N-acetylcysteine propyl ester | 67607-91-4

• 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-acetylcysteine propyl ester
• 英文别名: N-acetyl L-cysteine n-propyl ester；N-acetyl-L-cysteine propyl ester；N-Acetyl-L-cystein-propylester；L-2-Acetamino-3-mercapto-propionsaeure-propylester；propyl (2R)-2-acetamido-3-sulfanylpropanoate
• CAS: 67607-91-4
• 化学式: C₈H₁₅NO₃S
• 分子量: 205.278
• InChiKey: URESFVPLRNYXLP-ZETCQYMHSA-N

物化性质

• 沸点：
  349.6±32.0 °C(Predicted)
• 密度：
  1.112±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  56.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetylcysteine propyl ester 、 N-((5-(dimethylamino)naphthalen-1-yl)sulfonyl)acrylamide 在 三乙胺 作用下， 生成 C₂₃H₃₁N₃O₆S₂
  参考文献：
  名称：

  Protection of human retinal pigment epithelial cells from oxidative damage using cysteine prodrugs

  摘要：

  Age -related macular degeneration (AMD) is one of the major causes of vision loss in the elderly in most de- veloped countries. Among other causes, oxidative stress in the retinal pigment epithelium (RPE) has been hy- pothesized to be a major driving force of AMD pathology. Oxidative stress could be treated by antioxidant administration into the RPE cells. However, to achieve high in -vivo e fficacy of an antioxidant, it is imperative that the agent be able to penetrate the tissues and cells. Evidence suggests that lipophilicity governs cellular penetrance. Out of many antioxidant candidates, N -acetyl- L -cysteine (a prodrug of L -cysteine) (NAC) is a potent antioxidant as the bioavailability of the parent drug, L -cysteine, determines the production of glutathione; the universal antioxidant that regulates ROS. To increase the lipophilicity, four ester derivatives of N -acetylcysteine: N -acetylcysteine methyl ester, N -acetylcysteine ethyl ester, N -acetylcysteine propyl ester, and N -acetylcysteine butyl ester were synthesized. To mimic in vitro AMD conditions, hydroquinone, a component of cigarette smoke, was used as the oxidative insult. Cytosolic and mitochondrial protection against oxidative stress were tested using cytosolic and mitochondrial speci fic assays. The results provide evidence that these lipophilic cysteine prodrugs provide increased protection against oxidative stress in human RPE cells compared with NAC.

  DOI：

  10.1016/j.freeradbiomed.2020.03.024
• 作为产物：
  描述：

  N,N'-diacetyl-L-cystine dipropyl ester 在 硫酸 、 锌 作用下， 生成 N-acetylcysteine propyl ester
  参考文献：
  名称：

  Pirie, Biochemical Journal, 1931, vol. 25, p. 619

  摘要：

  DOI：

文献信息

• Visible‐Light‐Mediated S−H Bond Insertion Reactions of Diazoalkanes with Cysteine Residues in Batch and Flow
  作者：Long‐Zhou Qin、Xin Yuan、Yu‐Sheng Cui、Qi Sun、Xiu Duan、Kai‐Qiang Zhuang、Lin Chen、Jiang‐Kai Qiu、Kai Guo

  DOI：10.1002/adsc.202000716

  日期：2020.11.18

  diazoacetates with cysteine residues that enabled metal‐free, S−H functionalization under visible‐light conditions. Moreover, this process could be intensified by a continuous‐flow photomicroreactor on the acceleration of the reaction (6.5 min residence time). The batch and flow protocols described were applied to obtain a wide range of functionalized cysteine derivatives and cysteine‐containing dipeptides

  我们描述了芳基重氮乙酸酯与半胱氨酸残基的S-H键插入反应的应用，该反应可在可见光条件下实现无金属的S-H功能化。此外，连续反应光微反应器可加快反应速度（6.5分钟的停留时间），从而增强该过程。所描述的批次和流程方案可用于获得各种功能化的半胱氨酸衍生物和含半胱氨酸的二肽，从而为其在温和条件下的功能化提供了一个简单而通用的平台。
• Combination Therapies for Treating Metabolic Disorders
  申请人：Mayoux Eric

  公开号：US20100239552A1

  公开（公告）日：2010-09-23

  This invention is directed to pharmaceutical combinations comprising an antioxidant agent, an anti-inflammatory agent, and optionally at least one other anti-diabetic agent useful for treating metabolic disorders. This invention also encompasses pharmaceutically acceptable compositions comprising an antioxidant agent, an anti-inflammatory agent, optionally at least one other anti-diabetic agent, and at least one pharmaceutically acceptable carrier. The combinations and compositions of this invention are useful as methods for treating metabolic disorders including diabetes, particularly Type I and Type II diabetes, as well as diseases and disorders associated with diabetes, including but not limited to atherosclerosis, cardiovascular disease, inflammatory disorders, nephropathy, neuropathy, retinopathy, β-cell dysfunction, dyslipidemia, LADA, metabolic syndrome, hyperglycemia, insulin resistance, and/or chronic obstructive pulmonary disease in a mammal, particularly a diabetic mammal, and specifically a human patient. This invention is particularly directed to pharmaceutical compositions comprising an lipoic acid, one or more anti-inflammatories selected from the group consisting of diflunisal, diclofenac, dexibuprofen, dexketoprofen, naproxen, and salicylate, and optionally one or more pharmaceutically acceptable carriers. The compositions of this invention are useful as methods for treating metabolic disorders including type II diabetes, insulin resistance, beta-cell dysfunction, and hyperglycemia in a patient, particularly a diabetic patient.

