sodium 4-(2-methoxyphenyl)piperazine-1-carbodithioate | 1174408-29-7

• 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 4-(2-methoxyphenyl)piperazine-1-carbodithioate
• 英文别名: sodium 4-(2-methoxyphenyl)piperazine-1-dithiocarbamate；sodium;4-(2-methoxyphenyl)piperazine-1-carbodithioate
• CAS: 1174408-29-7
• 化学式: C₁₂H₁₅N₂OS₂*Na
• 分子量: 290.386
• InChiKey: IQDPBCGDXQUPAW-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -1.35
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  sodium 4-(2-methoxyphenyl)piperazine-1-carbodithioate 在 盐酸 、 sodium nitrite 作用下， 以 甲醇 、 水 为溶剂， 反应 0.33h， 以60%的产率得到bis[4-(2-methoxyphenyl)-1-piperazinylthiocarbonyl] disulfide
  参考文献：
  名称：

  二硫键在双（二烷基胺硫代羰基）二硫作为有效的双刃杀微生物杀精子剂中的作用：设计，合成和生物学

  摘要：

  滴虫病和念珠菌病是最常见的致病性生殖道感染，通常分别用甲硝唑和氟康唑治疗。阴道功效差，耐药性和非杀精性限制了它们作为局部杀微生物避孕药的使用。双（二烷基胺硫代羰基）二硫化物（4 – 38）被设计为具有双重活性的非表面活性剂分子，能够消除阴道毛滴虫和念珠菌菌株，并且能够以不可细胞毒性的剂量立即不可逆地固定100％人类精子，对人类宫颈上皮细胞和体外阴道菌群。化合物12，16，17它们的活性是非氧化酚9，OTC阴道杀精子剂的50倍，并且化合物12和17在兔模型中显示出显着的体内活性。最有前途的化合物17由于具有更高的活性和安全性以及显着的体内滴虫杀菌活性，已显示出有望进一步发展为双刃阴道杀微生物剂。二硫化物基团的作用是由于化学修饰过程中杀精子活性的丧失而确立的（39 – 56）。这些二硫化物可能靶向存在于人精子和滴虫的细胞膜上的巯基，如游离巯基的荧光标记所示。

  DOI：

  10.1016/j.ejmech.2016.03.012
• 作为产物：
  描述：

  二硫化碳 、 1-(2-methoxyphenyl)piperazine hydrochloride 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成 sodium 4-(2-methoxyphenyl)piperazine-1-carbodithioate
  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 <i>S</i>-(2-Thioxo-1,3-dithiolan-4-yl)methyl Dialkylcarbamothioate and <i>S</i>-Thiiran-2-ylmethyl Dialkylcarbamothioate via Intermolecular O−S Rearrangement in Water^,
  作者：Nand Lal、Lalit Kumar、Amit Sarswat、Santosh Jangir、Vishnu Lal Sharma

  DOI：10.1021/ol2005825

  日期：2011.5.6

  3-dithiolan-4-yl)methyl dialkylcarbamothioates (3) and S-thiiran-2-ylmethyl dialkylcarbamothioate (5) has been reported by the reaction of 5-(chloromethyl)-1,3-oxathiolane-2-thione (1) with sodium dialkylcarbamodithioate (2) and dialkylamine (4), respectively, through intermolecular O−S rearrangement in water. A plausible mechanism of formation of the title compounds has also been proposed.

  据报道，通过5-（氯甲基）的反应可以轻松合成S-（2-硫代-1,3-二硫杂环戊-4-基）甲基二烷基氨基甲酸酯（3）和S-噻喃-2-基甲基二烷基氨基甲酸酯（5）。 -1,3-氧杂硫杂环戊烷-2-硫酮（1）与二烷基氨基甲磺酸二钠（2）和二烷基胺（4）通过在水中的分子间OS重排。还提出了标题化合物形成的合理机理。
• 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
• Novel [^99mTc^III(PS)₂(Ln)] Mixed-Ligand Compounds (PS = Phosphino-thiolate; L = Dithiocarbamate) Useful in Design and Development of Tc^III-Based Agents: Synthesis, in Vitro, and ex Vivo Biodistribution Studies
  作者：Nicola Salvarese、Nicolò Morellato、Antonio Rosato、Laura Meléndez-Alafort、Fiorenzo Refosco、Cristina Bolzati

  DOI：10.1021/jm501088w

  日期：2014.11.13

  pyrrolidine dithiocarbamate) was determined by HPLC comparison with the corresponding 99gTc-complex. All complexes comprise the stable [99mTcIII(PS)2]+ moiety, where the remaining two coordination positions are saturated by a dithiocarbamate chelate, also carrying bioactive molecules (e.g., 2-methoxyphenylpiperazine). [99mTc(PS)2(Ln)] complexes were inert toward ligand exchange reactions. No significant in

