N-Pyruvylphenylalanine | 16947-06-1

• 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: N-Pyruvylphenylalanine
• 英文别名: N-pyruvoyl-phenylalanine；N-Pyruvoyl-phenylalanin；pyruvyl-phenylalanine；2-(2-Oxopropanoylamino)-3-phenylpropanoic acid
• CAS: 16947-06-1
• 化学式: C₁₂H₁₃NO₄
• 分子量: 235.24
• InChiKey: YEALFOYYKCROFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  83.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Pyruvylphenylalanine 在 1,4-二氧六环 、 盐酸 、 氯仿 、 五氯化磷 作用下， 生成 1-(N-pyruvoyl-L-phenylalanyl)-L-proline
  参考文献：
  名称：

  N-丙酮酰基-dl-苯丙氨酰基-dl-脯氨酸-内酰胺。Überdas thermische Abbauprodukt von Ergotamin

  摘要：

  麦角胺碱的热裂解产物C 17 H 18 O 4 N 2被显示为N-丙酮酰-苯丙氨酸-脯氨酸莱坦（Ia）的旋光形式，其非活性形式已被合成。迄今为止，通过向Ia中添加酰胺来合成与V型麦角胺有关的化合物的尝试均未成功。

  DOI：

  10.1002/hlca.19560390319
• 作为产物：
  描述：

  DL-丙氨酰基-DL-苯基丙氨酸 在 sodium sulfide 、 水 、 氯 作用下， 以 phosphate buffer 为溶剂， 生成 N-Pyruvylphenylalanine
  参考文献：
  名称：

  Chloramines VII:  Chlorination of Alanylphenylalanine in Model Solutions and in a Wastewater

  摘要：

  Products of the 30-min chlorination of the dipeptide alanylphenylalanine were determined at pH 7.0 in model solutions. At Cl-2/peptide mole ratios less than or equal to 1, N-chloroalanylphenylalanine (I) is the only product. I is very stable at 23 degrees C (t(1/2) = 111 +/- 8.8 h). At mole ratios greater than or equal to 2, N,N-dichloroalanylphenylalanine (II) is the only product. II decomposes in model solutions (t(1/2) = 4.1 +/- 0.2 h) at pH 7.0 to form a compound identified as the N-chloroketimine N-[2-(N'-chloroimino)propanoyl]phenylalanine (III). The structure of III was identified by converting it to N-pyruvylphenylalanine tert-butyl ester by reduction, hydrolysis, and esterification and correlating the mass spectrum and GC retention time of this derivative with those of an authentic sample. III is unusually stable and decomposes slowly (t(1/2) = 125 +/- 6.5 h) to phenylalanine. In order to monitor the reactions of the dipeptide at low concentrations in a wastewater, alanyl-p-[H-3]-phenylalanine was synthesized. A primary wastewater (TKN = 19.82 mg/L; [NH3] = 19.79 mg/L) was inoculated with the radiolabeled dipeptide and chlorinated to seven different chlorine concentrations spanning the breakpoint curve of the wastewater. Products identical to those observed in model solutions were formed. The stabilities of the tritiated analogs of II and III in the wastewater were similar to those determined in model solutions. Time studies of the decomposition of N,N-dichloroalanyl-p-[H-3]-phenylalanine revealed the formation of an intermediate (A) not previously recognized. Modeling of the reactions of II suggested that A was a decomposition product of III in the formation of phenylalanine and was probably either an isocyanate or a carbamic acid formed from hydrolysis of an isocyanate intermediate.

  DOI：

  10.1021/es9607953

文献信息

• Nitric Oxide Releasing Pyruvate Compounds, Compositions and Methods of Use
  申请人：Garvey David S.

  公开号：US20080287407A1

  公开（公告）日：2008-11-20

  The invention describes novel nitrosated and/or nitrosylated pyruvate compounds and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated and/or nitrosylated pyruvate compound, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one pyruvate compound and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one pyruvate compound, that is optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating diseases resulting from oxidative stress, diabetes, reperfusion injury following ischemia, preservation of tissues, organs, organ parts and/or limbs.

  该发明描述了新颖的硝化和/或亚硝化丙酮酸盐及其药用可接受盐，以及包含至少一种硝化和/或亚硝化丙酮酸化合物的新型组合物，以及可选地，至少一种捐赠、转移或释放一氧化氮、刺激内源性一氧化氮合成、提高内源性内皮源性舒张因子水平或是一氧化氮合酶底物的化合物，和/或至少一种治疗剂。该发明还提供了包含至少一种丙酮酸化合物和至少一种捐赠、转移或释放一氧化氮、提高内源性内皮源性舒张因子水平、刺激内源性一氧化氮合成或是一氧化氮合酶底物和/或至少一种治疗剂的新型组合物。该发明还提供了包含至少一种丙酮酸化合物的新型试剂盒，该丙酮酸化合物可选地硝化和/或亚硝化，以及可选地至少一种一氧化氮供体和/或至少一种治疗剂。该发明还提供了治疗由氧化应激、糖尿病、缺血后再灌注损伤、组织、器官、器官部分和/或肢体保护引起的疾病的方法。
• Inhibitors of serine proteases, particularly HCV NS3-NS4A protease
  申请人：Perni Robert B.

  公开号：US20080311079A1

  公开（公告）日：2008-12-18

  The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention. The invention further relates to processes for preparing these compounds.

