cyclohexylammonium S,S-diphenyl phosphorodithioate | 67941-87-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: cyclohexylammonium S,S-diphenyl phosphorodithioate
• 英文别名: Bis(phenylsulfanyl)phosphinic acid;cyclohexanamine
• CAS: 67941-87-1
• 化学式: C₆H₁₃N*C₁₂H₁₁O₂PS₂
• 分子量: 381.5
• InChiKey: VUBVCQVRZXEWLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  cyclohexylammonium S,S-diphenyl phosphorodithioate 在 吡啶 、 2,4-二磺酰氯基均三甲苯 、 次磷酸 作用下， 反应 0.34h， 生成 [(2R,3S,5R)-5-(4-benzamido-2-oxopyrimidin-1-yl)-2-[[[3-(imidazol-1-ylmethyl)phenyl]-bis(4-methoxyphenyl)methoxy]methyl]oxolan-3-yl]oxy-phenylsulfanylphosphinic acid;N,N-diethylethanamine
  参考文献：
  名称：

  3-(Imidazol-1-ylmethyl)-4',4"-dimethoxytrityl: a new functionalized 5'-hydroxyl protecting group capable of rapid internucleotidic bond formation in the phosphorothio ester approach

  摘要：

  DOI：

  10.1021/jo00381a047
• 作为产物：
  描述：

  trimethylsilyl dichlorophosphate 、 苯硫酚锂 以44%的产率得到
  参考文献：
  名称：

  KAZUO YAMAGUCHI; SHINKICHI HONDA; TSUJIAKI HATA, CHEM. LETT., 1979, NO 9, 1057-1058

  摘要：

  DOI：

文献信息

• Trifluoromethylated cyclic-ADP-ribose mimic: synthesis of 8-trifluoromethyl-N1-[(5′′-O-phosphorylethoxy)methyl]-5′-O-phosphorylinosine-5′,5′′-cyclic pyrophosphate (8-CF3-cIDPRE) and its calcium release activity in T cells
  作者：Min Dong、Tanja Kirchberger、Xiangchen Huang、Zhen Jun Yang、Liang Ren Zhang、Andreas H. Guse、Li He Zhang

  DOI：10.1039/c0ob00090f

  日期：——

  A convenient trifluoromethylation method was firstly applied to the synthesis of 8- CF3-purine nucleosides. On the basis of this method, new protection and deprotection strategies were developed for the successful synthesis of the trifluoromethylated cyclic-ADP-ribose mimic, 8-CF3-cIDPRE 1. Using intact, fura-2-loaded Jurkat T cells compound 1 and 2′,3′-O-isopropylidene 8-CF3-cIDPRE 14 were characterized as membrane-permeant cADPR agonists. Contrary to the 8-substituted cADPR analogues that mainly act as antagonists of cADPR in cells, 8-substituted cIDPRE derivatives were shown to be Ca2+ mobilizing agonists. Here we report that even compound 1, the 8-substituted cIDPRE with the strong electron withdrawing CF3 group, behaves as an agonist in T cells. Interestingly, also the partially protected 2′,3′-O-isopropylidene 8-CF3-cIDPRE activated Ca2+ signaling indicating only a minor role for the hydroxyl groups of the southern ribose of cADPR for its biological activity. To our knowledge 8-CF3-cIDPRE 1 is the first reported fluoro substituted cADPR mimic and 8-CF3-cIDPRE 1 and compound 14 are promising molecular probes for elucidating the mode of action of cADPR.

  首先应用了一种便捷的三氟甲基化方法合成8-三氟甲基嘌呤核苷。在此基础上,研发了新颖的保护和去保护策略,顺利合成了三氟甲基化环状ADP核糖模拟物,即8-CF\(}_3}\)-cIDPRE 1。利用完整、装载了fura-2的Jurkat T细胞,化合物1和2′,3′-O-异亚丙基-8-CF\(}_3}\)-cIDPRE 14被鉴定为膜渗透性cADPR激动剂。与主要作为细胞内cADPR拮抗剂的8-取代cADPR类似物相反,8-取代cIDPRE衍生物显示为钙动员激动剂。本文报道,即使化合物1,即含有强吸电子CF\(}_3}\)基团的8-取代cIDPRE,在T细胞中亦表现激动剂性质。有趣的是,部分保护的2′,3′-O-异亚丙基-8-CF\(}_3}\)-cIDPRE也激活了钙信号,表明cADPR南侧核糖上的羟基对其生物活性仅有微小作用。据我们所知,8-CF\(}_3}\)-cIDPRE 1是首个报道的含氟cADPR模拟物,而8-CF\(}_3}\)-cIDPRE 1及化合物14则是阐明cADPR作用机制的有前景的分子探针。
• NEW TYPE OF PREFABRICATED FULLY PROTECTED RIBONUCLEOTIDE MONOMER UNITS AS USEFUL SYNTHETIC INTERMEDIATES IN RAPID OLIGORIBONUCLEOTIDE SYNTHESIS
  作者：Sinkichi Honda、Kazunori Terada、Yoshinobu Sato、Mitsuo Sekine、Tsujiaki Hata

  DOI：10.1246/cl.1982.15

  日期：1982.1.5

  Oligoribonucleotide synthesis has been done by employing newly constructed fully protected ribonucleotide units, S,S-diphenyl 5′-O-dimethoxytrityl-2′-O-tetrahydropyranyl-N-monomethoxytritylnucleoside 3′-phosphorodithioates 7. The units were found to be useful synthetic intermediates for rapid oligoribonucleotide synthesis.

