2-Hydroxymethyl-5-(p-bromophenyl)thiophene | 344417-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Hydroxymethyl-5-(p-bromophenyl)thiophene
• 英文别名: (5-(4-bromophenyl)thiophen-2-yl)methanol；[5-(4-bromophenyl)thiophen-2-yl]methanol
• CAS: 344417-31-8
• 化学式: C₁₁H₉BrOS
• 分子量: 269.162
• InChiKey: RVXUWYAOFXFKMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Hydroxymethyl-5-(p-bromophenyl)thiophene 在 六甲基磷酰三胺 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 生成 2-(4-Bromophenyl)-5-(chloromethyl)thiophene
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009
• 作为产物：
  描述：

  5-(4-溴苯基)噻吩-2-羧酸 在 lithium aluminium tetrahydride 、 硫酸 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 7.0h， 生成 2-Hydroxymethyl-5-(p-bromophenyl)thiophene
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents

  摘要：

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.08.009

文献信息

• Development of dual functional SPECT/fluorescent probes for imaging cerebral β-amyloid plaques
  作者：Masahiro Ono、Manami Ishikawa、Hiroyuki Kimura、Shun Hayashi、Kenji Matsumura、Hiroyuki Watanabe、Yoichi Shimizu、Yan Cheng、Mengchao Cui、Hidekazu Kawashima、Hideo Saji

  DOI：10.1016/j.bmcl.2010.05.027

  日期：2010.7

  he imaging of beta-amyloid (A beta) aggregates in the brain may lead to the early detection of Alzheimer's disease (AD) and monitoring of the progression and effectiveness of treatment. The purpose of this study was to develop dual modality SPECT and fluorescent probes based on boron dipyrromethane (BODIPY) as a core structure. We designed and synthesized an I-125-labeled derivative of BODIPY (BODIPY7). BOD-IPY7 had a K-i value of 108 nM for A beta(1-42) aggregates and exhibited peaks of absorption/emission aL 606/613 nm. It detected A beta plaques in sections of brain tissue from an animal model of AD and displayed low uptake in the brain and high uptake in the liver in normal mice. Although additional modifications of the BODIPY scaffold are necessary to improve brain uptake, these results should aid the development of dual functional SPECT/fluorescent probes for the imaging of Ab plaques in the brain. (c) 2010 Elsevier Ltd. All rights reserved.
• Antimicrobial activity of 2-arylfuran derivatives and their structural analogs
  作者：A. F. Oleinik、T. I. Vozyakova、L. N. Filitis、O. V. Okinshevich、G. N. Pershin、V. M. Shestakovskii

  DOI：10.1007/bf00776796

  日期：1984.6
• OLEJNIK, A. F.;VOZYAKOVA, T. I.;FILITIS, L. N.;OKINSHEVICH, O. V.;PERSHIN+, XIM.-FARMATS. ZH., 1984, 18, N 6, 697-699
  作者：OLEJNIK, A. F.、VOZYAKOVA, T. I.、FILITIS, L. N.、OKINSHEVICH, O. V.、PERSHIN+

  DOI：——

  日期：——
• Synthesis and structure–activity relationships of 5-phenylthiophenecarboxylic acid derivatives as antirheumatic agents
  作者：Toshiya Noguchi、Masahiro Hasegawa、Kazuyuki Tomisawa、Morihiro Mitsukuchi

  DOI：10.1016/j.bmc.2003.08.009

  日期：2003.11

  5-(Phenylthiophene)-3-carboxylic acid (2a), a metabolite of esonarimod (1), which was developed as a new antirheumatic drug, was considered as a lead compound for new antirheumatic drugs. A new series of 2a derivatives were synthesized and their characteristic pharmacological effects, that is their antagonistic effect toward interleukin (IL)-1 in mice and the suppressive effect against adjuvant-induced arthritis (AIA) in rats, were evaluated and compared with those of 1. The structure-activity relationships indicated that [5-(4-bromophenyl)- thiophen-3-yl]acetic acid (5d), methyl [5-(4-chlorophenyl)-thiophen-3-yl]acetate acid (5d), and methyl [5-(4-bromophenyl)-thiophen-3-yl]acetate (5i) suppressed AIA more potently than 1 and all of the other synthesized compounds. (C) 2003 Elsevier Ltd. All rights reserved.