1-甲基-鸟苷环-3',5'-(氢磷酸酯) | 78033-41-7

• 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: 1-甲基-鸟苷环-3',5'-(氢磷酸酯)
• 英文名称: 1-methyl-cGMP
• 英文别名: N(1)-methyl-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-1-methylpurin-6-one
• CAS: 78033-41-7
• 化学式: C₁₁H₁₄N₅O₇P
• 分子量: 359.235
• InChiKey: FBEZEINIPFPIME-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  162
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  溴甲基乙酸酯 、 1-甲基-鸟苷环-3',5'-(氢磷酸酯) 在 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 以22%的产率得到[(4aR,6R,7R,7aS)-6-(2-amino-1-methyl-6-oxopurin-9-yl)-7-hydroxy-2-oxido-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-ium-2-yl]oxymethyl acetate
  参考文献：
  名称：

  Membrane-permeant, bioactivatable analogues of cGMP as inducers of cell death in IPC-81 leukemia cells

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(00)00050-0

文献信息

• NEW POLYMER LINKED MULTIMERS OF GUANOSINE-3', 5'-CYCLIC MONOPHOSPHATES
  申请人：MIRECA MEDICINES GMBH

  公开号：US20210317156A1

  公开（公告）日：2021-10-14

  Embodiments of the invention are directed to new polymer linked multimeric guanosine-3′, 5′-cyclic monophosphate (cGMP) analogues that modulate the cGMP-signaling system, preferably having activating properties, and more preferably being activators of cGMP dependent protein kinase (PKG), and related monomeric precursors thereof. The invention is also directed to related monomeric compounds, which may also show modulating activity and/or may serve as monomeric precursors of the multimers. The invention further relates to the use of such compounds as reagents for signal transduction research and as modulators of cyclic nucleotide-regulated binding proteins and isoenzymes thereof, and as ligands for affinity chromatography, for antibody production or for diagnostic applications e.g. on chip surfaces.