DCIBzL | 1025796-40-0

• 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: DCIBzL
• 英文别名: N-{[(1s)-1-Carboxy-5-{[(4-Iodophenyl)carbonyl]amino}pentyl]carbamoyl}-L-Glutamic Acid；(2S)-2-[[(1S)-1-carboxy-5-[(4-iodobenzoyl)amino]pentyl]carbamoylamino]pentanedioic acid
• CAS: 1025796-40-0
• 化学式: C₁₉H₂₄IN₃O₈
• 分子量: 549.319
• InChiKey: ROXRILBFJQYPNZ-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 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：
  8

反应信息

• 作为产物：
  描述：

  L-谷氨酸二叔丁酯盐酸盐 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 DCIBzL
  参考文献：
  名称：

  前列腺特异性膜抗原的新型β-和γ-氨基酸衍生抑制剂。

  摘要：

  前列腺特异性膜抗原（PSMA）是前列腺癌进展和转移的早期诊断的极佳生物标志物。在临床阶段，最有希望的PSMA靶向药物是基于Lys-尿素-Glu基序，其中Lys和Glu是α-（L）-氨基酸。在这项研究中，我们旨在确定S1口袋中β-和γ-氨基酸对PSMA结合亲和力的影响。我们合成并评估了具有（S）-或（R）-构型的β-和γ-氨基酸类似物，并保持α-（L）-Glu作为S1'结合药效基团。结构活性关系研究确定，化合物13c（具有（R）-构型的β-氨基酸类似物）表现出最有效的PSMA抑制活性，IC50值为3.97 nM。

  DOI：

  10.1021/acs.jmedchem.9b02022

文献信息

• HETERODIMERS OF GLUTAMIC ACID
  申请人：Babich John W.

  公开号：US20080193381A1

  公开（公告）日：2008-08-14

  Compounds of Formula (Ia) wherein R is a C 6 -C 12 substituted or unsubstituted aryl, a C 6 -C 12 substituted or unsubstituted heteroaryl, a C 1 -C 6 substituted or unsubstituted alkyl or —NR′R′, Q is C(O), O, NR′, S, S(O) 2 , C(O) 2 (CH2)p Y is C(O), O, NR′, S, S(O) 2 , C(O) 2 (CH2) p Z is H or C 1 -C 4 alkyl, R′ is H, C(O), S(O) 2 , C(O) 2 , a C 6 -C 12 substituted or unsubstituted aryl, a C 6 -C 12 substituted or unsubstituted heteroaryl or a C 1 -C 6 substituted or unsubstituted alkyl, when substituted, aryl, heteroaryl and alkyl are substituted with halogen, C 6 -C 12 heteroaryl, —NR′R′ or COOZ, which have diagnostic and therapeutic properties, such as the treatment and management of prostate cancer and other diseases related to NAALADase inhibition. Radiolabels can be incorporated into the structure through a variety of prosthetic groups attached at the X amino acid side chain via a carbon or hetero atom linkage.

  化合物的化学式（Ia），其中R是C6-C12取代或未取代的芳基，C6-C12取代或未取代的杂环芳基，C1-C6取代或未取代的烷基或-NR′R′，Q是C（O），O，NR′，S，S（O）2，C（O）2（CH2）p，Y是C（O），O，NR′，S，S（O）2，C（O）2（CH2）p，Z是H或C1-C4烷基，R′是H，C（O），S（O）2，C（O）2，C6-C12取代或未取代的芳基，C6-C12取代或未取代的杂环芳基或C1-C6取代或未取代的烷基，当取代时，芳基，杂环芳基和烷基取代为卤素，C6-C12杂环芳基，-NR′R′或COOZ，具有诊断和治疗特性，如治疗和管理前列腺癌和其他与NAALADase抑制相关的疾病。放射性标记可以通过连接到X氨基酸侧链的多种假体基团结构中。
• Heterodimers of Glutamic Acid
  申请人：Babich John W.

