Benzo[b]thiophene-3-carboxaldehyde, 2-(3-pyridinyl)- | 874945-93-4

• 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: Benzo[b]thiophene-3-carboxaldehyde, 2-(3-pyridinyl)-
• 英文别名: 2-pyridin-3-yl-1-benzothiophene-3-carbaldehyde
• CAS: 874945-93-4
• 化学式: C₁₄H₉NOS
• 分子量: 239.298
• InChiKey: GEJKTQGUQWJEAB-UHFFFAOYSA-N

物化性质

• 熔点：
  96-98 °C
• 沸点：
  460.3±35.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Benzo[b]thiophene-3-carboxaldehyde, 2-(3-pyridinyl)- 在 甲醇 、 sodium tetrahydroborate 作用下， 反应 2.0h， 以100%的产率得到2-(3'-pyridinyl)-3-(hydroxymethyl)-benzo[b]thiophene
  参考文献：
  名称：

  苯并[ b ]噻吩衍生物作为碱性磷酸酶抑制剂的合成与评价

  摘要：

  骨关节炎患者膝关节中碱性磷酸钙的存在可以通过抑制组织非特异性碱性磷酸酶（TNAP）活性来预防。左旋咪唑或丁苯甲醚的L立体异构体（已知的TNAP抑制剂）已被用作治疗类风湿性关节炎的治疗方法，但由于副作用，其治疗用途受到限制。我们报告了苯并[ b ]噻吩衍生物的合成和TNAP抑制特性，其中苯并噻吩-四咪唑和苯并噻吩-2,3-脱氢四甲酚可能参与骨关节炎的药物治疗。两种水溶性外消旋苯并噻吩四咪唑和-2,3-脱氢四咪唑，其表观抑制常数K i  = 85± 6μM和135±3μM（n = 3）与对映体左旋咪唑相当，为93±4μM。几种新型衍生物对肠道碱性磷酸酶的抑制作用比TNAP更为明显。

  DOI：

  10.1016/j.bmc.2009.08.048
• 作为产物：
  描述：

  3-溴吡啶 、 3-甲醛苯并噻吩 在 palladium diacetate potassium carbonate 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以51%的产率得到Benzo[b]thiophene-3-carboxaldehyde, 2-(3-pyridinyl)-
  参考文献：
  名称：

  Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus

  摘要：

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.04.023

文献信息

• [EN] COMPOSITION CONTAINING A THIOPHENIC OR BENZOTHIOPHENIC COMPOUND AND EXHIBITING A PUMP NORA INHIBITING ACTIVITY<br/>[FR] COMPOSITIONS CONTENANT UN COMPOSE THIOPHENIQUE OU BENZOTHIOPHENIQUE, PRESENTANT UNE ACTIVITE INHIBITRICE DE POMPE NORA
  申请人：UNIV CLAUDE BERNARD LYON

  公开号：WO2006018544A1

  公开（公告）日：2006-02-23

  La présente invention concerne l'utilisation d'inhibiteurs de pompe efflux NorA de formule (I) : tels que définis à la revendication 1, pour la préparation d'un médicament destiné à potentialiser l'effet d'un agent antimicrobien, ainsi que des compositions pour potentialiser l'effet d'un agent antimicrobien contenant, en tant qu'agent potentialisateur, un tel inhibiteur de pompe efflux NorA.
• Synthesis and evaluation of new arylbenzo[b]thiophene and diarylthiophene derivatives as inhibitors of the NorA multidrug transporter of Staphylococcus aureus
  作者：Jérémie Fournier dit Chabert、Béatrice Marquez、Luc Neville、Lionel Joucla、Sylvie Broussous、Pascale Bouhours、Emilie David、Stéphane Pellet-Rostaing、Bernard Marquet、Nicole Moreau、Marc Lemaire

  DOI：10.1016/j.bmc.2007.04.023

  日期：2007.7

  The synthesis based on palladium catalytic coupling of 38 new-arylated benzo[b]thiophenes or thiophenes is described in a few steps. We also report the direct arylation of the position 3 of the benzo[b]thiophenic structure, a 'one pot' 2,5-heterodiarylation of thiophenes as well as the synthesis of precursors of amino-acids with a 2-arylated benzo[b]thiophene core. These compounds were evaluated on bacteria strains: most of them did not exhibit any antibiotic activity but were found to selectively inhibit the NorA multidrug transporter of Staphylococcus aureus. As such, they restored the activity of the NorA substrates ciprofloxacin against a resistant S. aureus strain in which this efflux pump is over-expressed. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis and evaluation of benzo[b]thiophene derivatives as inhibitors of alkaline phosphatases
  作者：Lina Li、Lei Chang、Stéphane Pellet-Rostaing、François Liger、Marc Lemaire、René Buchet、Yuqing Wu

  DOI：10.1016/j.bmc.2009.08.048

  日期：2009.10

  prevented by inhibiting tissue non-specific alkaline phosphatase (TNAP) activity. Levamisole or the L stereoisomer of tetramisole (a known TNAP inhibitor) has been used as a treatment for curing rheumatoid arthritis but its therapeutical use is limited due to side effects. We report the synthesis and the TNAP inhibition property of benzo[b]thiophene derivatives, among which benzothiopheno-tetramisole

  骨关节炎患者膝关节中碱性磷酸钙的存在可以通过抑制组织非特异性碱性磷酸酶（TNAP）活性来预防。左旋咪唑或丁苯甲醚的L立体异构体（已知的TNAP抑制剂）已被用作治疗类风湿性关节炎的治疗方法，但由于副作用，其治疗用途受到限制。我们报告了苯并[ b ]噻吩衍生物的合成和TNAP抑制特性，其中苯并噻吩-四咪唑和苯并噻吩-2,3-脱氢四甲酚可能参与骨关节炎的药物治疗。两种水溶性外消旋苯并噻吩四咪唑和-2,3-脱氢四咪唑，其表观抑制常数K i  = 85± 6μM和135±3μM（n = 3）与对映体左旋咪唑相当，为93±4μM。几种新型衍生物对肠道碱性磷酸酶的抑制作用比TNAP更为明显。