2-(4-(2-methoxyphenyl)piperazin-1-yl)-N-(4-nitrobenzylidene)ethylamine | 524678-18-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(4-(2-methoxyphenyl)piperazin-1-yl)-N-(4-nitrobenzylidene)ethylamine
• 英文别名: N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-1-(4-nitrophenyl)methanimine
• CAS: 524678-18-0
• 化学式: C₂₀H₂₄N₄O₃
• 分子量: 368.436
• InChiKey: WFAQFKHAVHXCRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(4-(2-methoxyphenyl)piperazin-1-yl)-N-(4-nitrobenzylidene)ethylamine 在 盐酸 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 2.0h， 以96.2%的产率得到1-(2-aminoethyl)-4-(2-methoxyphenyl)piperazine
  参考文献：
  名称：

  Synthesis and biological evaluation of new [Tc(N)(PS)]-based mixed-ligand compounds useful in the design of target-specific radiopharmaceuticals: the 2-methoxyphenylpiperazine dithiocarbamate derivatives as an example

  摘要：

  This study presents the first application of a general procedure based on the use of the [Tc(N)Cl(PS) (PPh3)] species (PS is an alkyl phosphinothiolate ligand) for the preparation of Tc(N) target-specific compounds. [Tc(N)Cl(PS)(PPh3)] selectively reacts with an appropriate dithiocarbamate ligand (S boolean AND Y) to give [Tc(N)(PS)(S boolean AND Y)] compounds. 1-(2-Methoxyphenyl)piperazine, which displays a potent and specific affinity for 5HT(1A) receptors, was selected as a functional group and conjugated to the dithiocarbamate unit through different spacers (L-n). [Tc-99m(N)(PS)(L-n)] complexes were prepared in high yield (more than 90%). The chemical identity of Tc-99m complexes was determined by high performance liquid chromatography comparison with the corresponding Tc-99g complexes. All complexes were found to be inert toward transchelation with an excess of glutathione and cysteine. No notable biotransformation of the native compound into different species by the in vitro action of the serum and liver enzymes was shown. Nanomolar affinity for the 5HT(1A) receptor was obtained for [Tc-99m(N)(PSiso)L-3] (IC50 = 1.5 nM); a reduction of the affinity was observed for the other complexes as a function of the shortening of the alkyl chain interposed between the dithiocarbamate and the pharmacophore. Negligible brain uptake was found from in vivo distribution data of [Tc-99m(N)(PSiso)L-3]. The key finding of this study is that the complexes maintained good affinity and selectivity for 5HT(1A) receptors, and the IC50 value for [Tc-99g(N)(PSiso)L-3] being comparable to the IC50 value found for WAY 100635. This result confirmed the possibility of preparing [Tc-99m(N)(PS)]-based target-specific compounds without affecting the affinity and selectivity of the bioactive molecules for the corresponding receptors.

  DOI：

  10.1007/s00775-010-0712-4
• 作为产物：
  描述：

  对硝基苯甲醛 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 2-(4-(2-methoxyphenyl)piperazin-1-yl)-N-(4-nitrobenzylidene)ethylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of new [Tc(N)(PS)]-based mixed-ligand compounds useful in the design of target-specific radiopharmaceuticals: the 2-methoxyphenylpiperazine dithiocarbamate derivatives as an example

  摘要：

  This study presents the first application of a general procedure based on the use of the [Tc(N)Cl(PS) (PPh3)] species (PS is an alkyl phosphinothiolate ligand) for the preparation of Tc(N) target-specific compounds. [Tc(N)Cl(PS)(PPh3)] selectively reacts with an appropriate dithiocarbamate ligand (S boolean AND Y) to give [Tc(N)(PS)(S boolean AND Y)] compounds. 1-(2-Methoxyphenyl)piperazine, which displays a potent and specific affinity for 5HT(1A) receptors, was selected as a functional group and conjugated to the dithiocarbamate unit through different spacers (L-n). [Tc-99m(N)(PS)(L-n)] complexes were prepared in high yield (more than 90%). The chemical identity of Tc-99m complexes was determined by high performance liquid chromatography comparison with the corresponding Tc-99g complexes. All complexes were found to be inert toward transchelation with an excess of glutathione and cysteine. No notable biotransformation of the native compound into different species by the in vitro action of the serum and liver enzymes was shown. Nanomolar affinity for the 5HT(1A) receptor was obtained for [Tc-99m(N)(PSiso)L-3] (IC50 = 1.5 nM); a reduction of the affinity was observed for the other complexes as a function of the shortening of the alkyl chain interposed between the dithiocarbamate and the pharmacophore. Negligible brain uptake was found from in vivo distribution data of [Tc-99m(N)(PSiso)L-3]. The key finding of this study is that the complexes maintained good affinity and selectivity for 5HT(1A) receptors, and the IC50 value for [Tc-99g(N)(PSiso)L-3] being comparable to the IC50 value found for WAY 100635. This result confirmed the possibility of preparing [Tc-99m(N)(PS)]-based target-specific compounds without affecting the affinity and selectivity of the bioactive molecules for the corresponding receptors.

