3-(2-chlorophenyl)-2-sulfanylpropenoic acid | 7282-55-5

• 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: 3-(2-chlorophenyl)-2-sulfanylpropenoic acid
• 英文别名: (2-chlorophenyl)-2-mercaptoacrylic acid；H2Clpspa；3-(2-Chlorophenyl)-2-sulfanylprop-2-enoic acid
• CAS: 7282-55-5；7282-56-6；5765-72-0
• 化学式: C₉H₇ClO₂S
• 分子量: 214.672
• InChiKey: MDRWHBKNJMNZNG-UHFFFAOYSA-N

物化性质

• 熔点：
  110 °C
• 沸点：
  372.8±42.0 °C(Predicted)
• 密度：
  1.423±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：

  氯(三乙基膦)金(I) 、 3-(2-chlorophenyl)-2-sulfanylpropenoic acid 在 NaOH 作用下， 以 甲醇 、 水 为溶剂， 以82%的产率得到bis(triethylphosphine)digold(I) 3-(2-chlorophenyl)-2-sulfanylpropenoate
  参考文献：
  名称：

  Synthesis, Structural Characterization, and Antiinflammatory Activity of Triethylphosphinegold(I) Sulfanylpropenoates of the Type [(AuPEt₃)₂xspa] [H₂xspa = 3-(Aryl)-2-sulfanylpropenoic acid]: an (H₂O)₆ Cluster in the Lattice of the Complexes [(AuPEt₃)₂xspa]·3H₂O

  摘要：

  Gold complexes of the type [(AuPEt3)(2)xspa] were prepared by reacting AuPEt3Cl in basic media with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x = p, Clp, -o-mp, -p-mp, -o-hp, -p-hp, diBr-o-hp, f, t, -o-py; p = 3-phenyl, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, -diBr-o-hp = 3-(3,5- dibromo-2-hydroxyphenyl)-, t = 3-(2-furyl)-, t = 3-(2-thienyl)-, -o-py = 3-(2-pyridyl); spa = 2-sulfanylpropenoato], and 2-cyclopentylidene-2-sulfanylacetic acid (H(2)cpa). The complexes were characterized by spectroscopic methods (IR, H-1, C-13 and P-31 NMR) and mass spectrometry, and the complexes [(AuPEt3)(2)pspa]center dot 3H(2)O, [(AuPEt3)(2)-p-hpspa]center dot 3H(2)O, [(AuPEt3)(2)tspa)]center dot 3H(2)O, and [(AuPEt3)(2)-o-hpspa] by X-ray diffractometry. The crystals of the first three complexes contain (H2O)(6) clusters hydrogen bonded to [(AuPEt3)2xspa]2 dimer units, whereas in the -o-hpspa derivative the hydrogen bonds are between the monomer [(AuPEt3)2-o-hpspa] units. The antiinflammatory activity of the complexes against plantar edema induced by carrageenan in rats is generally significant, with the values for the o-hpspa and tspa derivatives being particularly high.

  DOI：

  10.1021/ic800314p
• 作为产物：
  描述：

  (E,Z)-5-(2-chlorophenylmethylene)-4-oxo-2-thioxothiazolidine 在 sodium hydroxide 、 盐酸 作用下， 以81%的产率得到3-(2-chlorophenyl)-2-sulfanylpropenoic acid
  参考文献：
  名称：

  三苯基膦银（I）硫烷基羧酸盐的新结构特征。

  摘要：

  我们研究了三苯基膦，硝酸银和3-（芳基）-2-硫烷基丙酸H（2）xspa以1.5：1：1摩尔比的混合物在氯仿/水中的反应，其中在酸命名法中，spa = 2-硫烷基丙酸酯并且x = p，Clp，mp，diBr-o-hp或f，其中p = 3-苯基-，Clp = 3-（2-氯苯基）-，mp = 3-甲氧基苯基-，diBr-o-hp = 3- （3，5-二溴-2-羟基苯基）-和f ＝ 3-（2-呋喃基）-。化合物[Ag（PPh（3））（Hpspa）]（1），[（AgPPh3）2（xspa）] [x = Clp（2），o-mp（3），p-mp（4），diBr -o-hp（5）和f（6）]和[Ag（PPh3）3（Hfspa）]（7）进行了分离，除7个以外的所有化合物均通过IR，拉曼和FAB质谱以及1H，13C和31P表征NMR光谱。化合物6还通过（13）C CP / MAS表征，化合物1和6通过（109）Ag