  报告了制备新型中性六配位混合配体[ 99m Tc III（PS）2（Ln）]化合物（PS =三烷基膦基硫代硫酸盐； Ln =二硫代氨基甲酸酯）的一般步骤及其制备方法。体外稳定性和离体组织分布研究。按照一锅法，在几乎生理条件下以高收率制备了[ 99m Tc（PS）2（Ln）]复合物。例如，的化学特性[ 99米TC（PSiso）2（L1）]（PSiso = 2-（二异丙基）乙硫醇; L1 =二硫代氨基甲酸吡咯烷）通过与相应的HPLC比较确定99克复杂的Tc。所有复合物均包含稳定的[ 99m Tc III（PS）2 ] +部分，其中其余的两个配位位置被二硫代氨基甲酸酯螯合物饱和，还带有生物活性分子（例如2-甲氧基苯基哌嗪）。[ 99m Tc（PS）2（Ln）]复合物对配体交换反应呈惰性。没有观察到明显的体外和体内生物转化，突显了其显着的热力学稳定性和动力学惰性。这些结果可方便地用于设计一类新的基于99m
• [EN] CARBODITHIOATES WITH SPERMICIDAL ACTIVITY AND PROCESS FOR PREPARATION THEREOF<br/>[FR] CARBODITHIOATES AYANT UNE ACTIVITÉ SPERMICIDE ET LEUR PROCÉDÉ DE PRÉPARATION
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2014122670A1

  公开（公告）日：2014-08-14

  The present invention relates to the synthesis and biological evaluation of compound of formula I as spermicidal agents, and its pharmaceutically acceptable acid salt thereof. The invention provides bis(4- substituted-1-piperazinylthiocarbonyl) disulfide (when n = 0) and alkane-1,n-diylbis(4-substituted piperazine-1-carbodithioate) (when n = 0, 1, 2 or 3) as shown in figure 1 of the accompanying drawing. These compounds are found to be useful for spermicidal activity.

  本发明涉及将式I化合物合成为杀精子剂，并其在药学上可接受的酸盐。该发明提供了双(4-取代-1-哌嗪基硫代羰基)二硫化物(当n = 0)和烷基-1,n-二基(4-取代哌嗪-1-羰基二硫代酸酯)(当n = 0, 1, 2或3)如附图1所示。这些化合物被发现对杀精子活性有用。
• New heteroleptic palladium(II) dithiocarbamates: synthesis, characterization, packing and anticancer activity against five different cancer cell lines
  作者：Shahan Zeb Khan、Muhammad Kashif Amir、Imdad Ullah、Asma Aamir、John M. Pezzuto、Tamara Kondratyuk、Francine Bélanger-Gariepy、Akbar Ali、Sajid Khan、Zia-ur-Rehman

  DOI：10.1002/aoc.3445

  日期：2016.6

  Two new heteroleptic palladium(II) complexes have been synthesized by reacting equimolar quantities of palladium(II) chloride, sodium 4‐(2‐methoxyphenyl)piperazine‐1‐carbodithioate and diphenyl‐p‐tolylphosphine (1) or tri‐p‐tolylphosphine (2). Complexes 1 and 2 have been characterized using elemental analysis, Fourier transform infrared spectroscopy, multinuclear NMR (1H, 13C and 31P) spectroscopy

  通过使等摩尔量的氯化钯（II），4-（2-甲氧基苯基）哌嗪-1-碳二硫代硫酸钠和二苯基对甲苯基膦（1）或三对甲苯基膦反应，合成了两种新的杂合钯（II）配合物。（2）。配合物1和2已使用元素分析，傅里叶变换红外光谱，多核NMR（1 H，13 C和31P）光谱学和单晶X射线分析。后一种技术证实了伪正方形平面的几何结构，其中两个相邻的位置被二齿二硫代氨基甲酸酯占据，而氯和取代的三苯基膦则存在于其余两个位置。两种复合物对五种不同癌细胞系的抗癌活性（LU –人肺癌，在UIC，外科肿瘤学系建立； MCF7 –人乳腺腺癌，ATCC编号为HTB‐22™； MDA‐MB‐231 –人乳腺腺癌，ATCC编号为HTB‐26™； Hepa-1c1c7 –小鼠肝肝癌，ATCC编号为CRL-2026™； PC‑3 –人前列腺腺癌，ATCC编号为CRL‐1435™）是​​通过MTT分析测定的，显示2的活性高于1个。药物