diethyl ((furan-2-ylcarbonyl)amino)propanedioate | 117975-98-1

• 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: diethyl ((furan-2-ylcarbonyl)amino)propanedioate
• 英文别名: diethyl furoylaminopropanedioate；[(2-furanylcarbonyl)amino]propanedioic acid, diethyl ester；Diethyl [(furan-2-carbonyl)amino]propanedioate；diethyl 2-(furan-2-carbonylamino)propanedioate
• CAS: 117975-98-1
• 化学式: C₁₂H₁₅NO₆
• mdl: MFCD12644178
• 分子量: 269.254
• InChiKey: IGIGKXUBGKMHCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  94.8
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl ((furan-2-ylcarbonyl)amino)propanedioate 在 吡啶 、 tetraphosphorus decasulfide 、 乙醇 、 sodium 作用下， 反应 4.17h， 生成 2-(furan-2-yl)-5-methylthiazolo[5,4-d]pyrimidin-7-one
  参考文献：
  名称：

  Exploring the 7-oxo-thiazolo[5,4-d]pyrimidine core for the design of new human adenosine A3 receptor antagonists. Synthesis, molecular modeling studies and pharmacological evaluation

  摘要：

  A new series of 5-methyl-thiazolo[5,4-d]pyrimidine-7-ones bearing different substituents at position 2 (aryl, heteroaryl and arylamino groups) was synthesized and evaluated in radioligand binding assays to determine their affinities at the human (h) A(1), A(2A), and A(3) adenosine receptors (ARs). Efficacy at the hA(2B) and antagonism of selected ligands at the hA(3) were also assessed through cAMP experiments. Some of the new derivatives exhibited good to high hA(3)AR affinity and selectivity versus all the other AR subtypes. Compound 2-(4-chlorophenyl)-5-methyl-thiazolo[5,4-d]pyrimidine-7-one 4 was found to be the most potent and selective ligand of the series (K-i hA(3) = 18 nM). Molecular docking studies of the reported derivatives were carried out to depict their hypothetical binding mode in our hA(3) receptor model. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.010
• 作为产物：
  描述：

  呋喃甲酰氯 、 氨基丙二酸二乙酯盐酸盐 在 碳酸氢钠 作用下， 以 乙醚 、 水 为溶剂， 反应 2.0h， 以88%的产率得到diethyl ((furan-2-ylcarbonyl)amino)propanedioate
  参考文献：
  名称：

  Exploring the 7-oxo-thiazolo[5,4-d]pyrimidine core for the design of new human adenosine A3 receptor antagonists. Synthesis, molecular modeling studies and pharmacological evaluation

  摘要：

  A new series of 5-methyl-thiazolo[5,4-d]pyrimidine-7-ones bearing different substituents at position 2 (aryl, heteroaryl and arylamino groups) was synthesized and evaluated in radioligand binding assays to determine their affinities at the human (h) A(1), A(2A), and A(3) adenosine receptors (ARs). Efficacy at the hA(2B) and antagonism of selected ligands at the hA(3) were also assessed through cAMP experiments. Some of the new derivatives exhibited good to high hA(3)AR affinity and selectivity versus all the other AR subtypes. Compound 2-(4-chlorophenyl)-5-methyl-thiazolo[5,4-d]pyrimidine-7-one 4 was found to be the most potent and selective ligand of the series (K-i hA(3) = 18 nM). Molecular docking studies of the reported derivatives were carried out to depict their hypothetical binding mode in our hA(3) receptor model. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.010

文献信息

• 2-furyl-oxazolo[5,4-d]-pyrimidines
  申请人：Imperial Chemical Industries PLC

  公开号：US05300509A1

  公开（公告）日：1994-04-05

  Compounds of formula I, and pharmaceutically acceptable salts thereof, ##STR1## in which R1 is hydrogen (1-6C)alkyl or (1-4C)alkanoyl; A is --N.dbd.CQ--O--, N.dbd.CQ--NR.sup.8 --, --N.dbd.CQ--CH.dbd.N-- or --N.dbd.CH--CQ.dbd.N--; Q is 2-furyl; R.sup.8 is hydrogen or C1-4C)alkyl; and R.sup.2 has any of the meanings given in the specification, processes for preparing the compounds and pharmaceutical compositions containing them. The compounds are useful as adenosine antagonists.

  公式I的化合物及其药用盐，其中R1是氢(1-6C)烷基或(1-4C)酰基；A是--N.dbd.CQ--O--，N.dbd.CQ--NR.sup.8--，--N.dbd.CQ--CH.dbd.N--或--N.dbd.CH--CQ.dbd.N--；Q是2-呋喃基；R.sup.8是氢或C1-4C)烷基；R.sup.2具有规范中给出的任何含义，制备这些化合物的方法以及含有它们的药物组合物。这些化合物可用作腺苷拮抗剂。
• 一种新型吲哚甘氨酸衍生物的合成方法
  申请人：常州大学

  公开号：CN106316920B

  公开（公告）日：2018-12-04

  本发明涉及一种新型吲哚甘氨酸衍生物的合成方法。该方法所用的原料为吲哚、酰胺基丙二酸酯和氧化剂。本发明的合成方法为吲哚、酰胺基丙二酸酯和氧化剂在有机溶剂中氮气保护下加热至60‑100℃发生交叉脱氢偶联反应，得到丰富的新型吲哚甘氨酸衍生物。本发明的底物范围很广，官能团兼容性好，各种取代的吲哚和酰胺基丙二酸酯都能以较好的产率获得吲哚甘氨酸衍生物。本发明具有合成路线短，反应原料低毒，反应时间短，氧化剂便宜易得，分离提纯方便等许多优点，在合成这一类化合物上具有重要的实际应用价值。
• HYPOGLYCEMIC HYDROXYUREA DERIVATIVES
  申请人：PFIZER INC.

  公开号：EP0544696B1

  公开（公告）日：1995-01-11
• US5646168A
  申请人：——

  公开号：US5646168A

  公开（公告）日：1997-07-08
• US5763467A
  申请人：——

  公开号：US5763467A

  公开（公告）日：1998-06-09