1-[[4-(三丁基锡烷基)苯甲酰基]氧基]-2,5-吡咯烷二酮 | 107759-58-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-[[4-(三丁基锡烷基)苯甲酰基]氧基]-2,5-吡咯烷二酮
• 英文名称: N-succinimidyl 4-(tri-n-butylstannyl)benzoate
• 英文别名: N-succinimidyl 4-tributylstannylbenzoate；(2,5-dioxopyrrolidin-1-yl) 4-tributylstannylbenzoate
• CAS: 107759-58-0
• 化学式: C₂₃H₃₅NO₄Sn
• 分子量: 508.245
• InChiKey: LOYKOFHWTNBVBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  63.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[[4-(三丁基锡烷基)苯甲酰基]氧基]-2,5-吡咯烷二酮 在 N-氯代丁二酰亚胺 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 N-succinimidyl-4-[125I]iodobenzoate
  参考文献：
  名称：

  [EN] NEW SCAFFOLDS AND MULTIFUNCTIONAL INTERMEDIATES FOR IMAGING PSMA AND CANCER THERAPY
  [FR] NOUVEAUX ÉCHAFAUDAGES ET INTERMÉDIAIRES MULTIFONCTIONNELS POUR L'IMAGERIE DE ET LE TRAITEMENT DU CANCER

  摘要：

  公开号：

  WO2016065142A3
• 作为产物：
  描述：

  六正丁基二锡 在 四(三苯基膦)钯 、 水 、 N,N'-二环己基碳二亚胺 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 生成 1-[[4-(三丁基锡烷基)苯甲酰基]氧基]-2,5-吡咯烷二酮
  参考文献：
  名称：

  Synthesis and evaluation of novel radioiodinated PSMA targeting ligands for potential radiotherapy of prostate cancer

  摘要：

  Radioligand therapy (RLT) using prostate-specific membrane antigen (PSMA) targeting ligands is an attractive option for the treatment of Prostate cancer (PCa) and its metastases. We report herein a series of radioiodinated glutamate-urea-lysine-phenylalanine derivatives as new PSMA ligands in which L-tyrosine and L-glutamic acid moieties were added to increase hydrophilicity concomitant with improvement of in vivo targeting properties. Compounds 8, 15, 19a/19b and 23a/23b were synthesized and radiolabeled with I-125 by iododestannylation. All iodinated compounds displayed high binding affinities toward PSMA (IC50 = 1-13 nM). In vitro cell uptake studies demonstrated that compounds containing an L-tyrosine linker moiety (8, 15 and 19a/19b) showed higher internalization than MIP-1095 and 23a/23b, both without the L-tyrosine linker moiety. Biodistribution studies in mice bearing PC3-PIP and PC3 xenografts showed that [I-125]8 and [I-125]15 with higher lipophilicity exhibited higher nonspecific accumulations in the liver and intestinal tract, whereas [I-125]19a/19b and [I-125]23a/23b containing additional glutamic acid moieties showed higher accumulations in the kidney and implanted PC3-PIP (PSMA+) tumors. [I-125]23b displayed a promising biodistribution profile with favorable tumor retention, fast clearance from the kidney, and 2-3-fold lower uptake in the liver and blood than that observed for [I-125]MIP-1095. [I-125/131]23b may serve as an optimal PSMA ligand for radiotherapy treatment of prostate cancer over-expressing PSMA.

  DOI：

  10.1016/j.bmc.2020.115319

文献信息

• Labeling approaches for the GE11 peptide, an epidermal growth factor receptor biomarker
  作者：Samar Dissoki、Aviv Hagooly、Smadar Elmachily、Eyal Mishani

  DOI：10.1002/jlcr.1910

  日期：2011.9

  The epidermal growth factor receptor (EGFR) is involved in the proliferation and differentiation of normal and malignant cells and is a major therapeutic target for a variety of human cancers. The peptide GE11 was reported to bind efficiently to the EGFR. Labeling GE11 with radionuclides may aid in the quantification of EGFR expression in tumors via noninvasive imaging. To this end, a GGGK linker was

  表皮生长因子受体（EGFR）参与正常和恶性细胞的增殖和分化，是多种人类癌症的主要治疗靶点。据报道，肽 GE11 与 EGFR 有效结合。用放射性核素标记 GE11 可能有助于通过无创成像量化肿瘤中 EGFR 的表达。为此，将 GGGK 接头连接到肽 (GE11') 上，该接头与辅基标记的基团缀合，例如 [18F]N-琥珀酰亚胺 4-氟苯甲酸酯 ([18F]SFB)、[18F](2- 2-[2-(2-氟-乙氧基)-乙氧基]-乙氧基}-乙氧基)-丙炔([18F]F-PEG4-丙炔)、[124I]N-琥珀酰亚胺4-碘苯甲酸酯和NOTA-Bn-用于 111In 标记的 NCS 螯合剂。所有标记的类似物均以放射化学纯度成功制备 > 95% 并根据其未标记的标准通过 HPLC 进行鉴定。[18F]SFB 和[18F]F-PEG4-丙炔的衰减校正产率 (DCY) 分别为 26% 和 30%，比活性 (SA)
• [EN] IN VIVO STABLE HG-197(M) COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND USE THEREOF IN NUCLEAR MEDICAL DIAGNOSTICS AND ENDORADIONUCLIDE THERAPY (THERANOSTICS)<br/>[FR] COMPOSÉS DE HG-197(M) STABLES IN VIVO, PROCÉDÉ DE PRODUCTION ASSOCIÉ ET UTILISATION ASSOCIÉE EN DIAGNOSTIC MEDICAL NUCLÉAIRE ET EN THÉRAPIE UTILISANT DES ENDORADIONUCLÉIDES (THÉRANOSTIC)
  申请人：HELMHOLTZ ZENTRUM DRESDEN

