4-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-4-oxobutanoic acid | 891781-87-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-4-oxobutanoic acid
• 英文别名: n-(2-Boc-amino-ethyl)-succinamic acid；4-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethylamino]-4-oxobutanoic acid
• CAS: 891781-87-6
• 化学式: C₁₁H₂₀N₂O₅
• 分子量: 260.29
• InChiKey: JKZIRNMWZZZHEQ-UHFFFAOYSA-N

物化性质

• 沸点：
  513.1±35.0 °C(Predicted)
• 密度：
  1.167±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2924199090

反应信息

• 作为反应物：
  描述：

  4-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-4-oxobutanoic acid 在 palladium 10% on activated carbon 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 2,2-dimethyl-4,8,13,16,21-pentaoxo-3-oxa-5,9,12,17,20-pentaazatetracosan-24-oic acid
  参考文献：
  名称：

  Dimeric argininamide-type neuropeptide Y receptor antagonists: Chiral discrimination between Y1 and Y4 receptors

  摘要：

  The structurally related peptides neuropeptide Y (NPY), peptide YY (PYY) and pancreatic polypeptide (PP) are endogenous agonists of the NPY receptor (YR) family, which in humans comprises four functionally expressed subtypes, designated Y1R, Y2R, Y4R and Y5R. Nonpeptide antagonists with high affinity and selectivity have been described for the Y1R, Y2R and Y5R, but such compounds are still lacking for the Y4R. In this work, the structures of the high affinity selective (R)-argininamide-type Y1R antagonists BIBP3226 and BIBO3304 were linked via the guanidine or urea moieties to give homo-dimeric argininamides with linker lengths ranging from 31 to 41 atoms. Interestingly, the twin compounds proved to be by far less selective for the Y1R than the R-configured monovalent parent compounds. The decrease in selectivity ratio was most pronounced for Y1R versus Y4R subtype, resulting in comparable affinities of bivalent ligands for Y1R and Y4R (e.g. UR-MK177 ((R, R)-49): K-i = 230 nM (Y1R) and 290 nM (Y4R)). With a Ki value of 130 nM and a K-b value of 20 nM, UR-MK188 ((R,R)-51) was superior to all Y4R antagonists known to date. The S, S-configured optical antipodes of UR-MK177 and UR-MK188 (UR-MEK381 ((S, S)-49) and UR-MEK388 ((S,S)-51)) were synthesized to investigate the stereochemical discrimination by the different receptor subtypes. Whereas preference for R, R-configured argininamides was characteristic of the Y1R, stereochemical discrimination by the Y4R was not observed. This may pave the way to selective Y4R antagonists. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.065
• 作为产物：
  描述：

  benzyl 4-[2-(tert-butoxycarbonylamino)ethylamino]-4-oxobutanoate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 以99%的产率得到4-((2-((tert-butoxycarbonyl)amino)ethyl)amino)-4-oxobutanoic acid
  参考文献：
  名称：

  Dimeric argininamide-type neuropeptide Y receptor antagonists: Chiral discrimination between Y1 and Y4 receptors

  摘要：

  The structurally related peptides neuropeptide Y (NPY), peptide YY (PYY) and pancreatic polypeptide (PP) are endogenous agonists of the NPY receptor (YR) family, which in humans comprises four functionally expressed subtypes, designated Y1R, Y2R, Y4R and Y5R. Nonpeptide antagonists with high affinity and selectivity have been described for the Y1R, Y2R and Y5R, but such compounds are still lacking for the Y4R. In this work, the structures of the high affinity selective (R)-argininamide-type Y1R antagonists BIBP3226 and BIBO3304 were linked via the guanidine or urea moieties to give homo-dimeric argininamides with linker lengths ranging from 31 to 41 atoms. Interestingly, the twin compounds proved to be by far less selective for the Y1R than the R-configured monovalent parent compounds. The decrease in selectivity ratio was most pronounced for Y1R versus Y4R subtype, resulting in comparable affinities of bivalent ligands for Y1R and Y4R (e.g. UR-MK177 ((R, R)-49): K-i = 230 nM (Y1R) and 290 nM (Y4R)). With a Ki value of 130 nM and a K-b value of 20 nM, UR-MK188 ((R,R)-51) was superior to all Y4R antagonists known to date. The S, S-configured optical antipodes of UR-MK177 and UR-MK188 (UR-MEK381 ((S, S)-49) and UR-MEK388 ((S,S)-51)) were synthesized to investigate the stereochemical discrimination by the different receptor subtypes. Whereas preference for R, R-configured argininamides was characteristic of the Y1R, stereochemical discrimination by the Y4R was not observed. This may pave the way to selective Y4R antagonists. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.08.065

