N-[(1R,2S)-2-羟基-1-甲基-2-苯基乙基]-十四烷酰胺 | 143492-38-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-[(1R,2S)-2-羟基-1-甲基-2-苯基乙基]-十四烷酰胺
• 英文名称: (1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol
• 英文别名: (1S,2R-D-erythro-2-N-myristoylamino)-1-phenyl-1-propanol；(1S,2R)-2N-myristoylamino-1-phenyl-1-propanol；(1S,2R)-N-myristoylamino-phenylpropanol-1；DMAPP；D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol；D-erythro-2-(N-myristoylamino)-l-phenyl-l-propanol；D-erythro-MAPP；N-[(1S,2R)-1-hydroxy-1-phenylpropan-2-yl]tetradecanamide
• CAS: 143492-38-0；60847-25-8
• 化学式: C₂₃H₃₉NO₂
• 分子量: 361.568
• InChiKey: YLAZEWZHIRBZDA-NFBKMPQASA-N

物化性质

• 沸点：
  536.7±43.0 °C(Predicted)
• 密度：
  0.965±0.06 g/cm3(Predicted)
• 溶解度：
  DMF：20mg/mL； DMSO：0.1mg/mL；乙醇：20mg/mL；乙醇:PBS (pH 7.2) (1:2): .5 mg/ml

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  26
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  左旋去甲麻黄碱 、 肉豆蔻酰氯 在 吡啶 作用下， 以 N-甲基吡咯烷酮 、 四氢呋喃 为溶剂， 生成 N-[(1R,2S)-2-羟基-1-甲基-2-苯基乙基]-十四烷酰胺
  参考文献：
  名称：

  The Synthesis and Biological Characterization of a Ceramide Library

  摘要：

  A facile synthesis of a combinatorial ceramide library and their activities in the NF-kappaB pathway and in apoptosis induction/prevention were demonstrated. A novel NF-kappaB activating molecule was discovered among ceramide containing beta-galactose, and the structural requirements of ceramides for apoptosis induction was elucidated.

  DOI：

  10.1021/ja017576o

文献信息

• Use of a sphingoid base for inhibiting ceramidase activity
  申请人：Cosmoferm B.V.

  公开号：EP1287815A1

  公开（公告）日：2003-03-05

  Use of an active compound selected from the group of a sphingoid base, a derivative of a sphingoid base, a salt of a sphingoid base, a ceramide or a mixture of two or more of these compounds for manufacturing a composition for topical application for inhibiting ceramidase activity in and on the skin.

  使用选自鞘磷脂基、鞘磷脂基的衍生物、鞘磷脂基的盐、神经酰胺或两种或两种以上此类化合物混合物的活性化合物，制造用于局部应用的组合物，以抑制皮肤内和皮肤上的神经酰胺酶活性。
• Compositions for the treatment of diseases associated with elevated sphingolipid concentrations
  申请人：Medlyte, Inc.

  公开号：EP1731161A1

  公开（公告）日：2006-12-13

  Methods and compositions are disclosed that are useful for the prevention and/or treatment of cardiovascular and cardiac diseases and disorders, or damage resulting from surgical or medical procedures that may cuase ischemic or ischemic/reperfusion damage in humans; and cardiovascular trauma. The beneficial effects of the compositions and methods are achieved through the use of pharmaceutical compositions that include agents that interfere with the production and/or biological activities of sphingolipids and their metabolites, particularly sphingosine (SPH) and sphingosine-1-phosphate (S-1-P). Also disclosed are methods for identifying and isolating therapeutic agents.

  本发明公开了一些方法和组合物，可用于预防和/或治疗心血管和心脏疾病和失调，或可能导致人体缺血或缺血/再灌注损伤的手术或医疗程序造成的损伤，以及心血管创伤。本发明组合物和方法的有益效果是通过使用药物组合物实现的，药物组合物包括干扰鞘磷脂及其代谢物，特别是鞘磷脂（SPH）和鞘磷脂-1-磷酸（S-1-P）的产生和/或生物活性的制剂。还公开了用于鉴定和分离治疗剂的方法。
• Compositions and methods for the treatment and prevention of cardiovascular diseases and disorders, and for identifying agents therapeutic therefor
  申请人：Medlyte, Inc.

  公开号：US20030026799A1

  公开（公告）日：2003-02-06

  Methods and compositions are disclosed that are useful for the prevention and/or treatment of cardiovascular and cardiac diseases and disorders, or damage resulting from surgical or medical procedures that may cause ischemic or ischemic/reperfusion damage in humans; and cardiovascular trauma. The beneficial effects of the compositions and methods are achieved through the use of pharmaceutical compositions that include agents that interfere with the production and/or biological activities of sphingolipids and their metabolites, particularly sphingosine (SPH) and sphingosine-1-phosphate (S-1-P). Also disclosed are methods for identifying and isolating therapeutic agents.

  所公开的方法和组合物有助于预防和/或治疗心血管和心脏疾病和失调，或可能导致人体缺血或缺血/再灌注损伤的手术或医疗程序造成的损伤；以及心血管创伤。这些组合物和方法的有益效果是通过使用药物组合物实现的，这些组合物包括干扰鞘磷脂及其代谢物，特别是鞘磷脂（SPH）和鞘磷脂-1-磷酸（S-1-P）的产生和/或生物活性的制剂。还公开了用于鉴定和分离治疗剂的方法。
• Use of sphingoid base for inhibiting ceramidase activity
  申请人：——

  公开号：US20030064936A1

  公开（公告）日：2003-04-03

  The present invention relates to the use of an active compound including a sphingoid base, a derivative of a sphingoid base, a salt of a sphingoid base, a ceramide or a mixture of two or more of these compounds for manufacturing a composition for topical application for inhibiting mammalian ceramidase activity in the skin and microbial ceramidase originating from micro-organisms present on the skin. The composition may further contain an amount of a compound capable of complexating divalent cations.

  本发明涉及一种活性化合物的用途，该化合物包括鞘氨醇碱、鞘氨醇碱的衍生物、鞘氨醇碱的盐、神经酰胺或两种或两种以上这些化合物的混合物，用于制造一种局部使用的组合物，以抑制皮肤中哺乳动物神经酰胺酶的活性和皮肤上微生物产生的微生物神经酰胺酶。该组合物还可含有一定量的能络合二价阳离子的化合物。
• Compositions and methods for the treatment and prevention of cancer, angiogenesis, and inflammation
  申请人：Medlyte, Inc.

  公开号：US20040247603A1

  公开（公告）日：2004-12-09

  Methods and compositions are disclosed that are useful for the prevention and/or treatment of cancer, angiogenesis, and inflammation. The beneficial effects of the compositions and methods are achieved through the use of pharmaceutical compositions that include agents that bind spingolipids or sphingolipid metabolites. In one embodiment the agent is an antibody or antibody derivative. In some embodiments, the agent is a receptor of a sphingolipid or a sphingolipid metabolite. Also disclosed are methods for identifying and isolating therapeutic agents.

  本文公开了可用于预防和/或治疗癌症、血管生成和炎症的方法和组合物。这些组合物和方法的有益效果是通过使用包含结合鞘磷脂或鞘磷脂代谢物的制剂的药物组合物来实现的。在一个实施方案中，药剂是抗体或抗体衍生物。在某些实施方案中，药剂是鞘磷脂或鞘磷脂代谢物的受体。还公开了鉴定和分离治疗剂的方法。