thioglycolic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 硫代羧酸及其衍生物
• 英文名称: thioglycolic acid ethyl ester
• 英文别名: ethyl thioglycolate；Ethylthioglykolat；S-ethyl 2-hydroxyethanethioate
• 化学式: C₄H₈O₂S
• 分子量: 120.172
• InChiKey: AKWUSYGCEGHCDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-5-硝基苯甲腈 、 thioglycolic acid ethyl ester 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 以93%的产率得到ethyl (3-amino-5-nitrobenzothiophen)-2-carboxylate
  参考文献：
  名称：

  High affinity ligands and potent antagonists for the α1D-adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives

  摘要：

  A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N(1)-methyl-N(5)-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N(1)-(phenylmethyl)pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.

  DOI：

  10.1016/j.ejmech.2014.06.057
• 作为试剂：
  描述：

  2-[7-chloro-4-(3-formylphenyl)-6-methyl-2-oxo-2H-chromen-3-yl]-N-[4-chloro-2-(trifluoromethyl)phenyl]acetamide 在 sodium tetrahydroborate 、 盐酸 、 氯化亚砜 、 thioglycolic acid ethyl ester 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 为溶剂， 反应 0.58h， 以80%的产率得到ethyl ({3-[7-chloro-3-(2-{[4-fluoro-2-(trifluoromethyl)phenyl]amino}-2-oxoethyl)-6-methyl-2-oxo-2H-chromen-4-yl]benzyl}thio) acetate
  参考文献：
  名称：

  EP1471064

  摘要：

  公开号：

文献信息

• Small-Molecule Inhibitors of the TLR3/dsRNA Complex
  作者：Kui Cheng、Xiaohui Wang、Hang Yin

  DOI：10.1021/ja111312h

  日期：2011.3.23

  The protein-RNA interface has been regarded as "undruggable" despite its importance in many biological processes. The toll-like receptor 3 (TLR3)/double-stranded RNA (dsRNA) complex provides an exciting target for a number of infectious diseases and cancers. We describe the development of a series of small-molecule probes that were shown to be competitive inhibitors of dsRNA binding to TLR3 with high affinity and specificity. In a multitude of assays, compound 4a was profiled as a potent antagonist to TLR3 signaling and also repressed the expression of downstream signaling pathways mediated by the TLR3/dsRNA complex, including TNF-alpha and IL-1 beta.
• Metabolic stability optimization and metabolite identification of 2,5-thiophene amide 17β-hydroxysteroid dehydrogenase type 2 inhibitors
  作者：Emanuele M. Gargano、Enrico Perspicace、Nina Hanke、Angelo Carotti、Sandrine Marchais-Oberwinkler、Rolf W. Hartmann

  DOI：10.1016/j.ejmech.2014.09.061

  日期：2014.11

  17 beta-HSD2 is a promising new target for the treatment of osteoporosis. In this paper, a rational strategy to overcome the metabolic liability in the 2,5-thiophene amide class of 17 beta-HSD2 inhibitors is described, and the biological activity of the new inhibitors. Applying different strategies, as lowering the cLogP or modifying the structures of the molecules, compounds 27, 31 and 35 with strongly improved metabolic stability were obtained. For understanding biotransformation in the 2,5-thiophene amide class the main metabolic pathways of three properly selected compounds were elucidated. (C) 2014 Elsevier Masson SAS. All rights reserved.
• High affinity ligands and potent antagonists for the α1D-adrenergic receptor. Novel 3,8-disubstituted [1]benzothieno[3,2-d]pyrimidine derivatives
  作者：Giuseppe Romeo、Loredana Salerno、Valeria Pittalà、Maria N. Modica、Maria A. Siracusa、Luisa Materia、Michela Buccioni、Gabriella Marucci、Kenneth P. Minneman

  DOI：10.1016/j.ejmech.2014.06.057

  日期：2014.8

  A new series of high affinity ligands and antagonists for the α1D-adrenergic receptor (AR) has been discovered. New molecules present a [1]benzothieno[3,2-d]pyrimidin-2,4(1H,3H)-dione or a [1]benzothieno[3,2-d]pyrimidin-4(3H)-one scaffold and bear a 2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl moiety in the 3-position and various amide substituents in the 8-position. In binding assays at the three human cloned α1A-, α1B-, and α1D-AR subtypes, they showed high affinity values, particularly for the α1D-AR subtype. Compound 22 (RX18), N(1)-methyl-N(5)-[3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2,4-dioxo-1,2,3,4-tetrahydro[1]benzothieno[3,2-d]pyrimidin-8-yl]-N(1)-(phenylmethyl)pentanediamide, was the most interesting in the series displaying very high affinity (pKi = 10.25) and potent antagonism (pKb = 9.15) when tested in a functional assay at the α1D-AR.