2,5-dioxopyrrolidin-1-yl quinoline-3-carboxylate | 127369-50-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2,5-dioxopyrrolidin-1-yl quinoline-3-carboxylate
• 英文别名: N-(3-carbonyloxy-quinoline)pyrrolidine-2,5-dione；3-quinolinecarboxylic acid N-hydroxysuccinimide ester；(2,5-Dioxopyrrolidin-1-yl) quinoline-3-carboxylate
• CAS: 127369-50-0
• 化学式: C₁₄H₁₀N₂O₄
• 分子量: 270.244
• InChiKey: JYOVEXFBBPZVAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl quinoline-3-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.17h， 生成 (R)-3-Phenyl-2-[(quinoline-3-carbonyl)-amino]-propionic acid
  参考文献：
  名称：

  N-酰基苯基丙氨酸和相关化合物。一类新的口服降糖药。

  摘要：

  N-苯甲酰基-DL-苯丙氨酸（1）被发现具有降血糖活性。制备了一系列化合物1的类似物，并评估了它们的降血糖活性。研究了苯丙氨酸部分的空间影响和酰基部分变化的影响。这项研究阐明了一些构效关系，并导致了N-（4-乙基苯甲酰基）-D-苯丙氨酸（34）的开发，其效力是初始化合物1的50倍。

  DOI：

  10.1021/jm00119a007
• 作为产物：
  描述：

  3-溴喹啉 、 2,5-dioxopyrrolidin-1-yl formate 在 palladium diacetate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 10.0h， 以73%的产率得到2,5-dioxopyrrolidin-1-yl quinoline-3-carboxylate
  参考文献：
  名称：

  Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

  摘要：

  An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)(2)/Xantphos catalyst system.

  DOI：

  10.1021/acs.joc.5b01119

文献信息

• Chemical Delivery System of Metaiodobenzylguanidine (MIBG) to the Central Nervous System
  作者：Fabienne Gourand、Guillaume Mercey、Méziane Ibazizène、Olivier Tirel、Joël Henry、Vincent Levacher、Cécile Perrio、Louisa Barré

  DOI：10.1021/jm901550z

  日期：2010.2.11

  The aim of the present investigation was to apply a chemical delivery system (CDS) to MIBG (4) with the purpose of delivering this drug to the CNS. Compound 4 has been linked to a 1,4-dihydroquinoline moiety in order to achieve its CNS penetration, and here we report the synthesis to link 4 to the chemical delivery system and the radiosynthesis with carbon-11 of the “CDS-4 entity”. After iv injection

  本研究的目的是将化学递送系统（CDS）应用于MIBG（4），以将该药物递送至CNS。化合物4已连接到1,4-二氢喹啉部分以实现其CNS渗透，在此我们报道了将4连接到化学传递系统的合成以及“ CDS- 4实体”的碳11的放射性合成。。静脉注射[ 11 C] CDS - 4大鼠后，对血液样品和脑匀浆中放射性分布的后续研究以及通过HPLC和LC-MS / MS的分析证实了4释放入中枢神经系统。
• Molecular Optical Diagnostic Probes: Rationally Designed Quinolines with Raman-Chiral-Fluorescent Activity
  作者：Dora Răsădean、Agathe Quesnel、Panagiota S. Filippou、G. Dan Pantoş、Priyanka Dey

  DOI：10.1021/acs.chemmater.3c00336

  日期：2023.7.11

  “quinoline fragment” nicotinamide and demonstrate their diagnostic capabilities. The molecular design strategically incorporates a pyridine ring with cysteine functionalization specifically at position 3, along with thiol and carboxyl end groups. The synthesized molecules demonstrated strong fluorescence and chiroptical activities. When functionalized onto gold nanostructures, the surface-enhanced Raman scattering

