N,N'-bis(2,4,6-triiodo-3,5-benzenedichlorocarbonyl)malonamide | 79944-44-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N,N'-bis(2,4,6-triiodo-3,5-benzenedichlorocarbonyl)malonamide
• 英文别名: 5,5′-[malonylbis(azanediyl)]bis(2,4,6-triiodoisophthaloyl dichloride)；N,N'-bis[3,5-bis(chlorocarbonyl)-2,4,6-triiodophenyl]-malondiamide；N,N'-bis-(2,4,6-triiodo-3,5-bis-chlorocarbonylphenyl)-malondiamide；5-[[3-(3,5-Dicarbonochloridoyl-2,4,6-triiodoanilino)-3-oxopropanoyl]amino]-2,4,6-triiodobenzene-1,3-dicarbonyl chloride
• CAS: 79944-44-8
• 化学式: C₁₉H₄Cl₄I₆N₂O₆
• 分子量: 1259.49
• InChiKey: SBZUWSFJCRJRJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N,N'-bis(2,4,6-triiodo-3,5-benzenedichlorocarbonyl)malonamide 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基乙酰胺 为溶剂， 反应 2.0h， 生成 5,5′-[malonylbis(azanediyl)]bis[N1,N3-bis(2-aminoethyl)-2,4,6-triiodoisophthalamide] tetratrifluoroacetate
  参考文献：
  名称：

  阳离子碘化造影剂（CA4 +）的合成，临床前表征及其在离体人体髋关节软骨定量计算机断层扫描中的应用

  摘要：

  超越定性可视化并能够对功能组织性能进行定量评估的造影剂代表了下一代临床有用的成像工具。阳离子碘化造影剂（CA4 +）的优化和高效大规模合成用于成像关节软骨。与相似的阴离子或非离子药物相比，使用CA4 +的增强CT（CECT）显示关节软骨中CA4 +的药物吸收明显更高，并且CA4 +的吸收遵循Donnan平衡理论。通过对离体人体髋关节软骨进行成像获得的CA4 + CECT衰减与糖胺聚糖含量，平衡模量和摩擦系数相关，这是软骨功能性能和骨关节炎阶段的关键指标。最后，

  DOI：

  10.1021/acs.jmedchem.7b00234
• 作为产物：
  描述：

  5-氨基间苯二甲酸 在 氯化亚砜 、 potassium chloride 、 一氯化碘 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 36.0h， 生成 N,N'-bis(2,4,6-triiodo-3,5-benzenedichlorocarbonyl)malonamide
  参考文献：
  名称：

  Highly-Iodinated Fullerene as a Contrast Agent For X-ray Imaging

  摘要：

  The first fullerene-based X-ray contrast agent (CA) has been designed, synthesized, and characterized. The new CA is an externally functionalized derivative Of C-60 that is conceptually based on contemporary X-ray CA, all of which use iodine as the X-ray attenuating vehicle and are based on the 2,4,6-triiodinated-benzene-ring substructure. Using a modified Bingel-type reaction, a single addend containing 6 iodine atoms and 8 protected hydroxyl groups was appended to C-60 followed by the addition of 4 more addends each containing 4 protected hydroxyl groups. Final deprotection afforded the highly water-soluble (>460 mg/mL), non-ionic, highly-iodinated (24% I) fullerene for application as an X-ray contrast agent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00252-3

文献信息

• Nonionic X-ray contrast agents, compositions and methods
  申请人：Mallinckrodt, Inc.

  公开号：US05075502A1

  公开（公告）日：1991-12-24

  Triiodinated isophthalamide derivatives, useful as X-ray contrast agents, having at least one amide group derived from the amino-alcohol, 3-(N-2-hydroxyethyl)amino-1,2-propanediol, which provides high water solubility and low mammalian toxicity, and methods of preparing them. Methods of preparing 3-(N-2-hydroxyethyl)amino-1,2-propanediol are provided.

