霉酚酸环丙烷类似物 | 125198-40-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 中文名称: 霉酚酸环丙烷类似物
• 中文别名: 霉酚酸环丙烷类似
• 英文名称: 1-Cyclopropane Mycophenolic Acid
• 英文别名: 3-[2-[(4-hydroxy-6-methoxy-7-methyl-3-oxo-1H-2-benzofuran-5-yl)methyl]-1-methylcyclopropyl]propanoic acid
• CAS: 125198-40-5
• 化学式: C₁₈H₂₂O₆
• 分子量: 334.369
• InChiKey: QVUZLDOXUBRWHS-UHFFFAOYSA-N

物化性质

• 熔点：
  130-135 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  611.8±55.0 °C(Predicted)
• 密度：
  1.316±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于氯仿（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  霉酚酸	mycophenolic acid	24280-93-1	C17H20O6	320.342

反应信息

• 作为产物：
  描述：

  二碘甲烷 、 霉酚酸 在 copper(l) chloride 、 锌 作用下， 生成 霉酚酸环丙烷类似物
  参考文献：
  名称：

  Synthesis and immunosuppressive activity of some side-chain variants of mycophenolic acid

  摘要：

  The syntheses and immunosuppressive bioassays of 12 side-chain variants of mycophenolic acid are described. The compounds were made either from mycophenolic acid itself or from 5-(chloromethyl)-1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisoben zofuran, a versatile intermediate for the synthesis of diverse side-chain variants. Replacement of the methylated E double bond of the natural product with a triple bond, a Z double bond, a saturated bond, or a sulfur atom, with overall chain lengths equal to or greater than that of mycophenolic acid, produced compounds devoid of significant activity. Replacement of the side-chain double bond with difluoro, dibromo, or unsubstituted cyclopropane rings also removed most activity. Replacement of the double bond with an allenic linkage yielded a compound with about one-fifth of the immunosuppressive activity of mycophenolic acid. Some possible causes for the unusual specificity of structure and activity are discussed.

  DOI：

  10.1021/jm00164a057

文献信息

• NELSON, PETER H.;EUGUI, ELSIE;WANG, CHING C.;ALLISON, ANTHONY C., J. MED. CHEM., 33,(1990) N, C. 833-838
  作者：NELSON, PETER H.、EUGUI, ELSIE、WANG, CHING C.、ALLISON, ANTHONY C.

  DOI：——

  日期：——
• COMPOUNDS AND COMPOSITIONS FOR EXTENDING LIFESPAN OF A SUBJECT
  申请人：YALE UNIVERSITY

  公开号：US20200108043A1

  公开（公告）日：2020-04-09

  The present invention relates in part to the unexpected discovery that certain compounds extend the lifespan of eukaryotic organisms. In certain embodiments, the invention comprises a method of extending the lifespan of a subject comprising administering to the subject a therapeutically effective amount of at least one compound selected from the group consisting of terreic acid and mycophenolic acid. The invention further relates to methods for screening potential compounds of interest for lifespan extending properties.
• [EN] COMPOUNDS AND COMPOSITIONS FOR EXTENDING LIFESPAN OF A SUBJECT<br/>[FR] COMPOSÉS ET COMPOSITIONS POUR PROLONGER LA DURÉE DE VIE D'UN SUJET
  申请人：UNIV YALE

  公开号：WO2018236747A1

  公开（公告）日：2018-12-27

  The present invention relates in part to the unexpected discovery that certain compounds extend the lifespan of eukaryotic organisms. In certain embodiments, the invention comprises a method of extending the lifespan of a subject comprising administering to the subject a therapeutically effective amount of at least one compound selected from the group consisting of terreic acid and mycophenolic acid. The invention also relates to methods for screening potential compounds of interest for lifespan extending properties.
• Synthesis and immunosuppressive activity of some side-chain variants of mycophenolic acid
  作者：Peter H. Nelson、Elsie Eugui、Ching C. Wang、Anthony C. Allison

  DOI：10.1021/jm00164a057

  日期：1990.2

  The syntheses and immunosuppressive bioassays of 12 side-chain variants of mycophenolic acid are described. The compounds were made either from mycophenolic acid itself or from 5-(chloromethyl)-1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxoisoben zofuran, a versatile intermediate for the synthesis of diverse side-chain variants. Replacement of the methylated E double bond of the natural product with a triple bond, a Z double bond, a saturated bond, or a sulfur atom, with overall chain lengths equal to or greater than that of mycophenolic acid, produced compounds devoid of significant activity. Replacement of the side-chain double bond with difluoro, dibromo, or unsubstituted cyclopropane rings also removed most activity. Replacement of the double bond with an allenic linkage yielded a compound with about one-fifth of the immunosuppressive activity of mycophenolic acid. Some possible causes for the unusual specificity of structure and activity are discussed.