  本发明涉及抑制丝氨酸蛋白酶活性的化合物，特别是抑制丙型肝炎病毒NS3-NS4A蛋白酶活性的化合物。因此，它们通过干扰丙型肝炎病毒的生命周期来发挥作用，并且也可用作抗病毒药物。本发明还涉及包含这些化合物的组合物，无论是用于体外使用还是用于治疗患有HCV感染的患者的给药。本发明还涉及通过给予包含本发明化合物的组合物来治疗患有HCV感染的患者的方法。本发明还涉及制备这些化合物的工艺。
• INHIBITORS OF SERINE PROTEASES, PARTICULARLY HCV NS3-NS4A PROTEASE
  申请人：Perni Robert B.

  公开号：US20110104115A1

  公开（公告）日：2011-05-05

  The present invention relates to compounds that inhibit serine protease activity, particularly the activity of hepatitis C virus NS3-NS4A protease. As such, they act by interfering with the life cycle of the hepatitis C virus and are also useful as antiviral agents. The invention further relates to compositions comprising these compounds either for ex vivo use or for administration to a patient suffering from HCV infection. The invention also relates to methods of treating an HCV infection in a patient by administering a composition comprising a compound of this invention. The invention further relates to processes for preparing these compounds.

  本发明涉及抑制丝氨酸蛋白酶活性的化合物，特别是乙型肝炎病毒NS3-NS4A蛋白酶的活性。因此，它们通过干扰乙型肝炎病毒的生命周期来发挥作用，并且也可用作抗病毒剂。本发明还涉及包含这些化合物的组合物，无论是用于体外使用还是用于治疗HCV感染的患者的给药。本发明还涉及通过给予包含本发明化合物的组合物来治疗患有HCV感染的患者的方法。本发明还涉及制备这些化合物的过程。
• Compositions and methods for the treatment and prevention of chronic hypoxemia and dyspnea
  申请人：Martin Alain

  公开号：US10813893B2

  公开（公告）日：2020-10-27

  The present invention has shown that not all salts of pyruvic acid enhance lung functions or enhance the synthesis of lung surfactants and that certain salts of pyruvic acid with the correct concentrations of calcium, phosphate and magnesium, are synergistic in their ability to enhance the synthesis of lung surfactants that will enhance lung alveoli functions, while decreasing coughing and lung tightness, and increasing oxygen saturation values to prevent hypoxemia. This patent demonstrates that the sodium pyruvate formula with calcium, phosphate and magnesium was superior over standard sodium pyruvate formula in saline alone in the removal of mucus, reduction of lung or sinus infections, and in reducing drug side effects and congestion. The use of this formula clearly demonstrated that it can be used to produce better efficacy in patients with hypoxemia, with lung and sinus diseases including, asthma, COPD, cystic fibrosis, interstitial lung disease, allergic rhinitis, sinusitis, Alzheimer's, disease, Parkinson's disease, brain trauma, nicotine addiction, sleep apnea, autism, migraine headaches, sleep disorders, lung and sinus infections, cancer therapy with cancer drugs, nicotine addiction, and medications that cause a decrease in lung surfactants.

  本发明表明，并非所有丙酮酸盐都能增强肺功能或促进肺表面活性物质的合成，某些丙酮酸盐与正确浓度的钙、磷酸盐和镁协同作用，能够促进肺表面活性物质的合成，从而增强肺泡功能，同时减少咳嗽和肺部紧绷感，提高血氧饱和度值，防止低氧血症。本专利证明，在清除粘液、减少肺部或鼻窦感染、减轻药物副作用和充血方面，含钙、磷酸盐和镁的丙酮酸钠配方优于仅在生理盐水中添加的标准丙酮酸钠配方。病、帕金森病、脑外伤、尼古丁上瘾、睡眠呼吸暂停、自闭症、偏头痛、睡眠障碍、肺部和鼻窦感染、使用抗癌药物进行癌症治疗、尼古丁上瘾以及导致肺表面活性物质减少的药物。
• Synergistic compositions to stimulate the synthesis of human lung and sinus surfactants to decrease coughing, increase FEV-1/FVC ratios, decrease lung fibrosis, by increasing apoptosis of myofibroblasts
  申请人：Martin Alain

  公开号：US11311505B2

  公开（公告）日：2022-04-26

  Methods for the treatment of patients with both Chronic Obstructive Pulmonary Disease (COPD) and pulmonary fibrosis, and of patients with idiopathic pulmonary fibrosis without COPD, by stimulating the synthesis of human and animal patient lung and sinus surfactants to increase lung functions, inhibiting fibrosis and reducing coughing and nasal erythema, include the following steps: A) analyzing and diagnosing a patient with a lung ailment selected from the group consisting of i) both COPD and pulmonary fibrosis; and ii) idiopathic pulmonary fibrosis without COPD; and, B) treating the patient to raise the patient's lung functions including FEV1/FVC ratio by contacting mammalian cells with a [therapeutically effective amount of a treatment] composition that includes: a) a pyruvate salt; b) a phosphate; c) a salt of calcium; and d) a salt of magnesium, in an aqueous carrier, containing no more than 2.2 grams of said pyruvate salt per liter.

  治疗慢性阻塞性肺病（COPD）和肺纤维化患者以及无慢性阻塞性肺病的特发性肺纤维化患者的方法，通过刺激人和动物患者肺和窦表面活性物质的合成来增加肺功能、抑制肺纤维化并减少咳嗽和鼻部红斑，包括以下步骤：A）分析和诊断一名肺部疾病患者，该患者选自以下组别：i）慢性阻塞性肺病和肺纤维化；ii）无慢性阻塞性肺病的特发性肺纤维化；B）通过将哺乳动物细胞与[治疗有效量的治疗]组合物接触，对患者进行治疗，以提高患者的肺功能，包括 FEV1/FVC 比率，该组合物包括：a) 丙酮酸盐；b) 磷酸盐；c) 钙盐；d) 镁盐。2 克的丙酮酸盐。