  三碘异苯二酰胺衍生物，作为X射线造影剂有用，至少有一个酰胺基团源自氨基醇3-(N-2-羟乙基)氨基-1,2-丙二醇，提供高水溶性和低哺乳动物毒性，并提供其制备方法。提供了制备3-(N-2-羟乙基)氨基-1,2-丙二醇的方法。
• Synthesis and evaluation of potential CT (computer tomography) contrast agents for bone structure and microdamage analysis
  作者：Raman Parkesh、Wolfgang Gowin、T. Clive Lee、Thorfinnur Gunnlaugsson

  DOI：10.1039/b606976b

  日期：——

  The design and synthesis of several novel X-ray contrast agents 1–3, developed for targeting bone structures, and in particularly microcracks in bones, using CT (Computer Tomography) detection is described. These contrast agents are based on the use of the well known triiodobenzene platform, which was conjugated into one or more phenyliminodiacetate moieties, which can be used to ‘lock’ onto bone matrices. Compounds 1–3 were all tested for their ability to visualise cracks in bone structures (bovine bones) using μ-CT imaging.

  描述了几种新型X射线对比剂1-3的设计与合成，这些对比剂旨在靶向骨结构，特别是骨中的微裂纹，采用计算机断层扫描（CT）检测。这些对比剂基于著名的三碘苯平台，该平台通过与一个或多个苯亚氨基二乙酸酯基团结合，以“锁定”骨基质。化合物1-3均经过测试，评估其在使用微CT成像时可视化骨结构（牛骨）裂纹的能力。
• Novel amino-dioxepane intermediates for the synthesis of new non-ionic
  申请人：The Regents of the University of California

  公开号：US04341756A1

  公开（公告）日：1982-07-27

  Novel intermediates for non-ionic polyiodo amino-substituted benzenepolyamides having polyol substituents on the amide nitrogens are provided which are 5-amino-6-hydroxy-1,3-dioxepanes. The compounds provide an economic and efficient route to novel contrast media having excellent chemical and physiological properties. Also provided are methods for preparing the subject compounds.

  本发明提供了一种新型中间体，用于非离子聚碘氨基取代苯基聚酰胺，其在酰胺氮上具有多元醇取代基，该中间体为5-氨基-6-羟基-1,3-二噁烷。这些化合物提供了一种经济高效的途径，制备出具有优异化学和生理性质的新型对比剂。本发明还提供了制备所述化合物的方法。
• Effect of Contrast Agent Charge on Visualization of Articular Cartilage Using Computed Tomography: Exploiting Electrostatic Interactions for Improved Sensitivity
  作者：Neel S. Joshi、Prashant N. Bansal、Rachel C. Stewart、Brian D. Snyder、Mark W. Grinstaff

  DOI：10.1021/ja9053306

  日期：2009.9.23

  The synthesis and evaluation of a new class of cationic iodinated contrast agents for the imaging of cartilage using computed tomography (CT) are described. In direct comparisons with anionic contrast agents, the cationic contrast agents afforded higher equilibrium concentrations in the articular cartilage of ex vivo rabbit femurs and thus greater imaging sensitivity. Variations in CT intensity across the sample reflected the inhomogeneous distribution of glycosaminoglycans in the tissue as confirmed by histological analysis. We anticipate that this work represents the first step in the development of sensitive, nondestructive CT-based methods to characterize the biochemical properties of cartilage using cationic contrast agents.
• Toward fullerene-based X-ray contrast agents: design and synthesis of non-ionic, highly-iodinated derivatives of C60
  作者：Tim Wharton、Lon J Wilson

  DOI：10.1016/s0040-4039(01)02119-0

  日期：2002.1

  An X-ray contrast agent precursor based on C-60 has been designed, synthesized, and characterized. The compound is the monoadduct of a malonodiamide containing six iodine atoms and eight acetal-protected alcohols with multiple hindered rotations at ambient temperature. (C) 2002 Elsevier Science Ltd. All rights reserved.