3-(2-thienyl)-2-sulfanylpropenoic acid | 29529-84-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 3-(2-thienyl)-2-sulfanylpropenoic acid
• 英文别名: 3-(2-thienyl)-2-sulfanylpropeonic acid；H2tspa；2-Mercapto-3-thien-2-ylpropenoic acid；2-sulfanyl-3-thiophen-2-ylprop-2-enoic acid
• CAS: 29529-84-8
• 化学式: C₇H₆O₂S₂
• 分子量: 186.255
• InChiKey: ABROOERZVAKZQQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  11
• 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：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(2-thienyl)-2-sulfanylpropenoic acid 在 盐酸 、 氯 作用下， 以 1,1,2-三氯乙烷 为溶剂， 反应 4.0h， 生成 噻吩并[3,2-b!噻吩-2-羧酸甲酯
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.

  DOI：

  10.1021/jm00150a023
• 作为产物：
  描述：

  5-(2-噻吩基亚甲基)-2-硫酮噻唑烷-4-酮 在 sodium hydroxide 作用下， 反应 0.5h， 以93 g的产率得到3-(2-thienyl)-2-sulfanylpropenoic acid
  参考文献：
  名称：

  Orally absorbable cephalosporin antibiotics. 2. Structure-activity studies of bicyclic glycine derivatives of 7-aminodeacetoxycephalosporanic acid

  摘要：

  Three positional analogues (4-, 5-, and 7-) of benzothienylglycine and (N-acetylindolinyl)-5-glycine were prepared and coupled to 7-aminodeacetoxycephalosporanic acid (7-ADCA) to give the cephalosporins 17a-c. In addition two isomeric (2,3-b and 3,2-b) thienothiopheneglycines were synthesized and coupled to 7-ADCA to yield cephalosporins 30d and 30e. In vitro testing of these new cephalosporins indicates good activity against Gram-positive bacteria. Against Streptococcus pneumoniae infections compound 25 displayed better mouse protection (both orally and subcutaneously) than cephalexin.

  DOI：

  10.1021/jm00150a023

文献信息

• Au–O Interactions and others in triphenylphosphinegold(<scp>i</scp>) sulfanylpropenoates with diverse structures
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、José Sordo、José M. Varela、Ezequiel M. Vázquez-López

  DOI：10.1039/b307192h

  日期：——

  We investigated the reactions of triphenylphosphinegold(I) chloride in ethanol or methanol with the 3-(2-aryl)-2-sulfanylpropenoic acids H2xspa [x = f, t, p; f = 3-(2-furyl)-, t = 3-(2-thienyl)-, p = 3-phenyl-; spa = 2-sulfanylpropenoato] in 1 ∶ 1 and 2 ∶ 1 mole ratios, and the reactions of diisopropylamine with the 1 ∶ 1 complexes. Compounds of types [Au(PPh3)(Hxspa)], [HQ][Au(PPh3)(xspa)] (HQ =

  我们研究了三苯基膦氯化金（I）在水中的反应。乙醇 或者 甲醇与3-（2-芳基）-2-硫烷基丙二酸H 2 xspa [x = f，t，p; f ＝ 3-（2-呋喃基）-，t ＝ 3-（2-噻吩基）-，p ＝ 3-苯基-；spa = 2-硫烷基丙酸酯]的摩尔比为1：1和2：1，二异丙胺与1：1配合物。分离[Au（PPh 3）（Hxspa）]，[HQ] [Au（PPh 3）（xspa）]（HQ =二异丙基铵）和[（AuPPh 3）2（xspa）]类型的化合物，并进行表征红外，拉曼和FAB 质谱并在1 H，13 C和31 P NMR光谱。（Htspa）2 ·Me 2 CO和配合物[Au（PPh 3）（Hfspa）]（1），[HQ] [Au（PPh 3）（pspa）]（6），[（AuPPh 3）2（fspa）]（7），[（AuPPh 3）2（tspa）]·2MeOH（8 ·2MeOH）和[（AuPPh
• 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
• Synthesis and Characterization of Triphenylphosphinesilver(I) Sulfanylcarboxylates of Types [(AgPPh3)(HL)] and [Ag(PPh3)3(HL)]
  作者：Elena Barreiro、José S. Casas、María D. Couce、Agustín Sánchez、José Sordo、José M. Varela、Ezequiel M. Vázquez-López

