N-carboxy-2-imidazolidinone | 17607-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-carboxy-2-imidazolidinone
• 英文别名: N-Carboxy-2-imidazolidone；N-Carboxy-imidazolidon-2；N-Caboxy-2-imidazolidon；2-Oxo-imidazolidin-1-carbonsaeure；2-oxo-imidazolidine-1-carboxylic acid；N-Carbonyl-2-imidazolidinon；2-Oxoimidazolidine-1-carboxylic acid
• CAS: 17607-02-2
• 化学式: C₄H₆N₂O₃
• 分子量: 130.103
• InChiKey: VLJHNNJRRSLTLE-UHFFFAOYSA-N

物化性质

• 密度：
  1.538±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-carboxy-2-imidazolidinone 在 氯化亚砜 作用下， 以 苯 为溶剂， 反应 0.5h， 生成 N-氯甲酰基-2-咪唑烷酮
  参考文献：
  名称：

  Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines

  摘要：

  A series of N-substituted tetrahydro-beta-carbolines were synthesized and screened for antileishmanial activity through an in vitro assay that involves promastigotes and axenic amastigotes of Leishmania donovani, the causative agent for visceral leishmaniasis. The thiophen-2-yl analogs 9b and 11f and naphthyl analog 11h were found to show significant activity against promastigotes with IC50 values of 12.7, 9.1 and 22.1 mu M, respectively. Analogs 9b and 11h were also effective against axenic amastigotes with IC50 values of 62.8 and 87.6 mu M, respectively. The antileishmanial activity of analogs was then tested in human macrophage cell line infected with L donovani amastigotes and 2-naphthyl linked analog 11h was found to be effective with IC50 value of 28.3 mu M. Several analogs also displayed antitrypanosomal activity against Tiypanosoma brucei, the causative agent for human African trypanosomiasis. Compounds 11e, 11f and 11h were more effective than others with IC50 values of 1.0, 8.9 and 10.2 mu M, respectively. All synthesized analogs were not cytotoxic towards mammalian cell lines including Vero (monkey kidney fibroblasts), HEPG2 (human hepatoma cells), LLC-PK1 (pig kidney epithelial cells) and THP-1 (human macrophages). (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.06.030
• 作为产物：
  描述：

  1-methoxycarbonyl-2-imidazolidinone 在 氢氧化钾 作用下， 生成 N-carboxy-2-imidazolidinone
  参考文献：
  名称：

  Comparison of the Structures and Vibrational Modes of Carboxybiotin and N-Carboxy-2-imidazolidone

  摘要：

  The spontaneous decarboxylation of N-carboxy-2-imidazolidone (a model for carboxybiotin) and N(1')carboxybiotin can be followed at high pH by Raman and FTIR spectroscopies, The major bands associated with vibrations of the carboxylate group have been assigned on the basis of quantum mechanical calculations of N-carboxy-2-imidazolidone and N(1')-carboxy-2-methylbiotin. The carboxylate modes are the asymmetric stretch, coupled to the ureido carbonyl stretch, near 1710 cm(-1), the symmetric stretch near 1340 cm(-1), and the -CO2- scissoring motion near 830 cm(-1). In the case of carboxybiotin, the last two modes are strongly coupled with biotin ring modes. All three carboxylate modes disappear as spontaneous decarboxylation occurs, to be replaced by features attributable to the noncarboxylated ring structures. The HF/6-31G* optimized structure of 2-methylbiotin revealed that the ureido ring portion is essentially planar, in accord with a number of X-ray crystallographic structures of biotin compounds. However, calculations at this level and at the B3LYP/631+G(d) level (using density functional theory) predict that the ureido ring in biotin puckers upon carboxylation. Comparison of the structures of carboxybiotin and carboxyimidazolidone, derived at the HF/6-31G* level, indicates that lengths of the ring-nitrogen-to-carboxylate bonds are equal and that the torsional angles about this linkage are very similar. This strong structural similarity provides a rationale for the observation that, at high pH, the spontaneous rates of decarboxylation of these two molecules are very similar.

  DOI：

  10.1021/jp984258b

文献信息

• Solvent-Accelerated Decarboxylation of <i>N</i>-Carboxy-2-imidazolidinone. Implications for Stability of Intermediates in Biotin-Dependent Carboxylations
  作者：Jubrail Rahil、Shaochun You、Ronald Kluger

  DOI：10.1021/ja962464w

  日期：1996.1.1

  by association of the substrate and protein. In addition, a report on the decarboxylation of N-carboxy-2-imidazolidinone in organic solvents containing macrocycles (Kluger, R.; Tsao, B. J. Am. Chem. Soc. 1993, 115, 2089−90) must be reinterpreted on the basis of the inherent instability of the substrate under the reaction conditions.