  分子治疗诊断剂由于其亚纳米尺寸，具有血液循环时间长的优点，从而以最小的注射剂量获得更好的靶向效率。为此，喹啉衍生物作为药物很有吸引力，并且正在探索用于癌症治疗。因此，对它们进行结构调整和重新利用以用于诊断将显着改善疾病部位的定位。在这项研究中，我们报告了喹啉和“喹啉片段”烟酰胺的战略修饰，并展示了它们的诊断能力。该分子设计策略性地将吡啶环与硫醇和羧基末端基团（特别是在第 3 位进行半胱氨酸官能化）结合在一起。合成的分子表现出很强的荧光和手性光学活性。当功能化到金纳米结构上时，合成分子的表面增强拉曼散射（SERS）与商业喹啉硫醇拉曼探针相似。该分子的强拉曼手性荧光光学活性有望用作多模式诊断探针。与市售的喹啉硫醇相比，合成的衍生物在健康和癌性人类细胞中都具有较高的细胞活力，并且具有选择性杀死癌细胞而不会对周围健康细胞的生长产生负面影响的潜力。因此，报告的工作展示了定制设计的分子，具有生物相容性
• Development of potent and selective CCK-A receptor agonists from Boc-CCK-4: tetrapeptides containing Lys(N.epsilon.)-amide residues
  作者：Kazumi Shiosaki、Chun Wel Lin、Hana Kopecka、Richard A. Craig、Bruce R. Bianchi、Thomas R. Miller、David G. Witte、Michael Stashko、Alex M. Nadzan

  DOI：10.1021/jm00089a010

  日期：1992.5

  A series of Boc-CCK-4 derivatives represented by the general structure Boc-Trp-Lys(N(epsilon)-COR)-Asp-Phe-NH2, where R is an aromatic, heterocyclic, or aliphatic group, are potent and selective CCK-AT receptor agonists. These amide-bearing compounds complement the previously described urea-based tetrapeptides (Shiosaki et al. J. Med. Chem. 1991, 34, 2837-2842); structure-activity studies revealed parallel as well as divergent trends between these two series. A significant correlation was observed between pancreatic binding affinity and the resonance constant R of the phenyl substituent in one particular series of derivatives. Sulfation of phenolic amides appended onto the epsilon-amino group of the lysine did not affect affinity for the CCK-AT receptor in contrast to the 500-fold increase in binding potency observed upon sulfation of CCK-8, suggesting that the lysine appendage and the sulfated tyrosine in CCK-8, both key structural elements that impart high affinity for the CCK-A receptor, are interacting differently with the receptor. The amide-bearing tetrapeptides are full agonists relative to CCK-8 in stimulating pancreatic amylase release while being partial agonists in eliciting phosphoinositide (PI) hydrolysis. Both effects were blocked by selective CCK-A receptor antagonists.
• Delivering FLT to the Central Nervous System by Means of a Promising Targeting System: Synthesis, [¹¹C]Radiosynthesis, and in Vivo Evaluation
  作者：Fabienne Gourand、Mihaela-Liliana Ţînţaş、Axelle Henry、Méziane Ibazizène、Martine Dhilly、Fabien Fillesoye、Cyril Papamicaël、Vincent Levacher、Louisa Barré

  DOI：10.1021/acschemneuro.7b00218

  日期：2017.11.15

  The development of delivery systems to transport some specific radiotracers across the blood-brain barrier (BBB) needs to be investigated for brain imaging. [F-18]FLT (3'-deoxy-3'-F-18-fluoro-L-thymidine), an analogue substrate of the nucleoside thymidine, has been developed as a proliferation tracer for oncological PET studies. Unfortunately, low-grade brain tumors are poorly visualized due to the low uptake of [18F]FLT in brain tissue, preventing its use in PET imaging to detect brain tumors at an early stage. Based on our previous work, a redox chemical delivery system (CDS) related to Bodor's strategy was developed to enable the penetration of FLT into the brain. To this end, FLT was covalently linked to a series of lipophilic carriers based on a 1,4-dihydroquinoline structure. To determine the best carrier, various sets of [C-11]CDS-FLT were prepared and injected into rats. Pleasingly, in vivo results let us suggest that this CDS is a promising approach to overcome the BBB to target low-grade brain tumors for PET imaging.
• SAWAYAMA, TADAHIRO;TSUKAMOTO, MASATOSHI;SASAGAWA, TAKASHI;NISHIMURA, KAZU+, CHEM. AND PHARM. BULL., 38,(1990) N, C. 110-115
  作者：SAWAYAMA, TADAHIRO、TSUKAMOTO, MASATOSHI、SASAGAWA, TAKASHI、NISHIMURA, KAZU+

  DOI：——

  日期：——