thiazol-2-yl-carbamic acid 2,5-dioxo-pyrrolidin-1-yl-ester | 238094-27-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: thiazol-2-yl-carbamic acid 2,5-dioxo-pyrrolidin-1-yl-ester
• 英文别名: (2,5-dioxopyrrolidin-1-yl) N-(1,3-thiazol-2-yl)carbamate
• CAS: 238094-27-4
• 化学式: C₈H₇N₃O₄S
• 分子量: 241.227
• InChiKey: QBRKKVSKURVDRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  thiazol-2-yl-carbamic acid 2,5-dioxo-pyrrolidin-1-yl-ester 、 Phe-D-Leu-Phe-D-Leu-Phe-OMe 在 N-甲基吗啉 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 生成 2-thiazolyl-ureido-Phe-D-Leu-Phe-D-Leu-Phe-OMe
  参考文献：
  名称：

  C- and N-terminal residue effect on peptide derivatives' antagonism toward the formyl-peptide receptor

  摘要：

  The biological action of several X-Phe-D-Leu-Phe-D-Leu-Z (X=3',5'-dimethylphenyl-ureido; Z=Phe, Lys, Glu, Tyr) analogues was analysed on human neutrophils to evaluate their ability to antagonize formyl-peptide receptors. X-Phe-D-Leu-Phe-D-Leu-Phe analogues obtained as C-terminal olo or amido derivatives and T-Phe-D-Leu-Phe-D-Leu-Phe analogues (T=thiazolyl-ureido) were also analysed. The activities of pentapeptide derivatives were compared with those of X-Phe-D-Leu-Phe-D-Leu-Phe chosen as reference antagonist. Our results demonstrate that X-Phe-D-Leu-Phe-D-Leu-Phe-olo, X-Phe-D-Leu-Phe-D-Leu-Glu and X-Phe-D-Leu-Phe-D-Leu-Tyr are more active antagonists than X-Phe-D-Leu-Phe-D-Leu-Phe. The presence of Lys (X-Phe-D-Leu-Phe-D-Leu-Lys) seems, instead, to inhibit the formyl-peptide receptor antagonist properties. The presence of the N-terminal thiazolyl-ureido group seems to considerably contribute to the receptor antagonist properties of T-Phe-D-Leu-Phe-D-Leu-Phe-OH. The introduction of the C-terminal methyl ester (T-Phe-D-Leu-Phe-D-Leu-Phe-OMe) or amido group (X-Phe-D-Leu-Phe-D-Leu-Phe-NH2) appears detrimental for the affinity and formyl-peptide receptor antagonist properties of the Phe-D-Leu-Phe-D-Leu-Phe derivatives. The examined peptides inhibit superoxide anion production and lysozyme release more efficaciously than neutrophil chemotaxis. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0014-2999(01)01627-2
• 作为产物：
  描述：

  2-氨基噻唑 、 N,N'-二琥珀酰亚胺基碳酸酯 以 甲苯 为溶剂， 生成 thiazol-2-yl-carbamic acid 2,5-dioxo-pyrrolidin-1-yl-ester
  参考文献：
  名称：

  3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9 β-amine衍生的一些脲的合成、结构和构象研究

  摘要：

  摘要 合成了一系列以3-甲基-2,4-二苯基-3-氮杂双环[3.3.1]壬烷-9 β-胺为原料的脲类化合物，并采用红外光谱、拉曼光谱、 1 H 和 13 C NMR 光谱对其进行了研究。这些化合物在CDCl 3 中采用优选的扁平椅椅构象，环己烷环比哌啶部分更扁平，N-CH 3 基团位于赤道位置。IR 和 1 H 和 13 C NMR 数据显示在尿素单元中存在至少两种构象。这些结果得到了分子模型研究的支持。

  DOI：

  10.1016/s0022-2860(98)00946-6

文献信息

• Synthesis, structural and conformational study of some ureas derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9α-amine
  作者：I. Iriepa、B. Gil-Alberdi、E. Gálvez、J. Bellanato、P. Carmona

  DOI：10.1016/s0022-2860(96)09561-0

  日期：1997.6

  A series of ureas derived from 3-methyl-2,4-diphenyl-3-azabicyclo[3.3.1] nonan-9 alpha-amine were synthesized and studied by IR, Raman, H-1 and C-13 NMR spectroscopy. These compounds adopt, in CDCl3, a preferred flattened chair-chair conformation with the cyclohexane ring more flattened than the piperidine moiety and the N-CH3 groups in equatorial positions. IR and H-1 and C-13 NMR data show the presence of two conformations at the urea unity. These results are supported by molecular modeling studies. (C) 1997 Elsevier Science B.V.