2-[3-[1-carboxy-5-(4-fluoro-benzoylamino)-pentyl]-ureido]-pentanedioic acid | 1093733-10-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-[3-[1-carboxy-5-(4-fluoro-benzoylamino)-pentyl]-ureido]-pentanedioic acid
• 英文别名: (S)-2-(3-((S)-1-carboxy-5-(4-fluorobenzamido)pentyl)ureido)pentanedioic acid；(2S)-2-[[(1S)-1-carboxy-5-[(4-fluorobenzoyl)amino]pentyl]carbamoylamino]pentanedioic acid
• CAS: 1093733-10-8
• 化学式: C₁₉H₂₄FN₃O₈
• 分子量: 441.413
• InChiKey: BQJLVCYAYCTTKJ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  182
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-[3-[5-(4-fluoro-benzoylamino)-1-(4-methoxy-benzyloxycarbonyl)-pentyl]-ureido]-pentanedioic acid bis-(4-methoxy-benzyl)ester 在 苯甲醚 、 三氟乙酸 作用下， 以79%的产率得到2-[3-[1-carboxy-5-(4-fluoro-benzoylamino)-pentyl]-ureido]-pentanedioic acid
  参考文献：
  名称：

  Radiohalogenated Prostate-Specific Membrane Antigen (PSMA)-Based Ureas as Imaging Agents for Prostate Cancer

  摘要：

  To extend our development of new imaging agents targeting the prostate-specific membrane antigen (PSMA), we have used the versatile intermediate 2-[3-(5-amino-1-carboxy-pentyl)-ureido]-pentanedioic acid (Lys-C(O)-Glu), which allows ready incorporation of radiohalogens for single photon emission computed tomography (SPECT) and positron emission tomography (PET). We prepared 2-[3-[1-carboxy-5-(4-[I-125]iodobenzoylamino)-pentyl]-ureido]-pentanedioic acid ([I-125]3), 2-[3-[1-carboxy-5-(4-[F-18]fluoro-benzoylamino)-pentyl-ureido]-pentanedioic acid ([F-18]6), and 2-(3-[1-carboxy-5-[(5-[I-125]iodo-pyridine-3-carbonyl)-amino]-pentyl ureido)-pentanedioic acid ([I-125]8) in 65-80% (nondecay-corrected), 30-35% (decay corrected), and 59-75% (nondecay-corrected) radiochemical yields. Compound [I-125]3 demonstrated 8.8 +/- 4.7% injected close per gram (%ID/g) within PSMA(+) PC-3 PIP tumor at 30 min postinjection, which persisted, with clear delineation of the tumor by SPECT. similar tumor uptake values at early time points were demonstrated for [F-18]6 (using PET) and [I-125]8. Because of the many radiohalogenated moieties that call be attached via the e amino group, the intermediate Lys-C(O)-Glu is an attractive template upon which to develop new imaging agents for prostate cancer.

  DOI：

  10.1021/jm801055h

文献信息

• PSMA imaging agents
  申请人：Wang Eric

  公开号：US10011632B2

  公开（公告）日：2018-07-03

  Compounds for targeting and agents for imaging, Prostate-specific membrane antigen (PSMA) are disclosed. Methods of synthesizing compounds and imaging agents, as well as methods for imaging PSMA are also disclosed. The imaging agents disclosed are suitable for PET and SPECT imaging.

  本研究公开了用于靶向前列腺特异性膜抗原（PSMA）的化合物和成像剂。还公开了合成化合物和成像剂的方法，以及 PSMA 的成像方法。所公开的成像剂适用于 PET 和 SPECT 成像。
• METHOD FOR THE PRODUCTION OF 18F-LABELED ACTIVE ESTERS AND THEIR APPLICATION EXEMPLIFIED BY THE PREPARATION OF A PSMA-SPECIFIC PET-TRACER
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften

  公开号：EP3183236B1

  公开（公告）日：2022-04-20
• PSMA Imaging Agents
  申请人：WANG Eric

  公开号：US20160304555A1

  公开（公告）日：2016-10-20

  Compounds for targeting and agents for imaging, Prostate-specific membrane antigen (PSMA) are disclosed. Methods of synthesizing compounds and imaging agents, as well as methods for imaging PSMA are also disclosed. The imaging agents disclosed are suitable for PET and SPECT imaging.
• Novel method for the production of 18F-labeled active esters and their application exemplified by the preparation of a PSMA-specific PET-tracer
  申请人：Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.

  公开号：US20170267717A1

  公开（公告）日：2017-09-21

  Novel efficient, time-saving and reliable radiofluorination procedures for the production of 18 F-labelled active esters via nucleophilic substitution of the corresponding onium precursors with 18 F − are described. The active ester including [ 18 F]F-Py-TFP and [ 18 F]TFB produced by one of these methods was used to prepare PSMA-specific PET tracers such as [ 18 F]DCFPyL. The key advantages of these inventive methods are efficiency, short time of preparation and excellent amenability to automation. A pharmaceutical composition containing at least one PSMA-specific PET tracers prepared by the inventive method is useful for positron emission tomography (PET) imaging, especially imaging prostate tumor.
• Radiohalogenated Prostate-Specific Membrane Antigen (PSMA)-Based Ureas as Imaging Agents for Prostate Cancer
  作者：Ying Chen、Catherine A. Foss、Youngjoo Byun、Sridhar Nimmagadda、Mrudula Pullambhatla、James J. Fox、Mark Castanares、Shawn E. Lupold、John W. Babich、Ronnie C. Mease、Martin G. Pomper

  DOI：10.1021/jm801055h

  日期：2008.12.25

  To extend our development of new imaging agents targeting the prostate-specific membrane antigen (PSMA), we have used the versatile intermediate 2-[3-(5-amino-1-carboxy-pentyl)-ureido]-pentanedioic acid (Lys-C(O)-Glu), which allows ready incorporation of radiohalogens for single photon emission computed tomography (SPECT) and positron emission tomography (PET). We prepared 2-[3-[1-carboxy-5-(4-[I-125]iodobenzoylamino)-pentyl]-ureido]-pentanedioic acid ([I-125]3), 2-[3-[1-carboxy-5-(4-[F-18]fluoro-benzoylamino)-pentyl-ureido]-pentanedioic acid ([F-18]6), and 2-(3-[1-carboxy-5-[(5-[I-125]iodo-pyridine-3-carbonyl)-amino]-pentyl ureido)-pentanedioic acid ([I-125]8) in 65-80% (nondecay-corrected), 30-35% (decay corrected), and 59-75% (nondecay-corrected) radiochemical yields. Compound [I-125]3 demonstrated 8.8 +/- 4.7% injected close per gram (%ID/g) within PSMA(+) PC-3 PIP tumor at 30 min postinjection, which persisted, with clear delineation of the tumor by SPECT. similar tumor uptake values at early time points were demonstrated for [F-18]6 (using PET) and [I-125]8. Because of the many radiohalogenated moieties that call be attached via the e amino group, the intermediate Lys-C(O)-Glu is an attractive template upon which to develop new imaging agents for prostate cancer.