((4-甲酰基-5-羟基-6-甲基-3-吡啶基)甲基)-膦酸 | 26210-18-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: ((4-甲酰基-5-羟基-6-甲基-3-吡啶基)甲基)-膦酸
• 英文名称: (4-formyl-3-hydroxy-2-methyl-5-pyridyl)methylphosphonic acid
• 英文别名: (4-Formyl-5-hydroxy-6-methylpyridin-1-ium-3-yl)methyl-hydroxyphosphinate
• CAS: 26210-18-4
• 化学式: C₈H₁₀NO₅P
• 分子量: 231.145
• InChiKey: MJHZPNZKADTPDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4-氨基苯基)磷酸 、 ((4-甲酰基-5-羟基-6-甲基-3-吡啶基)甲基)-膦酸 在 盐酸 、 sodium carbonate 、 sodium nitrite 、 sodium hydroxide 作用下， 反应 0.17h， 生成
  参考文献：
  名称：

  Structure−Activity Relationships of Pyridoxal Phosphate Derivatives as Potent and Selective Antagonists of P2X₁ Receptors

  摘要：

  Novel analogues of the P2 receptor antagonist pyridoxal-5'-phosphate 6-azophcnyl-2',5'-disulfonate (2) were synthesized and studied as antagonists in functional assays at recombinant rat P2X(1), P2X(2), and P2X(3) receptors expressed in Xenopus oocytes lion flux stimulation) and at turkey erythrocyte P2Y(1) receptors (phospholipase C activation). Selected compounds were also evaluated as antagonists of ion flux and the opening of a large pore at the recombinant human P2X(7) receptor. Modifications were made in the 4-aldehyde and 5'-phosphate groups of the pyridoxal moiety: i.e. a CH2OH group at the 4-position in pyridoxine was either condensed as a cyclic phosphate or phosphorylated separately to form a bisphosphate, which reduced potency at P2 receptors. 5-Methylphosphonate substitution, anticipated to increase stability to hydrolysis, preserved P2 receptor potency. At the g-position, halo, carboxylate, sulfonate, and phosphonate variations made on the phenylazo ring modulated potency at P2 receptors. The p-carboxyphenylazo analogue, 4, of phosphate 2 displayed an IC50 value of 9 nM at recombinant P2X(1) receptors and was 1300-, 16-, and >10000-fold selective for P2X(1) versus P2X(2), P2X(3), and P2Y(1) subtypes, respectively. The corresponding Ei-methylphosphonate was equipotent at P2X(1) receptors. The 5-methylphosphonate analogue containing a 6-[3,5-bis(methylphosphonate)]phenylazo moiety, 9, had IC50 values of 11 and 25 nM at recombinant P2X(1) and P2X(3) receptors, respectively. The analogue containing a phenylazo 4-phosphonate group, 11, was also very potent at both P2X(1) and P2X(3) receptors. However, the corresponding 2,5-disulfonate analogue, 10, was 28-fold selective for P2X(1) versus P2X(3) receptors. None of the analogues were more potent at P2X(7) and P2Y(1) receptors than 2, which acted in the micromolar range at these two subtypes.

  DOI：

  10.1021/jm9904203
• 作为产物：
  描述：

  diethyl α4,3-O-isopropylidene-α5-pyridoxylphosphonate 在 盐酸 、 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 反应 17.25h， 生成 ((4-甲酰基-5-羟基-6-甲基-3-吡啶基)甲基)-膦酸
  参考文献：
  名称：

  具有缩短的侧链的吡side醛磷酸盐的膦酸酯类似物。

  摘要：

  已经制备了含有5'-膦酰基甲基的吡ido醛5'-磷酸的膦酸酯类似物及其单乙酯和二乙酯。除二乙酯外，这些化合物似乎结合到天冬氨酸转氨酶的活性位点中。但是，它们缺乏该酶和大肠杆菌的谷氨酸脱羧酶的可检测催化活性。分光光度法观察结果表明，与天冬氨酸转氨酶结合的膦酰基甲基类似物确实会与底物缓慢反应。单甲酯的反应速度降低了约20倍。由于膦酸酯键的稳定性，这些化合物可用作各种蛋白质的修饰剂。

  DOI：

  10.1021/jm00358a027

文献信息

• Dipyridoxyl phosphate nuclear magnetic resonance imagery contrast agents
  申请人：NYCOMED SALUTAR, INC.

