ethyl 3-aminothieno[2,3-b]pyrazine-2-carboxylate-4-oxide | 208993-99-1

• 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-aminothieno[2,3-b]pyrazine-2-carboxylate-4-oxide
• 英文别名: ethyl 7-amino-1-oxido-thieno[2,3-b]pyrazine-6-carboxylate；Thieno[2,3-b]pyrazine-6-carboxylic acid, 7-amino-, ethyl ester, 1-oxide；ethyl 7-amino-1-oxidothieno[2,3-b]pyrazin-1-ium-6-carboxylate
• CAS: 208993-99-1
• 化学式: C₉H₉N₃O₃S
• 分子量: 239.255
• InChiKey: SXUZSRMVGATVKG-UHFFFAOYSA-N

物化性质

• 沸点：
  457.9±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  119
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-aminothieno[2,3-b]pyrazine-2-carboxylate-4-oxide 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 6.0h， 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
• 作为产物：
  描述：

  2-氯-3-氰基吡嗪 在 dipotassium peroxodisulfate 、 硫酸 、 sodium ethanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 37.0h， 生成 ethyl 3-aminothieno[2,3-b]pyrazine-2-carboxylate-4-oxide
  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（也称为良性前列腺肥大）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征。
• [EN] BENZOPYRANOPYRROLE AND BENZOPYRANOPYRIDINE ALPHA-1 ADRENERGIC COMPOUNDS<br/>[FR] COMPOSES ALPHA-1 ADRENERGIQUES A BASE DE BENZOPYRANOPYRROLE ET DE BENZOPYRANOPYRIDINE
  申请人：ABBOTT LABORATORIES

  公开号：WO1998024791A1

  公开（公告）日：1998-06-11

  (EN) The present invention relates to a compound of formula (I) and the pharmaceutically acceptable salts thereof wherein W is a bicyclic heterocyclic ring system. The compounds are $g(a)-1 adrenergic antagonists and are useful in the treatment of BPH; also disclosed are $g(a)-1 antagonist compositions and a method for antagonizing $g(a)-1 adrenoreceptors and treating BPH.(FR) La présente invention concerne un composé de la formule (I) ainsi que les sels de celui-ci, acceptables sur le plan pharmacologique. Dans cette formule W représente un système de noyau hétérocyclique bicyclique. Ces composés sont des antagonistes $g(a)-1 adrénergiques et ils sont utiles dans le traitement de l'hyperplasie prostatique bénigne. L'invention concerne également des compositions antagonistes $g(a)-1 adrénergiques ainsi qu'un procédé destiné à antagoniser les adrénorécepteurs $g(a)-1 et à traiter l'hyperplasie prostatique bénigne.

  本发明涉及一种公式(I)的化合物及其药学上可接受的盐，其中W是一个双环杂环环系统。这些化合物是$g(a)-1肾上腺素受体拮抗剂，可用于治疗BPH；还披露了$g(a)-1拮抗剂组合物和拮抗$g(a)-1肾上腺素受体和治疗BPH的方法。
• BENZOPYRANOPYRROLE AND BENZOPYRANOPYRIDINE ALPHA-1 ADRENERGIC COMPOUNDS
  申请人：Abbott Laboratories

  公开号：EP0942911B1

  公开（公告）日：2001-10-17
• US5891882A
  申请人：——

  公开号：US5891882A

  公开（公告）日：1999-04-06
• US6046207A
  申请人：——

  公开号：US6046207A

  公开（公告）日：2000-04-04