6-chloromethyl-7-hydroxy-5-methoxy-4-methyl-3H-isobenzofuran-1-one | 24953-92-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 6-chloromethyl-7-hydroxy-5-methoxy-4-methyl-3H-isobenzofuran-1-one
• 英文别名: 6-Chlormethyl-7-hydroxy-5-methoxy-4-methyl-phthalid；6-(chloromethyl)-7-hydroxy-5-methoxy-4-methyl-3H-2-benzofuran-1-one
• CAS: 24953-92-2
• 化学式: C₁₁H₁₁ClO₄
• 分子量: 242.659
• InChiKey: CHDQGBWRZUVNKE-UHFFFAOYSA-N

物化性质

• 沸点：
  516.8±50.0 °C(Predicted)
• 密度：
  1.406±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-chloromethyl-7-hydroxy-5-methoxy-4-methyl-3H-isobenzofuran-1-one 在 palladium on activated charcoal 乙基溴化镁 、 氢气 、 copper(l) cyanide 作用下， 以 乙酸乙酯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 18.5h， 生成 7-(1,3-dihydro-4-hydroxy-6-methoxy-7-methyl-3-oxo-5-isobenzofuranyl)heptanoic acid
  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

• Enhancing the efficiency of RNA polymerase inhibitors by using inosine monophosphate dehydrogenase inhibitors
  申请人：Bantia Shanta

  公开号：US20050187170A1

  公开（公告）日：2005-08-25

  The present invention relates generally to pharmaceutical compositions useful to treat viral diseases. The present invention relates particularly RNA polymerase inhibitors and inosine monophosphate dehydrogenase (IMPDH) inhibitors such as mycophenolate compounds.

  本发明一般涉及用于治疗病毒性疾病的药物组合物。本发明尤其涉及 RNA 聚合酶抑制剂和单磷酸肌苷脱氢酶（IMPDH）抑制剂，如霉酚酸化合物。
• 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：——
• US6514979B1
  申请人：——

  公开号：US6514979B1

  公开（公告）日：2003-02-04
• [EN] SYNERGISTIC COMBINATIONS OF GUANOSINE ANALOG REVERSE TRANSCRIPTASE INHIBITORS AND INOSINE MONOPHOSPHATE DEHYDROGENESE INHIBITORS AND USES THEREFOR<br/>[FR] COMBINAISONS SYNERGIQUES D'INHIBITEURS DE GUANOSINE ANALOGUE TRANSCRIPTASE INVERSE ET D'INHIBITEURS D'INOSINE MONOPHOSPHATE DESHYDROGENASE, ET UTILISATIONS CORRESPONDANTES
  申请人：UNIV MARYLAND BIOTECH INST

  公开号：WO2000051615A1

  公开（公告）日：2000-09-08

  Synergistic combinations of guanosine nucleoside analog reverse transcriptase inhibitors such as abacavir with inosine monophosphate dehydrogenase inhibitors such as mycophenolates, pharmaceutical compositions comprising such combinations, and therapeutic methods comprising administering the synergistic combinations to subjects in need thereof, for treating a viral infection, such as an HIV-1 infection.