3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-benzylamine | 713497-18-8

• 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: 3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-benzylamine
• 英文别名: 1-{3-Iodo-5-[3-(trifluoromethyl)-3H-diaziren-3-yl]phenyl}methanamine；[3-iodo-5-[3-(trifluoromethyl)diazirin-3-yl]phenyl]methanamine
• CAS: 713497-18-8
• 化学式: C₉H₇F₃IN₃
• 分子量: 341.074
• InChiKey: ABDUSQQQKYDEKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-Iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-benzylamine 、 (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy)phenyl]piperazin-1-yl]propyl]-2,4-pentadienamide hydrochloride 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以48%的产率得到(2Z,4E)-5-(5,6-Dichloro-1H-indol-2-yl)-2-methoxy-penta-2,4-dienoic acid {3-[4-(3-{[3-iodo-5-(3-trifluoromethyl-3H-diazirin-3-yl)-benzylcarbamoyl]-methoxy}-phenyl)-piperazin-1-yl]-propyl}-amide
  参考文献：
  名称：

  Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase

  摘要：

  Amides of (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy)phenyl)] piperazin-1-yl]propyl]-2,4-pentadienamide (1) and of 5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid (2) are strong inhibitors of the vacuolar ATPase located on the plasma membrane of osteoclasts. In order to understand which V-ATPase subunit is involved in the interaction with these novel inhibitors, analogues containing a photoactivable group and an iodine atom were designed. A series of alcohols or amines containing the photoactivable trifluoroaziridinophenyl or benzophenone moiety and an iodine atom were linked to the above acids via an ester or amide group. These compounds could be thereafter used as a radioactive photoprobe to label the protein. Whereas the compounds containing the photoactivable groups maintained good inhibitory activity, the introduction of the bulky iodine atom was generally detrimental, decreasing potency significantly. Better results were obtained by linking. 3-(4-amino-piperidinomethyl)-3'-iodobenzophenone to 3-ethoxy-4-(2-(5,6-dichlorobenzimidazolyl))benzoic acid to give the corresponding amide 27, that inhibited vacuolar ATP-ase with a IC50 = 140 nM. The feasibility of introducing a radioactive 1211 atom,was ascertained by exchanging the iodine with a tributylstannyl group, that was again substituted by iodine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00106-8

文献信息

• Synthesis of photoactivable inhibitors of osteoclast vacuolar ATPase
  作者：Barbara Biasotti、Sabrina Dallavalle、Lucio Merlini、Carlo Farina、Stefania Gagliardi、Carlo Parini、Pietro Belfiore

  DOI：10.1016/s0968-0896(03)00106-8

  日期：2003.5

  Amides of (2Z,4E)-5-[(5,6-dichloroindol-2-yl)]-2-methoxy-N-[3-[4-[3-(carboxymethoxy)phenyl)] piperazin-1-yl]propyl]-2,4-pentadienamide (1) and of 5-(5,6-dichloro-2-indolyl)-2-methoxy-2,4-pentadienoic acid (2) are strong inhibitors of the vacuolar ATPase located on the plasma membrane of osteoclasts. In order to understand which V-ATPase subunit is involved in the interaction with these novel inhibitors, analogues containing a photoactivable group and an iodine atom were designed. A series of alcohols or amines containing the photoactivable trifluoroaziridinophenyl or benzophenone moiety and an iodine atom were linked to the above acids via an ester or amide group. These compounds could be thereafter used as a radioactive photoprobe to label the protein. Whereas the compounds containing the photoactivable groups maintained good inhibitory activity, the introduction of the bulky iodine atom was generally detrimental, decreasing potency significantly. Better results were obtained by linking. 3-(4-amino-piperidinomethyl)-3'-iodobenzophenone to 3-ethoxy-4-(2-(5,6-dichlorobenzimidazolyl))benzoic acid to give the corresponding amide 27, that inhibited vacuolar ATP-ase with a IC50 = 140 nM. The feasibility of introducing a radioactive 1211 atom,was ascertained by exchanging the iodine with a tributylstannyl group, that was again substituted by iodine. (C) 2003 Elsevier Science Ltd. All rights reserved.