2-(3,4,5-trimethoxyphenyl)ethaneisonitrile | 165459-75-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(3,4,5-trimethoxyphenyl)ethaneisonitrile
• 英文别名: 5-(2-Isocyanoethyl)-1,2,3-trimethoxybenzene
• CAS: 165459-75-6
• 化学式: C₁₂H₁₅NO₃
• 分子量: 221.256
• InChiKey: ZQMBKJSONUTTKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  32
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  仙人球毒碱 、 氯仿 在 sodium hydroxide 、 四丁基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以17%的产率得到2-(3,4,5-trimethoxyphenyl)ethaneisonitrile
  参考文献：
  名称：

  Novel Hexakis(areneisonitrile)technetium(I) Complexes as Radioligands Targeted to the Multidrug Resistance P-Glycoprotein

  摘要：

  Transport substrates and modulators of the human multidrug resistance (MDR1) P-glycoprotein (Pgp) are generally lipophilic cationic compounds, many with substituted aryl moieties, We sought to synthesize aromatic technetium-isonitrile complexes to enable functional detection in vivo of Pgp expression in tissues. A series of substituted aromatic isonitrile analogs were synthesized from their corresponding amines by reaction with dichlorocarbene under phase transfer-catalyzed conditions, and the non-carrier-aaded hexakis(areneisonitrile)Tc-99m(I) complexes were produced by reaction with pertechnetate in the presence of sodium dithionite. Cellular accumulation in. vitro, whole body biodistribution, and the imaging properties of these lipophilic, monocationic organometallic complexes were determined in Chinese hamster lung fibroblasts expressing MDR Pgp, in normal rats, and in rabbits, respectively. For this initial series, verapamil (50 mu M), the classical Pgp modulator, significantly enhanced cellular accumulation or displaced binding of Tc complexes of 1b, 1d, 1h, 2a, 2d, 3a, and 3b, indicative of targeted interactions with Pgp. Most complexes, despite their modestly high lipophilicity, were excluded by the blood/brain barrier, and several complexes displayed simultaneously high hepatobiliary and renal excretion in vivo, consistent with the physiological expression pattern of Pgp in these tissues. Selected Tc- and Re-areneisonitrile complexes of this class have potential applicability to the functional imaging and modulation, respectively, of MDR Pgp in human tissues.

  DOI：

  10.1021/jm00015a018

文献信息

• US5403574A
  申请人：——

  公开号：US5403574A

  公开（公告）日：1995-04-04
• [EN] EVALUATION AND TREATMENT OF THE MULTIDRUG RESISTANCE PHENOTYPE
  申请人：——

  公开号：WO1993000064A2

  公开（公告）日：1993-01-07

  [EN] The present invention relates to methods for detecting the multidrug resistance phenotype in vivo and in vitro. The invention particularly relates to methods of diagnosing the multidrug resistance phenotype by imaging, particularly scintigraphic imaging, in solid tumors in vivo or in tumors and biopsies in vitro. The methods of the present invention allow the diagnosis of multidrug-resistant tumor and other multidrug-resistant phenotypes without invasive surgical methods. The present invention is also directed to methods of treating multidrug resistant tumors with novel agents that bind to P-glycoprotein. The novel compounds of the present invention are co-administered with a chemotherapeutic agent in order to enhance accumulation of the drug.
  [FR] La présente invention concerne des procédés de détection du phénotype de résistance multimédicamenteuse in vivo et in vitro. L'invention concerne en particulier des procédés de diagnostic du phénotype de résistance aux multimédicaments par imagerie, en particulier imagerie scintigraphique, dans des tumeurs solides in vivo ou dans des tumeurs et des biopsies in vitro. Les procédés de la présente invention permettent le diagnostic de la tumeur résistant aux multiples médicaments et autres phénotypes résistant aux multimédicaments sans avoir recours à des méthodes chirurgicales de type à invasion. La présente invention concerne également des procédés de traitement de tumeurs résistant à de multiples médicaments à l'aide de nouveaux agents qui se lient à la P-glycoprotéine. Les nouveaux composés de la présente invention sont administrés en association avec un agent chimiothérapeutique de manière à améliorer l'accumulation du médicament.