1-mercapto-2-(p-bromophenyl)cinnamic acid | 5765-89-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-mercapto-2-(p-bromophenyl)cinnamic acid
• 英文别名: (4-bromophenyl)-2-mercaptoacrylic acid；3-(4-bromophenyl)-2-sulfanylprop-2-enoic acid
• CAS: 5765-89-9
• 化学式: C₉H₇BrO₂S
• 分子量: 259.123
• InChiKey: QXTGSYHLHVXDPD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  lead(II) acetate trihydrate 、 1-mercapto-2-(p-bromophenyl)cinnamic acid 以 乙醇 、 水 为溶剂， 以67%的产率得到
  参考文献：
  名称：

  3-(4-X-Phenyl)-2-sulfanylpropenoic Acids 与 PbIIIon 的螯合行为 - 2:1 配合物超分子结构中孤电子对的相关性

  摘要：

  3-(4-X-苯基)-2-硫烷基丙烯酸[H2(X-pspa); X = –F, –Cl, –Br, –I, –OCH3, –OCF3, –OH] 与醋酸铅 (II) 在酒精介质中的探索是为了寻找新的 Pb2+ 离子螯合剂。直接反应以 67 (X = –Br) 到 95% (X = –OCH3) 的产率提供了 [Pb(X-pspa)] 配合物。当在二异丙胺 (Q) 存在下进行 PbII/H2(X-pspa) 反应时，得到衍生物 [HQ]2[Pb(X-pspa)2] (X = Cl, Br)。所有配合物均通过光谱（FAB-MS 和 ESI-MS）和光谱（IR、1H 和 13C NMR 光谱）方法表征，这些方法表明配体与二甲亚砜中金属离子的 O、S 配位的持久性(DMSO) 溶液。H2(Cl-pspa), [HQ]2[Pb(Cl-pspa)2] 和 [HQ]2[Pb(Br-pspa)2] 也通过

  DOI：

  10.1002/ejic.201300633
• 作为产物：
  描述：

  N-(4-bromobenzylidene)aniline 在 盐酸 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 生成 1-mercapto-2-(p-bromophenyl)cinnamic acid
  参考文献：
  名称：

  将杂环CH酸加到甲亚胺的C = N键上

  摘要：

  DOI：

  10.1007/bf00503664

文献信息

• [EN] BETA LACTAMASE INHIBITORS<br/>[FR] INHIBITEURS DE LA BÊTA-LACTAMASE
  申请人：ISIS INNOVATION

  公开号：WO2016051133A1

  公开（公告）日：2016-04-07

  A compound which is a thienolate of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein R1, R3, Ring A1, n and Ring A2 are as defined herein, are found to be useful in inhibiting metallo-beta-lactamase and therefore in potentiating the activity of beta lactamase antibiotics. The compound can be used alone or in combination with a rhodanine of formula (II) or a pharmaceutically acceptable salt thereof: (II) wherein R3, Ring A1, n, Ring A2, L and Ring B are as defined herein. Treatment or prevention of bacterial infection in combination with beta-lactam antibiotic agents is also provided.

  一种化合物，其为式（I）的硫代醇酸盐或其药用可接受的盐：（I）其中R1、R3、环A1、n和环A2如本文所定义，被发现在抑制金属β-内酰胺酶方面有用，因此可以增强β-内酰胺酶抗生素的活性。该化合物可以单独使用或与式（II）的罗丹啉或其药用可接受的盐结合使用：（II）其中R3、环A1、n、环A2、L和环B如本文所定义。还提供了与β-内酰胺抗生素联合治疗或预防细菌感染。
• Structure activity relationship studies on rhodanines and derived enethiol inhibitors of metallo-β-lactamases
  作者：Dong Zhang、Marios S. Markoulides、Dmitrijs Stepanovs、Anna M. Rydzik、Ahmed El-Hussein、Corentin Bon、Jos J.A.G. Kamps、Klaus-Daniel Umland、Patrick M. Collins、Samuel T. Cahill、David Y. Wang、Frank von Delft、Jürgen Brem、Michael A. McDonough、Christopher J. Schofield

  DOI：10.1016/j.bmc.2018.02.043

  日期：2018.7

  antibiotics. We report studies on enethiol containing MBL inhibitors, which were prepared by rhodanine hydrolysis. The enethiols inhibit MBLs from different subclasses. Crystallographic analyses reveal that the enethiol sulphur displaces the di-Zn(II) ion bridging 'hydrolytic' water. In some, but not all, cases biophysical analyses provide evidence that rhodanine/enethiol inhibition involves formation

