3-trimethylmethylcarbonyl-6-(benzyl)pyridoxal monomethyl acetal | 258531-72-5

• 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
• 英文名称: 3-trimethylmethylcarbonyl-6-(benzyl)pyridoxal monomethyl acetal
• 英文别名: 3-tert-butylcarbonyl-6-(benzyl)pyridoxal monomethylacetal；(4-Benzyl-1-methoxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl) 2,2-dimethylpropanoate；(4-benzyl-1-methoxy-6-methyl-1,3-dihydrofuro[3,4-c]pyridin-7-yl) 2,2-dimethylpropanoate
• CAS: 258531-72-5
• 化学式: C₂₁H₂₅NO₄
• 分子量: 355.434
• InChiKey: RIOWRSQKIIKIMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-trimethylmethylcarbonyl-6-(benzyl)pyridoxal monomethyl acetal 在 氢氧化钾 、 硫酸 作用下， 以 水 、 丙酮 为溶剂， 反应 48.17h， 生成 6-(benzyl)pyridoxal-4-dimethylacetal
  参考文献：
  名称：

  Synthesis of pyridoxal phosphate derivatives with antagonist activity at the P2Y13 receptor

  摘要：

  We have synthesized a series of derivatives of the known P2 receptor antagonist PPADS (pyridoxit-5'-phosphate-6-azo-phenyl-2.4-disulfonate) and examined their ability to inhibit functional activity of the recombinant human P2Ytt nucleotide receptor expressed in 1321N1 human astrocytoma cells co-expressing G alpha(16) protein (AG32). Analogues of PPADS modified through substitution of the phenylazo ring, including halo and nitro substitution, and 5'-alkyl phosphonate analogues were synthesized and tested. A 6-benzyl-5'-methyl phosphonate analogue was prepared to examine the effect of stable replacement of the azo linkage, The highest antagonistic poteney was observed for 6-(3-nitrophenylazo) derivatives of pyridoxal-5'-phosphate, The 2-chloro-5-nitro analogue (MRS 2211) and 4-chloro-3-nitro analogue (MRS 2603) inhibited ADP (100 nM)-induced inositol trisphosphate (IP3) formation with pIC(50) values of 5.97 and 6.18, respectively, being 45- and 74-fold more potent than PPADS. The antagonism of MRS 2211 was competitive with a pA(2) value of 6.3. MRS2211 and MRS2603 inhibited phospholipase C (PLC) responses to 30 nM 2-methylthio-ADP in human P2Y(1) receptor-mediated 1321N1 astrocytoma cells with IC50 values of > 10and 0.245 mu M, respectively. Both analogues were inactive(> 10 mu M) as antagonists of human P2Y(12) receptor-mediated PLC responses in 1321N1 astrocytoma cells, Thus. MRS2211 displayed > 20-fold selectivity as antagonist of the P2Y(13) receptor in comparison to P2Y(1) and P2Y12 receptors, while MRS2603 antagonized both P2Y(1) and P2Y(13), receptors. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bcp.2005.04.021
• 作为产物：
  描述：

  吡哆醛盐酸盐 在 碳酸氢钠 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.5h， 生成 3-trimethylmethylcarbonyl-6-(benzyl)pyridoxal monomethyl acetal
  参考文献：
  名称：

  Versatile Synthesis of 6-Alkyl and Aryl Substituted Pyridoxal Derivatives

  摘要：

  开发了一种通用且方便的方法，用于在吡哆醛的 6 位上使用碳取代基进行功能衍生化，使用受保护的 N-异丁氧基羰氧基吡哆醛氯化物上的格氏反应和与受保护的 6-乙烯基吡哆醛的 Heck 反应。

  DOI：

  10.1055/s-2000-6228