sodium 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyldithiocarbamate | 524678-13-5

• 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: sodium 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyldithiocarbamate
• 英文别名: Sodium 2-(4-(2-methoxyphenyl)piperazin-1-yl)ethyldithiocarbamate；sodium;N-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]carbamodithioate
• CAS: 524678-13-5
• 化学式: C₁₄H₂₀N₃OS₂*Na
• 分子量: 333.454
• InChiKey: VZWVJDOGLHDGTL-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.76
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  galium(III) nitrate monohydrate 、 sodium 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyldithiocarbamate 以 水 为溶剂， 以62.9 %的产率得到
  参考文献：
  名称：

  二硫代氨基甲酸镓复合物的合成、表征及体外细胞毒性

  摘要：

  报道了通式[Ga(DTC) 3 ]的均配单核Ga( III )配合物库，其中DTC是脂环族或线性二硫代氨基甲酸酯螯合剂。该配合物以Ga(NO 3 ) 3 ·6H 2 O为起始原料，以高产率制备，并通过元素分析、红外和核磁共振光谱进行了充分表征。获得了其中五个配合物的晶体。评估了新合成的化合物针对一组人类癌细胞系的抗肿瘤活性。 DTC 的化学性质对最终化合物的结构特征没有显着影响。 X射线晶体结构分析表明，所有这些配合物都具有三角棱柱几何形状，具有三个相同的螯合DTCs配位Ga（ III ）离子。值得注意的是，在配合物22 ，[Ga(NHEt) 3 ]（NHEt= N-乙基二硫代氨基甲酸酯）中，不对称单元由两个独立且结构不同的分子形成。细胞研究表明，所有合成的 Ga-DTC 复合物均表现出显着的细胞毒活性，甚至针对对顺铂不太敏感的人类结肠癌细胞。在测试的化合物中， 6个（[Ga(CEPipDTC)

  DOI：

  10.1039/d3dt03552b
• 作为产物：
  描述：

  1-(2-methoxyphenyl)piperazine hydrochloride 在 盐酸 、 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.0h， 生成 sodium 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyldithiocarbamate
  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

• Synthesis of several MPP derivatives for 99mTc-labelling and evaluated as potential 5-HT1A receptor imaging agents
  作者：WenJiang Yang、Yan Lin、XianZhong Zhang、JunBo Zhang、XueBin Wang

  DOI：10.1007/s11426-011-4271-5

  日期：2011.7

  The (2-methoxyphenyl) piperazine (MPP) was selected as the functional group and conjugated to dithiocarbamate through different spacers. A series of new MPP derivatives (MPPnDTC, n = 2–6) were synthesized and radiolabelled with 99mTc-nitrido core or 99mTc-tricarboxyl core as potential 5-HT1A receptor imaging agents. All the six 99mTc-labelled complexes were lipophilic and neutral. Biodistribution results showed that those radiotracers had moderate initial brain and hippocampus uptake. There have no significant relation was observed between the biological properties of these tracers with the length of its carbon chain. The radioactivity concentrations of hippocampus of 99mTcN-MPP2DTC, 99mTcN-MPP3DTC, 99mTcN-MPP4DTC, 99mTcN-MPP5DTC, 99mTcN-MPP6DTC and 99mTc(CO)3-MPP3DTC at 2 min post-injection time (p.i.) were 0.43, 1.15, 0.99, 1.04, 1.13 and 0.83 %ID/g, respectively.

  选择（2-甲氧基苯基）哌嗪（MPP）作为功能团，通过不同间隔基与二硫代氨基甲酸盐偶联。合成了一系列新的MPP衍生物（MPPnDTC，n = 2–6），并以99mTc-氮杂核或99mTc-三羧基核进行放射性标记，作为潜在的5-HT1A受体成像剂。所有六个99mTc标记的配合物都是亲脂性的和中性的。生物分布结果显示，这些放射性示踪剂在初始阶段具有适度的脑和海马体摄取。这些示踪剂的生物学特性与其碳链长度之间没有显著关系。99mTcN-MPP2DTC、99mTcN-MPP3DTC、99mTcN-MPP4DTC、99mTcN-MPP5DTC、99mTcN-MPP6DTC和99mTc(CO)3-MPP3DTC在注射后2分钟的海马体放射性浓度分别为0.43、1.15、0.99、1.04、1.13和0.83 %ID/g。
• Synthesis and Characterization of [M^III(PS)₂(L)] Mixed-Ligand Compounds (M = Re, ⁹⁹Tc; PS = Phosphinothiolate; L = Dithiocarbamate) as Potential Models for the Development of New Agents for SPECT Imaging and Radiotherapy
  作者：N. Salvarese、N. Morellato、A. Venzo、F. Refosco、A. Dolmella、C. Bolzati

  DOI：10.1021/ic400094s

  日期：2013.6.3

  The synthesis and characterization of a new series of neutral, six-coordinated mixed-ligand compounds [MIII(PS)2(L)] (M = Re; 99Tc), where PS is bis(arylalkyl)- or trialkylphosphinothiolate and L is dithiocarbamate, are reported. Stable [MIII(PS)2(L)] complexes were easily synthesized, in good yield, starting from precursors where the metal was in different oxidation states (III, V, and VII), involving

  一系列新的中性，六配位混合配体化合物[M III（PS）2（L）]（M = Re; 99 Tc）的合成和表征，其中PS是双（芳烷基）-或三烷基硫代磷酸酯，L是二硫代氨基甲酸酯，据报道。从金属处于不同氧化态（III，V和VII）的前体开始，容易合成高收率的稳定[M III（PS）2（L）]配合物，涉及配体交换和/或氧化还原-取代反应。通过元素分析，阳离子电喷雾电离质谱，多核NMR光谱，循环伏安法和X射线衍射分析对化合物进行表征。所有配合物均由[MIII（PS）2 ] +部分，其中两个硫代硫醇盐配体紧密结合到金属上，其余两个位置被二硫代氨基甲酸酯螯合物饱和，还带有庞大的生物活性分子[例如，（2-甲氧基苯基）哌嗪]。X射线分析是对四种不同的Re / 99 Tc化合物的晶体样品进行的，它们具有扭曲的三角棱柱几何形状，并带有P 2 S 4配位体。从相应的过金属酸盐阴离子开始，在温和的反应条件下以高收率轻松制备这些[M
• 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。
• TECHNETIUM OR RHENIUM COMPLEXES, RADIOPHARMACEUTICAL PRODUCTS COMPRISING THEM
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP1453841A1

  公开（公告）日：2004-09-08
• [EN] TECHNETIUM OR RHENIUM COMPLEXES, RADIOPHARMACEUTICAL PRODUCTS COMPRISING THEM<br/>[FR] COMPLEXES DE TECHNETIUM OU DE RHENIUM, PRODUITS RADIOPHARMACEUTIQUES LES CONTENANT
  申请人：SCHERING AG

  公开号：WO2003044031A1

  公开（公告）日：2003-05-30

  The invention relates to a technetium or rhenium complex of formula (I): [M(R1CS3)2L] (I)in which M is Tc or Re, R1 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 R2CS2 in which R2 is identical to R1. The dithiolate ligand is preferably a dithiocarbamate.The invention also relates to a radiopharmaceutical product comprising a complex of formula (I) with M representing 99Tc, 186Re or 188Re.