1-(5-nitrobenzo[b]thiophen-2-yl)-2-bromoethanone | 120992-60-1

• 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: 1-(5-nitrobenzo[b]thiophen-2-yl)-2-bromoethanone
• CAS: 120992-60-1
• 化学式: C₁₀H₆BrNO₃S
• 分子量: 300.133
• InChiKey: AMNIMAGMKXRYPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-(5-nitrobenzo[b]thiophen-2-yl)-2-bromoethanone 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 氯仿 、 异丙醇 为溶剂， 生成 N-[3-(5-nitro-2-benzo[b]thiophen-3-yl-2-hydroxyethyl)-3H-thiazol-2-ylidene]acetamide
  参考文献：
  名称：

  Inhibitors of tissue-nonspecific alkaline phosphatase: Design, synthesis, kinetics, biomineralization and cellular tests

  摘要：

  Chronic kidney disease (CKD) is associated with numerous metabolic and endocrine disturbances, including abnormalities of calcium and phosphate metabolism and an inflammatory syndrome. The latter occurs early in the course of CKD and contributes to the development and progression of vascular calcification. A few therapeutic strategies are today contemplated to target vascular calcification in patients with CKD: vitamin K2, calcimimetics and phosphate binders. However, none has provided complete prevention of vascular calcification and there is an urgent need for alternate efficient treatments. Recent findings indicate that tissue-nonspecific alkaline phosphatase (TNAP) may represent a very promising drug target due to its participation in mineralization by vascular smooth muscle cells. We report the synthesis of four levamisole derivatives having better inhibition property on TNAP than levamisole. Their IC50, Ki and water solubility have been determined. We found that the four inhibitors bind to TNAP in an uncompetitive manner and are selective to TNAP. Indeed, they do not inhibit intestinal and placental alkaline phosphatases. Survival MTT tests on human MG-63 and Saos-2 osteoblast-like cells have been performed in the presence of inhibitors. All the inhibitors are not toxic at concentrations that block TNAP activity. Moreover, they are able to significantly reduce mineralization in MG63 and Saos-2 osteoblast-like cells, indicating that they are promising molecules to prevent vascular calcification. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.053
• 作为产物：
  描述：

  2-氯-5-硝基苯甲醛 在 吡啶溴化氢盐 、 potassium carbonate 作用下， 以 氯仿 、 水 为溶剂， 反应 6.0h， 生成 1-(5-nitrobenzo[b]thiophen-2-yl)-2-bromoethanone
  参考文献：
  名称：

  Inhibitors of tissue-nonspecific alkaline phosphatase: Design, synthesis, kinetics, biomineralization and cellular tests

  摘要：

  Chronic kidney disease (CKD) is associated with numerous metabolic and endocrine disturbances, including abnormalities of calcium and phosphate metabolism and an inflammatory syndrome. The latter occurs early in the course of CKD and contributes to the development and progression of vascular calcification. A few therapeutic strategies are today contemplated to target vascular calcification in patients with CKD: vitamin K2, calcimimetics and phosphate binders. However, none has provided complete prevention of vascular calcification and there is an urgent need for alternate efficient treatments. Recent findings indicate that tissue-nonspecific alkaline phosphatase (TNAP) may represent a very promising drug target due to its participation in mineralization by vascular smooth muscle cells. We report the synthesis of four levamisole derivatives having better inhibition property on TNAP than levamisole. Their IC50, Ki and water solubility have been determined. We found that the four inhibitors bind to TNAP in an uncompetitive manner and are selective to TNAP. Indeed, they do not inhibit intestinal and placental alkaline phosphatases. Survival MTT tests on human MG-63 and Saos-2 osteoblast-like cells have been performed in the presence of inhibitors. All the inhibitors are not toxic at concentrations that block TNAP activity. Moreover, they are able to significantly reduce mineralization in MG63 and Saos-2 osteoblast-like cells, indicating that they are promising molecules to prevent vascular calcification. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.09.053

文献信息

• A Straightforward Expeditious synthesis of 5-nitrobenzo[b]thiophene-2-carbaldehyde
  作者：Hongtao Wei、Min Sun、Min Ji

  DOI：10.3184/030823409x460669

  日期：2009.6

  A high yielding one-pot synthesis of 5-nitrobenzo[b]thiophene-2-carbaldehyde is reported using the readily available, cheap starting material 2,5-dihydroxy-1,4-dithiane and 2-chloro-5-nitrobenzaldehyde.

  本研究报告采用易于获得的廉价起始原料 2,5-二羟基-1,4-二噻烷和 2-氯-5-硝基苯甲醛，高产地一步合成了 5-硝基苯并[b]噻吩-2-甲醛。