[125I]-Iodopride | 115655-34-0

• 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: [125I]-Iodopride
• 英文别名: Iodopride；(S)-N-<(1-ethyl-2-pyrrolidinyl)methyl>-5-iodo-2-methoxybenzamide；(S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-5-iodo-2-methoxybenzamide；N-(1-Ethyl-pyrrolidin-2-ylmethyl)-5-iodo-2-methoxy-benzamide；N-[[(2S)-1-ethylpyrrolidin-2-yl]methyl]-5-iodo-2-methoxybenzamide
• CAS: 115655-34-0
• 化学式: C₁₅H₂₁IN₂O₂
• 分子量: 388.248
• InChiKey: JHMTYLJMPBFCTD-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [125I]-Iodopride 、 六正丁基二锡 、 醋酸钯 、 四(三苯基膦)钯 以40%的产率得到
  参考文献：
  名称：

  DE, PAULIS TOMAS;JANOWSKY, AARON;KESSLER, ROBERT M.;CLANTON, JEFFREY A.;S+, J. MED. CHEM., 31,(1988) N 10, C. 2027-2033

  摘要：

  DOI：
• 作为产物：
  描述：

  5-碘-2-甲氧基苯甲酸 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 生成 [125I]-Iodopride
  参考文献：
  名称：

  (S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-5-[125I]iodo-2-methoxybenzamide hydrochloride, a new selective radioligand for dopamine D-2 receptors

  摘要：

  From salicyclic acid, the two enantiomers of N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-iodo-2-methoxybenzamide (6b) were prepared in a five-step synthesis. With use of Heindel's triazene method for introduction of the radionuclide, the iodine-125-labeled substituted benzamide was obtained with a calculated specific activity of 136 Ci/mmol and 14% radiochemical yield. For the preparation of the iodine-125-labeled benzamide with higher specific activity, this method was unsuccessful and utilization of the corresponding tri-n-butyltin derivative was required. Treatment of the latter in dilute hydrochloric acid with sodium iodide-125 and chloramine-T gave [125I](S)-6b in 56% radiochemical yield and at least 97% radiochemical purity. The displacement of [125I](S)-6b and [3H](S)-sulpiride from their respective binding sites in striatal rat brain homogenates using various neuroleptic agents showed that (S)-6b has the same binding profile but more potent binding for dopamine D-2 receptors than has sulpiride. These experiments also indicate that the S enantiomer of 6b is a specific ligand (KD = 1.2 nM) for the D-2 receptor. Further, the octanol-water partition coefficient of (S)-6b as determined by reverse-phase high-performance liquid chromatography was found to be 40 times greater than that for sulpiride. Thus (S)-6b has a lipophilicity that will allow a relatively higher uptake into the brain compared to sulpiride. In vivo experiments with rats show that [125I](S)-6b penetrates readily into the brain and is preferentially localized in the striatum as compared to the cerebellum, the ratio of uptake being 7.2 to 1, 60 min after injection. These observations of good brain penetration and high affinity and selectivity for D-2 receptors indicate that the corresponding iodine-123-labeled benzamide may be a useful ligand for the noninvasive visualization study of dopamine D-2 receptor sites in vivo by single photon emission computed tomography.

  DOI：

  10.1021/jm00118a031

文献信息

• DE, PAULIS TOMAS;JANOWSKY, AARON;KESSLER, ROBERT M.;CLANTON, JEFFREY A.;S+, J. MED. CHEM., 31,(1988) N 10, C. 2027-2033
  作者：DE, PAULIS TOMAS、JANOWSKY, AARON、KESSLER, ROBERT M.、CLANTON, JEFFREY A.、S+

  DOI：——

  日期：——
• JPH01160955A
  申请人：——

  公开号：JPH01160955A

  公开（公告）日：1989-06-23
• (S)-N-[(1-Ethyl-2-pyrrolidinyl)methyl]-5-[125I]iodo-2-methoxybenzamide hydrochloride, a new selective radioligand for dopamine D-2 receptors
  作者：Tomas De Paulis、Aaron Janowsky、Robert M. Kessler、Jeffrey A. Clanton、Howard E. Smith

  DOI：10.1021/jm00118a031

  日期：1988.10

  From salicyclic acid, the two enantiomers of N-[(1-ethyl-2-pyrrolidinyl)methyl]-5-iodo-2-methoxybenzamide (6b) were prepared in a five-step synthesis. With use of Heindel's triazene method for introduction of the radionuclide, the iodine-125-labeled substituted benzamide was obtained with a calculated specific activity of 136 Ci/mmol and 14% radiochemical yield. For the preparation of the iodine-125-labeled benzamide with higher specific activity, this method was unsuccessful and utilization of the corresponding tri-n-butyltin derivative was required. Treatment of the latter in dilute hydrochloric acid with sodium iodide-125 and chloramine-T gave [125I](S)-6b in 56% radiochemical yield and at least 97% radiochemical purity. The displacement of [125I](S)-6b and [3H](S)-sulpiride from their respective binding sites in striatal rat brain homogenates using various neuroleptic agents showed that (S)-6b has the same binding profile but more potent binding for dopamine D-2 receptors than has sulpiride. These experiments also indicate that the S enantiomer of 6b is a specific ligand (KD = 1.2 nM) for the D-2 receptor. Further, the octanol-water partition coefficient of (S)-6b as determined by reverse-phase high-performance liquid chromatography was found to be 40 times greater than that for sulpiride. Thus (S)-6b has a lipophilicity that will allow a relatively higher uptake into the brain compared to sulpiride. In vivo experiments with rats show that [125I](S)-6b penetrates readily into the brain and is preferentially localized in the striatum as compared to the cerebellum, the ratio of uptake being 7.2 to 1, 60 min after injection. These observations of good brain penetration and high affinity and selectivity for D-2 receptors indicate that the corresponding iodine-123-labeled benzamide may be a useful ligand for the noninvasive visualization study of dopamine D-2 receptor sites in vivo by single photon emission computed tomography.