IMB-05 | 148520-10-9

• 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: IMB-05
• 英文别名: 2-(2-(methylsulfinyl)acetyl)benzothiophene；1-(benzo[b]thiophen-2-yl)-2-(methylsulfinyl)ethanone；1-(1-benzothiophen-2-yl)-2-methylsulfinylethanone
• CAS: 148520-10-9
• 化学式: C₁₁H₁₀O₂S₂
• 分子量: 238.331
• InChiKey: XFRACMIQFCPUDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  120-123 °C
• 沸点：
  495.4±25.0 °C(Predicted)
• 密度：
  1.397±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  81.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  IMB-05 在 氯化铵 、 锌 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以93%的产率得到2-乙酰基苯并噻吩
  参考文献：
  名称：

  Practical Synthesis of 2-Acetylbenzo[b]thiophene

  摘要：

  2-Acetyl-benzo[b]thiophene and its oxime were prepared from 2-nitrobenzaldehyde in good yields and under convenient conditions.

  DOI：

  10.1080/00397919308009834
• 作为产物：
  描述：

  1-苯并噻吩-2-羧酸乙酯 在 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 0.5h， 生成 IMB-05
  参考文献：
  名称：

  新型取代苯并噻吩或苯并呋喃衍生物作为BMP-2上调剂的合成及其对BMP-2上调作用的评价及对糖皮质激素引起的大鼠骨质疏松的影响

  摘要：

  BMP途径是设计用于治疗低骨量的治疗剂的有希望的新目标。为了丰富我们对SAR的理解，并基于我们先前得出的结构效应关系，在这项工作中准备了23种衍生物。提出了这些化合物在糖皮质激素诱导的骨质疏松症大鼠中的合成，上调其BMP-2表达的活性以及预防骨丢失的功效。通过光学显微镜评估所测试的大鼠的骨组织学表明，化合物1，21，35，和与模型组相比，38显著增加了小梁，以及与治疗的组的小梁8A与雷洛昔芬和阿法骨化醇相似。该化合物显示出发展为同化剂的潜力。

  DOI：

  10.1016/j.ejmech.2015.04.016

文献信息

• Substituted Benzothiophene or Benzofuran Derivatives as a Novel Class of Bone Morphogenetic Protein-2 Up-Regulators: Synthesis, Structure−Activity Relationships, and Preventive Bone Loss Efficacies in Senescence Accelerated Mice (SAMP6) and Ovariectomized Rats
  作者：Hui-fang Guo、Hua-yi Shao、Zhao-yong Yang、Si-tu Xue、Xue Li、Zong-ying Liu、Xiao-bo He、Jian-dong Jiang、Yue-qin Zhang、Shu-yi Si、Zhuo-rong Li

  DOI：10.1021/jm901685n

  日期：2010.2.25

  In this work, substituted benzothiophene and benzofuran compounds were found to be a new class of potential anabolic agents by enhancing BMP-2 expression. A series of benzothiophene and benzofuran derivatives have been synthesized, and their activities of up-regulating BMP-2 and bone loss prevention efficacies in SAMP6 mice and OVX rats have been studied. Benzothiophenes 1, 3, 14, 4a, 7a, 8a, and benzofuran analogue 2 showed higher BMP-2 up-regulation rates in vitro. Compound 8111 was found to significantly affect the bone formation rate of tested SAMP6 mice. Compound I showed an improved bone quality in SAMP6 mice and also showed activity in OVX rats. We have demonstrated that Substituted benzothiophene and benzofuran derivatives, especially compounds I and 8a, enhance BMP-2 expression in vitro and in vivo and stimulate bone formation and trabecular connectivity restoration ill vivo. The compounds represent potential leads in the development of a new class of anabolic agents.
• Kolasa Teodozyj, Brooks Dee W., Synth. Commun., 23 (1993) N 6, S 743-748
  作者：Kolasa Teodozyj, Brooks Dee W.

  DOI：——

  日期：——
• [EN] BENZO 5-MEMBERED UNSATURATED HETEROCYCLIC COMPOUNDS AND PREPARATION METHODS THEREOF<br/>[FR] COMPOSÉS DE BENZO HÉTÉROCYCLIQUES INSATURÉS À 5 ÉLÉMENTS ET PROCÉDÉS POUR LES PRÉPARER
  申请人：INST MED BIOTECHNOLOGY CAMS

  公开号：WO2012068702A1

  公开（公告）日：2012-05-31

  Disclosed are benzo 5-membered unsaturated heterocyclic compounds represented by formula I and their pharmaceutically acceptable salts, preparation methods and uses thereof in the preparation of the drugs for treating osteoporosis, wherein each substituent of formula (I) is defined as the description.
• Synthesis of a novel class of substituted benzothiophene or benzofuran derivatives as BMP-2 up-regulators and evaluation of the BMP-2-up-regulating effects in vitro and the effects on glucocorticoid-induced osteoporosis in rats
  作者：Si-tu Xue、Hui-fang Guo、Mei-jie Liu、Jie Jin、Da-hong Ju、Zong-ying Liu、Zhuo-rong Li

  DOI：10.1016/j.ejmech.2015.04.016

  日期：2015.5

  therapeutic agents for the treatment of low bone mass. To enrich our understanding of SAR and based on our previously concluded structure–effect relationship, 23 derivatives were prepared in this work. The synthesis, up-regulating activities on BMP-2 expression, and bone loss prevention efficacies of these compounds in rats with glucocorticoid-induced osteoporosis are presented. The bone histology of

  BMP途径是设计用于治疗低骨量的治疗剂的有希望的新目标。为了丰富我们对SAR的理解，并基于我们先前得出的结构效应关系，在这项工作中准备了23种衍生物。提出了这些化合物在糖皮质激素诱导的骨质疏松症大鼠中的合成，上调其BMP-2表达的活性以及预防骨丢失的功效。通过光学显微镜评估所测试的大鼠的骨组织学表明，化合物1，21，35，和与模型组相比，38显著增加了小梁，以及与治疗的组的小梁8A与雷洛昔芬和阿法骨化醇相似。该化合物显示出发展为同化剂的潜力。
• Practical Synthesis of 2-Acetylbenzo[b]thiophene
  作者：Teodozyj Kolasa、Dee W. Brooks

  DOI：10.1080/00397919308009834

  日期：1993.3

  2-Acetyl-benzo[b]thiophene and its oxime were prepared from 2-nitrobenzaldehyde in good yields and under convenient conditions.