N-hydroxysuccinimidyl 2-[(triphenylmethylthio)methylcarbonylamino]ethanoate | 91425-33-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-hydroxysuccinimidyl 2-[(triphenylmethylthio)methylcarbonylamino]ethanoate
• CAS: 91425-33-1
• 化学式: C₂₇H₂₄N₂O₅S
• 分子量: 488.564
• InChiKey: FXKKJRWYAMNSSR-UHFFFAOYSA-N

物化性质

• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  35.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  92.78
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-hydroxysuccinimidyl 2-[(triphenylmethylthio)methylcarbonylamino]ethanoate 在 镍 4-二甲氨基吡啶 、 一水合肼 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 10.0h， 生成 Ethyl 3-[[4-hydroxy-3-[[2-[(2-tritylsulfanylacetyl)amino]acetyl]amino]phenyl]carbamothioylamino]propanoate
  参考文献：
  名称：

  基于 ON2S 配体的原始双功能螯合剂的便捷合成及其与氧铼（V）核的配位化学

  摘要：

  用于氧铼核心的半刚性、四齿双功能螯合剂 (BFC) 已通过五个步骤合成，总产率为 46%。芳香胺可通过异硫氰酸酯功能与肽结合。该 BFC 是第一个包含酰胺基和硫醇官能团的胺官能化四齿配体。Monooxorhenium 配合物很容易从双功能螯合剂和 β-丙氨酸-共轭系统制备。这些复合物以良好的收率获得并且被充分表征。此外，发现它们对配体交换反应稳定。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

  DOI：

  10.1002/ejoc.200500810
• 作为产物：
  描述：

  3-氮杂-4-氧代-5-[(三苯基甲基)硫代]戊酸乙酯 在 sodium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 N-hydroxysuccinimidyl 2-[(triphenylmethylthio)methylcarbonylamino]ethanoate
  参考文献：
  名称：

  新的半刚性配体家族的设计和合成：用于制备99mTc放射性药物的通用化合物。

  摘要：

  已开发出设计用于协调99 99m的一系列新型半刚性四齿配体（具有硫，酰胺基或氨基供体基团）的合成途径。制备了-99m配合物，并比较了它们在血清中的稳定性以及通过半胱氨酸交换反应进行的复分解反应的稳定性。两种（99m）Tc配合物及其their类似物的HPLC比较导致我们放射性配合物性质的第一个证明。

  DOI：

  10.1039/b313996d

文献信息

• Rhenium(<scp>v</scp>) oxocomplexes with novel pyrazolyl-based N₄- and N₃S-donor chelators
  作者：Carolina Moura、Rute F. Vítor、Leonor Maria、António Paulo、Isabel C. Santos、Isabel Santos

  DOI：10.1039/b611034g

  日期：——

  The novel pyrazolyl-based ligands 3,5-Me2pz(CH2)2NH(CH2)2NH(CH2)2NH2 (1) and pz*(CH2)2NH-Gly-CH2STrit (pz* = pz (8), 3,5-Me2pz (9), 4-(EtOOC)CH2-3,5-Me2pz (10)) were synthesized, and their suitability to stabilize Re(V) oxocomplexes was evaluated using different starting materials, namely (NBu4)[ReOCl4], [ReOCl3(PPh3)2] and trans-[ReO2(py)4]Cl. Compound 1 reacts with trans-[ReO2(py)4]Cl yielding the cationic compound [ReO(OMe)3,5-Me2pz(CH2)2N(CH2)2NH(CH2)2NH2}](BPh4) (11) in a low isolated yield. In contrast, the neutral complexes [ReOpz*(CH2)2NH-Gly-CH2S}] (pz* = pz (12), 3,5-Me2pz (13), 4-(EtOOCCH2)-3,5-Me2pz (14)) were synthesized almost quantitatively by reacting [ReOCl3(PPh3)2] or (NBu4)[ReOCl4] with the trityl-protected chelators 8–10. The X-ray diffraction analysis of 11 and 13 confirmed the tetradentate coordination mode of the respective ancillary ligands. In 11 the monoanionic chelator coordinates to the metal through four nitrogen atoms, while in 13 the chelator is trianionic, coordinating to the metal through three nitrogens and one sulfur atom. Solution NMR studies of 12–14, including two-dimensional NMR techniques (1H COSY and 1H/13C HSQC), confirmed that the N3S coordination mode of the chelators is retained in solution. Unlike 11, complexes 12–14 may be considered relevant in the development of radiopharmaceuticals, as further corroborated by the synthesis of the congener [99mTcOpz(CH2)2-NH-Gly-CH2S}] (12a). This radioactive compound was obtained from 99mTcO4− in aqueous medium, in almost quantitative yield and with high specific activity and radiochemical purity.

