ethyl 3-isocyanato-2-thiophenecarboxylate | 179114-84-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: ethyl 3-isocyanato-2-thiophenecarboxylate
• 英文别名: Ethyl 3-isocyanatothiophene-2-carboxylate
• CAS: 179114-84-2
• 化学式: C₈H₇NO₃S
• 分子量: 197.214
• InChiKey: ACCDQMIERGSXJI-UHFFFAOYSA-N

物化性质

• 沸点：
  295.6±25.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  84
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-isocyanato-2-thiophenecarboxylate 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 5.0h， 生成 3-[2-(6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-2,4-dioxo-1,2,3,4-tetrahydro-thieno[3,2-d]pyrimidine-6-carboxylic acid methyl ester
  参考文献：
  名称：

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

  摘要：

  In search of a uroselective alpha (1A) subtype selective antagonist, a novel series of 6-OMe hexahydrobenz [e]isoindoles attached to a bicyclic heterocyclic moiety via a two-carbon linker was synthesized. It was found that in contrast to the previously described series of tricyclic heterocycles,l this bicyclic series has very specific requirements for the heterocyclic attachments. The most important structural features contributing to the alpha (1A)/alpha (1B) selectivity of these compounds were identified. In vitro functional assays for the al adrenoceptor subtypes were used to further characterize the most selective compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity. Compound 48 showed the highest degree of selectivity in the radioligand binding assays (56-fold), in the in vitro functional tests (80-fold), and for in vivo prostate selectivity (960-fold).

  DOI：

  10.1021/jm000541z
• 作为产物：
  描述：

  三光气 、 3-氨其噻吩-2-甲酸乙酯 以 甲苯 为溶剂， 生成 ethyl 3-isocyanato-2-thiophenecarboxylate
  参考文献：
  名称：

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

  摘要：

  In search of a uroselective alpha (1A) subtype selective antagonist, a novel series of 6-OMe hexahydrobenz [e]isoindoles attached to a bicyclic heterocyclic moiety via a two-carbon linker was synthesized. It was found that in contrast to the previously described series of tricyclic heterocycles,l this bicyclic series has very specific requirements for the heterocyclic attachments. The most important structural features contributing to the alpha (1A)/alpha (1B) selectivity of these compounds were identified. In vitro functional assays for the al adrenoceptor subtypes were used to further characterize the most selective compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity. Compound 48 showed the highest degree of selectivity in the radioligand binding assays (56-fold), in the in vitro functional tests (80-fold), and for in vivo prostate selectivity (960-fold).

  DOI：

  10.1021/jm000541z

文献信息

• Structure−Activity Studies for a Novel Series of Bicyclic Substituted Hexahydrobenz[<i>e</i>]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia
  作者：Michael D. Meyer、Robert J. Altenbach、Hao Bai、Fatima Z. Basha、William A. Carroll、James F. Kerwin、Suzanne A. Lebold、Edmund Lee、John K. Pratt、Kevin B. Sippy、Karin Tietje、Michael D. Wendt、Michael E. Brune、Steven A. Buckner、Arthur A. Hancock、Irene Drizin

  DOI：10.1021/jm000541z

  日期：2001.6.1

  In search of a uroselective alpha (1A) subtype selective antagonist, a novel series of 6-OMe hexahydrobenz [e]isoindoles attached to a bicyclic heterocyclic moiety via a two-carbon linker was synthesized. It was found that in contrast to the previously described series of tricyclic heterocycles,l this bicyclic series has very specific requirements for the heterocyclic attachments. The most important structural features contributing to the alpha (1A)/alpha (1B) selectivity of these compounds were identified. In vitro functional assays for the al adrenoceptor subtypes were used to further characterize the most selective compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity. Compound 48 showed the highest degree of selectivity in the radioligand binding assays (56-fold), in the in vitro functional tests (80-fold), and for in vivo prostate selectivity (960-fold).