  DOI：

  10.1007/s00775-010-0712-4

文献信息

• Technetium or rhenium complexes, radiopharmaceutical products comprising them
  申请人：Mevellec Franck

  公开号：US20050008568A1

  公开（公告）日：2005-01-13

  The invention relates to a technetium or rhenium complex of formula (I): [M (R 1 CS 3 ) 2 L]  (I) in which M is Tc or Re, R 1 represents an alkyl, cycloalkyl, aralkyl or aryl group which is unsubstituted or substituted by one or more substituents chosen from halogen atoms, the hydroxyl group, alkyl groups and alkoxy groups, and L is a dithiolate ligand, with the exception of the ligand of formula R 2 CS 2 in which R 2 is identical to R 1 . The dithiolate ligand is preferably a dithiocarbamate. The invention also relates to a radiopharmaceutical product comprising a complex of formula (I) with M representing 99 Tc, 186 Re or 188 Re.

  该发明涉及公式（I）的锝或铼配合物： [M（R 1 CS 3 ） 2 L]  （I） 其中M为Tc或Re，R 1 代表未取代或取代为一个或多个卤素原子、羟基、烷基和烷氧基中的一种取代基的烷基、环烷基、芳基或芳基，L为二硫醚配体，但不包括公式R 2 CS 2 中R 2 与R 1 相同的配体。 该二硫醚配体优选为二硫代氨基甲酸酯。 该发明还涉及包含公式（I）中M代表 99 Tc、 186 Re或 188 Re的放射性药物产品。
• Synthesis and biological evaluation of new [Tc(N)(PS)]-based mixed-ligand compounds useful in the design of target-specific radiopharmaceuticals: the 2-methoxyphenylpiperazine dithiocarbamate derivatives as an example
  作者：Cristina Bolzati、Nicola Salvarese、Davide Carta、Fiorenzo Refosco、Alessandro Dolmella、Hans Jürgen Pietzsch、Ralf Bergmann、Giuliano Bandoli

  DOI：10.1007/s00775-010-0712-4

  日期：2011.1

  This study presents the first application of a general procedure based on the use of the [Tc(N)Cl(PS) (PPh3)] species (PS is an alkyl phosphinothiolate ligand) for the preparation of Tc(N) target-specific compounds. [Tc(N)Cl(PS)(PPh3)] selectively reacts with an appropriate dithiocarbamate ligand (S boolean AND Y) to give [Tc(N)(PS)(S boolean AND Y)] compounds. 1-(2-Methoxyphenyl)piperazine, which displays a potent and specific affinity for 5HT(1A) receptors, was selected as a functional group and conjugated to the dithiocarbamate unit through different spacers (L-n). [Tc-99m(N)(PS)(L-n)] complexes were prepared in high yield (more than 90%). The chemical identity of Tc-99m complexes was determined by high performance liquid chromatography comparison with the corresponding Tc-99g complexes. All complexes were found to be inert toward transchelation with an excess of glutathione and cysteine. No notable biotransformation of the native compound into different species by the in vitro action of the serum and liver enzymes was shown. Nanomolar affinity for the 5HT(1A) receptor was obtained for [Tc-99m(N)(PSiso)L-3] (IC50 = 1.5 nM); a reduction of the affinity was observed for the other complexes as a function of the shortening of the alkyl chain interposed between the dithiocarbamate and the pharmacophore. Negligible brain uptake was found from in vivo distribution data of [Tc-99m(N)(PSiso)L-3]. The key finding of this study is that the complexes maintained good affinity and selectivity for 5HT(1A) receptors, and the IC50 value for [Tc-99g(N)(PSiso)L-3] being comparable to the IC50 value found for WAY 100635. This result confirmed the possibility of preparing [Tc-99m(N)(PS)]-based target-specific compounds without affecting the affinity and selectivity of the bioactive molecules for the corresponding receptors.