文献信息

• TETRACYCLIC ANTHRAQUINONES POSSESSING ANTI-CANCER PROPERTIES
  申请人：Zhang Hesheng

  公开号：US20090325894A1

  公开（公告）日：2009-12-31

  The present invention provides aminoside tetracyclic anthraquinones represented by formula (I) or formula (II), wherein the peptides are introduced to connect tetracyclic anthraquinones and fatty acid saturated or unsaturated in order to make the anticancer agents to be absorbed and released selectively; meanwhile some water-solubility groups are also introduced into the branched chain, aminosaccharide and tetracyclic moiety of the compounds to improve the water-solubility. The present invention also provides the preparative method and the use thereof as pharmaceutically active components for treating the diseases cured by aminoside tetracyclic anthraquinone, for example cancer, such as intestines, liver, gastric, breast, lung, ovary, prostate, brain glioma, lymph, skin, pigment, thyroid gland, multiple bone marrow cancer and leukemia.

  本发明提供了由式(I)或式(II)表示的氨基四环蒽醌类化合物，其中引入肽连接四环蒽醌和饱和或不饱和脂肪酸，以使抗癌药物能够被选择性地吸收和释放；同时还在化合物的支链、氨基糖和四环蒽基团中引入了一些水溶性基团，以提高水溶性。本发明还提供了制备方法以及将其用作药用活性成分治疗由氨基四环蒽醌类化合物治愈的疾病，例如癌症，如肠癌、肝癌、胃癌、乳腺癌、肺癌、卵巢癌、前列腺癌、脑胶质瘤、淋巴癌、皮肤癌、色素瘤、甲状腺癌、多发性骨髓癌和白血病。
• Peptide nanotube aligning side chains onto one side
  作者：Yuki Tabata、Shota Mitani、Shunsaku Kimura

  DOI：10.1002/psc.2881

  日期：2016.6

  ic acid (CP5ES) is synthesized and investigated on peptide nanotube (PNT) formation. When the PNT is formed with the maximum number of intermolecular hydrogen bonds between the cyclic peptides, the sequence enables the alignment of the side chains, naphthyl groups, on one side of the PNT. Microscopic and spectroscopic observations of CP5ES crystals reveal that CP5ES forms rod‐ or needle‐shaped molecular

  合成了由β-萘基丙氨酸，两个β-丙氨酸和乙二胺-琥珀酸（CP5ES）序列组成的新型伪环状五-β-肽，并研究了肽纳米管（PNT）的形成。当在环状肽之间形成具有最大数目的分子间氢键的PNT时，该序列可在PNT的一侧进行侧链萘基的比对。CP5ES晶体的显微镜和光谱观察表明，CP5ES形成杆状或针状分子组装体，显示出棉花效应的激子耦合和主要的单体发射，这与由β-萘丙氨酸和两个β-丙氨酸。因此，建议将乙二胺-琥珀酸序列插入环状骨架的β-氨基酸中，可有效使侧链在PNT的一侧对齐。版权所有©2016欧洲多肽协会和John Wiley＆Sons，Ltd.
• Synthesis and Preclinical Evaluation of [¹⁸F]SiFA-PSMA Inhibitors in a Prostate Cancer Model
  作者：Justin J. Bailey、Melinda Wuest、Michael Wagner、Atul Bhardwaj、Carmen Wängler、Bjoern Wängler、John F. Valliant、Ralf Schirrmacher、Frank Wuest