  DOI：10.1002/zaac.200700005

  日期：2007.5

  Compounds of types [(AgPPh3)(HL)] and [Ag(PPh3)3(HL)] H2L = H2xspa: x = p (3-phenyl-), t [3-(2-thienyl)-], f [3-(2-furyl)-]; spa = 2-sulfanylpropenoato} were synthesized and characterized by IR, 1H, 13C and 31P NMR spectroscopy and FAB mass spectrometry. The structures of [(AgPPh3)(Htspa)] (2) and [Ag(PPh3)3(Hpspa)] (4) were determined by X-ray diffractometry. Complex 2 has a supramolecular structure

  [(AgPPh3)(HL)] 和 [Ag(PPh3)3(HL)] 类型的化合物 H2L = H2xspa: x = p (3-苯基-), t [3-(2-噻吩基)-], f [3-(2-呋喃基)-]; spa = 2-sulFAnylpropenoato} 被合成并通过 IR、1H、13C 和 31P NMR 光谱和 FAB 质谱进行表征。[(AgPPh3)(Htspa)] (2) 和 [Ag(PPh3)3(Hpspa)] (4) 的结构通过 X 射线衍射测定。配合物 2 具有基于双核单元之间氢键的超分子结构，可以看作是由 Ag(PPh3)(Htspa) 单体通过 Ag-S 键连接形成的，每个单体中的金属原子都被 O,S 螯合。配合物 4 具有单核结构，具有 Ag-S 和 Ag-P 键以及分子内氢键。
• 3-(Aryl)-2-sulfanylpropenoates of mercury(II) and phenylmercury(II)
  作者：José S. Casas、Alfonso Castiñeiras、María D. Couce、Manuel García-Vega、Manuel Rosende、Agustín Sánchez、José Sordo、José M. Varela、Ezequiel M. Vázquez López

  DOI：10.1016/j.poly.2008.04.034

  日期：2008.8

  Compounds [HQ]2[Hg(L)2] and [HQ][PhHg(L)] [where HQ = diisopropylammonium cation; L = pspa, fspa, tspa, where p = 3-(phenyl), f = 3-(2-furyl), t = 3-(2-thienyl), and spa = 2-sulfanylpropenoato] have been prepared by the reaction of mercury(II) acetate or phenylmercury(II) acetate with the corresponding acid in the presence of diisopropylamine in ethanol. The compounds have been characterized by elemental

  化合物[HQ] 2 [Hg（L）2 ]和[HQ] [PhHg（L）] [其中HQ =二异丙基铵阳离子；通过反应制备了L ＝ pspa，fspa，tspa，其中p ＝ 3-（苯基），f ＝ 3-（2-呋喃基），t ＝ 3-（2-噻吩基）和spa ＝ 2-硫烷基丙酸酯）。在乙醇中的二异丙胺存在下，用乙酸将乙酸汞（II）或乙酸苯汞（II）与相应的酸反应。通过元素分析，FAB质谱，IR和NMR（1 H，13 C）光谱对化合物进行了表征。[HQ] 2 [Hg（L）2 ]化合物的晶体结构显示存在二异丙基铵阳离子和[Hg（L）2 ] 2-阴离子。在每个阴离子中，Hg原子都处于HgO 2 S 2环境中，这可以描述为nido -tbp。[HQ] [PhHg（L）]化合物的晶体结构显示存在二异丙基铵阳离子和[PhHg（L）] -阴离子，其中Hg原子采用HgCOS扭曲的T环境。NMR数据表明，通过X射线衍射法测定的固体中的配体L
• 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。