2-[[5-[(Dimethylamino)methyl]furan-2-yl]methyl]isoindole-1,3-dione | 1026064-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-[[5-[(Dimethylamino)methyl]furan-2-yl]methyl]isoindole-1,3-dione
• CAS: 1026064-16-3
• 化学式: C₁₆H₁₆N₂O₃
• 分子量: 284.315
• InChiKey: VPFRCIOJXYVIBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  53.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[[5-[(Dimethylamino)methyl]furan-2-yl]methyl]isoindole-1,3-dione 在 一水合肼 作用下， 以 乙二醇二甲醚 、 乙醇 为溶剂， 反应 5.0h， 生成 (+/-)-N-<5-(1'-phenyl-1'-cyclohexylacetamidomethyl)-2-furfuryl>-dimethylamine
  参考文献：
  名称：

  Cholinergic agents structurally related to furtrethonium. 1

  摘要：

  A series of 5-substituted-2-(dimethylaminomethyl)-furyl derivatives 4 was prepared, with the aim of discovering novel antimuscarinic agents which are selective for smooth muscle as opposed to cardiac tissue. Both non-quaternary and quaternary ammonium compounds were synthesised. The agonist starting point, furtrethonium 3, was gradually transformed into antagonist by introduction of lipophilic and bulky groups in position 5 of this molecule. In particular, the introduction of alpha-hydroxy-alpha-cyclohexylbenzyl moiety (compound 9b), a lipophilic group characteristic of antimuscarinic agents, caused an appreciable increase of the antagonist's potency, and the lengthening of the distance between this lipophilic group and the furan ring, obtained by introduction of an ester, ether or amide group, led to some selectivity towards smooth muscle (compounds 19, 21, 25). Interestingly, compound 19, with an ester moiety as a spacer group, proved to be at least 20 times more potent in rat ileum (pK(B) = 7.3) and rat bladder (pK(B) = 7.2) than guinea-pig atria (pK(B) = 5.9).

  DOI：

  10.1016/0223-5234(94)90213-5
• 作为产物：
  描述：

  二甲胺 、 5-[(1,3-二氧代-1,3-二氢-2H-异吲哚-2-基)甲基]-2-糠醛 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以95%的产率得到2-[[5-[(Dimethylamino)methyl]furan-2-yl]methyl]isoindole-1,3-dione
  参考文献：
  名称：

  WO2008/124703

  摘要：

  公开号：

文献信息

• DEVELOPMENT OF MOLECULAR IMAGING PROBES FOR CARBONIC ANHYDRASE-IX USING CLICK CHEMISTRY
  申请人：Kolb Hartmuth C.

  公开号：US20090123372A1

  公开（公告）日：2009-05-14

  The present application discloses methods for identifying inhibitors with high binding-affinity for the carbonic anhydrase-IX (CA-IX) enzyme using click chemistry and uses the candidates thereof as positron emission tomography (PET) imaging agents.

  本申请公开了使用点击化学方法鉴定高亲和力的碳酸酐酶IX（CA-IX）酶抑制剂的方法，并将其候选物作为正电子发射断层扫描（PET）成像剂。
• Development of Molecular Imaging Probes for Carbonic Anhydrase-IX Using Click Chemistry
  申请人：Kolb Hartmuth C.

  公开号：US20100317842A1

  公开（公告）日：2010-12-16

  The present application discloses methods for identifying inhibitors with high binding-affinity for the carbonic anhydrase-IX (CA-IX) enzyme using click chemistry and uses the candidates thereof as positron emission tomography (PET) imaging agents.

  本申请公开了一种使用点击化学方法鉴定高亲和力碳酸酐酶IX（CA-IX）酶抑制剂的方法，并将其候选物作为正电子发射断层扫描（PET）成像剂。
• Development of molecular imaging probes for carbonic anhydrase-IX using click chemistry
  申请人：Siemens Medical Solutions USA, Inc.

  公开号：EP2468734A1

  公开（公告）日：2012-06-27

  The present application discloses methods for identifying inhibitors with high binding-affinity for the carbonic anhydrase-IX (CA-IX) enzyme using click chemistry and uses the candidates thereof as positron emission tomography (PET) imaging agents.

  本申请公开了利用点击化学方法鉴定对碳酸酐酶-IX（CA-IX）酶具有高结合亲和力的抑制剂的方法，并将其候选物用作正电子发射断层扫描（PET）成像剂。
• US7829063B2
  申请人：——

  公开号：US7829063B2

  公开（公告）日：2010-11-09
• US8354092B2
  申请人：——

  公开号：US8354092B2

  公开（公告）日：2013-01-15