  寡核糖核苷酸合成是通过使用新构建的完全受保护的核糖核苷酸单元 S,S-二苯基 5'-O-二甲氧基三苯甲基-2'-O-四氢吡喃基-N-单甲氧基三苯甲基核苷 3'-二硫代磷酸酯 7 完成的。发现这些单元是有用的合成用于快速寡核糖核苷酸合成的中间体。
• Synthesis of a novel N-1 carbocyclic, N-9 butyl analogue of cyclic ADP ribose (cADPR)
  作者：Aldo Galeone、Luciano Mayol、Giorgia Oliviero、Gennaro Piccialli、Michela Varra

  DOI：10.1016/s0040-4020(01)01162-0

  日期：2002.1

  A new analogue 1 of cADPR was prepared through a synthetic pathway starting from 6-chloropurine 2 which underwent two sequential alkylations at N-9 and N-1, with formation of the intermediate 8. The successive bis-phosphorylation of hydroxyalkyl functions, followed by deprotection and reprotection steps, afforded the derivative 13, the substrate for the cyclization reaction. This was carried out according

  通过从6-氯嘌呤2开始的合成途径制备了cADPR的新类似物1，后者在N-9和N-1经历了两个连续的烷基化，形成了中间体8。羟基烷基官能团的连续双磷酸化，然后进行脱保护和再保护步骤，得到衍生物13，其为环化反应的底物。这是根据松田程序进行的，并导致分子内焦磷酸盐键的形成，从而得到14。在碱性条件下最终的14脱保护，以高收率得到目标化合物1。
• Synthesis of a New N1-Pentyl Analogue of Cyclic Inosine Diphosphate Ribose (cIDPR) as a Stable Potential Mimic of Cyclic ADP Ribose (cADPR)
  作者：Aldo Galeone、Luciano Mayol、Giorgia Oliviero、Gennaro Piccialli、Michela Varra

  DOI：10.1002/1099-0690(200212)2002:24<4234::aid-ejoc4234>3.0.co;2-8

  日期：2002.12

  7 of cADPR (1), a cyclic nucleotide bis(phosphate) involved in Ca2+ metabolism, was prepared starting from 2′,3′-isopropylideneinosine (8) which was alkylated at N-1, leading to the intermediate 11. Bis(phosphorylation) of 11 through two alternative procedures, followed by phosphate deprotection steps, afforded derivatives 15 and 16, the substrates for the intramolecular pyrophosphate bond formation

  cADPR (1) 的新类似物 7 是一种参与 Ca2+ 代谢的环核苷酸双（磷酸酯），从 2',3'-异亚丙基肌苷 (8) 开始制备，其在 N-1 处被烷基化，产生中间体 11。通过两个替代程序对 11 进行双（磷酸化），然后进行磷酸脱保护步骤，得到衍生物 15 和 16，它们是分子内焦磷酸键形成的底物。15 和 16 均以高产率转化为衍生物 17，最终脱保护得到目标化合物 7。 (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2002)
• Synthesis of Oligoribonucleotides by Use of 4,4′,4″-Tris(acyloxy)trityl Groups for Protection of the 6-Amino Group of Adenosine
  作者：Mitsuo Sekine、Reiko Iwase、Narihiro Masuda、Tsujiaki Hata

  DOI：10.1246/bcsj.61.1669

  日期：1988.5

  been examined as protecting groups of the amino group of adenosine in oligoribonucleotide synthesis. The former was used for a 3′-terminal adenosine unit and the latter was introduced into an building block of internal adenosine. These protecting groups were successfully applied to the liquid-phase synthesis of pGUA and pGUAUUA which were the 5′-terminal oligoribonucleotide fragments of brome mosaic

  两种取代的三苯甲基，即 4,4',4"-tris(benzoyloxy)trityl (TBTr) 和 4,4',4"-tris(p-anisoyloxy)trityl (TAnTr)，已被用作保护基团寡核糖核苷酸合成中腺苷的氨基。前者用于 3'-末端腺苷单元，后者被引入内部腺苷的构建块中。这些保护基团成功地应用于 pGUA 和 pGUAUUA 的液相合成，它们是雀麦花叶病毒 mRNA 4 的 5'-末端寡核糖核苷酸片段。