  合成了新型的以吡唑基为基础的配体3,5-Me2pz(CH2)2NH( )2NH( )2NH2 (1)和pz*( )2NH-Gly- STrit（pz* = pz (8)，3,5-Me2pz (9)，4-(EtOOC) -3,5-Me2pz (10)），并评估了它们稳定Re(V)氧化络合物的适用性，使用的起始材料分别为(NBu4)[ReOCl4]、[ReOCl3(PPh3)2] 和 trans-[ReO2(py)4]Cl。化合物1与trans-[ReO2(py)4]Cl反应，生成阳离子化合物[ReO(OMe)3,5-Me2pz( )2N( )2NH( )2NH2}](BPh4) (11)，其孤立产率较低。相比之下，几乎定量合成了中性复合物[ReOpz*( )2NH-Gly- S}] (pz* = pz (12)，3,5-Me2pz (13)，4-(EtOOC )-3,5-Me2pz (14))，通过将[ReOCl3(PPh3)2]或(NBu4)[ReOCl4]与三苯基保护的螯合剂8–10反应。对11和13的X射线衍射分析确认了各自辅助配体的四齿配位模式。在11中，单阴离子螯合剂通过四个氮原子与金属配位，而在13中，螯合剂是三阴离子，通过三个氮和一个硫原子与金属配位。对12–14的溶液NMR研究，包括二维NMR技术（1H COSY和1H/13C HSQC），确认了螯合剂的N3S配位模式在溶液中的保留。与11不同，复合物12–14被认为在放射药物开发中具有相关性，进一步通过合成同类物[99mTcOpz( )2-NH-Gly- S}] (12a)得到了印证。该放射性化合物在水相中从99mTcO4−获得，几乎定量收率，并具有高特异活性和放射化学纯度。
• Synthesis, metal complexation and biological evaluation of a novel semi-rigid bifunctional chelating agent for 99mTc labelling
  作者：Julien Le Gal、Sandra Michaud、Marie Gressier、Yvon Coulais、Eric Benoist

  DOI：10.1016/j.bmc.2005.12.005

  日期：2006.5

  A novel bifunctional chelating agent bearing an aromatic ring has been synthesised and characterised. This ligand formed well-defined oxorhenium complexes. The analogous 99mTcO-complex was obtained in an excellent yield with high radiochemical purity (>95%). The biodistribution of the 99mTc-complex after intravenous injection studied in normal rats showed that the activity was excreted mainly via renal-urinary

  合成并表征了新型的带有芳香环的双官能螯合剂。该配体形成明确的氧络合物。以优异的收率获得了类似的99mTcO复合物，并具有较高的放射化学纯度（> 95％）。正常大鼠静脉注射后99mTc复合物的生物分布研究表明，该活性主要通过肾泌尿途径排泄，表明其可用于标记99mTc肽。
• Qi, Chuan-Min; Feng, Shu-Juan; Zhang, Hua-Bei, Medicinal Chemistry Research, 2003, vol. 12, # 9, p. 471 - 480
  作者：Qi, Chuan-Min、Feng, Shu-Juan、Zhang, Hua-Bei、Huang, Hai-Bo、Li, Bo

  DOI：——

  日期：——
• SYNTHESIS BIODISTRIBUTION AND QSAR STUDIES OF FIVE Tc-99M LABELED NOVEL N3S PSEUDO-PEPTIDE COMPLEXES
  作者：Hua-bei Zhang、Hai-hong Ye、Ya-ling Zhang、Xuefang Zheng、Jian-sheng Han、Hua Li、Chun-ping Liu

  DOI：10.1007/s00044-004-0124-5

  日期：2005.1

  Five novel N3S pseudo-peptide chelators derived from mercaptoacetic acid have been synthesized and characterized based on the spectroscopic data. All the chelators were labeled with Technicium-99m to evaluate their biological activities. Investigations of their biodistribution in mice showed all five pseudo-peptide chelators (MGQ, MGGQ, MAGQ, MVGQ, MFGQ) are rapidly cleared from blood, mainly through renal clearance. Tc-99m-MGGQ and Tc-99m-MVGQ had high kidney uptake, quick blood clearance and high activity ratios of kidney to blood, thus showing potential application as renal imaging agents. Quantitative structure-activity relationship studies were performed. Linear regression analysis between the logarithm of renal uptake value (log%ID) and the parameters obtained from the ZINDO/1 method elicited several equations that possessed certain predictive qualities, and may play a direct part in drug design and synthesis.