thiophosphate di-tributylamine salt

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机硫代磷酸及其衍生物
• 英文名称: thiophosphate di-tributylamine salt
• 英文别名: N,N-dibutylbutan-1-amine;trihydroxy(sulfanylidene)-lambda5-phosphane；N,N-dibutylbutan-1-amine;trihydroxy(sulfanylidene)-λ5-phosphane
• 化学式: 2C₁₂H₂₇N*H₃O₃PS
• 分子量: 484.768
• InChiKey: MOYPQDNWHYMHEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  18
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  96
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-碘-5-脱氧环磷腺苷 、 thiophosphate di-tributylamine salt 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 Thiophosphoric acid S-[(2S,3S,4R,5R)-5-(6-amino-purin-9-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethyl] ester; compound with tributyl-amine
  参考文献：
  名称：

  5′-Deoxy-5′-thioribonucleoside-5′-triphosphates

  摘要：

  5'-Deoxy-5'-thiouridine- and 5'-deoxy-5'-thioadenosine-5'-triphosphate 6 and 7 were chemically synthesised by two methods, Their incorporation into RNA to produce a 5'-S-bridging phosphorothioate internucleotide linkages, using T7 RNA polymerase, was investigated. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00084-1
• 作为产物：
  描述：

  三正丁胺 在 trisodium thiophosphate 作用下， 以 乙醇 为溶剂， 生成 thiophosphate di-tributylamine salt
  参考文献：
  名称：

  Identification of Highly Promising Antioxidants/Neuroprotectants Based on Nucleoside 5′-Phosphorothioate Scaffold. Synthesis, Activity, and Mechanisms of Action

  摘要：

  With a view to identify novel and biocompatible neuroprotectants, we designed nucleoside 5'-thiophosphate analogues, 6-11. We identified 2-SMe-ADP(alpha-S), 7A, as a most promising neuroprotectant. 7A reduced ROS production in PC12 cells under oxidizing conditions, IC50 of 0.08 vs 21 mu M for ADP. Furthermore, 7A rescued primary neurons subjected to oxidation, EC50 of 0.04 vs 19 mu M for ADP. 7A is a most potent P2Y(1)-R agonist, EC50 of 0.0026 mu M. Activity of 7A in cells involved P2Y(1/12)-R as indicated by blocking P2Y(12)-R or P2Y(1)-R Compound 7A inhibited Fenton reaction better than EDTA, IC50 of 37 vs 54 mu M, due to radical scavenging, IC50 of 12.5 vs 30 mu M for ADP, and Fe(II)-chelation, IC50 of 80 vs >200 mu M for ADP (ferrozine assay). In addition, 7A was stable in human blood serum, 412 of 15 vs 1.5 h for ADP, and resisted hydrolysis by NPP1/3, 2-fold vs ADP. Hence, we propose 7A as a highly promising neuroprotectant.

  DOI：

  10.1021/acs.jmedchem.5b00575
• 作为试剂：
  描述：

  adenosine 5'-methylenebis(phosphonate) triethylammonium 、 三乙基碳酸氢铵缓冲液 、 乙酸–三乙胺 在 N,N'-羰基二咪唑 、 三辛胺 、 thiophosphate di-tributylamine salt 、 zinc(II) chloride 作用下， 以 N,N-二甲基甲酰胺 、 甲醇 为溶剂， 反应 6.0h， 以19%的产率得到adenosine 5'-[γ-thio]-α,β-methylene triphosphate triethylamine salt
  参考文献：
  名称：

  [EN] NUCLEOSIDE 5'-PHOSPHOROTHIOATE ANALOGUES AND USES THEREOF
  [FR] ANALOGUES DE NUCLÉOSIDE 5'-PHOSPHOROTHIOATE ET LEURS UTILISATIONS

  摘要：

  该发明提供了特定的单核苷酸和二核苷酸5'-磷硫酸酯类似物，更具体地说是单腺苷或尿苷5'-二磷硫酸酯类似物或三磷硫酸酯类似物，其中磷硫酸酯的桥氧原子之一被类似于-CH2-的基团取代，并且磷硫酸酯的非桥接原子或负电荷原子之一是硫原子或硫离子；以及其药物组合物。这些化合物可用于治疗神经退行性疾病或障碍，如阿尔茨海默病。

