5-methoxy-3,4-dihydro-naphthalene-1,2-dicarboxylic acid-anhydride | 859986-28-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 5-methoxy-3,4-dihydro-naphthalene-1,2-dicarboxylic acid-anhydride
• 英文别名: 5-Methoxy-3,4-dihydro-naphthalin-1,2-dicarbonsaeure-anhydrid；6-Methoxy-4,5-dihydrobenzo[e][2]benzofuran-1,3-dione
• CAS: 859986-28-0
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: MJNLYAQGUAESJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methoxy-3,4-dihydro-naphthalene-1,2-dicarboxylic acid-anhydride 在 10percent Pd/C 氢气 作用下， 以 乙酸乙酯 、 xylene 为溶剂， 反应 20.0h， 生成 (3aR,9bR)-6-methoxy-((S)-α-methylbenzyl)-2,3,3a,4,5,9b-[1H]-hexahydrobenz[e]isoindole-1,3-dione
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of Tricyclic Substituted Hexahydrobenz[e]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia (BPH)

  摘要：

  In search of a uroselective agent that exhibits a high level of selectivity for the alpha(1A) receptor, a novel series of tricyclic hexahydrobenz[e]isoindoles was synthesized. A generic pharmacophoric model was developed requiring the presence of a basic amine core and a fused heterocyclic side chain separated by an alkyl chain. It was shown that the 6-OMe substitution with R, R stereochemistry of the ring junction of the benz[e]isoindole and a two-carbon spacer chain were optimal. In contrast to the highly specific requirements for the benz[e]isoindole portion and linker chain, a wide variety of tricyclic fused heterocyclic attachments were tolerated with retention of potency and selectivity. In vitro functional assays for the alpha(1) adrenoceptor subtypes were used to further characterize these compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity.

  DOI：

  10.1021/jm990567u
• 作为产物：
  描述：

  ethyl (2-methoxyphenyl)-2-oxo-3-carboethoxypentanoate 在 硫酸 作用下， 反应 6.0h， 以51%的产率得到5-methoxy-3,4-dihydro-naphthalene-1,2-dicarboxylic acid-anhydride
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of Tricyclic Substituted Hexahydrobenz[e]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia (BPH)

  摘要：

  In search of a uroselective agent that exhibits a high level of selectivity for the alpha(1A) receptor, a novel series of tricyclic hexahydrobenz[e]isoindoles was synthesized. A generic pharmacophoric model was developed requiring the presence of a basic amine core and a fused heterocyclic side chain separated by an alkyl chain. It was shown that the 6-OMe substitution with R, R stereochemistry of the ring junction of the benz[e]isoindole and a two-carbon spacer chain were optimal. In contrast to the highly specific requirements for the benz[e]isoindole portion and linker chain, a wide variety of tricyclic fused heterocyclic attachments were tolerated with retention of potency and selectivity. In vitro functional assays for the alpha(1) adrenoceptor subtypes were used to further characterize these compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity.

  DOI：

  10.1021/jm990567u

文献信息

• The Synthesis of 5-Hydroxy-1,2-naphthalic Anhydride
  作者：William G. Dauben、Masato. Tanabe

  DOI：10.1021/ja01176a088

  日期：1949.8
• Structure−Activity Studies for a Novel Series of Tricyclic Substituted Hexahydrobenz[<i>e</i>]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia (BPH)
  作者：Michael D. Meyer、Robert J. Altenbach、Fatima Z. Basha、William A. Carroll、Stephen Condon、Steven W. Elmore、James F. Kerwin、Kevin B. Sippy、Karin Tietje、Michael D. Wendt、Arthur A. Hancock、Michael E. Brune、Steven A. Buckner、Irene Drizin

  DOI：10.1021/jm990567u

  日期：2000.4.1

  In search of a uroselective agent that exhibits a high level of selectivity for the alpha(1A) receptor, a novel series of tricyclic hexahydrobenz[e]isoindoles was synthesized. A generic pharmacophoric model was developed requiring the presence of a basic amine core and a fused heterocyclic side chain separated by an alkyl chain. It was shown that the 6-OMe substitution with R, R stereochemistry of the ring junction of the benz[e]isoindole and a two-carbon spacer chain were optimal. In contrast to the highly specific requirements for the benz[e]isoindole portion and linker chain, a wide variety of tricyclic fused heterocyclic attachments were tolerated with retention of potency and selectivity. In vitro functional assays for the alpha(1) adrenoceptor subtypes were used to further characterize these compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity.