(E)-1-(1-(2-(2-(3-iodoallyloxy)-4-(1-(methylsulfonyl)piperidin-4-yloxy)phenyl)acetyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one | 1369357-96-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (E)-1-(1-(2-(2-(3-iodoallyloxy)-4-(1-(methylsulfonyl)piperidin-4-yloxy)phenyl)acetyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one
• 英文别名: 1-[1-[2-[2-[(E)-3-iodoprop-2-enoxy]-4-(1-methylsulfonylpiperidin-4-yl)oxyphenyl]acetyl]piperidin-4-yl]-3,4-dihydroquinolin-2-one
• CAS: 1369357-96-9
• 化学式: C₃₁H₃₈IN₃O₆S
• 分子量: 707.63
• InChiKey: ZJWAEMNLDJQLSS-SYZQJQIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (Z)-1-(1-(2-(4-(1-(methylsulfonyl)piperidin-4-yloxy)-2-(3-(tributylstannyl)allyloxy)phenyl)acetyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one 在 碘 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以83%的产率得到(E)-1-(1-(2-(2-(3-iodoallyloxy)-4-(1-(methylsulfonyl)piperidin-4-yloxy)phenyl)acetyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one
  参考文献：
  名称：

  Synthesis and evaluation of C-11, F-18 and I-125 small molecule radioligands for detecting oxytocin receptors

  摘要：

  Compounds 1-4 were synthesized and investigated for selectivity and potency for the oxytocin receptor (OTR) to determine their viability as radioactive ligands. Binding assays determined 1-4 to have high binding affinity for both the human and rodent OTR and also have high selectivity for the human OTR over human vasopressin V1a receptors (V1aR). Inadequate selectivity for OTR over V1aR was found for rodent receptors in all four compounds. The radioactive (C-11, F-18, and I-125) derivatives of 1-4 were synthesized and investigated for use as autoradiography and positron emission tomography (PET) ligands. Receptor autoradiography performed with [I-125]1 and [I-125]2 on rodent brain slices provided the first small molecule radioligand images of the OTR and V1aR. Biodistribution studies determined [I-125]1 and [I-125]2 were adequate for in vivo peripheral investigations, but not for central investigations due to low uptake within the brain. A biodistribution study with [F-18]3 suggested brain uptake occurred slowly over time. PET imaging studies with [F-18]3 and [C-11]4 using a rat model provided insufficient uptake in the brain over a 90 and 45 min scan times respectively to merit further investigations in non-human primates. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.019