N-acetylcysteine butyl ester | 34233-59-5

• 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 butyl ester
• 英文别名: N-acetyl L-cysteine butyl ester；N-Acetyl-L-cysteine butyl ester；butyl (2R)-2-acetamido-3-sulfanylpropanoate
• CAS: 34233-59-5
• 化学式: C₉H₁₇NO₃S
• 分子量: 219.305
• InChiKey: WVSUZTRZSBUVMD-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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-((5-(dimethylamino)naphthalen-1-yl)sulfonyl)acrylamide 、 N-acetylcysteine butyl ester 在 三乙胺 作用下， 生成
  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-乙酰-L-半胱氨酸 、 正丁醇 在 氯化亚砜 作用下， 生成 N-acetylcysteine butyl ester
  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

文献信息

• [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。
• STABILIZED LIPID FORMULATION OF APOPTOSIS PROMOTER
  申请人：Abbott Laboratories

  公开号：EP2424499A1

  公开（公告）日：2012-03-07
• SALT OF ABT-263 AND SOLID-STATE FORMS THEREOF
  申请人：Abbott Laboratories

  公开号：EP2424849A1

  公开（公告）日：2012-03-07
• STABLE NANOPARTICULATE DRUG SUSPENSION
  申请人：Abbott Laboratories

  公开号：EP2442789A1

  公开（公告）日：2012-04-25
• ABT-263 CRYSTALLINE FORMS AND SOLVATES FOR USE IN TREATING BCL-2 PROTEIN RELATED DISEASES
  申请人：Abbott Laboratories

  公开号：EP2477972A1

  公开（公告）日：2012-07-25