  公开号：EP0290047A2

  公开（公告）日：1988-11-09

  N,N′-bis-(pyridoxal-5-phosphate)-alkylenediamine-­N,N′-diacetic acids, N,N′-bis-(pyridoxal-5-phosphate)-­1,2-cycloalkylenediamine N,N′-diacetic acids, and N,N′-bis-(pyridoxal-5-phosphate)-1,2-arylenediamine-­N,N′-diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective NMRI contrast agents. Preferred contrast agents are paramagnetic ion chelates of N,N′-bis-(pyridoxal-5-phosphate)ethylene diamine-N,N′-diacetic acid, N,N′-bis-(pyridoxal-­5-phosphate)trans-1,2-cyclohexylenediamine-N,N′-diacetic acid, N,N′-bis-(pyridoxal-5-phosphate)trans-1,2-arylened­iamine-N,N′-diacetic acid, and the soluble calcium salts thereof. Novel intermediates for forming these compounds are N,N′-bis(pyridoxal-5-phosphate)alkylenediimines, N,N′-bis(pyridoxal-5-phosphate)alkylenediamines, N,N′-bis(pyridoxal-5-phosphate)-1,2-cycloalkylenedi­imines, N,N′-bis(pyridoxal-5-phosphate)-1,2-cycloalky­lenediamines, N,N′-bis(pyridoxal-5-phosphate)-1,2-ary­lenediamines, and the corresponding monophosphate compounds.

  N,N′-双-(5-磷酸吡哆醛)-烷基二胺-N,N′-二乙酸、N,N′-双-(5-磷酸吡哆醛)-1,2-环烷基二胺-N,N′-二乙酸、N,N′-双-(5-磷酸吡哆醛)-1,2-芳基二胺-N、N′-二乙酸、相应的单磷酸化合物和单乙酸化合物及其盐和酯与顺磁性金属离子形成稳定、高溶解度的螯合物，是高效的 NMRI 造影剂。首选的造影剂是 N,N′-双（5-磷酸吡哆醛）乙二胺-N,N′-二乙酸、N,N′-双（5-磷酸吡哆醛）反式-1、2-环己二胺-N,N′-二乙酸、N,N′-双-(5-磷酸吡哆醛)反式-1,2-芳二胺-N,N′-二乙酸及其可溶性钙盐。 形成这些化合物的新型中间体有 N,N′-双（5-磷酸吡哆醛）烷二亚胺、N,N′-双（5-磷酸吡哆醛）烷二胺、N,N′-双（5-磷酸吡哆醛）-1、2-环烷基二亚胺、N,N′-双(5-磷酸吡哆醛)-1,2-环烷基二胺、N,N′-双(5-磷酸吡哆醛)-1,2-芳基二胺以及相应的单磷酸盐化合物。
• Radioactive metal chelates of dipyridoxyl phosphate
  申请人：NYCOMED SALUTAR, INC.

  公开号：EP0290041A2

  公开（公告）日：1988-11-09

  Radioactive metal ion chelates of N,N-bis-(pyridoxal-5-phosphate)-alkylenediamine-N,N'-diacetic acids, N ,N'-bis-(pyridoxal-5-phosphate)-1,2-cycloalkylenediamine-N,N'-diacetic acids, and N,N -bis-(pyridoxal-5-phosphate)-1,2-aryienediamine-N,N -diacetic acids, the corresponding monophosphate compounds and monoacetic acid compounds, and their salts and esters form stable, highly soluble chelates with paramagnetic metal ions, and are highly effective agents for radiopharmaceutical imaging. Preferred contrast agents are radioactive metal ion such as technetium-99m and indium-111 ion chelates of N,N'-bis-(pyridoxal-5-phosphate)ethylenediamine-N,N-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-cyclohexylenediamine-N,N'-diacetic acid, N,N'-bis-(pyridoxal-5-phosphate)trans-1,2-arylenediamine-N,N'-diacetic acid, and the soluble calcium salts thereof.

  N,N-双-(吡哆醛-5-磷酸)-烷基二胺-N,N'-二乙酸、N,N'-双-(吡哆醛-5-磷酸)-1,2-环烷基二胺-N,N'-二乙酸、N,N-双-(吡哆醛-5-磷酸)-1,2-芳二胺-N,N'-二乙酸的放射性金属离子螯合物、相应的单磷酸盐化合物和单乙酸化合物及其盐和酯与顺磁性金属离子形成稳定的高溶解性螯合物、N-二乙酸、相应的单磷酸化合物和单乙酸化合物及其盐和酯与顺磁性金属离子形成稳定、高溶解度的螯合物，是放射性药物成像的高效制剂。首选的造影剂是放射性金属离子，如 N,N'-双（吡哆醛-5-磷酸）乙二胺-N,N-二乙酸、N、N,N'-双-(5-磷酸吡哆醛)反式-1,2-环己二胺-N,N'-二乙酸、N,N'-双-(5-磷酸吡哆醛)反式-1,2-芳二胺-N,N'-二乙酸及其可溶性钙盐。
• US4992554A
  申请人：——

  公开号：US4992554A

  公开（公告）日：1991-02-12
• US4933456A
  申请人：——

  公开号：US4933456A

  公开（公告）日：1990-06-12
• US4992555A
  申请人：——

  公开号：US4992555A

  公开（公告）日：1991-02-12