5-(4-溴苯基)噻吩-2-羧酸 | 40133-13-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 5-(4-溴苯基)噻吩-2-羧酸
• 英文名称: 5-(4-bromophenyl)thiophene-2-carboxylic acid
• CAS: 40133-13-9
• 化学式: C₁₁H₇BrO₂S
• mdl: MFCD07375953
• 分子量: 283.145
• InChiKey: VZLAAWUSRTYBGI-UHFFFAOYSA-N

物化性质

• 沸点：
  438.8±35.0 °C(Predicted)
• 密度：
  1.637±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  1. 摩尔折射率：63.84
  2. 摩尔体积（m³/mol）：172.9
  3. 等张比容（90.2K）：476.4
  4. 表面张力（dyne/cm）：57.6
  5. 极化率：25.31
  6. 介电常数：未确定

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(4-溴苯基)噻吩-2-羧酸 在 六甲基磷酰三胺 、 lithium aluminium tetrahydride 、 氯化亚砜 、 硫酸 作用下， 以 四氢呋喃 、 乙醚 、 甲苯 为溶剂， 反应 7.0h， 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-甲醛 在 sodium hydroxide 、 silver(l) oxide 作用下， 以 水 为溶剂， 以76%的产率得到5-(4-溴苯基)噻吩-2-羧酸
  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

• Antifungal Application of Rosin Derivatives from Renewable Pine Resin in Crop Protection
  作者：Pan Tao、Chengyu Wu、Jin Hao、Yanqing Gao、Xiaohua He、Jian Li、Shibin Shang、Zhanqian Song、Jie Song

  DOI：10.1021/acs.jafc.0c00562

  日期：2020.4.8

  metabolism. Furthermore, QSAR and SAR studies revealed that charge distribution of rosin-based amides derivatives have a key role in the antifungal activity through the hydrogen bonding, conjugation, and electrostatic interaction between the compounds and the receptors of the target. To sum up, this study contributes to the development of rosin-based antifungal agents with a novel structure and preferable

  在当前的工作中，我们从天然产物松香中合成了两个系列的脱氢松香酰胺衍生物，并评估了它们对ValSA mali，Phytophthora capsici，Botrytis cinerea，Sclerotiania sclerotiorum和FuSArium oxysporum的抗真菌作用。体外和体内抗真菌活性结果表明，含噻吩杂环的松香基酰胺化合物对灰葡萄孢的抑制作用更好。尤其是，化合物5b（5-氟-2-噻吩脱氢松香基酰胺）对EC的灰葡萄孢表现出优异的抗真菌性能。50为0.490 mg / L，低于阳性对照戊硫吡py（0.562 mg / L）。生理生化研究表明，化合物5b对灰葡萄孢的主要作用机制是改变菌丝体形态，增加细胞膜通透性，并抑制呼吸代谢中的TCA途径。此外，QSAR和SAR研究表明，松香类酰胺衍生物的电荷分布通过化合物与目标受体之间的氢键键合，结合和静电相互作用，在抗真菌活性中起着关键
• Small-Molecule Thioesters as SARS-CoV-2 Main Protease Inhibitors: Enzyme Inhibition, Structure–Activity Relationships, Antiviral Activity, and X-ray Structure Determination
  作者：Thanigaimalai Pillaiyar、Philipp Flury、Nadine Krüger、Haixia Su、Laura Schäkel、Elany Barbosa Da Silva、Olga Eppler、Thales Kronenberger、Tianqing Nie、Stephanie Luedtke、Cheila Rocha、Katharina Sylvester、Marvin R.I. Petry、James H. McKerrow、Antti Poso、Stefan Pöhlmann、Michael Gütschow、Anthony J. O’Donoghue、Yechun Xu、Christa E. Müller、Stefan A. Laufer

  DOI：10.1021/acs.jmedchem.2c00636

  日期：2022.7.14

  The main protease (Mpro, 3CLpro) of SARS-CoV-2 is an attractive target in coronaviruses because of its crucial involvement in viral replication and transcription. Here, we report on the design, synthesis, and structure–activity relationships of novel small-molecule thioesters as SARS-CoV-2 Mpro inhibitors. Compounds 3w and 3x exhibited excellent SARS-CoV-2 Mpro inhibition with kinac/Ki of 58,700 M–1

  SARS-CoV-2 的主要蛋白酶（M pro、 3CL pro）是冠状病毒中一个有吸引力的靶点，因为它在病毒复制和转录中发挥着至关重要的作用。在这里，我们报告了作为 SARS-CoV-2 M前抑制剂的新型小分子硫酯的设计、合成和构效关系。化合物3w和3x表现出优异的 SARS-CoV-2 M pro抑制作用，k inac / K i分别为 58,700 M –1 s –1 ( K i = 0.0141 μM) 和 27,200 M –1 s –1 ( K i = 0.0332 μM) ， 分别。在 Calu-3 和 Vero76 细胞中，化合物3h、3i 、 3l、3r、3v、3w和3x显示纳摩尔范围内的抗病毒活性，且没有宿主细胞毒性。完成了3w和3af与 SARS-CoV-2 M pro的共结晶，X 射线结构显示与蛋白酶的催化 Cys145 残基共价结合。有效的 SARS-CoV-2 Mpro
• BEATON C. M.; CHAPMAN N. B.; CLARKE K.; WILLIS J. M., J. CHEM. SOC. PERKIN TRANS., PART 1 <JCPK-BH>, 1976, NO 22, 2355-2363
  作者：BEATON C. M.、 CHAPMAN N. B.、 CLARKE K.、 WILLIS J. M.

  DOI：——

  日期：——