  公开号：WO2018146116A1

  公开（公告）日：2018-08-16

  The present invention relates to in vivo stable 197(m)Hg compounds according to formula (I) for use in nuclear medical diagnostics and endoradionuclide therapy (theranostics), particularly the treatment of cancer, a method for the production of the 197(m)Hg compounds comprising the step of radiolabeling of organic precursor compounds with NCA 197(m)Hg by electrophilic substitution; and the use of the 197(m)Hg compounds for nuclear medical diagnostics and endoradionuclide therapy (theranostics), particularly the treatment of cancer.

  本发明涉及用于核医学诊断和内放射性核素治疗（治疗学）的体内稳定的197(m)Hg化合物，特别是用于癌症治疗的公式（I）所述的化合物，包括将有机前体化合物与NCA 197(m)Hg进行电亲核取代的步骤的197(m)Hg化合物的制备方法；以及用于核医学诊断和内放射性核素治疗（治疗学），特别是用于癌症治疗的197(m)Hg化合物的用途。
• FORMATION OF 18F AND 19F FLUOROARENES BEARING REACTIVE FUNCTIONALITIES
  申请人：Carroll Michael Andrew

  公开号：US20090286992A1

  公开（公告）日：2009-11-19

  An iodonium compound of formula (I): where R AR1 is a C 5-6 aryl group, bearing at least one substituent selected from formyl, thionoacyl, acylamidocarboxy, thionoester, azo, C 2-20 alkenyl, C 2-20 alkynyl, and (CH 2 ) n R C , where R C is selected from ether, amino, azo and thioether; R AR2 is a C 5-10 aryl group, optionally substituted by one or more groups selected from C 1-12 alkyl, C 5-12 aryl, C 3-12 heterocyclyl, ether, thioether, nitro, cyano and halo, and may be linked to a solid support or fluorous tag; and X is a counteranion.

  化学式(I)的碘化物：其中RAR1是一个C5-6芳基，至少带有一种取代基，选自甲酰基、硫代酰基、酰胺羧基、硫酯、偶氮、C2-20烯基、C2-20炔基和(CH2)nRC，其中RC选自醚、氨基、偶氮和硫醚；RAR2是一个C5-10芳基，可选择地被一个或多个取代基取代，选自C1-12烷基、C5-12芳基、C3-12杂环烷基、醚、硫醚、硝基、氰基和卤素，并且可以连接到固体支撑物或氟标记；X是一个对阴离子。
• [EN] RADIOHALIDE-LABELED TARGETED DIAGNOSTICS AND THERAPEUTICS<br/>[FR] AGENTS THÉRAPEUTIQUES ET DE DIAGNOSTIC CIBLÉS MARQUÉS AVEC UN RADIOHALOGÉNURE
  申请人：SLOAN KETTERING INST CANCER

  公开号：WO2016033293A1

  公开（公告）日：2016-03-03

  Disclosed are chemical entities of formula (I) wherein R1, R2 and n are defined herein, and methods of use thereof. These chemical entities are radiative emitters and are useful, e.g., as therapeutic agents for the treatment of, or as diagnostic (e.g., imaging) agents for cancers, e.g., cancers in which PARP1 is overexpressed.

  揭示了具有化学式（I）的化学实体，其中R1、R2和n在此处定义，并且其使用方法。这些化学实体是放射性发射体，可用作治疗剂，例如用于治疗PARP1过度表达的癌症，或作为诊断（例如，成像）剂。
• [EN] PROSTATE-SPECIFIC MEMBRANE ANTIGEN (PSMA) INHIBITORS AS DIAGNOSTIC AND RADIONUCLIDE THERAPEUTIC AGENTS<br/>[FR] INHIBITEURS DE L'ANTIGÈNE MEMBRANAIRE SPÉCIFIQUE DE LA PROSTATE (PSMA) EN TANT QU'AGENTS DIAGNOSTIQUES ET AGENTS THÉRAPEUTIQUES DE TYPE RADIONUCLÉIDES
  申请人：FIVE ELEVEN PHARMA INC

  公开号：WO2020220023A1

  公开（公告）日：2020-10-29

  The present disclosure relates to compounds according to Formula I. These compounds display very good binding affinities to the PSMA binding sites. They comprise a radioactive isotope or a chelating moiety that can be labeled with a radioactive metal such as [68Ga]or [177Lu]. The present disclosure also relates to pharmaceutical compositions comprising a pharmaceutical acceptable carrier and a compound of Formula I or a complex thereof, or a pharmaceutically acceptable salt thereof.

  本公开涉及符合式I的化合物。这些化合物显示出对PSMA结合位点非常好的结合亲和力。它们包括一个放射性同位素或一个能够用放射性金属标记的螯合基团，如[68Ga]或[177Lu]。本公开还涉及包括药用可接受载体和符合式I的化合物或其复合物，或其药用可接受盐的制药组合物。