methyl 1,2-dihydroxy-8-methoxy-6,6-dimethyl-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate | 1070298-33-7

• 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: methyl 1,2-dihydroxy-8-methoxy-6,6-dimethyl-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate
• CAS: 1070298-33-7
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: FGASAXTZBODMMB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.56
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 1,2-dihydroxy-8-methoxy-6,6-dimethyl-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.5h， 以95%的产率得到1,2-dihydroxy-8-methoxy-6,6-dimethyl-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylic acid
  参考文献：
  名称：

  Illudalic acid as a potential LAR inhibitor: Synthesis, SAR, and preliminary studies on the mechanism of action

  摘要：

  A novel synthesis of the human leukocyte common antigen-related (LAR) phosphatase inhibitor, illudalic acid, has been achieved by a route more amenable to structure modi. cations. A series of simpler analogues of illudalic acid was synthesized and evaluated for potency in inhibiting LAR. The structure -activity relationship (SAR) study has shown that the 5-formyl group and the hemi-acetal lactone are crucial for effective inhibition of LAR activity, and are the key pharmacophores of illudalic acid. The fused dimethylcyclopentene ring moiety evidently helps to enhance the potency of illudalic acid against LAR. A preliminary study of the mechanism of action of illudalic acid against LAR was conducted using electrospray ionization mass spectrometry (ESI-MS) and molecular docking techniques. The results are in full agreement with the described mechanism. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.06.014
• 作为产物：
  描述：

  methyl 8-methoxy-2,2-dimethyl-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate 在 chromium(VI) oxide 、 溶剂黄146 、 sodium tetrahydroborate 作用下， 以98%的产率得到methyl 1,2-dihydroxy-8-methoxy-6,6-dimethyl-1,2,3,5,6,7-hexahydro-s-indacene-4-carboxylate
  参考文献：
  名称：

  [EN] SELECTIVE PHOSPHATASE INHIBITORS BASED ON ILLUDALIC ACID
  [FR] INHIBITEURS SÉLECTIFS DE PHOSPHATASE À BASE DE L'ACIDE ILLUDALIQUE

  摘要：

  本公开提供基于伊卢达酸的新型选择性磷酸酶抑制剂化合物。本公开提供了一种简化的合成伊卢达酸的方法和一种合成磷酸酶抑制剂化合物的方法。本发明的方法提供了β-酮酰胺和酯的汇合苯环化，随后进行一锅法还原/水解序列。本发明提供的简洁合成方法使得能够快速组装本发明的伊卢达酸化合物，这些化合物是有效的蛋白酪氨酸磷酸酶受体D型（PTPRD）抑制剂。

  公开号：

  WO2022026717A1