3-iodo-5-(3-(trifluoromethyl)-3H-diazirine-3-yl)benzyl alcohol | 713497-17-7

• 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-diazirine-3-yl)benzyl alcohol
• 英文别名: 3-[3-iodo-5-(hydroxymethyl)phenyl]-3-trifluoromethyl-3H-diazirine；{3-Iodo-5-[3-(trifluoromethyl)-3H-diaziren-3-yl]phenyl}methanol；[3-iodo-5-[3-(trifluoromethyl)diazirin-3-yl]phenyl]methanol
• CAS: 713497-17-7
• 化学式: C₉H₆F₃IN₂O
• 分子量: 342.059
• InChiKey: PSIQIKVXWDNGRW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  45
• 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-diazirine-3-yl)benzyl alcohol 在 四溴化碳 、 双硫磷 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以81%的产率得到3-(5-(bromomethyl)-3-iodo-phenyl)-3-trifluoromethyl-3H-diazirine
  参考文献：
  名称：

  A novel photoaffinity probe for the LTD4 receptor

  摘要：

  A novel photoaffinity probe for the leukotriene D-4 receptor (LTD4) is described. L-745310, which is structurally related to the potent LTD4 antagonist MK-0476 (Singulair(TM)), was found to selectively label a 43-kDa protein in guinea-pig lung membrane previously identified as the LTD4 receptor. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10011-6
• 作为产物：
  描述：

  3,5-二碘苯甲醇 在 咪唑 、 4-二甲氨基吡啶 、 正丁基锂 、 盐酸羟胺 、 四丁基氟化铵 、 氨 、 三乙胺 、 silver(l) oxide 作用下， 以 四氢呋喃 、 吡啶 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 55.5h， 生成 3-iodo-5-(3-(trifluoromethyl)-3H-diazirine-3-yl)benzyl alcohol
  参考文献：
  名称：

  A novel photoaffinity probe for the LTD4 receptor

  摘要：

  A novel photoaffinity probe for the leukotriene D-4 receptor (LTD4) is described. L-745310, which is structurally related to the potent LTD4 antagonist MK-0476 (Singulair(TM)), was found to selectively label a 43-kDa protein in guinea-pig lung membrane previously identified as the LTD4 receptor. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10011-6

文献信息

• Novel bifunctional probe for radioisotope-free photoaffinity labeling: compact structure comprised of photospecific ligand ligation and detectable tag anchoring unitsElectronic supplementary information (ESI) available: Photo-decomposition study of phenyl and benzyl azides. Experimental details for photoreactions of 1 and 5. Synthetic procedures and characterization of new compounds. See http://www.rsc.org/suppdata/ob/b3/b316221d/.
  作者：Takamitsu Hosoya、Toshiyuki Hiramatsu、Takaaki Ikemoto、Masayuki Nakanishi、Hiroshi Aoyama、Ayako Hosoya、Tomoya Iwata、Kei Maruyama、Makoto Endo、Masaaki Suzuki

  DOI：10.1039/b316221d

  日期：——

  A novel method for radioisotope-free photoaffinity labeling was developed, in which a bifunctional ligand is connected to a target protein by activation of a photoreactive group, such as an aromatic azido or 3-trifluoromethyl-3H-diazirin-3-yl group, and identification of the ligated product is achieved by anchoring of a detectable tag through the Staudinger-Bertozzi reaction with an alkyl azido moiety

  开发了一种无放射性同位素的光亲和标记的新方法，其中双功能配体通过激活光反应性基团（例如芳族叠氮基或3-三氟甲基-3H-二氮杂-3-基）与靶蛋白连接，并且通过Staudinger-Bertozzi反应与可在光解中幸存的烷基叠氮基部分锚定可检测标签，可实现对连接产物的鉴定。该方法的化学基础已通过使用具有双官能团的模型化合物在光辐射下，存在用于反应性中间体的捕集剂的条件下进行了确认。该方法的实用性已经通过人HMG-CoA还原酶的催化部分的特异性标记得到证明。
• 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.