3-氰基-5-碘代(1H)吲唑 | 885278-27-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 中文名称: 3-氰基-5-碘代(1H)吲唑
• 中文别名: 5-碘-3-氰基吲唑
• 英文名称: 5-iodo-1H-indazole-3-carbonitrile
• CAS: 885278-27-3
• 化学式: C₈H₄IN₃
• mdl: MFCD07371568
• 分子量: 269.044
• InChiKey: URWUCPSDBLQGSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-氰基-5-碘代(1H)吲唑 在 copper(l) iodide 、 偶氮二甲酸二异丙酯 、 potassium carbonate 、 三苯基膦 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 0.08h， 生成
  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 盐酸 、 N-碘代丁二酰亚胺 、 sodium nitrite 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 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