thioxanthen-9-yl-methanol | 17394-18-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻喃类
• 英文名称: thioxanthen-9-yl-methanol
• 英文别名: 9H-thioxanthen-9-ylmethanol
• CAS: 17394-18-2
• 化学式: C₁₄H₁₂OS
• 分子量: 228.315
• InChiKey: GOGXIFCTYHCFER-UHFFFAOYSA-N

物化性质

• 沸点：
  368.7±21.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  thioxanthen-9-yl-methanol 在 双氧水 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 8.0h， 生成 2-[(10,10-dioxo-9H-thioxanthen-9-yl)methoxycarbonylamino]acetic acid
  参考文献：
  名称：

  Thioxanthene dioxide based amino-protecting groups sensitive to pyridine bases and dipolar aprotic solvents

  摘要：

  DOI：

  10.1021/jo00286a019
• 作为产物：
  描述：

  9-噻吨酮 在 sodium tetrahydroborate 、 高氯酸 、 sodium hexamethyldisilazane 作用下， 以 1,4-二氧六环 、 乙醚 、 乙醇 为溶剂， 生成 thioxanthen-9-yl-methanol
  参考文献：
  名称：

  2-Substituted (2SR)-2-Amino-2-((1SR,2SR)-2-carboxycycloprop-1-yl)glycines as Potent and Selective Antagonists of Group II Metabotropic Glutamate Receptors. 1. Effects of Alkyl, Arylalkyl, and Diarylalkyl Substitution

  摘要：

  In this paper, we describe the synthesis of a series of a-substituted analogues of the potent and selective group II metabotropic glutamate receptor (mGluR) agonist (1S,1'S,2'S)-carboxy-cyclopropylglycine (2, L-CCG 1). Incorporation of a substituent on the amino acid carbon converted the agonist 2 into antagonist. Ail of the compounds were prepared and tested as a series of four isomers, i.e., two racemic diastereomers. We explored alkyl substitution, both normal and terminally branched; phenylalkyl and diphenylalkyl substitution; and a variety of aromatic and carbocyclic surrogates for phenyl. Affinity for group II mGluRs was measured using [H-3]glutamic acid (Glu) binding in rat forebrain membranes. Antagonist activity was confirmed for these compounds by measuring their ability to antagonize (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid-induced inhibition of forskolin-stimulated cyclic-AMP in RGT cells transfected with human mGluR2 and mGluR3. We found that while alkyl substitution provided no increase in affinity relative to 2, phenylethyl and diphenylethyl substitution, as in 105 and 109, respectively, were quite beneficial, The affinity of 109 was further enhanced when the two aromatic rings were joined by an oxygen or sulfur atom to form the tricyclic xanthylmethyl and thioxanthylmethyl amino acids 113 and 114, respectively. Amino acid 113, with an IC50 of 0.10 mu M in the [H-3]Glu binding assay, was 52-fold more patent than 2, whose IC50 was 0.47 mu M.

  DOI：

  10.1021/jm970497w

文献信息

• CARPINO, LOUIS A.;GAO, HEAU-SHAN;TI, GEN-SHING;SEGEV, DAVID, J. ORG. CHEM., 54,(1989) N5, C. 5887-5897
  作者：CARPINO, LOUIS A.、GAO, HEAU-SHAN、TI, GEN-SHING、SEGEV, DAVID

  DOI：——

  日期：——
• Thioxanthene dioxide based amino-protecting groups sensitive to pyridine bases and dipolar aprotic solvents
  作者：Louis A. Carpino、Heau Shan Gao、Gen Shing Ti、David Segev

  DOI：10.1021/jo00286a019

  日期：1989.12
• 2-Substituted (2<i>SR</i>)-2-Amino-2-((1<i>SR</i>,2<i>SR</i>)-2-carboxycycloprop-1-yl)glycines as Potent and Selective Antagonists of Group II Metabotropic Glutamate Receptors. 1. Effects of Alkyl, Arylalkyl, and Diarylalkyl Substitution
  作者：Paul L. Ornstein、Thomas J. Bleisch、M. Brian Arnold、Rebecca A. Wright、Bryan G. Johnson、Darryle D. Schoepp

  DOI：10.1021/jm970497w

  日期：1998.1.1

  In this paper, we describe the synthesis of a series of a-substituted analogues of the potent and selective group II metabotropic glutamate receptor (mGluR) agonist (1S,1'S,2'S)-carboxy-cyclopropylglycine (2, L-CCG 1). Incorporation of a substituent on the amino acid carbon converted the agonist 2 into antagonist. Ail of the compounds were prepared and tested as a series of four isomers, i.e., two racemic diastereomers. We explored alkyl substitution, both normal and terminally branched; phenylalkyl and diphenylalkyl substitution; and a variety of aromatic and carbocyclic surrogates for phenyl. Affinity for group II mGluRs was measured using [H-3]glutamic acid (Glu) binding in rat forebrain membranes. Antagonist activity was confirmed for these compounds by measuring their ability to antagonize (1S,3R)-1-aminocyclopentane-1,3-dicarboxylic acid-induced inhibition of forskolin-stimulated cyclic-AMP in RGT cells transfected with human mGluR2 and mGluR3. We found that while alkyl substitution provided no increase in affinity relative to 2, phenylethyl and diphenylethyl substitution, as in 105 and 109, respectively, were quite beneficial, The affinity of 109 was further enhanced when the two aromatic rings were joined by an oxygen or sulfur atom to form the tricyclic xanthylmethyl and thioxanthylmethyl amino acids 113 and 114, respectively. Amino acid 113, with an IC50 of 0.10 mu M in the [H-3]Glu binding assay, was 52-fold more patent than 2, whose IC50 was 0.47 mu M.