1-(1,3-dioxan-2-yl)-1'-(tri-n-butyltin)ferrocene | 1241848-87-2

• 英文名称: 1-(1,3-dioxan-2-yl)-1'-(tri-n-butyltin)ferrocene
• CAS: 1241848-87-2
• 化学式: C₂₆H₄₂FeO₂Sn
• 分子量: 561.175
• InChiKey: IXXSLLSMXGYWPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  1,2-二碘乙烷 、 1-(1,3-dioxan-2-yl)-1'-(tri-n-butyltin)ferrocene 在 正丁基锂 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 以78%的产率得到1-(1,3-dioxan-2-yl)-1'-iodoferrocene
  参考文献：
  名称：

  1,1′-Disubstituted Ferrocenyl Carbohydrate Chloroquine Conjugates as Potential Antimalarials

  摘要：

  This work presents a new class of organometallic antimalarials, based on a ferrocene scaffold, bearing a chloroquine derivative and a 1,2;3,5-(diisopropylidene)-alpha-D-glucofuranose moiety in a 1,1'-heteroannular substitution pattern. Synthesis proceeds via orthogonal functionalization of ferrocene, giving 1-acetoxy-1'-(1,3-dioxan-2-yl)ferrocene (15) as the precursor for modular introduction of the carbohydrate (16, 17) followed by subsequent reductive amination with chloroquine building blocks 8-10, yielding the 1-[3-(7-chloroquinolin-4-ylamino)alkylamino]-1'-[6-(1,2;3,5-diisopropylidene)-alpha-D-glucofuranosidyl]ferrocenes 18-20. After complete characterization of these new, trifunctional conjugates, they were examined for their antiplasmodial activity in a chloroquine-susceptible strain of Plasmodium falciparum (D10) and in two chloroquine-resistant strains (Dd2 and K1). Their activity was compared to that of the monosubstituted reference conjugates 1-3 and the 1,2-disubstituted regioisomers 4-6. Compounds 19 and 20 exhibited consistently high activity in in vitro antiplasmodial activity assays performed in Dd2 and K1 strains, performing better than the reference compounds chloroquine and the monosubstituted and 1,2-disubstituted compounds 1-6.

  DOI：

  10.1021/om300354x
• 作为产物：
  描述：

  1'-(tri-n-butylstannyl)-1-ferrocenecarboxaldehyde 、 1,3-丙二醇 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 6.0h， 以88%的产率得到1-(1,3-dioxan-2-yl)-1'-(tri-n-butyltin)ferrocene
  参考文献：
  名称：

  1,1′-Disubstituted Ferrocenyl Carbohydrate Chloroquine Conjugates as Potential Antimalarials

  摘要：

  This work presents a new class of organometallic antimalarials, based on a ferrocene scaffold, bearing a chloroquine derivative and a 1,2;3,5-(diisopropylidene)-alpha-D-glucofuranose moiety in a 1,1'-heteroannular substitution pattern. Synthesis proceeds via orthogonal functionalization of ferrocene, giving 1-acetoxy-1'-(1,3-dioxan-2-yl)ferrocene (15) as the precursor for modular introduction of the carbohydrate (16, 17) followed by subsequent reductive amination with chloroquine building blocks 8-10, yielding the 1-[3-(7-chloroquinolin-4-ylamino)alkylamino]-1'-[6-(1,2;3,5-diisopropylidene)-alpha-D-glucofuranosidyl]ferrocenes 18-20. After complete characterization of these new, trifunctional conjugates, they were examined for their antiplasmodial activity in a chloroquine-susceptible strain of Plasmodium falciparum (D10) and in two chloroquine-resistant strains (Dd2 and K1). Their activity was compared to that of the monosubstituted reference conjugates 1-3 and the 1,2-disubstituted regioisomers 4-6. Compounds 19 and 20 exhibited consistently high activity in in vitro antiplasmodial activity assays performed in Dd2 and K1 strains, performing better than the reference compounds chloroquine and the monosubstituted and 1,2-disubstituted compounds 1-6.

  DOI：

  10.1021/om300354x