N-((4-nitrophenoxy)carbonyl)-3-phenylsydnonimine | 1446512-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-((4-nitrophenoxy)carbonyl)-3-phenylsydnonimine
• 英文别名: (1E)-1-(4-nitrophenoxy)-N-(3-phenyloxadiazol-3-ium-5-yl)methanimidate
• CAS: 1446512-86-2
• 化学式: C₁₅H₁₀N₄O₅
• 分子量: 326.268
• InChiKey: BSUCLKILERXUJP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  120
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-((4-nitrophenoxy)carbonyl)-3-phenylsydnonimine 在 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 (S)-N-((4-(2-amino-3-methoxy-3-oxopropyl)phenyl)carbamoyl)-3-phenylsydnonimine hydrochloride
  参考文献：
  名称：

  Novel amino acids: synthesis of furoxan and sydnonimine containing amino acids and peptides as potential nitric oxide releasing motifs

  摘要：

  将呋喃噁唑和吡啶亚胺环系统引入氨基酸侧链的工作通过制备四种具有这些释放一氧化氮结构的新型氨基酸得到了证明。N-((4-硝基苯氧)羧基)-3-苯基吡啶亚胺9和双（苯基磺酰）呋喃噁唑10是将杂环侧链引入适当的胺和醇功能的关键中间体。呋喃噁唑5和7均显示出基于亚硝酸盐生成的NO释放。采用正交氨基酸保护基团策略，证明这些氨基酸可以被嵌入肽框架中。作为示例，这些氨基酸被置于几个三肽结构的中心。Griess试验显示，这些氨基酸在存在γ-谷胱甘肽（GST）时释放NO。

  DOI：

  10.1039/c3ob41047a
• 作为产物：
  描述：

  苯胺 在 potassium carbonate 、 三乙胺 、 sodium iodide 、 亚硝酸异戊酯 作用下， 以 乙醚 、 二氯甲烷 、 丙酮 为溶剂， 反应 44.25h， 生成 N-((4-nitrophenoxy)carbonyl)-3-phenylsydnonimine
  参考文献：
  名称：

  Novel amino acids: synthesis of furoxan and sydnonimine containing amino acids and peptides as potential nitric oxide releasing motifs

  摘要：

  将呋喃噁唑和吡啶亚胺环系统引入氨基酸侧链的工作通过制备四种具有这些释放一氧化氮结构的新型氨基酸得到了证明。N-((4-硝基苯氧)羧基)-3-苯基吡啶亚胺9和双（苯基磺酰）呋喃噁唑10是将杂环侧链引入适当的胺和醇功能的关键中间体。呋喃噁唑5和7均显示出基于亚硝酸盐生成的NO释放。采用正交氨基酸保护基团策略，证明这些氨基酸可以被嵌入肽框架中。作为示例，这些氨基酸被置于几个三肽结构的中心。Griess试验显示，这些氨基酸在存在γ-谷胱甘肽（GST）时释放NO。

  DOI：

  10.1039/c3ob41047a

文献信息

• Synthesis and anticancer properties of RGD peptides conjugated to nitric oxide releasing functional groups and abiraterone
  作者：Andrew Nortcliffe、Ian N. Fleming、Nigel P. Botting、David O'Hagan

  DOI：10.1016/j.tet.2014.09.004

  日期：2014.11

  A series of analogues of the integrin binding aspartic acid-glycine-arginine (RGD) peptide sequence were synthesised conjugated to nitric oxide (NO) donating functional groups. Also the cytotoxicity of abiraterone, a prostate cancer drug, was explored when it was conjugated in three part constructs to RGD sequences and NO releasing heterocycles. In general the analogues showed integrin binding affinity comparable to RGD reference compounds, and all released NO by the Griess test assay. Two analogues exhibited significant cytotoxic effects against PO and MCF7 cell lines. (C) 2014 Published by Elsevier Ltd.
• Synthesis and biological evaluation of nitric oxide-donating analogues of sulindac for prostate cancer treatment
  作者：Andrew Nortcliffe、Alexander G. Ekstrom、James R. Black、James A. Ross、Fouad K. Habib、Nigel P. Botting、David O’Hagan

  DOI：10.1016/j.bmc.2013.12.014

  日期：2014.1

  A series of analogues of the non-steroidal anti-inflammatory drug (NSAID) sulindac 1 were synthesised tethered to nitric oxide (NO) donating functional groups. Sulindac shows antiproliterative effects against immortal PC3 cell lines. It was previously demonstrated that the effect can be enhanced when tethered to NO releasing groups such as nitrate esters, furoxans and sydnonimines. To explore this approach further, a total of fifty-six sulindac-NO analogues were prepared and they were evaluated as NO-releasing cytotoxic agents against prostate cancer (PCa) cell lines. Compounds 1k and 1n exhibited significant cytotoxic with IC50 values of 6.1 +/- 4.1 and 12.1 +/- 3.2 mu M, respectively, coupled with observed nitric oxide release. (C) 2013 Elsevier Ltd. All rights reserved.
• Novel amino acids: synthesis of furoxan and sydnonimine containing amino acids and peptides as potential nitric oxide releasing motifs
  作者：Andrew Nortcliffe、Nigel P. Botting、David O'Hagan

  DOI：10.1039/c3ob41047a

  日期：——

  The incorporation of furoxan and sydnonimine ring systems into amino acid side chains is demonstrated with the preparation of four novel amino acids which carry these nitric oxide-releasing motifs. N-((4-Nitrophenoxy)carbonyl)-3-phenylsydnonimine 9 and bis(phenylsulfonyl)furoxan 10 are the key intermediates for introducing the heterocycle side chains onto appropriate amine and alcohol functionalities respectively. Furoxan 5 and 7 both displayed NO release based on determination of nitrite production. Orthogonal amino acid protecting group strategies were deployed to demonstrate that the amino acids could be incorporated into peptide frameworks. By way of demonstration the amino acids were placed centrally into several tripeptide motifs. Griess test assays showed that these amino acids released NO in the presence of γ-glutathione (GST).

  将呋喃噁唑和吡啶亚胺环系统引入氨基酸侧链的工作通过制备四种具有这些释放一氧化氮结构的新型氨基酸得到了证明。N-((4-硝基苯氧)羧基)-3-苯基吡啶亚胺9和双（苯基磺酰）呋喃噁唑10是将杂环侧链引入适当的胺和醇功能的关键中间体。呋喃噁唑5和7均显示出基于亚硝酸盐生成的NO释放。采用正交氨基酸保护基团策略，证明这些氨基酸可以被嵌入肽框架中。作为示例，这些氨基酸被置于几个三肽结构的中心。Griess试验显示，这些氨基酸在存在γ-谷胱甘肽（GST）时释放NO。