  本发明涉及包含抗氧化剂、抗炎剂和可选地至少一种其他抗糖尿病药物的药物组合，用于治疗代谢紊乱。本发明还包括包含抗氧化剂、抗炎剂、可选地至少一种其他抗糖尿病药物和至少一种药用载体的药用可接受的组合物。本发明的这些组合和组合物作为治疗代谢紊乱的方法是有用的，包括糖尿病，特别是I型和II型糖尿病，以及与糖尿病相关的疾病和紊乱，包括但不限于动脉粥样硬化、心血管疾病、炎症性疾病、肾病、神经病、视网膜病变、β细胞功能障碍、血脂异常、LADA、代谢综合征、高血糖、胰岛素抵抗和/或慢性阻塞性肺疾病在哺乳动物，特别是糖尿病哺乳动物，特别是人类患者中。本发明特别涉及包含硫辛酸、来自二氟尼索、双氯芬酸、右布洛芬、右侧氧布洛芬、萘普生和水杨酸的一种或多种抗炎药物以及可选地一种或多种药用可接受的载体的药物组合。本发明的组合物作为治疗代谢紊乱的方法是有用的，包括II型糖尿病、胰岛素抵抗、β细胞功能障碍和高血糖在患者，特别是糖尿病患者中。
• [EN] N-ACETYL L-CYSTEINE CHELATES AND METHODS FOR MAKING AND USING THE SAME<br/>[FR] CHÉLATES DE N-ACÉTYLE L-CYSTÉINE ET LEURS PROCÉDÉS DE FABRICATION ET D'UTILISATION
  申请人：VIVA PHARMACEUTICAL INC

  公开号：WO2014209412A1

  公开（公告）日：2014-12-31

  A nutritional supplement for a human, the supplement having a chelate comprised of an N-acetyl-L-cysteine ligand bonded to a metal to form a chelate ring. A method for preparing a chelate comprised of N-acetyl-L-cysteine ligand and a metal having the steps of: dissolving an amount of N-acetyl-L-cysteine in an aqueous solution, adding a metal to the aqueous solution, stirring and heating the aqueous solution, and removing the solvent under reduced pressure. A method of treating a human for one or more of oxidative stress, cardiovascular disease, cerebrovascular disease, neurodegenerative diseases, Alzheimer's disease, ADHD, bipolar, schizophrenia, autism, dementia, and HIV in a human comprising administering an effective amount of a composition having N-acetyl-L-cysteine in a chelate formation with a metal. A compound having a chelate formulation with a metal being chelated by an N-acetyl-L-cysteine ligand.

  一种用于人类的营养补充剂，该补充剂具有一个螯合物，由N-乙酰-L-半胱氨酸配体与金属结合形成一个螯合环。一种制备由N-乙酰-L-半胱氨酸配体和金属组成的螯合物的方法包括以下步骤：在水溶液中溶解一定量的N-乙酰-L-半胱氨酸，向水溶液中加入金属，搅拌和加热水溶液，然后在减压下去除溶剂。一种治疗人类氧化应激、心血管疾病、脑血管疾病、神经退行性疾病、阿尔茨海默病、注意力缺陷多动障碍、躁郁症、精神分裂症、自闭症、痴呆症和艾滋病等的方法，包括向人类施用含有N-乙酰-L-半胱氨酸与金属形成螯合物的有效量的组合物。一种具有金属与N-乙酰-L-半胱氨酸配体螯合的螯合制剂的化合物。
• [EN] SALT OF ABT-263 AND SOLID-STATE FORMS THEREOF<br/>[FR] SEL DE ABT-263 ET FORMES SOLIDES DE CELUI-CI
  申请人：ABBOTT LAB

  公开号：WO2010127190A1

  公开（公告）日：2010-11-04

  ABT-263 bis-HCl and crystalline polymorphs thereof are suitable active pharmaceutical ingredients for pharmaceutical compositions useful in treatment of a disease characterized by overexpression of one or more anti-apoptotic Bcl-2 family proteins, for example cancer.

  ABT-263 bis-HCl及其结晶多形体是适用于制备药物组合物的有效药物成分，用于治疗一种疾病，该疾病以一个或多个抗凋亡Bcl-2家族蛋白质的过度表达为特征，例如癌症。
• Topical macqui berry formula
  申请人：Tracie Martyn International, Inc.

  公开号：US10993897B2

  公开（公告）日：2021-05-04

  The present invention provides a topical formulation and method of use where the formulation comprises macqui berry or a macqui berry extract containing anthocyanins having a very high oxygen radical absorbance capacity (ORAC). The formulation provides the macqui berry in a stabilized form which includes a glucuronide or glycuronide, a photostabilizing agent, encapsulation, or light—and/or air-blocking packaging.

  本发明提供了一种外用制剂和使用方法，其中的制剂包含具有极高氧自由基吸收能力（ORAC）的马奎莓或含有花青素的马奎莓提取物。本发明的制剂提供了稳定形式的马奎莓，其中包括葡萄糖醛酸或糖醛酸、光稳定剂、封装或阻光和/或阻气包装。