IB-MECA acetonide | 152918-48-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: IB-MECA acetonide
• 英文别名: (3aS,4S,6R,6aR)-6-(6-((3-iodobenzyl)amino)-9H-purin-9-yl)-N,2,2-trimethyltetrahydrofuro[3,4-d][1,3]dioxole-4-carboxamide；(3aR,4R,6S,6aS)-4-[6-[(3-iodophenyl)methylamino]purin-9-yl]-N,2,2-trimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxamide
• CAS: 152918-48-4
• 化学式: C₂₁H₂₃IN₆O₄
• 分子量: 550.356
• InChiKey: VDRFIZJIZAPWBO-UIVXKWKOSA-N

物化性质

• 密度：
  1.83±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  IB-MECA acetonide 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 8.0h， 生成 N6-(3-碘苄基)腺苷-5'-N-甲基糖酰胺
  参考文献：
  名称：

  WO2008/111082

  摘要：

  公开号：
• 作为产物：
  描述：

  (3AS,4S,6R,6AR)-6-(6-氯-9H-嘌呤-9-基)-2,2-二甲基四氢呋喃并[3,4 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 42.0h， 生成 IB-MECA acetonide
  参考文献：
  名称：

  WO2008/111082

  摘要：

  公开号：

文献信息

• PROCESS FOR THE SYNTHESIS OF IB-MECA
  申请人：Bruzinski Paul

  公开号：US20100087636A1

  公开（公告）日：2010-04-08

  The present disclosure provides a method for the synthesis of IB-MECA. More specifically, the present disclosure provides a simple and high yield method for Good Manufacturing Production (GMP) of IB-MECA. The method involves the reaction of 6-halopurine-9-riboside with a diol protecting reagent; oxidation of the primary alcohol in the diol protected 6-halopurine-9-riboside with a diol protecting reagent; oxidation of the primary alcohol in the diol protected 6-halopurine; reaction of the diol protected 6-halopurine with a nucleophile (e.g. methylamine); substitution of the halogen group with iodobenzylamine and removal of the diol protecting group.

  本公开提供了一种IB-MECA的合成方法。更具体地说，本公开提供了一种简单且高产的Good Manufacturing Production (GMP) IB-MECA方法。该方法涉及将6-卤代嘌呤-9-核苷与二元醇保护试剂反应；将二元醇保护的6-卤代嘌呤-9-核苷的一级醇氧化为醛；将二元醇保护的6-卤代嘌呤与亲核试剂（例如甲基胺）反应；用碘代苯胺取代卤素基团并去除二元醇保护基。
• Structure-Activity Relationships of N6-Benzyladenosine-5'-uronamides as A3-Selective Adenosine Agonists
  作者：Carola Gallo-Rodriguez、Xiao-duo Ji、Neli Melman、Barry D. Siegman、Lawrence H. Sanders、Jeraldine Orlina、Bilha Fischer、Quanlong Pu、Mark E. Olah

  DOI：10.1021/jm00031a014

  日期：1994.3

  Adenosine analogues modified at the 5'-position as uronamides and/or as N-6-benzyl derivatives were synthesized. These derivatives were examined for affinity in radioligand binding assays at the newly discovered rat brain A(3) adenosine receptor and at rat brain A(1) and Az, receptors. 5'Uronamide substituents favored AS selectivity in the order N-methyl > N-ethyl approximate to unsubstituted carboxamide > N-cyclopropyl. 5'-(N-Methylcarboxamido)-N-6-benzyladenosine was 37-56-fold more selective for Ag receptors. Potency at A(3) receptors was enhanced upon substitution of the benzyl substituent with nitro and other groups. 5'-N-Methyluronamides and N-6-(3-substituted-benzyl) adenosines are optimal for potency and selectivity at A(3) receptors. A series of 3-(halobenzyl)5'-N-ethyluronamide derivatives showed the order of potency at A(1) and A(2)a receptors of I similar to Br > Cl > F. At A(3) receptors the 3-F derivative was weaker than the other halo derivatives. 5'-N-Methyl-N-6- (3-iodobenzyl) adenosine displayed a K-i value of 1.1 nM at A(3) receptors and selectivity versus A(1) and A(2a), receptors of 50-fold. A series of methoxybenzyl derivatives showed that a C-methoxy group best favored A(3) selectivity. A 4-sulfobenzyl derivative was a specific ligand at A(3) receptors of moderate potency. An aryl amino derivative was prepared as a probe for radioiodination and receptor cross-linking.
• US9102698B2
  申请人：——

  公开号：US9102698B2

  公开（公告）日：2015-08-11