  公开号：US20120269726A1

  公开（公告）日：2012-10-25

  Compounds of Formula (Ia) wherein R is a C 6 -C 12 substituted or unsubstituted aryl, a C 6 -C 12 substituted or unsubstituted heteroaryl, a C 1 -C 6 substituted or unsubstituted alkyl or —NR′R′, Q is C(O), O, NR′, S, S(O) 2 , C(O) 2 (CH2)p Y is C(O), O, NR′, S, S(O) 2 , C(O) 2 (CH2)p Z is H or C 1 -C 4 alkyl, R′ is H, C(O), S(O) 2 , C(O) 2 , a C 6 -C 12 substituted or unsubstituted aryl, a C 6 -C 12 substituted or unsubstituted heteroaryl or a C 1 -C 6 substituted or unsubstituted alkyl, when substituted, aryl, heteroaryl and alkyl are substituted with halogen, C 1 -C 12 heteroaryl, —NR′R′ or COOZ, which have diagnostic and therapeutic properties, such as the treatment and management of prostate cancer and other diseases related to NAALADase inhibition. Radiolabels can be incorporated into the structure through a variety of prosthetic groups attached at the X amino acid side chain via a carbon or hetero atom linkage.

  化合物的式子(Ia)，其中R是C6-C12取代或未取代芳基，C6-C12取代或未取代杂芳基，C1-C6取代或未取代烷基或—NR′R′，Q是C(O)，O，NR′，S，S(O)2，C(O)2(CH2)p，Y是C(O)，O，NR′，S，S(O)2，C(O)2(CH2)p，Z是H或C1-C4烷基，R′是H，C(O)，S(O)2，C(O)2，C6-C12取代或未取代芳基，C6-C12取代或未取代杂芳基或C1-C6取代或未取代烷基，当取代时，芳基，杂芳基和烷基被卤素，C1-C12杂芳基，—NR′R′或COOZ取代，具有诊断和治疗性能，例如治疗和管理前列腺癌和其他与NAALADase抑制有关的疾病。可以通过连接到X氨基酸侧链的碳或杂原子连接处的各种假体团将放射性标记纳入结构中。
• Heterodimers of glutamic acid
  申请人：Molecular Insight Pharmaceuticals, Inc.

  公开号：US10131627B2

  公开（公告）日：2018-11-20

  Compounds of Formula (Ia) wherein R is a C6-C12 substituted or unsubstituted aryl, a C6-C12 substituted or unsubstituted heteroaryl, a C1-C6 substituted or unsubstituted alkyl or —NR′R′, Q is C(O), O, NR′, S, S(O)2, C(O)2 (CH2)p Y is C(O), O, NR′, S, S(O)2, C(O)2 (CH2)p Z is H or C1-C4 alkyl, R′ is H, C(O), S(O)2, C(O)2, a C6-C12 substituted or unsubstituted aryl, a C6-C12 substituted or unsubstituted heteroaryl or a C1-C6 substituted or unsubstituted alkyl, when substituted, aryl, heteroaryl and alkyl are substituted with halogen, C6-C12 heteroaryl, —NR′R′ or COOZ, which have diagnostic and therapeutic properties, such as the treatment and management of prostate cancer and other diseases related to NAALADase inhibition. Radiolabels can be incorporated into the structure through a variety of prosthetic groups attached at the X amino acid side chain via a carbon or hetero atom linkage.

  式（Ia）化合物 其中 R 是 C6-C12 取代或未取代的芳基、C6-C12 取代或未取代的杂芳基、C1-C6 取代或未取代的烷基或 -NR′R′、 Q 是 C(O)、O、NR′、S、S(O)2、C(O)2 (CH2)p Y 是 C(O)、O、NR′、S、S(O)2、C(O)2 (CH2)p Z 是 H 或 C1-C4 烷基、 R′ 是 H、C(O)、S(O)2、C(O)2、取代或未取代的 C6-C12 芳基、取代或未取代的 C6-C12 杂芳基或取代或未取代的 C1-C6 烷基，当芳基、杂芳基和烷基被卤素取代时、C6-C12杂芳基、-NR′R′或 COOZ，它们具有诊断和治疗特性，如治疗和控制前列腺癌以及与 NAALADase 抑制有关的其他疾病。放射性标记可通过碳原子或杂原子连接在 X 氨基酸侧链上的各种人工基团掺入结构中。
• ERG targeted therapy
  申请人：The Regents of the University of Michigan

  公开号：US10774122B2

  公开（公告）日：2020-09-15

  The present disclosure relates to compositions and methods for cancer therapy, including but not limited to, targeted inhibition of cancer markers. In particular, the present disclosure relates to recurrent gene fusions as clinical targets for cancer.

  本公开涉及用于癌症治疗的组合物和方法，包括但不限于靶向抑制癌症标志物。特别是，本公开涉及作为癌症临床靶点的复发性基因融合。
• 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.