  公开号：

  WO2013132489A1

文献信息

• Characterization of Complexes of Nucleoside-5′-Phosphorothioate Analogues with Zinc Ions
  作者：Alon Haim Sayer、Yehudit Itzhakov、Noa Stern、Yael Nadel、Bilha Fischer

  DOI：10.1021/ic400878k

  日期：2013.10.7

  On the basis of the high affinity of Zn2+ to sulfur and imidazole, we targeted nucleotides such as GDP-beta-S, ADP-beta-S, and AP(3)(beta-S)A, as potential biocompatible Zn2+-chelators. The thiophosphate moiety enhanced the stability of the Zn2+-nucleotide complex by about 0.7 log units. ATP-alpha,beta-CH2-gamma-S formed the most stable Zn2+-complex studied here, log K 6.50, being similar to 0.8 and similar to 1.1 log units more stable than ATP-gamma-S-Zn2+ and ATP-Zn2+ complexes, and was the major species, 84%, under physiological pH. Guanine nucleotides Zn2+ complexes were more stable by 0.3-0.4 log units than the corresponding adenine nucleotide complexes. Likewise, AP(3)(beta-S)A-zinc complex was similar to 0.5 log units more stable than AP(3)A complex. H-1- and P-31 NMR monitored Zn2+ titration showed that Zn2+ coordinates with the purine nucleotide N7-nitrogen atom, the terminal phosphate, and the adjacent phosphate. In conclusion, replacement of a terminal phosphate by a thiophosphate group resulted in decrease of the acidity of the phosphate moiety by approximately one log unit, and increase of stability of Zn2+-complexes of the latter analogues by up to 0.7 log units. A terminal phosphorothioate contributed more to the stability of nucleotide-Zn2+ complexes than a bridging phosphorothioate.
• PURINE NUCLEOTIDE DERIVATIVES
  申请人：Lauras AS

  公开号：EP1765844A2

  公开（公告）日：2007-03-28
• PROCESS FOR THE PREPARATION OF AN (RP)-8-SUBSTITUTED CAMPS
  申请人：Lauras AS

  公开号：EP2081947A2

  公开（公告）日：2009-07-29
• [EN] PURINE NUCLEOTIDE DERIVATIVES<br/>[FR] DERIVES DE NUCLEOTIDE PURIQUE
  申请人：LAURAS AS

  公开号：WO2005123755A2

  公开（公告）日：2005-12-29

  This invention provides novel 8-carbyl substituted Camps (adenosine 3′, 5′-cyclic monophosphorothioate) and a novel procedures for the preparation of 8-Br-cAMP, a key starting material.
• [EN] PROCESS FOR THE PREPARATION OF AN (RP)-8-SUBSTITUTED CAMPS<br/>[FR] PROCÉDÉ DE PRÉPARATION D'UN cAMPS (Rp)-8-SUBSTITUÉ
  申请人：LAURAS AS

  公开号：WO2008032103A2

  公开（公告）日：2008-03-20

  [EN] This invention relates to a process for the preparation of an (Rp)-8-substituted adenosine-3',5'-cyclic phosphorothioic acid, or a salt or ester thereof, which comprises P-amidating 8-bromoadenosine-3',5'-cyclic phosphoric acid, and reacting the P-amidate with a base and with carbon disulphide to yield (Rp)-8-bromoadenosine-3',5'-cyclic phosphorothioic acid or a salt or ester thereof.
  [FR] L'invention porte sur un procédé de préparation d'un acide phosphorothioique (Rp)-8-substitué adénosine-3',5'-cyclique, ou d'un sel ou un ester de ce dernier, procédé selon lequel on effectue la P-amidation d'un acide phosphorique 8-bromoadénosine-3',5'-cyclique, et on fait réagir le P-amidate avec une base et avec du disulfure de carbone afin d'obtenir un acide phosphorothioique (Rp)-8-bromoadénosine-3',5'-cyclique, ou un sel ou un ester de ce dernier.