2-(Dibutylamino-methylsulfanyl-methylene)-malononitrile | 85106-65-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(Dibutylamino-methylsulfanyl-methylene)-malononitrile
• 英文别名: 2-[(Dibutylamino)-methylsulfanylmethylidene]propanedinitrile
• CAS: 85106-65-6
• 化学式: C₁₃H₂₁N₃S
• 分子量: 251.396
• InChiKey: CMKTXGMBEHAFIC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  76.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(Dibutylamino-methylsulfanyl-methylene)-malononitrile 在 ammonium sulfate 、 lithium tert-butoxide 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(5-Cyano-4-dibutylamino-6'-morpholin-4-yl-[2,3']bipyridinyl-6-yl)-formimidic acid ethyl ester
  参考文献：
  名称：

  Synthesis and structure-activity relationships of 5-heteroatom-substituted pyridopyrimidines as adenosine kinase inhibitors

  摘要：

  Under stressful conditions, many cells release adenosine to minimize tissue damage. Inhibition of intracellular adenosine kinase (AK) increases the local extracellular concentration of adenosine and its effect on traumatized tissue. The synthesis and SAR of a new series of pyridopyrimidines for the inhibition of AK are described. It was found that a range of analogs with position five substituted by an amine or ether functionality increased aqueous solubility while retaining the in vitro potency of initial leads. A narrower range of analogs was active in vivo in a rat inflammatory hyperalgesia model. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(03)00019-9
• 作为产物：
  描述：

  [双(甲硫基)亚甲基]丙烷二腈 、 二正丁胺 以 苯 为溶剂， 以99%的产率得到2-(Dibutylamino-methylsulfanyl-methylene)-malononitrile
  参考文献：
  名称：

  SYNTHESIS OF THIENO[3,2-b]PYRIDINES

  摘要：

  通过使用 LDA 直接从 3-（二取代氨基）-2-氰基-3-甲硫基丙烯腈进行甲氧基化，可以轻松合成多种噻吩并[3,2-b]吡啶。

  DOI：

  10.1246/cl.1982.1933

文献信息

• SYNTHESIS OF THIENO[3,2-<i>b</i>]PYRIDINES
  作者：Masataka Yokoyama、Masanori Tohnishi、Akemi Kurihara、Tsuneo Imamoto

  DOI：10.1246/cl.1982.1933

  日期：1982.12.5

  Several thieno[3,2-b]pyridines could be easily synthesized by methallation using LDA directly from 3-(disubstituted amino)-2-cyano-3-methylthioacrylonitriles.

  通过使用 LDA 直接从 3-（二取代氨基）-2-氰基-3-甲硫基丙烯腈进行甲氧基化，可以轻松合成多种噻吩并[3,2-b]吡啶。
• YOKOYAMA, MASATAKA;TOHNISHI, MASANORI;KURIHARA, AKEMI;IMAMOTO, TSUNEO, CHEM. LETT., 1982, N 12, 1933-1936
  作者：YOKOYAMA, MASATAKA、TOHNISHI, MASANORI、KURIHARA, AKEMI、IMAMOTO, TSUNEO

  DOI：——

  日期：——
• Synthesis and structure-activity relationships of 5-heteroatom-substituted pyridopyrimidines as adenosine kinase inhibitors
  作者：Gregory A Gfesser、Erol K Bayburt、Marlon Cowart、Stanley DiDomenico、Arthur Gomtsyan、Chih-Hung Lee、Andrew O Stewart、Michael F Jarvis、Elizabeth A Kowaluk、Shripad S Bhagwat

  DOI：10.1016/s0223-5234(03)00019-9

  日期：2003.3

  Under stressful conditions, many cells release adenosine to minimize tissue damage. Inhibition of intracellular adenosine kinase (AK) increases the local extracellular concentration of adenosine and its effect on traumatized tissue. The synthesis and SAR of a new series of pyridopyrimidines for the inhibition of AK are described. It was found that a range of analogs with position five substituted by an amine or ether functionality increased aqueous solubility while retaining the in vitro potency of initial leads. A narrower range of analogs was active in vivo in a rat inflammatory hyperalgesia model. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.