1-(benzofuran-2-yl)-2-(2-iminothiazol-3(2H)-yl)ethanol | 116923-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 1-(benzofuran-2-yl)-2-(2-iminothiazol-3(2H)-yl)ethanol
• 英文别名: 1-(1-Benzofuran-2-yl)-2-(2-imino-1,3-thiazol-3-yl)ethanol
• CAS: 116923-24-1
• 化学式: C₁₃H₁₂N₂O₂S
• 分子量: 260.316
• InChiKey: RBKCVSKQANFBMN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  85.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(benzofuran-2-yl)-2-(2-iminothiazol-3(2H)-yl)ethanol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到(benzofurannyl-2)-6 dihydro-5,6 imidazo<2,1-b>thiazole
  参考文献：
  名称：

  Synthesis of benzofuran derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase: effects on cell toxicity and osteoblast-induced mineralization

  摘要：

  Tissue-nonspecific alkaline phosphatase (TNAP) by hydrolyzing pyrophosphate, an inhibitor of apatite formation, promotes extracellular matrix calcification during bone formation and growth, as well as during ectopic calcification under pathological conditions. TNAP is a target for the treatment of soft tissue pathological ossification. We synthesized a series of benzofuran derivatives. Among these, SMA14, displayed TNAP activity better than levamisole. SMA14 was found to be not toxic at doses of up to 40 mu M in osteoblast-like Saos-2 cells and primary osteoblasts. As probed by Alizarin Red staining, this compound inhibited mineral formation in murine primary osteoblast and in osteoblast-like Saos-2 cells. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.061
• 作为产物：
  描述：

  2-(溴乙酰基)苯并呋喃 在 sodium tetrahydroborate 作用下， 以 甲烷磺酸 、 异丙醇 为溶剂， 反应 15.0h， 生成 1-(benzofuran-2-yl)-2-(2-iminothiazol-3(2H)-yl)ethanol
  参考文献：
  名称：

  Synthesis of benzofuran derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase: effects on cell toxicity and osteoblast-induced mineralization

  摘要：

  Tissue-nonspecific alkaline phosphatase (TNAP) by hydrolyzing pyrophosphate, an inhibitor of apatite formation, promotes extracellular matrix calcification during bone formation and growth, as well as during ectopic calcification under pathological conditions. TNAP is a target for the treatment of soft tissue pathological ossification. We synthesized a series of benzofuran derivatives. Among these, SMA14, displayed TNAP activity better than levamisole. SMA14 was found to be not toxic at doses of up to 40 mu M in osteoblast-like Saos-2 cells and primary osteoblasts. As probed by Alizarin Red staining, this compound inhibited mineral formation in murine primary osteoblast and in osteoblast-like Saos-2 cells. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.01.061

文献信息

• Amarouch, H.; Loiseau, P. R.; Bonnafous, M., Farmaco, Edizione Scientifica, 1988, vol. 43, # 5, p. 421 - 438
  作者：Amarouch, H.、Loiseau, P. R.、Bonnafous, M.、Caujolle, R.、Payard, M.、et al.

  DOI：——

  日期：——
• AMAROUCH, H.;LOISEAU, P. R.;BONNAFOUS, M.;CAUJOLLE, R.;PAYARD, M.;LOISEAU+, FARMACO: ED. SCI., 43,(1988) N 5, C. 421-437
  作者：AMAROUCH, H.、LOISEAU, P. R.、BONNAFOUS, M.、CAUJOLLE, R.、PAYARD, M.、LOISEAU+

  DOI：——

  日期：——
• Synthesis of benzofuran derivatives as selective inhibitors of tissue-nonspecific alkaline phosphatase: effects on cell toxicity and osteoblast-induced mineralization
  作者：Stéphanie Marquès、René Buchet、Florence Popowycz、Marc Lemaire、Saïda Mebarek

  DOI：10.1016/j.bmcl.2016.01.061

  日期：2016.3

  Tissue-nonspecific alkaline phosphatase (TNAP) by hydrolyzing pyrophosphate, an inhibitor of apatite formation, promotes extracellular matrix calcification during bone formation and growth, as well as during ectopic calcification under pathological conditions. TNAP is a target for the treatment of soft tissue pathological ossification. We synthesized a series of benzofuran derivatives. Among these, SMA14, displayed TNAP activity better than levamisole. SMA14 was found to be not toxic at doses of up to 40 mu M in osteoblast-like Saos-2 cells and primary osteoblasts. As probed by Alizarin Red staining, this compound inhibited mineral formation in murine primary osteoblast and in osteoblast-like Saos-2 cells. (C) 2016 Elsevier Ltd. All rights reserved.