ethyl 2-(6-ethoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2-(6-ethoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate
• 英文别名: (6-ethoxy-benzothiazol-2-yl)-oxalamic acid ethyl ester；N-(6-Aethoxybenzthiazol-2-yl)-oxamidsaeureaethylester；Ethyl [(6-ethoxy-1,3-benzothiazol-2-yl)carbamoyl]formate；ethyl 2-[(6-ethoxy-1,3-benzothiazol-2-yl)amino]-2-oxoacetate
• 化学式: C₁₃H₁₄N₂O₄S
• mdl: MFCD02671785
• 分子量: 294.331
• InChiKey: JBKKYTGZESQHRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-氨基-6-乙氧基苯并噻唑 、 草酰氯单乙酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以44%的产率得到ethyl 2-(6-ethoxybenzo[d]thiazol-2-ylamino)-2-oxoacetate
  参考文献：
  名称：

  Synthesis, in vitro and in silico screening of ethyl 2-(6-substituted benzo[d]thiazol-2-ylamino)-2-oxoacetates as protein-tyrosine phosphatase 1B inhibitors

  摘要：

  The ethyl 2-(6-substituted benzo[d]thiazol-2-ylamino)-2-oxoacetate derivatives (OX 1-9) were prepared using a one-step reaction. The in vitro inhibitory activity of the compounds against protein tyrosine phosphatase 1B (PTP-1B) was evaluated. Compounds OX-(1, 6 and 7) were rapid reversible (mixed-type) inhibitors of PTP-1B with IC50 values in the low micro-molar range. The most active compounds OX-(1, 6 and 7) were docked into the crystal structure of PTP-1B. Docking results indicate potential hydrogen bond interactions between the oxamate group in all compounds and the catalytic amino acid residues Arg221 and Ser216. The compounds were evaluated for their in vivo hypoglycemic activity, showing significant lowering of plasma glucose concentration in acute normoglycemic model and oral glucose tolerance test similarly at the effect exerted for hypoglycemic drug glibenclamide. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.025

文献信息

• Synthesis, in vitro and in silico screening of ethyl 2-(6-substituted benzo[d]thiazol-2-ylamino)-2-oxoacetates as protein-tyrosine phosphatase 1B inhibitors
  作者：Gabriel Navarrete-Vazquez、Marleth Ramírez-Martínez、Samuel Estrada-Soto、Carlos Nava-Zuazo、Paolo Paoli、Guido Camici、Jaime Escalante-García、José L. Medina-Franco、Fabian López-Vallejo、Rolffy Ortiz-Andrade

  DOI：10.1016/j.ejmech.2012.04.025

  日期：2012.7

  The ethyl 2-(6-substituted benzo[d]thiazol-2-ylamino)-2-oxoacetate derivatives (OX 1-9) were prepared using a one-step reaction. The in vitro inhibitory activity of the compounds against protein tyrosine phosphatase 1B (PTP-1B) was evaluated. Compounds OX-(1, 6 and 7) were rapid reversible (mixed-type) inhibitors of PTP-1B with IC50 values in the low micro-molar range. The most active compounds OX-(1, 6 and 7) were docked into the crystal structure of PTP-1B. Docking results indicate potential hydrogen bond interactions between the oxamate group in all compounds and the catalytic amino acid residues Arg221 and Ser216. The compounds were evaluated for their in vivo hypoglycemic activity, showing significant lowering of plasma glucose concentration in acute normoglycemic model and oral glucose tolerance test similarly at the effect exerted for hypoglycemic drug glibenclamide. (C) 2012 Elsevier Masson SAS. All rights reserved.