2-(2-amino-5-iodophenyl)acetonitrile | 1261758-49-9

• 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: 2-(2-amino-5-iodophenyl)acetonitrile
• 英文别名: (2-amino-5-iodophenyl)acetonitrile
• CAS: 1261758-49-9
• 化学式: C₈H₇IN₂
• 分子量: 258.061
• InChiKey: RQMRWCACCRIQLK-UHFFFAOYSA-N

物化性质

• 沸点：
  378.0±37.0 °C(Predicted)
• 密度：
  1.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-amino-5-iodophenyl)acetonitrile 在 盐酸 、 sodium nitrite 、 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以54%的产率得到3-氰基-5-碘代(1H)吲唑
  参考文献：
  名称：

  [¹⁸F]ZCDD083: A PFKFB3-Targeted PET Tracer for Atherosclerotic Plaque Imaging

  摘要：

  PFKFB3, a glycolysis-related enzyme upregulated in inflammatory conditions and angiogenesis, is an emerging target for diagnosis and therapy of atherosclerosis. The fluorinated phenoxindazole [F-18]ZCDD083 was synthesized, radiolabeled in 17 +/- 5% radiochemical yield and >99% radiochemical purity, and formulated for preclinical PET/CT imaging in mice. In vivo stability analysis showed no significant metabolite formation. Biodistribution studies showed high blood pool activity and slow hepatobiliary clearance. Significant activity was detected in the lung 2 h postinjection (pi) (11.0 +/- 1.5%ID/g), while at 6 h pi no pulmonary background was observed. Ex vivo autoradiography at 6 h pi showed significant high uptake of [F-18]ZCDD083 in the arch region and brachiocephalic artery of atherosclerotic mice, and no uptake in control mice, matching plaques distribution seen by lipid staining along with PFKFB3 expression seen by immunofluorescent staining. In vivo PET scans showed higher aortic region uptake of [F-18]ZCDD083 in atherosclerotic ApoE(-/-)Fbn1(C1039G+/-) than in control mice (0.78 +/- 0.05 vs 0.44 +/- 0.09%ID/g). [F-18]ZCDD083 was detected in aortic arch and brachiocephalic artery of ApoE(-/-) (with moderate atherosclerosis) and ApoE(-/-)Fbn1(C1039G+/-) (with severe, advanced atherosclerosis) mice, suggesting this tracer may be useful for the noninvasive detection of atherosclerotic plaques in vivo.

  DOI：

  10.1021/acsmedchemlett.9b00677
• 作为产物：
  描述：

  2-氨基苯乙腈 在 N-碘代丁二酰亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以89%的产率得到2-(2-amino-5-iodophenyl)acetonitrile
  参考文献：
  名称：

  [¹⁸F]ZCDD083: A PFKFB3-Targeted PET Tracer for Atherosclerotic Plaque Imaging

  摘要：

  PFKFB3, a glycolysis-related enzyme upregulated in inflammatory conditions and angiogenesis, is an emerging target for diagnosis and therapy of atherosclerosis. The fluorinated phenoxindazole [F-18]ZCDD083 was synthesized, radiolabeled in 17 +/- 5% radiochemical yield and >99% radiochemical purity, and formulated for preclinical PET/CT imaging in mice. In vivo stability analysis showed no significant metabolite formation. Biodistribution studies showed high blood pool activity and slow hepatobiliary clearance. Significant activity was detected in the lung 2 h postinjection (pi) (11.0 +/- 1.5%ID/g), while at 6 h pi no pulmonary background was observed. Ex vivo autoradiography at 6 h pi showed significant high uptake of [F-18]ZCDD083 in the arch region and brachiocephalic artery of atherosclerotic mice, and no uptake in control mice, matching plaques distribution seen by lipid staining along with PFKFB3 expression seen by immunofluorescent staining. In vivo PET scans showed higher aortic region uptake of [F-18]ZCDD083 in atherosclerotic ApoE(-/-)Fbn1(C1039G+/-) than in control mice (0.78 +/- 0.05 vs 0.44 +/- 0.09%ID/g). [F-18]ZCDD083 was detected in aortic arch and brachiocephalic artery of ApoE(-/-) (with moderate atherosclerosis) and ApoE(-/-)Fbn1(C1039G+/-) (with severe, advanced atherosclerosis) mice, suggesting this tracer may be useful for the noninvasive detection of atherosclerotic plaques in vivo.

  DOI：

  10.1021/acsmedchemlett.9b00677

文献信息

• Palladium-catalyzed tandem addition/cyclization in aqueous medium: synthesis of 2-arylindoles
  作者：Shuling Yu、Kun Hu、Julin Gong、Linjun Qi、Jianghe Zhu、Yetong Zhang、Tianxing Cheng、Jiuxi Chen

  DOI：10.1039/c7ob00572e

  日期：——

  was developed through palladium-catalyzed tandem addition/cyclization of potassium aryltrifluoroborates with aliphatic nitriles in aqueous medium. The use of water as the reaction medium makes the synthesis process environmentally benign. A plausible mechanism for the formation of 2-arylindoles involving sequential nucleophilic addition followed by an intramolecular cyclization is proposed. Moreover

  通过在水性介质中钯催化的芳基三氟硼酸钾与脂肪族腈的串联/串联加成/环化反应，开发了构建2-芳基吲哚的有效方案。使用水作为反应介质使合成过程对环境无害。提出了一个合理的机制，形成2-芳基吲哚涉及亲核加成顺序，然后进行分子内环化。此外，这种催化串联转化的效用也在有效的克级合成中得到了证明。该方法提供了另一种可替代的合成工具，可用于获得更多种类的2-芳基吲哚。
• Synthesis of 2,5-disubstituted-3-cyanoindoles
  作者：Mark A. Bobko、Karen A. Evans、Arun C. Kaura、Leanna E. Shuster、Dai-Shi Su

  DOI：10.1016/j.tetlet.2011.11.009

  日期：2012.1

  An efficient synthesis of 2,5-disubstituted-3-cyanoindoles is described. This approach utilizes a highly selective iodination together with the modified Made lung reaction to generate an intermediate which can be readily transformed to more fully elaborated 2,5-disubstituted-3-cyanoindole templates that were previously difficult to access. Detailed examples and utility of this approach are presented herein. (C) 2011 Elsevier Ltd. All rights reserved.