甲基(4E)-6-(4,6-二羟基-7-甲基-3-氧代-1,3-二氢-2-苯并呋喃-5-基)-4-甲基-4-己烯酸酯 | 33431-38-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 甲基(4E)-6-(4,6-二羟基-7-甲基-3-氧代-1,3-二氢-2-苯并呋喃-5-基)-4-甲基-4-己烯酸酯
• 中文别名: O-去甲基麦考酚酸甲酯；吗替麦考酚酯杂质
• 英文名称: methyl ester of (E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methyl-4-hexenoic acid
• 英文别名: O-Desmethyl Mycophenolic Acid Methyl Ester；methyl (E)-6-(4,6-dihydroxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)-4-methylhex-4-enoate
• CAS: 33431-38-8
• 化学式: C₁₇H₂₀O₆
• 分子量: 320.342
• InChiKey: ONBUUVPMBJOPQE-RUDMXATFSA-N

物化性质

• 沸点：
  544.1±50.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

制备方法与用途

生物活性方面，O-脱甲基麦考酚酸甲酯是合成麦考酚酸的一个中间体。

反应信息

• 作为反应物：
  描述：

  甲基(4E)-6-(4,6-二羟基-7-甲基-3-氧代-1,3-二氢-2-苯并呋喃-5-基)-4-甲基-4-己烯酸酯 在 吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 [7-(2-methoxyethoxymethoxy)-6-[(E)-6-methoxy-3-methyl-6-oxohex-2-enyl]-4-methyl-1-oxo-3H-2-benzofuran-5-yl] pyridine-3-carboxylate
  参考文献：
  名称：

  Mycophenolic acid as a latent agonist of PPARγ

  摘要：

  Mycophenolic acid (MPA), known as an inhibitor of inosine monophosphate dehydrogenase (IMPDH), was found to inhibit the differentiation of 3T3-L1 pre-adipocytes into mature adipocytes. Although the effect of MPA was attributed to inhibition of IMPDH, we uncovered a hidden biological property of MPA as an agonist of peroxisome proliferator activated receptor gamma (PPAR gamma). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.059
• 作为产物：
  描述：

  霉酚酸 在 吡啶 、 2,3,5-三甲基吡啶 、 对甲苯磺酸 、 lithium iodide 作用下， 反应 27.0h， 生成 甲基(4E)-6-(4,6-二羟基-7-甲基-3-氧代-1,3-二氢-2-苯并呋喃-5-基)-4-甲基-4-己烯酸酯
  参考文献：
  名称：

  Mycophenolic acid as a latent agonist of PPARγ

  摘要：

  Mycophenolic acid (MPA), known as an inhibitor of inosine monophosphate dehydrogenase (IMPDH), was found to inhibit the differentiation of 3T3-L1 pre-adipocytes into mature adipocytes. Although the effect of MPA was attributed to inhibition of IMPDH, we uncovered a hidden biological property of MPA as an agonist of peroxisome proliferator activated receptor gamma (PPAR gamma). (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.06.059

文献信息

• Structure−Activity Relationships for Inhibition of Inosine Monophosphate Dehydrogenase by Nuclear Variants of Mycophenolic Acid
  作者：Peter H. Nelson、Stephen F. Carr、Bruce H. Devens、Elsie M. Eugui、Fidencio Franco、Carlos Gonzalez、Ronald C. Hawley、David G. Loughhead、David J. Milan、Eva Papp、John W. Patterson、Sussan Rouhafza、Eric B. Sjogren、David B. Smith、Rebecca A. Stephenson、Francisco X. Talamas、Ann-Marie Waltos、Robert J. Weikert、John C. Wu

  DOI：10.1021/jm9603633

  日期：1996.1.1

  Structure-activity relationships in the region of the phthalide ring of the inosine monophosphate dehydrogenase inhibitor mycophenolic acid have been explored. Replacement of the lactone ring with other cyclic moieties resulted in loss of potency, especially for larger groups. Replacement of the ring by acyclic substituents also indicated a strong sensitivity to steric bulk. A phenolic hydroxyl group, with an adjacent hydrogen bond acceptor, was found to be essential for high potency. The aromatic methyl group was essential for activity; the methoxyl group could be replaced by ethyl to give a compound with 2-4 times the potency of mycophenolic acid in vitro and in vivo.
• Mycophenolic acid as a latent agonist of PPARγ
  作者：Makoto Ubukata、Hitomi Takamori、Misaki Ohashi、Shinya Mitsuhashi、Kaoru Yamashita、Tomohisa Asada、Noriyuki Nakajima、Nobuyasu Matsuura、Mie Tsuruga、Keiko Taki、Junji Magae

  DOI：10.1016/j.bmcl.2007.06.059

  日期：2007.9

  Mycophenolic acid (MPA), known as an inhibitor of inosine monophosphate dehydrogenase (IMPDH), was found to inhibit the differentiation of 3T3-L1 pre-adipocytes into mature adipocytes. Although the effect of MPA was attributed to inhibition of IMPDH, we uncovered a hidden biological property of MPA as an agonist of peroxisome proliferator activated receptor gamma (PPAR gamma). (c) 2007 Elsevier Ltd. All rights reserved.