ethyl 2-(6-fluorobenzo[d]thiazol-2-ylamino)-2-oxoacetate | 887405-95-0

• 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-fluorobenzo[d]thiazol-2-ylamino)-2-oxoacetate
• 英文别名: Ethyl 2-[(6-fluoro-1,3-benzothiazol-2-yl)amino]-2-oxoacetate
• CAS: 887405-95-0
• 化学式: C₁₁H₉FN₂O₃S
• 分子量: 268.268
• InChiKey: UDFXNMBUUULLGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  苄异腈 、 ethyl 2-(6-fluorobenzo[d]thiazol-2-ylamino)-2-oxoacetate 、 丁炔二酸二甲酯 以 1,4-二氧六环 为溶剂， 反应 12.17h， 以63%的产率得到dimethyl 2-[N-benzyl-2-ethoxy-2-oxoacetamido]-8-fluoro-4H-benzo[4,5]thiazolo[3,2-a]pyrimidine-3,4-dicarboxylate
  参考文献：
  名称：

  三组分[3 + 2 + 1]环化导致密集官能化的苯并[4,5]噻唑并[1,2- a ]嘧啶

  摘要：

  已经开发了一种通过三组分[3 + 2 + 1]环化来制备致密官能化的三环稠合嘧啶衍生物的简便方法。该方法的主要优点是产品的收率相当好（高达88％），低成本原料的现成可获得性，无催化剂和温和的条件。

  DOI：

  10.1016/j.tet.2015.12.075
• 作为产物：
  描述：

  2-氨基-6-氟苯并噻唑 、 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63%的产率得到ethyl 2-(6-fluorobenzo[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

• Three-component [3+2+1] cyclizations leading to densely functionalized benzo[4,5]thiazolo[1,2- a ]pyrimidines
  作者：Ming Bao、Bo Jiang、Haiying Wang、Liang Li

  DOI：10.1016/j.tet.2015.12.075

  日期：2016.2

  A facile method has been developed for the preparation of densely functionalized tricyclic fused pyrimidine derivatives by three-component [3+2+1] cyclization. Fairly good yields of the products (up to 88%), the ready availability of the low-cost starting materials, the catalyst-free and mild conditions are the main advantages of this method.

  已经开发了一种通过三组分[3 + 2 + 1]环化来制备致密官能化的三环稠合嘧啶衍生物的简便方法。该方法的主要优点是产品的收率相当好（高达88％），低成本原料的现成可获得性，无催化剂和温和的条件。
• 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.