Methyl 3-isocyanatothieno[3,2-b]pyridine-2-carboxylate | 187733-03-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: Methyl 3-isocyanatothieno[3,2-b]pyridine-2-carboxylate
• CAS: 187733-03-5
• 化学式: C₁₀H₆N₂O₃S
• 分子量: 234.235
• InChiKey: QLBJXSOBNVBNNZ-UHFFFAOYSA-N

物化性质

• 沸点：
  390.1±42.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  96.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 3-isocyanatothieno[3,2-b]pyridine-2-carboxylate 在 potassium tert-butylate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 A 131701
  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：

  光气 、 3-氨基噻吩[3,2-B]吡啶-2-甲酸甲酯 在 三乙胺 作用下， 生成 Methyl 3-isocyanatothieno[3,2-b]pyridine-2-carboxylate
  参考文献：
  名称：

  3- [2-（（3aR，9bR）-cis-6-甲氧基-2,3,3a，4,5,9b-六氢-1H-苯并[e]异吲哚-2-基）乙基的合成及药理学表征] pyrido- [3'，4'：4,5] thieno [3,2-d] pyrimidine-2,4（1H，3H）-dione（A-131701）：一种对症治疗的尿液选择性α1A肾上腺素受体拮抗剂前列腺增生。

  摘要：

  DOI：

  10.1021/jm970364a

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。
• Synthesis and Pharmacological Characterization of 3-[2-((3a<i>R</i>,9b<i>R</i>)-<i>cis</i>-6-Methoxy- 2,3,3a,4,5,9b-hexahydro-1<i>H</i>- benz[<i>e</i>]isoindol-2-yl)ethyl]pyrido[3‘,4‘:4,5]thieno[3,2-<i>d</i>]pyrimidine- 2,4(1<i>H</i>,3<i>H</i>)-dione (A-131701):  A Uroselective α_1A Adrenoceptor Antagonist for the Symptomatic Treatment of Benign Prostatic Hyperplasia
  作者：Michael D. Meyer、Robert J. Altenbach、Fatima Z. Basha、William A. Carroll、Irene Drizin、Steven W. Elmore、Paul P. Ehrlich、Suzanne A. Lebold、Karin Tietje、Kevin B. Sippy、Michael D. Wendt、Daniel J. Plata、Fred Plagge、Steven A. Buckner、Michael E. Brune、Arthur A. Hancock、James F. Kerwin

  DOI：10.1021/jm970364a

  日期：1997.9.1
• US6376488B1
  申请人：——

  公开号：US6376488B1

  公开（公告）日：2002-04-23
• 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.