3-p-hydroxyphenyl-2-mercaptoacrylic acid | 29529-80-4

• 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-p-hydroxyphenyl-2-mercaptoacrylic acid
• 英文别名: 4-Hydroxy-α-mercapto-zimtsaeure；3-(4-hydroxyphenyl)-2-sulfanylpropenoic acid；H2-p-hpspa；3-(4-Hydroxyphenyl)-2-sulfanylprop-2-enoic acid；3-(4-hydroxyphenyl)-2-sulfanylprop-2-enoic acid
• CAS: 29529-80-4
• 化学式: C₉H₈O₃S
• 分子量: 196.227
• InChiKey: FZQDISDUXJNJPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 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：
  58.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-p-hydroxyphenyl-2-mercaptoacrylic acid 在 氢氧化钾 、 potassium carbonate 、 乙酰氯 作用下， 以 甲醇 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 62.0h， 生成 methyl (Z)-2-β-D-glucopyranosylthio-3-p-benzyloxyphenylacrylate
  参考文献：
  名称：

  Synthetic inhibitor of leaf-closure that reveals the biological importance of leaf-movement for the survival of leguminous plants

  摘要：

  Nyctinasty has been known since pre-Christian era, whereas the question 'Why do leguminous plants sleep?' has always puzzled scientists. This paper gives a clue to the historical mystery: by using synthetic inhibitors for nyctinasty, we found that legumes cannot survive without nyctinasty. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00906-2
• 作为产物：
  描述：

  5-[(4-Hydroxy-phenyl)-phenylamino-methyl]-3-phenyl-2-thioxo-thiazolidin-4-one 在 氢氧化钾 作用下， 以 水 为溶剂， 以34%的产率得到3-p-hydroxyphenyl-2-mercaptoacrylic 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

• 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
• The Chelating Behaviour of 3‐(4‐X‐Phenyl)‐2‐sulfanylpropenoic Acids with the Pb ^II Ion – Relevance of the Lone Electron Pair in the Supramolecular Structures of the 2:1 Complexes
  作者：José S. Casas、M. Victoria Castaño、Maria D. Couce、Agustín Sánchez、José Sordo、M. Dolores Torres、Ezequiel M. Vázquez López

  DOI：10.1002/ejic.201300633

  日期：2013.10

  enoic acids [H2(X-pspa); X = –F, –Cl, –Br, –I, –OCH3, –OCF3, –OH] with lead(II) acetate in an alcoholic medium was explored in the search for new chelating agents for the Pb2+ ion. The direct reactions afforded [Pb(X-pspa)] complexes in yields of 67 (X = –Br) to 95 % (X = –OCH3). When the PbII/H2(X-pspa) reaction was performed in the presence of diisopropylamine (Q), the derivatives [HQ]2[Pb(X-pspa)2]

  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
• 10.1039/d4md00157e
  作者：Kamps, Jos J. A. G.、Zhang, Dong、Claridge, Timothy D. W.、Schofield, Christopher J.

  DOI：10.1039/d4md00157e

  日期：——

  to enethiols which are inhibitors of metallo-enzymes, such as metallo β-lactamases. We report that in DMSO, rhodanine derived enethiols undergo dimerisations to give 1,3-dithiolanes and mixed disulfides. The results highlight the potential of rhodanines and enethiols to give multiple products. They suggest that where possible DMSO should be avoided as a storage solvent for rhodanines/enethiols and

  绕丹宁被描述为“难以进展”的药用化合物，尽管其中一种绕丹宁用于治疗糖尿病，其他绕丹宁正在临床开发中。绕丹宁可以水解成烯硫醇，烯硫醇是金属酶（例如金属 β-内酰胺酶）的抑制剂。我们报道，在 DMSO 中，绕丹宁衍生的烯硫醇经历二聚化，得到 1,3-二硫戊环和混合二硫化物。结果凸显了绕丹宁和烯硫醇产生多种产品的潜力。他们建议，在可能的情况下，应避免使用 DMSO 作为绕丹宁/烯硫醇的储存溶剂，并强调需要对生物学相关的烯硫醇/混合二硫化物进行进一步研究。
• 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
  作者：Elena Barreiro、José S. Casas、María D. Couce、Ángeles Gato、Agustín Sánchez、José Sordo、José M. Varela、Ezequiel M. Vázquez López

  DOI：10.1021/ic800314p

  日期：2008.7.1

  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.
• 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.