  N-carboxy-2-imidazolidinone 的脱羧以前已被确立为从 N(1')-carboxybiotin 转移二氧化碳的模型。本论文报告了反应的 pH 依赖性以及在甲醇和乙腈中的反应加速。这些结果表明，如果去溶剂化的能量由底物和蛋白质的结合所提供的能量补偿，则 N(1')-羧基生物素在氢键减少的疏水活性位点中的酶促反应可能会很快。此外，一份关于 N-carboxy-2-imidazolidinone 在含有大环的有机溶剂中脱羧的报告 (Kluger, R.; Tsao, BJ Am. Chem. Soc. 1993, 115, 2089-90) 必须基于底物在反应条件下的固有不稳定性。
• Synthesis, antileishmanial and antitrypanosomal activities of N-substituted tetrahydro-β-carbolines
  作者：Sudhakar Manda、Shabana I. Khan、Surendra K. Jain、Shabber Mohammed、Babu L. Tekwani、Ikhlas A. Khan、Ram A. Vishwakarma、Sandip B. Bharate

  DOI：10.1016/j.bmcl.2014.06.030

  日期：2014.8

  A series of N-substituted tetrahydro-beta-carbolines were synthesized and screened for antileishmanial activity through an in vitro assay that involves promastigotes and axenic amastigotes of Leishmania donovani, the causative agent for visceral leishmaniasis. The thiophen-2-yl analogs 9b and 11f and naphthyl analog 11h were found to show significant activity against promastigotes with IC50 values of 12.7, 9.1 and 22.1 mu M, respectively. Analogs 9b and 11h were also effective against axenic amastigotes with IC50 values of 62.8 and 87.6 mu M, respectively. The antileishmanial activity of analogs was then tested in human macrophage cell line infected with L donovani amastigotes and 2-naphthyl linked analog 11h was found to be effective with IC50 value of 28.3 mu M. Several analogs also displayed antitrypanosomal activity against Tiypanosoma brucei, the causative agent for human African trypanosomiasis. Compounds 11e, 11f and 11h were more effective than others with IC50 values of 1.0, 8.9 and 10.2 mu M, respectively. All synthesized analogs were not cytotoxic towards mammalian cell lines including Vero (monkey kidney fibroblasts), HEPG2 (human hepatoma cells), LLC-PK1 (pig kidney epithelial cells) and THP-1 (human macrophages). (C) 2014 Elsevier Ltd. All rights reserved.
• Comparison of the Structures and Vibrational Modes of Carboxybiotin and <i>N</i>-Carboxy-2-imidazolidone
  作者：John Clarkson、Paul R. Carey

  DOI：10.1021/jp984258b

  日期：1999.4.1

  The spontaneous decarboxylation of N-carboxy-2-imidazolidone (a model for carboxybiotin) and N(1')carboxybiotin can be followed at high pH by Raman and FTIR spectroscopies, The major bands associated with vibrations of the carboxylate group have been assigned on the basis of quantum mechanical calculations of N-carboxy-2-imidazolidone and N(1')-carboxy-2-methylbiotin. The carboxylate modes are the asymmetric stretch, coupled to the ureido carbonyl stretch, near 1710 cm(-1), the symmetric stretch near 1340 cm(-1), and the -CO2- scissoring motion near 830 cm(-1). In the case of carboxybiotin, the last two modes are strongly coupled with biotin ring modes. All three carboxylate modes disappear as spontaneous decarboxylation occurs, to be replaced by features attributable to the noncarboxylated ring structures. The HF/6-31G* optimized structure of 2-methylbiotin revealed that the ureido ring portion is essentially planar, in accord with a number of X-ray crystallographic structures of biotin compounds. However, calculations at this level and at the B3LYP/631+G(d) level (using density functional theory) predict that the ureido ring in biotin puckers upon carboxylation. Comparison of the structures of carboxybiotin and carboxyimidazolidone, derived at the HF/6-31G* level, indicates that lengths of the ring-nitrogen-to-carboxylate bonds are equal and that the torsional angles about this linkage are very similar. This strong structural similarity provides a rationale for the observation that, at high pH, the spontaneous rates of decarboxylation of these two molecules are very similar.