  DOI：

  10.1039/b501309g

文献信息

• 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。
• Synthesis and antimicrobial activities of gold(I) sulfanylcarboxylates
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、Rafael Seoane、Antonio Perez-Estévez、José Sordo

  DOI：10.1007/s13404-011-0040-7

  日期：2012.3

  Reaction of NaAuCl4·H2O and thiodiglycol (1:3 molar ratio) with 3-(aryl)-2-sulfanylpropenoic acids, H2xspa = [x:p = 3-phenyl-, f = 3-(2-furyl)-, t = 3-(2-thienyl)-, o-py = 3-(2-pyridyl)-, Clp = 3-(2-chlorophenyl)-, -o-mp = 3-(2-methoxyphenyl)-, -p-mp = 3-(4-methoxyphenyl)-, -o-hp = 3-(2-hydroxyphenyl)-, -p-hp = 3-(4-hydroxyphenyl)-, diBr-o-hp = 3-(3,5-dibromo-2-hydroxyphenyl)] and 2-cyclopentylidene-2-sulfanylacetic

  NaAuCl4·H2O 和硫二甘醇（1:3 摩尔比）与 3-(芳基)-2-硫烷基丙烯酸反应，H2xspa = [x:p = 3-苯基-，f = 3-(2-呋喃基)-，t = 3-(2-噻吩基)-, o-py = 3-(2-吡啶基)-, Clp = 3-(2-氯苯基)-, -o-mp = 3-(2-甲氧基苯基)-, -p -mp = 3-(4-甲氧基苯基)-, -o-hp = 3-(2-羟基苯基)-, -p-hp = 3-(4-羟基苯基)-, diBr-o-hp = 3-(3 ,5-二溴-2-羟基苯基)] 和 2-亚环戊基-2-硫烷基乙酸 (H2cpa) 以 1:1 的金属/配体摩尔比得到 [Au(Hxspa)] 或 [Au(Hcpa)] 类型的化合物. 这些化合物与二异丙胺反应得到 [HQ][Au(xspa)] 或 [HQ][Au(cpa)]（HQ = 二异丙基铵），然后与 NaOH 反应得到
• Chemical and in vitro study of the potential of 3-(aryl)-2-sulfanylpropenoic acids and their Zn(ii) complexes as protective agents against cadmium toxicity
  作者：J. S. Casas、E. E. Castellano、M. D. Couce、M. García-Vega、A. Sánchez、A. Sánchez-González、J. Sordo、J. M. Varela、E. M. Vázquez López

  DOI：10.1039/b918361b

  日期：——

  The free H2xspa ligands [xspa = pspa, Clpspa, tspa or fspa where p = 3-(phenyl), Clp = 3-(2-chlorophenyl), t = 3-(2-thienyl), f = 3-(2-furyl) and spa = 2-sulfanylpropenoato], their Zn(II) complexes of formula [HQ]2[Zn(xspa)2] (HQ = diisopropylammonium) and the Cd(II) equivalents were prepared and characterized by elemental analysis and by IR, Raman and NMR (1H, 13C) spectroscopy. X-Ray studies of the crystal structures of [HQ]2[Zn(pspa)2], [HQ]2[Zn(Clpspa)2], [HQ]2[Zn(tspa)2] and [HQ]2[Zn(fspa)2] show that the zinc atom is coordinated to two O atoms and two S atoms of the ligands in a distorted tetrahedral ZnO2S2 environment. In the structures of [HQ]2[Cd(pspa)2] and [HQ]2[Cd(Clpspa)2] the cadmium atom is coordinated to three S atoms and two carboxylato O atoms of the ligands in a distorted trigonal bipyramidal environment. The interchange of ligands between Zn(II) and Cd(II) was studied by 113Cd NMR spectroscopy. The in vitro protective effect of H2xspa and their Zn(II) complexes against Cd toxicity was investigated using the human hepatocarcinoma HepG2 cell line and the pig renal proximal tubule LLC-PK1 cell line. The incorporation of Zn(II) was found to be relevant in the case of H2pspa, with an increase observed in the cell viability of the LCC-PK1 cells with respect to the value for the free ligand.

