Ethyl 2-chloro-7-isocyanatothieno[2,3-b]pyrazine-6-carboxylate | 403854-02-4

• 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 2-chloro-7-isocyanatothieno[2,3-b]pyrazine-6-carboxylate
• CAS: 403854-02-4
• 化学式: C₁₀H₆ClN₃O₃S
• 分子量: 283.695
• InChiKey: DLTRVWGYYWUEOT-UHFFFAOYSA-N

物化性质

• 沸点：
  413.1±45.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3aR,9bR)-2-氨基乙基-6-甲氧基-2,3,3a,4,5,9b-[1H]-六氢苯并[e]异吲哚 、 Ethyl 2-chloro-7-isocyanatothieno[2,3-b]pyrazine-6-carboxylate 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 3.0h， 生成 3-Chloro-7-[2-(6-methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-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：

  2-氯-3-氰基吡嗪 在 dipotassium peroxodisulfate 、 硫酸 、 sodium ethanolate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 43.0h， 生成 Ethyl 2-chloro-7-isocyanatothieno[2,3-b]pyrazine-6-carboxylate
  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

• Benzoxazine &agr;-1 adrenergic compounds
  申请人：Abbott Laboratories

  公开号：US06376488B1

  公开（公告）日：2002-04-23

  The present invention relates to compounds having formula I and to pharmaceutically acceptable salts thereof. Compounds of formula I inhibit &agr;1 adrenoreceptors and may be useful for treating benign prostatic hyperplasia (also called benign prostatic hypertrophy) and other urological diseases such as bladder outlet obstruction, neurogenic bladder and gynecological syndromes.

  本发明涉及具有公式I的化合物及其药学上可接受的盐。公式I的化合物抑制α1肾上腺素受体，可用于治疗良性前列腺增生（也称良性前列腺肥大）和其他泌尿系统疾病，如膀胱出口梗阻、神经源性膀胱和妇科综合症。
• US6376488B1
  申请人：——

  公开号：US6376488B1

  公开（公告）日：2002-04-23
• [EN] BENZOXAZINE ALPHA-1 ADRENERGIC COMPOUNDS<br/>[FR] COMPOSES DE BENZOXAZINE ALPHA-1 ADRENERGIQUE
  申请人：ABBOTT LAB

  公开号：WO2002020533A2

  公开（公告）日：2002-03-14

  The present invention relates to compounds having formula I and to pharmaceutically acceptable salts thereof. Compounds of formula I inhibit a1 adrenoreceptors and may be useful for treating benign prostatic hyperplasia (also called benign prostatic hypertrophy) and other urological diseases such as bladder outlet obstruction, neurogenic bladder and gynecological syndromes.
• 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.