(3S)-O-(N-methoxyglycyl)betulinic acid | 1101863-07-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (3S)-O-(N-methoxyglycyl)betulinic acid
• 英文别名: (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[2-(methoxyamino)acetyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
• CAS: 1101863-07-3
• 化学式: C₃₃H₅₃NO₅
• 分子量: 543.788
• InChiKey: KVTGNHSEGQHWKI-ISCFYSBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  39
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3S)-O-(N-methoxyglycyl)betulinic acid 、 2-脱氧-2-氟-D-葡萄糖 以 甲醇 、 二氯甲烷 为溶剂， 反应 48.0h， 生成 (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-[2-[[(3R,4S,5S,6R)-3-fluoro-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-methoxyamino]acetyl]oxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid
  参考文献：
  名称：

  Enhancing the Divergent Activities of Betulinic Acid via Neoglycosylation

  摘要：

  Using neoglycosylation, the impact of differential glycosylation upon the divergent anticancer and anti-HIV properties of the triterpenoid betulinic acid (BA) was examined. Each member from a library of 37 differentially glycosylated BA variants was tested for anticancer and anti-HIV activities. Enhanced analogs for both desired activities were discovered with the corresponding antitumor or antiviral enhancements diverging, on the basis of the appended sugar, into two distinct compound subsets.

  DOI：

  10.1021/ol8025704
• 作为产物：
  描述：

  3-氯苯甲酰乙腈 、 3-O-(chloroacetyl)betulinic acid 在 sodium iodide 作用下， 以 乙醇 、 四氢呋喃 为溶剂， 反应 19.67h， 以67%的产率得到(3S)-O-(N-methoxyglycyl)betulinic acid
  参考文献：
  名称：

  [EN] ENHANCED NEOGLYCOSIDES THROUGH NEOGLYCOSYLATION AND METHODS OF USE THEREOF
  [FR] NÉO-GLYCOSIDES AMÉLIORÉS PAR NÉO-GLYCOSYLATION ET LEURS PROCÉDÉS D'UTILISATION

  摘要：

  通过新糖基化技术，研究了巴西诺酸（BA）的不同糖基化对其抗癌和抗HIV特性的影响。对包含37种不同糖基化BA变体的库中的每个成员进行了抗癌和抗HIV活性测试。发现了增强的类似物，对于这两种期望的活性，根据附加的糖，分化为两个不同的化合物子集，分别具有抗肿瘤或抗病毒增强效果。

  公开号：

  WO2010080863A1

文献信息

• Suppression of glial fibrillary acidic protein
  申请人：Messing Albee

  公开号：US20100190705A1

  公开（公告）日：2010-07-29

  Provided herein are methods of decreasing glial fibrillary acidic protein (GFAP) levels in a cell. Such methods include administering an effective amount of a GFAP lowering compound to the cell. Also provided are compounds useful for the treatment of Alexander disease in subjects at risk of or diagnosed with Alexander disease and methods for the identification of such compounds.
• Enhanced Neoglycosides Through Neoglycosylation and Methods of Use Thereof
  申请人：Goff Randal D.

  公开号：US20120108530A1

  公开（公告）日：2012-05-03

  Using neoglycosylation, the impact of differential glycosylation upon the divergent anticancer and anti-HIV properties of the triterpenoid betulinic acid (BA) was examined. Each member from a library of 37 differentially glycosylated BA variants was tested for anticancer and anti-HIV activities. Enhanced analogs for both desired activities were discovered with the corresponding antitumor or antiviral enhancements diverging, based upon the appended sugar, into two distinct compound subsets.
• SUPPRESSION OF GLIAL FIBRILLARY ACIDIC PROTEIN
  申请人：Messing Albee

  公开号：US20130225540A1

  公开（公告）日：2013-08-29

  Provided herein are methods of decreasing glial fibrillary acidic protein (GFAP) levels in a cell. Such methods include administering an effective amount of a GFAP lowering compound to the cell. Also provided are compounds useful for the treatment of Alexander disease in subjects at risk of or diagnosed with Alexander disease and methods for the identification of such compounds.
• US8372808B2
  申请人：——

  公开号：US8372808B2

  公开（公告）日：2013-02-12
• US8653043B2
  申请人：——

  公开号：US8653043B2

  公开（公告）日：2014-02-18