  DOI：10.1021/acs.jmedchem.1c00812

  日期：2021.11.11

  tomography (PET) imaging of prostate-specific membrane antigen (PSMA) with gallium-68 (68Ga) and fluorine-18 (18F) radiotracers has aroused tremendous interest over the past few years. The use of organosilicon-[18F]fluoride acceptors (SiFA) conjugated to urea-based peptidomimetic PSMA inhibitors provides a “kit-like” multidose synthesis technology. Nine novel 18F-labeled SiFA-bearing PSMA inhibitors with different

  在过去几年中，使用 gal-68 ( 68 Ga) 和 18 ( 18 F) 放射性示踪剂对前列腺特异性膜抗原 (PSMA) 进行正电子发射断层扫描 (PET) 成像引起了极大的兴趣。使用有机硅-[ 18 F] 氟化物受体 (SiFA) 与基于尿素的拟肽 PSMA 抑制剂偶联，提供了一种“类似试剂盒”的多剂量合成技术。合成了九种具有不同接头部分的新型18 F 标记的带有 SiFA 的 PSMA 抑制剂，并分析了它们在 LNCaP 细胞中对 [ 125 I] I-TAAG-PSMA 的体外结合。IC 50值范围为 58–570 nM。在所有化合物中，[ 18 F]SiFA-Asp2 -PEG 3 -PSMA (IC 50 = 125 nM) 在 LNCaP 肿瘤中显示出最高的肿瘤摄取 (SUV 60 分钟0.73)。摩尔活性（A大幅增加阿米）（从7.5±0.5至86±3吉贝/微摩尔）导致在LNCaP肿瘤摄取一个显著增加（SUV
• [EN] FIBROBLAST ACTIVATION PROTEIN (FAP)-TARGETED IMAGING AND THERAPY OF CANCERS AND OTHER FIBROTIC AND INFLAMMATORY DISEASES<br/>[FR] IMAGERIE CIBLÉE DE PROTÉINE D'ACTIVATION DES FIBROBLASTES (FAP) ET THÉRAPIE DE CANCERS ET D'AUTRES MALADIES FIBROTIQUES ET INFLAMMATOIRES
  申请人：PURDUE RESEARCH FOUNDATION

  公开号：WO2021055641A1

  公开（公告）日：2021-03-25

  Fibroblast activation protein (FAP)-targeting compounds (e.g., conjugates); a method for imaging cancer or fibrosis; and methods for treating an inflammatory disease/disorder and cancer.

  纤维母细胞活化蛋白（FAP）靶向化合物（例如，共轭物）；一种用于影像癌症或纤维化的方法；以及治疗炎症性疾病/紊乱和癌症的方法。
• THE TETRACYCLIC ANTHRAQUINONES POSSESSING ANTI-CANCER EFFECT
  申请人：Tianjin Hemey Bio-Tech Co., Ltd.

  公开号：EP2123283A1

  公开（公告）日：2009-11-25

  The present invention provides aminoside tetracyclic anthraquinones represented by formula (I) or formula (II), wherein the piptides are introduced to connect tetracyclic anthraquinones and fatty acid saturated or unsaturated in order to make the anticancer agents to be absorbed and released selectively; meanwhile some water-solubility groups are also introduced into the branched chain, aminosaccharide and tetracyclic moiety of the compounds to improve the water-solubility. The present invention also provides the preparative method and the use thereof as pharmaceutically active components for treating the diseases cured by aminoside tetracyclic anthraquinone, for example cancer, such as intestines, liver, gastric, breast, lung, ovary, prostate, brain glioma, lymph, skin, pigment, thyroid gland, multiple bone marrow cancer and leukemia.

  本发明提供了以式(I)或式(II)为代表的氨基苷类四环蒽醌，其中引入了肽类连接四环蒽醌和饱和或不饱和脂肪酸，以使抗癌剂被选择性吸收和释放；同时在化合物的支链、氨基糖和四环分子中还引入了一些水溶性基团，以提高水溶性。本发明还提供了制备方法及其作为药物活性成分的用途，用于治疗氨基苷类四环蒽醌可治愈的疾病，例如癌症，如肠癌、肝癌、胃癌、乳腺癌、肺癌、卵巢癌、前列腺癌、脑胶质瘤、淋巴癌、皮肤癌、色素癌、甲状腺癌、多发性骨髓癌和白血病等。