N-[2-[2-[oxido-bis(phenylsulfanyl)phosphaniumyl]oxyethoxy]ethyl]prop-2-ynamide | 1021183-13-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[2-[2-[oxido-bis(phenylsulfanyl)phosphaniumyl]oxyethoxy]ethyl]prop-2-ynamide
• CAS: 1021183-13-0
• 化学式: C₁₉H₂₀NO₄PS₂
• 分子量: 421.478
• InChiKey: UDJOUNBOJXRTOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[2-[2-[oxido-bis(phenylsulfanyl)phosphaniumyl]oxyethoxy]ethyl]prop-2-ynamide 在 吡啶 、 copper(l) iodide 、 碘 、 三乙基碳酸氢铵缓冲液 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 反应 32.25h， 生成
  参考文献：
  名称：

  Synthesis and Calcium Mobilization Activity of cADPR Analogues Which Integrate Nucleobase, Northern and Southern Ribose Modifications

  摘要：

  我们合成了新型的 cADPR 模拟物，它整合了核碱基、北核糖和南核糖修饰。合成的关键步骤是 Cu（I）催化的 Hüisgen [3+2] 环加成和微波辅助的分子内焦磷酸化。初步的生物学研究表明，这些 cADPR 模拟物是钙信号通路的膜渗透激动剂。在南部核糖的 2'- 位上引入氯或氟会导致活性降低。南方核糖 3'-OH 上疏水基团的存在并不会明显改变其激动活性。

  DOI：

  10.3390/molecules17044343
• 作为产物：
  描述：

  、 丙炔酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-[2-[2-[oxido-bis(phenylsulfanyl)phosphaniumyl]oxyethoxy]ethyl]prop-2-ynamide
  参考文献：
  名称：

  通过点击化学制备核碱基简化的cADPR模拟物的简捷方法

  摘要：

  通过点击化学的应用合成了新的核碱基修饰的cADPR模拟物。Cu（I）-Huisgen环加成反应（点击反应）用于构建4-amide-1,2,3-三唑核碱基并有效连接两个构件。简洁的保护策略用于合成相应的环焦磷酸盐，目标化合物6a和6b在四个步骤中制备。

  DOI：

  10.1016/j.tetlet.2008.05.076

文献信息

• A Convenient Preparation of 5-Iodo-1,4-disubstituted-1,2,3-triazole: Multicomponent One-Pot Reaction of Azide and Alkyne Mediated by CuI−NBS
  作者：Lingjun Li、Guisheng Zhang、Anlian Zhu、Lihe Zhang

  DOI：10.1021/jo800035v

  日期：2008.5.1

  The system of CuI and NBS was found to provide both I+ and Cu+ for the first time. An efficient method for preparation of 5-iodo-1,4-disubstituted-1,2,3-triazole was achieved by multicomponent one-pot reaction of azides with alkynes in the presence of the novel CuI and NBS catalytic system. The high tolerance of various sensitive groups revealed the potential applications of this method in organic

  发现CuI和NBS系统首次提供I +和Cu +。在新型CuI和NBS催化体系的存在下，通过叠氮化物与炔烃的多组分一锅反应，实现了制备5-碘-1,4-二取代-1,2,3-三唑的有效方法。各种敏感性基团的高耐受性揭示了该方法在有机合成和药物发现中的潜在应用。
• A New Synthetic Protocol for One-Pot Preparations of 5-Halo-1,4-disubstituted-1,2,3-triazoles
  作者：Lingjun Li、Yanyan Li、Ran Li、Anlian Zhu、Guisheng Zhang

  DOI：10.1071/ch11067

  日期：——

  In this paper, a new synthetic protocol for one-pot preparations of 5-halo-1,4-disubstituted-1,2,3-triazoles is provided by rational combination of a CuI catalyzed azide–alkyne cycloaddition (CuAAC) reaction and an oxidative halogenation reaction. CuI- N-chlorosuccinimide (NCS) and CuBr-NCS reaction systems are developed, respectively, for effective preparations of 5-iodo-1,4-disubstituted-1,2,3-triazoles and 5-bromo-1,4-disubstituted-1,2,3-trizoles under mild conditions with a high tolerance of various sensitive groups.

