8-(4-氯苯基硫代)鸟苷-3,5-环单磷酸三乙基胺盐 | 54364-02-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 中文名称: 8-(4-氯苯基硫代)鸟苷-3,5-环单磷酸三乙基胺盐
• 英文名称: 8-pCPT-cGMP
• 英文别名: 8-(4-chlorophenylthio)guanosine 3',5'-cyclic monophosphate；8-CPT-cGMP；8-(4-chlorophenylthio)-cGMP；9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-8-(4-chlorophenyl)sulfanyl-1H-purin-6-one
• CAS: 54364-02-2
• 化学式: C₁₆H₁₅ClN₅O₇PS
• 分子量: 487.817
• InChiKey: ZDJHIEHUVPCEDK-IDTAVKCVSA-N

物化性质

• 稳定性/保质期：

  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  196
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  8-(4-氯苯基硫代)鸟苷-3,5-环单磷酸三乙基胺盐 在 Oxone 作用下， 以 甲醇 为溶剂， 以29%的产率得到8-(4-chlorophenylsulfonyl)guanosine-3',5'-cyclic monophosphate
  参考文献：
  名称：

  [EN] NEW POLYMER LINKED MULTIMERS OF GUANOSINE-3', 5'-CYCLIC MONOPHOSPHATES
  [FR] NOUVEAUX MULTIMÈRES LIÉS AU POLYMÈRE MONOPHOSPHATE DE GUANOSINE-3', 5'-CYCLIQUES

  摘要：

  公开号：

  WO2018041942A9

文献信息

• Membrane-permeant, bioactivatable analogues of cGMP as inducers of cell death in IPC-81 leukemia cells
  作者：Frank Schwede、Odd T Brustugun、Michaela Zorn-Kruppa、Stein O Døskeland、Bernd Jastorff

  DOI：10.1016/s0960-894x(00)00050-0

  日期：2000.3

  We report an improved single-step synthesis to generate the membrane-permeant acetoxymethyl esters (AM-esters) of cGMP and three cGMP-analogues. These bioactivatable compounds were found to induce cell death in rat IPC-81 cells, a model system for acute myelocytic leukemia, in micromolar doses, while the corresponding non-modified cGMP-analogues were inactive. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Novel N7- and N1-Substituted cGMP Derivatives Are Potent Activators of Cyclic Nucleotide-Gated Channels
  作者：Timothy Strassmaier、Jeffrey W. Karpen

  DOI：10.1021/jm0702581

  日期：2007.8.1

  Cyclic nucleotide-gated (CNG) channels, key players in olfactory and visual signal transduction, generate electrical responses to odorant- and light-induced changes in cyclic nucleotide concentration. Previous work suggests that substitutions are tolerated solely at the C8 position on the purine ring of cGMP. Our studies with C8, 2'-OH, and 2-NH2-modified cGMP derivatives support this assertion. To gain further insight into determinants important for CNG channel binding and activation, we targeted previously unexplored positions. Modifications at N7 of 8-SH-cGMP (6) are well tolerated by olfactory and retinal rod CNG channels. Toleration of a very large substituent, a 3400 molecular weight PEG, at either N7 or C8 argues for broad accommodation at these positions in the binding site. Modification at N1 of cGMP reduces the apparent affinity for the channel; however, when combined with 8-parachlorophenylthio derivatization, the resulting cGMP analogue is more potent than cGMP itself. These studies establish the N7 and N1 positions of cGMP as targets for modification in the design of novel CNG channel agonists.
• US5625056A
  申请人：——

  公开号：US5625056A

  公开（公告）日：1997-04-29