乙基3-氨基-5-甲氧基-噻吩-2-羧酸酯 | 460355-90-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 乙基3-氨基-5-甲氧基-噻吩-2-羧酸酯
• 英文名称: 4-amino-5-carboethoxy-2-methoxythiophene
• 英文别名: Ethyl 3-amino-5-methoxythiophene-2-carboxylate
• CAS: 460355-90-2
• 化学式: C₈H₁₁NO₃S
• 分子量: 201.246
• InChiKey: SVLSSNWSVYEHNN-UHFFFAOYSA-N

物化性质

• 沸点：
  365.3±37.0 °C(Predicted)
• 密度：
  1.260±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  乙基3-氨基-5-甲氧基-噻吩-2-羧酸酯 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 3.0h， 生成 6-Methoxy-3-[2-(6-methoxy-1,3,3a,4,5,9b-hexahydro-benzo[e]isoindol-2-yl)-ethyl]-1H-thieno[3,2-d]pyrimidine-2,4-dione
  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：

  甲氧基二硫代甲酸甲酯 、 溴乙酸乙酯 、 乙腈 在 lithium diisopropyl amide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成 乙基3-氨基-5-甲氧基-噻吩-2-羧酸酯
  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

• BICYCLIC SUBSTITUTED HEXAHYDROBENZ(E)ISOINDOLE ALPHA-1- ADRENERGIC ANTAGONISTS
  申请人：Abbott Laboratories

  公开号：EP0805812B1

  公开（公告）日：2001-06-13
• US5792767A
  申请人：——

  公开号：US5792767A

  公开（公告）日：1998-08-11
• [EN] BICYCLIC SUBSTITUTED HEXAHYDROBENZ[E]ISOINDOLE ALPHA-1- ADRENERGIC ANTAGONISTS<br/>[FR] ANTAGONISTES ALPHA-1-ADRENERGIQUES BICYCLIQUES SUBSTITUES D'HEXAHYDROBENZ(E)ISOINDOLE
  申请人：ABBOTT LABORATORIES

  公开号：WO1996022991A1

  公开（公告）日：1996-08-01

  (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 receptors and treating BPH.(FR) La présente invention concerne un composé de formule (I) ainsi que ses sels pharmaceutiquement acceptables, W étant un noyau hétérocyclique bicyclique. Les composés sont des antagonistes $g(a)-1 adrénergiques et ils sont utiles dans le traitement de l'hyperplasie prostatique bénigne. L'invention concerne aussi des compositions antagonistes $g(a)-1 adrénergiques et un procédé servant à rendre antagonistes des récepteurs $g(a)-1 et à traiter l'hyperplasie prostatique bénigne.
• 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).