  金属-β-内酰胺酶 (MBL) 使细菌对几乎所有类别的 β-内酰胺抗生素产生耐药性。我们报告了通过绕丹宁水解制备的含烯硫醇的 MBL 抑制剂的研究。烯硫醇抑制不同亚类的 MBL。晶体分析表明，烯硫醇硫取代了桥接“水解”水的二锌 (II) 离子。在某些（但不是全部）情况下，生物物理分析提供证据表明绕丹宁/烯硫醇抑制涉及三元 MBL 烯硫醇绕丹宁复合物的形成。结果证明低分子量活性位点 Zn(II) 螯合化合物如何抑制一系列临床相关的 MBL，并为绕丹宁水解为 MBL 蛋白折叠以及其他金属酶的有效抑制剂的潜力提供了额外的证据，也许有助于绕丹宁​​的复杂生物效应。结果意味着任何使用绕丹宁（和相关支架）作为抑制剂的药物化学研究当然应该包括对其水解产物的测试。
• Beta lactamase inhibitors
  申请人：Oxford University Innovation Limited

  公开号：US10351525B2

  公开（公告）日：2019-07-16

  A compound which is a thienolate of formula (I) or a pharmaceutically acceptable salt thereof: (I) wherein R1, R3, Ring A1, n and Ring A2 are as defined herein, are found to be useful in inhibiting metallo-beta-lactamase and therefore in potentiating the activity of beta lactamase antibiotics. The compound can be used alone or in combination with a rhodanine of formula (II) or a pharmaceutically acceptable salt thereof: (II) wherein R3, Ring A1, n, Ring A2, L and Ring B are as defined herein. Treatment or prevention of bacterial infection in combination with beta-lactam antibiotic agents is also provided.

  式 (I) 的噻吩酸盐或其药学上可接受的盐：(I) 其中 R1、R3、环 A1、n 和环 A2 如本文所定义，该化合物可抑制金属-β-内酰胺酶，从而增强β-内酰胺酶抗生素的活性。该化合物可单独使用，也可与式 (II) 的罗丹宁或其药学上可接受的盐结合使用：(II) 其中 R3、环 A1、n、环 A2、L 和环 B 如本文所定义。还提供了与β-内酰胺类抗生素制剂联合使用治疗或预防细菌感染的方法。
• New diorganolead(IV) sulfanylpropenoates: Synthesis, characterization and analysis of their evolution in DMSO solution
  作者：José S. Casas、M. Victoria Castaño、María D. Couce、Agustín Sánchez、José Sordo、M. Dolores Torres、Ezequiel M. Vázquez López

  DOI：10.1016/j.jorganchem.2015.04.036

  日期：2015.8

  The diorganolead(IV) sulfanylpropenoates [R2Pb(X-pspa)] R = Me, Ph; H-2(X-pspa) = 3-(4-X-phenyl)-2-sulfanylpropenoic acids; X = F, Cl, Br, I, CH3O, CF3O, HO} and [HQ](2)[Ph2Pb(X-pspa)(2)] (X = F, CH3O, HO; Q = diisopropylamine) were prepared. The structures of H-2(Br-pspa) and [HQ](2)[Ph2Pb(CH3O-pspa)(2)], 2H(2)O were fully characterized in the solid state using X-ray diffraction.All sulfanylpropenoates and free sulfanylpropenoic acids are fairly soluble in DMSO. The acids are in general oxidised to the corresponding disulfide by DMSO except H-2(I-pspa), a selective calpain inhibitor, which evolves to form two decomposition products neither of which is probably the disulfide. From the [Ph2Pb(X-pspa)] solutions in DMSO, several compounds have been isolated and identified by X-ray diffraction. Those with [Ph2Pb(Cl-pspa)(DMSO)] and [Ph2Pb(X-pspa)(DMSO)]center dot DMSO (X = Br, CH3O, F3CO) stoichiometries consist of molecules loosely associated in dimers. However, in solid [Ph2Pb(HO-pspa)(DMSO)]center dot 2DMSO, the [Ph2Pb(HO-pspa)(DMSO)] molecules are assembled in chains along the x axis. NMR and ESI-MS measurements in freshly prepared [Ph2Pb(X-pspa)] solutions are compatible with the presence of dimeric or polymeric species such as those isolated in the solid state. However, the NMR spectra of [Me2Pb(X-pspa)] revealed that these compounds decompose quickly in DMSO due to redistribution reactions suffered by the organometallic moiety and the concomitant partial decomposition of the sulfanylpropenoates. (c) 2015 Elsevier B.V. All rights reserved.
• EP3200776A1
  申请人：——

  公开号：EP3200776A1

  公开（公告）日：2017-08-09