4-(3,4-dimethoxyphenyl)-2,3-dimethyl-4-oxobutyric acid | 358369-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(3,4-dimethoxyphenyl)-2,3-dimethyl-4-oxobutyric acid
• 英文别名: 4-(3,4-Dimethoxy-phenyl)-2,3-dimethyl-4-oxo-buttersaeure；4-(3,4-Dimethoxyphenyl)-2,3-dimethyl-4-oxobutanoic acid；4-(3,4-dimethoxyphenyl)-2,3-dimethyl-4-oxobutanoic acid
• CAS: 358369-08-1
• 化学式: C₁₄H₁₈O₅
• 分子量: 266.294
• InChiKey: CPSIPHCFSMXGHW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(3,4-dimethoxyphenyl)-2,3-dimethyl-4-oxobutyric acid 在 盐酸 、 amalgamated zinc 作用下， 生成 6,7-dimethoxy-2,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one
  参考文献：
  名称：

  The role of human and mouse Y chromosome genes in male infertility

  摘要：

  It was suggested by Ronald Fisher in 1931 that genes involved in benefit to the male (including spermatogenesis genes) would accumulate on the Y chromosome. The analysis of mouse Y chromosome deletions and the discovery of microdeletions of the human Y chromosome associated with diverse defective spermatogenic phenotypes has revealed the presence of intervals containing one or more genes controlling male germ cell differentiation. These intervals have been mapped, cloned and examined in detail for functional genes. This review discusses the genes mapping to critical spermatogenesis intervals and the evidence indicating which are the most likely candidates underlying Y-linked male infertility. (C) 2000, Editrice Kurtis.

  DOI：

  10.1007/bf03343787
• 作为产物：
  描述：

  2,3-二甲基丁二酸 在 乙酸酐 、 magnesium 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 生成 4-(3,4-dimethoxyphenyl)-2,3-dimethyl-4-oxobutyric acid
  参考文献：
  名称：

  Novel Selective PDE4 Inhibitors. 1. Synthesis, Structure−Activity Relationships, and Molecular Modeling of 4-(3,4-Dimethoxyphenyl)-2H-phthalazin-1-ones and Analogues

  摘要：

  A number of 6-(3,4-dimethoxyphenyl)-4,5-dihydro-2H-pyridazin-3-ones and a novel series of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones were prepared and tested on the eGMP-inhibited phosphodiesterase (PDE3) and cAMP-specific phosphodiesterase (PDE4) enzymes. All tested compounds were found to specifically inhibit PDE4 except for pyridazinone 3b, which showed moderate PDE4 (pIC(50) = 6.5) as well as PDE3 (pIC(50) = 6.6) inhibitory activity. In both the pyridazinone and phthlazinone series it was found that N-substitution is beneficial for PDE4 inhibition, whereas in the pyridazinone series it also accounts for PDE4 selectivity. In the phthalazinone series, the cis-4a,5,6,7,8,8a-hexahydrophthalazinones and their corresponding 4a,5,8,8a-tetrahydro analogues showed potent PDE4 inhibitory potency (10/11c,d: pIC(50) = 7.6-8.4). A molecular modeling study revealed that the cis-fused cyclohexa(e)ne rings occupy a region in space different from that occupied by the other fused (un)saturated hydrocarbon rings applied; we therefore assume that the steric interactions of these rings with the binding site play an important role in enzyme inhibition.

  DOI：

  10.1021/jm010837k

文献信息

• 311. The constituents of guaiacum resin. Part II. Synthesis of dl-guaiaretic acid dimethyl ether
  作者：Robert D. Haworth、Cecil R. Mavin、George Sheldrick

  DOI：10.1039/jr9340001423

  日期：——
• Novel Selective PDE4 Inhibitors. 1. Synthesis, Structure−Activity Relationships, and Molecular Modeling of 4-(3,4-Dimethoxyphenyl)-2<i>H</i>-phthalazin-1-ones and Analogues
  作者：Margaretha Van der Mey、Armin Hatzelmann、Ivonne J. Van der Laan、Geert J. Sterk、Ulrich Thibaut、Hendrik Timmerman

  DOI：10.1021/jm010837k

  日期：2001.8.1

  A number of 6-(3,4-dimethoxyphenyl)-4,5-dihydro-2H-pyridazin-3-ones and a novel series of 4-(3,4-dimethoxyphenyl)-2H-phthalazin-1-ones were prepared and tested on the eGMP-inhibited phosphodiesterase (PDE3) and cAMP-specific phosphodiesterase (PDE4) enzymes. All tested compounds were found to specifically inhibit PDE4 except for pyridazinone 3b, which showed moderate PDE4 (pIC(50) = 6.5) as well as PDE3 (pIC(50) = 6.6) inhibitory activity. In both the pyridazinone and phthlazinone series it was found that N-substitution is beneficial for PDE4 inhibition, whereas in the pyridazinone series it also accounts for PDE4 selectivity. In the phthalazinone series, the cis-4a,5,6,7,8,8a-hexahydrophthalazinones and their corresponding 4a,5,8,8a-tetrahydro analogues showed potent PDE4 inhibitory potency (10/11c,d: pIC(50) = 7.6-8.4). A molecular modeling study revealed that the cis-fused cyclohexa(e)ne rings occupy a region in space different from that occupied by the other fused (un)saturated hydrocarbon rings applied; we therefore assume that the steric interactions of these rings with the binding site play an important role in enzyme inhibition.
• The role of human and mouse Y chromosome genes in male infertility
  作者：Nabeel A. Affara、M. J. Mitchell

  DOI：10.1007/bf03343787

  日期：2000.11

  It was suggested by Ronald Fisher in 1931 that genes involved in benefit to the male (including spermatogenesis genes) would accumulate on the Y chromosome. The analysis of mouse Y chromosome deletions and the discovery of microdeletions of the human Y chromosome associated with diverse defective spermatogenic phenotypes has revealed the presence of intervals containing one or more genes controlling male germ cell differentiation. These intervals have been mapped, cloned and examined in detail for functional genes. This review discusses the genes mapping to critical spermatogenesis intervals and the evidence indicating which are the most likely candidates underlying Y-linked male infertility. (C) 2000, Editrice Kurtis.