  本文通过合理结合 CuI 催化的叠氮-炔环加成反应（CuAAC）和氧化卤化反应，提供了一种一锅制备 5-卤代-1,4-二取代-1,2,3-三唑的新合成方案。CuI- N-氯代丁二酰亚胺（NCS）和 CuBr-NCS 反应体系分别用于在温和条件下有效制备 5-碘-1,4-二取代-1,2,3-三唑和 5-溴-1,4-二取代-1,2,3-三唑，对各种敏感基团具有很高的耐受性。
• Novel nucleobase-simplified cyclic ADP-ribose analogue: A concise synthesis and Ca2+-mobilizing activity in T-lymphocytes
  作者：Lingjun Li、Cornelia C. Siebrands、Zhenjun Yang、Liangren Zhang、Andreas H. Guse、Lihe Zhang

  DOI：10.1039/b925295a

  日期：——

  purine nucleobase-simplified cyclic ADP ribose (cADPR) analogue 6b was synthesized, in which a 1,2,3-triazole-4-amide was constructed, instead of a purine moiety, and the northern ribose was replaced by an ether strand. Compound 6b exhibits calcium release activity in intact T-lymphocytes and indicates that it is a membrane-permeable cADPR mimic. Thus, the cADPR analogue containing 1,2,3-triazole-4-amide

  合成了嘌呤核碱基简化的环状ADP核糖（cADPR）类似物6b，其中构造了1,2,3-三唑-4-酰胺，而不是嘌呤部分，而北部核糖被醚链取代。化合物6b在完整的T淋巴细胞中表现出钙释放活性，表明它是膜可渗透的cADPR模拟物。因此，包含1,2,3-三唑-4-酰胺的cADPR类似物为进一步设计cADPR类似物并阐明其结构-活性关系提供了新颖的模板。
• A concise route for the preparation of nucleobase-simplified cADPR mimics by click chemistry
  作者：Lingjun Li、Baichuan Lin、Zhenjun Yang、Liangren Zhang、Lihe Zhang

  DOI：10.1016/j.tetlet.2008.05.076

  日期：2008.7

  Novel nucleobase-modified cADPR mimics were synthesized by the application of click chemistry. Cu(I)-Huisgen cycloaddition (click reaction) was used to construct 4-amide-1,2,3-triazole nucleobase and connect two building blocks efficiently. A concise protection strategy was used for the synthesis of the corresponding cyclo-pyrophosphate, and the target compounds 6a and 6b were prepared within four

  通过点击化学的应用合成了新的核碱基修饰的cADPR模拟物。Cu（I）-Huisgen环加成反应（点击反应）用于构建4-amide-1,2,3-三唑核碱基并有效连接两个构件。简洁的保护策略用于合成相应的环焦磷酸盐，目标化合物6a和6b在四个步骤中制备。
• Synthesis and Calcium Mobilization Activity of cADPR Analogues Which Integrate Nucleobase, Northern and Southern Ribose Modifications
  作者：Yue Zhou、Peilin Yu、Hongwei Jin、Zhenjun Yang、Jianbo Yue、Liangren Zhang、Lihe Zhang

  DOI：10.3390/molecules17044343

  日期：——

  Novel cADPR mimics, which integrate nucleobase, northern and southern ribose modifications were synthesized. The key steps of the synthesis were a Cu(I)-catalyzed Hüisgen [3+2] cycloaddition and a microwave-assisted intramolecular pyrophosphorylation. Preliminary biological investigations showed that these cADPR mimics are membrane-permeating agonists of the calcium signaling pathway. The introduction of chlorine or fluorine at the 2'-position of the southern riboses led to a decrease of activity. The existence of a hydrophobic group on the 3'-OH of the southern riboses does not obviously alter the agonistic activity.

  我们合成了新型的 cADPR 模拟物，它整合了核碱基、北核糖和南核糖修饰。合成的关键步骤是 Cu（I）催化的 Hüisgen [3+2] 环加成和微波辅助的分子内焦磷酸化。初步的生物学研究表明，这些 cADPR 模拟物是钙信号通路的膜渗透激动剂。在南部核糖的 2'- 位上引入氯或氟会导致活性降低。南方核糖 3'-OH 上疏水基团的存在并不会明显改变其激动活性。