N-(2-chloroethyl)-N'-[3-[(2-methoxycarbonyl)benzothienyl]]urea | 167225-15-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: N-(2-chloroethyl)-N'-[3-[(2-methoxycarbonyl)benzothienyl]]urea
• 英文别名: N'-(2-chloroethyl)-N'-[3-(2-ethoxycarbonyl)benzothienyl]urea；3-[[[(2-Chloroethyl)amino]carbonyl]amino]benzo[b]thiophene-2-carboxylic acid ethyl ester；ethyl 3-(2-chloroethylcarbamoylamino)-1-benzothiophene-2-carboxylate
• CAS: 167225-15-2
• 化学式: C₁₄H₁₅ClN₂O₃S
• 分子量: 326.804
• InChiKey: FMTGRELBMHMGFG-UHFFFAOYSA-N

物化性质

• 沸点：
  474.6±45.0 °C(Predicted)
• 密度：
  1.377±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(5-chloro-2-methoxy-phenyl)-piperazine 、 N-(2-chloroethyl)-N'-[3-[(2-methoxycarbonyl)benzothienyl]]urea 反应 1.0h， 生成 3-[2-[4-(5-chloro-2-methoxyphenyl)piperazin-1-yl]ethyl]-1H-[1]benzothiolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  New pyrimido[5,4-b]indoles and [1]benzothieno[3,2-d]pyrimidines: High affinity ligands for the α1-adrenoceptor subtypes

  摘要：

  A number of new pyrimido[5,4-b]indole and [1]benzothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their binding and functional properties at alpha(1)-adrenergic receptor (alpha(1)-AR) subtypes. They behaved as potent alpha(1)-AR antagonists. In binding experiments, some of them (RC24 and RC23) showed very high affinity for the alpha(1D)-AR subtype. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.034
• 作为产物：
  描述：

  氯乙基异氰酸酯 、 3-氨基-苯并[b]噻吩-2-羧酸乙酯 生成 N-(2-chloroethyl)-N'-[3-[(2-methoxycarbonyl)benzothienyl]]urea
  参考文献：
  名称：

  New pyrimido[5,4-b]indoles and [1]benzothieno[3,2-d]pyrimidines: High affinity ligands for the α1-adrenoceptor subtypes

  摘要：

  A number of new pyrimido[5,4-b]indole and [1]benzothieno[3,2-d]pyrimidine derivatives were synthesized and evaluated for their binding and functional properties at alpha(1)-adrenergic receptor (alpha(1)-AR) subtypes. They behaved as potent alpha(1)-AR antagonists. In binding experiments, some of them (RC24 and RC23) showed very high affinity for the alpha(1D)-AR subtype. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.09.034

文献信息

• New Pyrimido[5,4-<i>b</i>]indoles as Ligands for α₁-Adrenoceptor Subtypes
  作者：Giuseppe Romeo、Luisa Materia、Fabrizio Manetti、Alfredo Cagnotto、Tiziana Mennini、Ferdinando Nicoletti、Maurizio Botta、Filippo Russo、Kenneth P. Minneman

  DOI：10.1021/jm0307741

  日期：2003.7.1

  A new series of compounds were designed as structural analogues of the alpha(1)-AR ligand RN5 (4), characterized by a tricyclic 5H-pyrimido[5,4-b]indole-(1H,3H)2,4-dione system connected through an alkyl. chain to a phenylpiperazine (PP) moiety. These compounds were synthesized and tested in binding assays on human alpha(1A)-AR, alpha(1B)-AR, and alpha(1D)-AR subtypes expressed in HEK293 cells. Several structural modifications were performed on the PP moiety, the tricyclic system, and the connecting alkyl chain. Many of the new molecules showed a preferential affinity for the alpha(1D)-AR subtype. Some compounds, including 39 and 40, displayed substantial alpha(1D)-AR selectivity with respect to alpha(1A)-AR, alpha(1B)-AR, serotonergic 5-HT1A, 5-HT1B, 5-HT2A, and dopaminergic D-1 and D-2 receptors. Two conformationally rigid analogues of 4, useful for studying the architecture of the receptor/ligand complex, were also prepared and tested. A subset of the new compounds was then used to evolve a preliminary pharmacophore model for alpha(1D)-AR antagonists, based on a more generalized model we had developed for alpha(1)-AR antagonists. This new model rationalized the relationships between structural properties and biological data of the pyrimido[5,4-b]indole compounds, as well as other compounds.
• 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.