5-(diethoxymethylfuran-2-yl)-tributyltin | 213261-65-5

• 分子结构分类: 有机化合物 - 有机金属化合物 - 金属芳基
• 英文名称: 5-(diethoxymethylfuran-2-yl)-tributyltin
• 英文别名: 2-(diethoxymethyl)-5-(tributylstannyl)furan；2-(Diethoxymethyl)-5-(tributylstannyl) furan；tributyl-[5-(diethoxymethyl)furan-2-yl]stannane
• CAS: 213261-65-5
• 化学式: C₂₁H₄₀O₃Sn
• 分子量: 459.257
• InChiKey: PQQKUFUTUONEGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.41
• 重原子数：
  25
• 可旋转键数：
  15
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(diethoxymethylfuran-2-yl)-tributyltin 在 四(三苯基膦)钯 盐酸羟胺 、 potassium tert-butylate 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 甲醇 、 二甲基亚砜 为溶剂， 反应 34.0h， 生成 5-{6-[4-(N-hydroxyamidino)phenyl]-pyridin-3-yl}-furan-2-N-hydroxyamidine
  参考文献：
  名称：

  Synthesis, DNA Affinity, and Antiprotozoal Activity of Linear Dications:  Terphenyl Diamidines and Analogues

  摘要：

  Diamidines 10a-g and 18a, b were obtained from dinitriles 9a-g and 15a, b by treatment with lithium trimethylsilylamide or upon hydrogenation of bis-O-acetoxyamidoximes. Dinitriles 9a-g were prepared via Suzuki reactions between arylboronic acids and arylnitriles. Potential prodrugs 12a-f and 17 were prepared via methylation of the diamidoximes 11a-f and 16a. Significant DNA affinities for rigid-rod molecules were observed. Compounds 10a, 10b, 10d, 18a, and 18b show IC50 values of 5 nM or less against Trypanosoma brucei rhodesiense ( T. b. r.) and 10a, 10b, 10e, 18a, and 18b gave similar ones against Plasmodium falciparum ( P. f.). The dications, 10a, 10d, 10f, and 10g are more active than furamidine in vivo. The prodrugs are only moderately effective on oral administration. Mouse liver microsome bioconversion of the methamidoxime prodrugs is significantly reduced from that of pafuramidine and suggests that the in vivo efficacy of these prodrugs is, in part, due to poor bioconversion.

  DOI：

  10.1021/jm060470p
• 作为产物：
  描述：

  2-(diethoxymethyl)-5-(tributylstannyl)-thiophene 、 2-糠醛缩二乙醇 生成 5-(diethoxymethylfuran-2-yl)-tributyltin
  参考文献：
  名称：

  Polyheterocyclic compounds

  摘要：

  本发明涉及一组多杂环化合物，其公式如下所示：##STR1##其中X.sub.1、X.sub.2、X.sub.3和X.sub.4分别独立地为O、S、NH或N（C.sub.1-6烷基），但其中一个必须为O、NH或N（C.sub.1-6烷基）；R.sub.1、R.sub.2、R.sub.5和R.sub.6分别独立地为H或取代基（例如，卤素、CN、NO.sub.2或C.sub.1-4卤代烷基），但其中至少一个必须为取代基；R.sub.3和R.sub.4分别独立地为H、C.sub.1-6烷基、CHO、CH.sub.2OH或CH.sub.2NH.sub.2；m和n分别独立地为0或1。

  公开号：

  US05994394A1

文献信息

• Synthesis, DNA Affinity, and Antiprotozoal Activity of Linear Dications:  Terphenyl Diamidines and Analogues
  作者：Mohamed A. Ismail、Reem K. Arafa、Reto Brun、Tanja Wenzler、Yi Miao、W. David Wilson、Claudia Generaux、Arlene Bridges、James E. Hall、David W. Boykin

  DOI：10.1021/jm060470p

  日期：2006.8.1

  Diamidines 10a-g and 18a, b were obtained from dinitriles 9a-g and 15a, b by treatment with lithium trimethylsilylamide or upon hydrogenation of bis-O-acetoxyamidoximes. Dinitriles 9a-g were prepared via Suzuki reactions between arylboronic acids and arylnitriles. Potential prodrugs 12a-f and 17 were prepared via methylation of the diamidoximes 11a-f and 16a. Significant DNA affinities for rigid-rod molecules were observed. Compounds 10a, 10b, 10d, 18a, and 18b show IC50 values of 5 nM or less against Trypanosoma brucei rhodesiense ( T. b. r.) and 10a, 10b, 10e, 18a, and 18b gave similar ones against Plasmodium falciparum ( P. f.). The dications, 10a, 10d, 10f, and 10g are more active than furamidine in vivo. The prodrugs are only moderately effective on oral administration. Mouse liver microsome bioconversion of the methamidoxime prodrugs is significantly reduced from that of pafuramidine and suggests that the in vivo efficacy of these prodrugs is, in part, due to poor bioconversion.
• Polyheterocyclic compounds
  申请人：Industrial Technology Research Institute

  公开号：US05994394A1

  公开（公告）日：1999-11-30

  The present invention relates to a group of polyheterocyclic compounds covered by the following formula: ##STR1## wherein each of X.sub.1, X.sub.2, X.sub.3, and X.sub.4, independently, is O, S, NH, or N(C.sub.1-6 alkyl), but one of them must be O, NH, or N(C.sub.1-6 alkyl); each of R.sub.1, R.sub.2, R.sub.5, and R.sub.6, independently, is H or a substituent (e.g., halogen, CN, NO.sub.2, or C.sub.1-4 haloalkyl), but at least one of them must be a substituent; each of R.sub.3 and R.sub.4, independently, is H, C.sub.1-6 alkyl, CHO, CH.sub.2 OH, or CH.sub.2 NH.sub.2 ; and each of m and n, independently, is 0 or 1.

  本发明涉及一组多杂环化合物，其公式如下所示：##STR1##其中X.sub.1、X.sub.2、X.sub.3和X.sub.4分别独立地为O、S、NH或N（C.sub.1-6烷基），但其中一个必须为O、NH或N（C.sub.1-6烷基）；R.sub.1、R.sub.2、R.sub.5和R.sub.6分别独立地为H或取代基（例如，卤素、CN、NO.sub.2或C.sub.1-4卤代烷基），但其中至少一个必须为取代基；R.sub.3和R.sub.4分别独立地为H、C.sub.1-6烷基、CHO、CH.sub.2OH或CH.sub.2NH.sub.2；m和n分别独立地为0或1。