皮质醇酸 | 160219-85-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 中文名称: 皮质醇酸
• 英文名称: 4'-(2,4-dihydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoic acid
• 英文别名: 2,4-dihydroxy-6-pentadecylbenzoic acid；aquastatin B；corticiolic acid；4-(2,4-Dihydroxy-6-pentadecylbenzoyloxy)-2-hydroxy-6-methylbenzoic acid；4-(2,4-dihydroxy-6-pentadecylbenzoyl)oxy-2-hydroxy-6-methylbenzoic acid
• CAS: 160219-85-2
• 化学式: C₃₀H₄₂O₇
• 分子量: 514.659
• InChiKey: QSTORXOHOONJBS-UHFFFAOYSA-N

物化性质

• 沸点：
  669.1±55.0 °C(Predicted)
• 密度：
  1.158±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  37
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  124
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  皮质醇酸 在 4 A molecular sieve 、 三氟化硼乙醚 、 potassium hydrogencarbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 生成 benzyl 4'-(4-O-(2'',3''-di-O-acetyl-4'',6''-O-benzylidene-β-D-glucopyranosyl)-2-hydroxy-6-pentadecanylbenzoyloxy)-2'-hydroxy-6'-methylbenzoate
  参考文献：
  名称：

  Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities

  摘要：

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

  DOI：

  10.1021/jo051384k
• 作为产物：
  描述：

  2,4-二羟基-6-甲基苯甲酸 在 palladium on activated charcoal 氢气 、 potassium hydrogencarbonate 、 三氟乙酸酐 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 98.0h， 生成 皮质醇酸
  参考文献：
  名称：

  Total Synthesis of CRM646-A and -B, Two Fungal Glucuronides with Potent Heparinase Inhibition Activities

  摘要：

  CRM646-A (1) and -B (2), two fungal glucuronides with a dimeric 2,4-dihydroxy-6-alkylbenzoic acid (orcinolp-depside) aglycone showing significant heparinase and telomerase inhibition activities, were synthesized for the first time. The successful approach involved construction of the phenol glucuronidic linkage, via coupling of the orsellinate derivative 27 with glucuronate bromide 7, before assembly of the phenolic ester linkage in the depside aglycone. Attempts via direct glycosylation of the depside aglycone derivatives were not successful.

  DOI：

  10.1021/jo051384k

文献信息

• Isolation of the protein tyrosine phosphatase 1B inhibitory metabolite from the marine-derived fungus Cosmospora sp. SF-5060
  作者：Changon Seo、Jae Hak Sohn、Hyuncheol Oh、Bo Yeon Kim、Jong Seog Ahn

  DOI：10.1016/j.bmcl.2009.09.025

  日期：2009.11

  In the course of bioassay-guided study on the EtOAc extract of a culture broth of the marine-derived fungus Cosmospora sp. SF-5060, aquastatin A (1) was isolated as a protein tyrosine phosphatase 1B (PTP1B) inhibitory component produced by the fungus. The compound was isolated by various chromatographic methods, and the structure was determined mainly by analysis of NMR spectroscopic data. Compound 1 exhibited potent inhibitory activity against PTP1B with IC50 value of 0.19 mu M, and the kinetic analyses of PTP1B inhibition by compound 1 suggested that the compound is inhibiting PTP1B activity in a competitive manner. Aquastatin A (1) also showed modest but selective inhibitory activity toward PTP1B over other protein tyrosine phosphatases, such as TCPTP, SHP-2, LAR, and CD45. In addition, the result of hydrolyzing aquastatin A (1) suggested that the dihydroxypentadecyl benzoic acid moiety in the molecule is responsible for the inhibitory activity. (C) 2009 Elsevier Ltd. All rights reserved.