methyl 7-amino-3-phenylthieno[2,3-b]pyrazine-6-carboxylate | 208993-97-9

• 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: methyl 7-amino-3-phenylthieno[2,3-b]pyrazine-6-carboxylate
• 英文别名: methyl 3-amino-5-phenylthieno[2,3-b]pyrazine-2-carboxylate；Thieno[2,3-b]pyrazine-6-carboxylic acid, 7-amino-2-phenyl-, methylester；methyl 7-amino-2-phenylthieno[2,3-b]pyrazine-6-carboxylate
• CAS: 208993-97-9
• 化学式: C₁₄H₁₁N₃O₂S
• 分子量: 285.326
• InChiKey: PZACMQHJOUOYGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 7-amino-3-phenylthieno[2,3-b]pyrazine-6-carboxylate 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 7-[2-(6-Methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-3-phenyl-5H-9-thia-1,4,5,7-tetraaza-fluorene-6,8-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：

  (E)-2,3-diamino-3-phenylsulfanylprop-2-enenitrile;4-methylbenzenesulfonic acid 在 sodium perborate 、 溶剂黄146 、 氯乙酸 、 三氟乙酸 作用下， 以 异丙醇 为溶剂， 反应 40.0h， 生成 methyl 7-amino-3-phenylthieno[2,3-b]pyrazine-6-carboxylate
  参考文献：
  名称：

  A REGIOSELECTIVE SYNTHESIS OF METHYL 7-AMINO-3-PHENYLTHIENO-[2,3-b]PYRAZINE-6-CARBOXYLATE

  摘要：

  A practical synthesis of methyl 7-amino-3-phenylthieno[2,3-b]pyrazine-6-carboxylate (1) has been achieved via a regioselective synthesis of 3-cyano-5-phenyl-3-phenylthiopyrazine (5a), by condensing 1,1 -diethoxyacetophenone with 2,3-diamino-3-phenylthioacrylonitrile.

  DOI：

  10.1081/scc-100103262

文献信息

• 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.
• A REGIOSELECTIVE SYNTHESIS OF METHYL 7-AMINO-3-PHENYLTHIENO-[2,3-<i>b</i>]PYRAZINE-6-CARBOXYLATE
  作者：Weijiang Zhang、Anthony R. Haight、Kelley L. Ford、Shyamal I. Parekh

  DOI：10.1081/scc-100103262

  日期：2001.1

  A practical synthesis of methyl 7-amino-3-phenylthieno[2,3-b]pyrazine-6-carboxylate (1) has been achieved via a regioselective synthesis of 3-cyano-5-phenyl-3-phenylthiopyrazine (5a), by condensing 1,1 -diethoxyacetophenone with 2,3-diamino-3-phenylthioacrylonitrile.