticin receptor type 1 and 2 antagonist, bradykinin receptor type 1 antagonist, melanocortin receptor MC4R antagonist, serotonin receptor 5-HT2B antagonist, and NB-kB signaling pathway inhibitor. The invention also relates to pharmaceutical compositions comprising a therapeutically effective amount of the compound according to the invention.

  本发明涉及有机化合物化学、药理学和医学，涉及肥胖症、牛皮癣、克罗恩病、结肠炎、肠易激综合征、腹泻、恶心和呕吐以及其他一些与酪蛋白酶 S 活性有关的疾病的治疗、通过使用(2S)-2-[2-(4-羟基苯基)乙酰氨基]-3-苯基丙酸苄酯化合物，还可以治疗大麻素受体 1 型、速激肽受体 1 型和 2 型、原激肽受体 1 型和 2 型、缓激肽受体 1 型、黑皮质素受体 MC4R、5-羟色胺受体 5-HT2B 和 NB-kB 信号通路相关的其他一些疾病。 该化合物及其药学上可接受的加合物、水合物和溶解物是一种酪蛋白酶 S 抑制剂、大麻素受体 1 型激动剂、速激肽受体 1 型和 2 型拮抗剂、原激肽受体 1 型和 2 型拮抗剂、缓激肽受体 1 型拮抗剂、黑皮质素受体 MC4R 拮抗剂、5-羟色胺受体 5-HT2B 拮抗剂和 NB-kB 信号通路抑制剂。本发明还涉及包含治疗有效量的根据本发明的化合物的药物组合物。
• NOVEL MODULATOR OF METABOTROPIC AND IONOTROPIC TRANSMEMBRANE RECEPTORS AND USE THEREOF
  申请人：IBD Therapeutics LLC

  公开号：EP3792247A1

  公开（公告）日：2021-03-17

  The invention relates to organic chemistry, pharmacology and medicine and is concerned with the treatment of inflammatory and autoimmune diseases, such as psoriasis, atopic dermatitis, prurigo, Crohn's disease, colitis, gastrointestinal diseases such as diarrhoea and irritable bowel syndrome, respiratory diseases such as asthma, COPD, bronchitis, rhinitis, and also cough and a series of other diseases associated with the activity of opioid and tachykinin receptors and of TRPV1 and TRPM8 ion channels using a 2-phenylethylamine N-(p-hydroxyphenylacetyl)phenylalanine compound The invention, and also pharmaceutically acceptable adducts, hydrates, solvates are agonists of opioid receptors, antagonists of tachykinin receptors and of TRPV1 and TRPM8 ion channels. The invention also relates to pharmaceutical compositions comprising a therapeutically effective amount of the compound according to the invention.

  本发明涉及有机化学、药理学和医学，主要用于治疗炎症和自身免疫性疾病，如牛皮癣、特应性皮炎、瘙痒症、克罗恩病、结肠炎、胃肠道疾病，如腹泻和肠易激综合征、呼吸系统疾病，如哮喘、慢性阻塞性肺病、支气管炎、鼻炎、咳嗽以及其他一系列与阿片类和速激肽受体以及 TRPV1 和 TRPM8 离子通道活性有关的疾病，使用 2-苯乙胺 N-（对羟基苯乙酰基）苯丙氨酸化合物 本发明以及药学上可接受的加成物、水合物、溶液剂是阿片受体的激动剂、速激肽受体的拮抗剂以及 TRPV1 和 TRPM8 离子通道的激动剂。本发明还涉及包含治疗有效量的本发明化合物的药物组合物。
• 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
• Phenyl-containing n-acyl amine and aminoacid derivatives, methods for the production thereof, a pharmaceutical composition and the use thereof
  申请人：Nebolsin Vladimir Evgenievich

  公开号：US20090111874A1

  公开（公告）日：2009-04-30

  The present invention relates to novel phenyl-N-acyl derivatives of biogenic amines and amino acids of general formula (I) as cyclooxynease inhibitors, possessing analgetic and anti-inflammatory properties and devoid of side effects in particular ulcerogeneity and pro-spasmodic actions, as well as capability to potentiate effect of other analgetics, and possessing in addition antihypoxic, antidepressant and anti-Parkinsonistic action; as well as to the processes for the preparation novel and known phenyl-N-acyl derivatives of biogenic amines, to a pharmaceutical composition and to an agent comprising compounds of general formula (I) as well as to use thereof and a method of treating.