  游离 H2xspa 配体 [xspa = pspa、Clpspa、tspa 或 fspa，其中 p = 3-(苯基)、Clp = 3-(2-氯苯基)、t = 3-(2-噻吩基)、f = 3-(2-呋喃基) 和 spa = 2-硫烷基丙烯酸]，它们的 Zn(II) 络合物，结构式为 [HQ]2[Zn(xspa)2] (HQ = 二异丙基铵) 和 Cd(II) 等价物的制备和表征通过元素分析以及红外、拉曼和核磁共振 (1H, 13C) 光谱进行。 [HQ]2[Zn(pspa)2]、[HQ]2[Zn(Clpspa)2]、[HQ]2[Zn(tspa)2] 和 [HQ]2[ 晶体结构的 X 射线研究Zn(fspa)2]表明，在扭曲的四面体ZnO2S2环境中，锌原子与配体的两个O原子和两个S原子配位。在[HQ]2[Cd(pspa)2]和[HQ]2[Cd(Clpspa)2]的结构中，镉原子在扭曲的三角双锥环境中与配体的三个S原子和两个羧基O原子配位。通过 113Cd NMR 光谱研究了 Zn(II) 和 Cd(II) 之间的配体互换。使用人肝癌 HepG2 细胞系和猪肾近曲小管 LLC-PK1 细胞系研究了 H2xspa 及其 Zn(II) 复合物对 Cd 毒性的体外保护作用。发现 Zn(II) 的掺入与 H2pspa 的情况相关，相对于游离配体的值，LCC-PK1 细胞的细胞活力有所增加。
• Andreasch, Monatshefte fur Chemie, 1928, vol. 49, p. 125
  作者：Andreasch

  DOI：——

  日期：——
• Mono and dinuclear phosphinegold(I) sulfanylcarboxylates: Influence of nuclearity and substitution of PPh 3 for PEt 3 on cytotoxicity
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、Angeles Sánchez-Gonzalez、José Sordo、Ezequiel M. Vázquez-López

  DOI：10.1016/j.jinorgbio.2014.05.010

  日期：2014.9

  Gold complexes of the type [Au(PEt3)(Hxspa)] were prepared by reacting triethylphosphinegold(I) chloride in ethanol/water (8:1) with the 3-(aryl)-2-sulfanylpropenoic acids H(2)xspa [x = p = 3-phenyl-; f = 3-(2-furyl)-; t = 3-(2-thienyl)-; py = 3-(2-pyridyl); Clp = 3-(2-Chlorophenyl)-; -o-mp = 3-(2-methoxyphenyl)-; -p-mp = 3-(4-methoxyphenyl)-; -o-hp = 3-(2-hydroxyphenyl)-; -p-hp = 3-(4-hydroxyphenyl)-; -diBr-o-hp = 3-(3,5-dibromo-2-hidroxyphenyl-); spa = 2-sulfanylpropenoato] or 2-cyclopentylidene-2-sulfanylacetic acid (H(2)cpa) and KOH in a 1:1:1 mole ratio. The compounds were characterized by IR spectroscopy and FAB mass spectrometry and by H-1, C-13 and P-31 NMR spectroscopy. The in vitro antitumor activity of these and of the previously described dinuclear [(AuPEt3)(2)(xspa)] complexes against the HeLa-229, A2780 and A2780cis cell lines was determined and compared with those of the analogous PPh3 complexes. The results show that the substitution of the PPh3 ligand by PEt3 is particularly effective in increasing the cytotoxicity of the dinuclear [(AuPR3)(2)(xspa)] complexes, giving rise to compounds that are significantly more active than cisplatin against the aforementioned cell lines. In addition, and as a preliminary test for nephrotoxicity, the cytotoxicity of the most active compounds against the normal renal LCC-PK1 cell line was evaluated and compared with that of cisplatin. (C) 2014 Elsevier Inc. All rights reserved.