N-[2-((triphenylmethyl)thio)ethyl]chloroacetamide | 258826-31-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-[2-((triphenylmethyl)thio)ethyl]chloroacetamide
• 英文别名: 2-Chloro-N-(2-tritylsulfanylethyl)-acetamide；2-chloro-N-(2-tritylsulfanylethyl)acetamide
• CAS: 258826-31-2
• 化学式: C₂₃H₂₂ClNOS
• 分子量: 395.953
• InChiKey: VIHVCPYAOQEHEP-UHFFFAOYSA-N

物化性质

• 熔点：
  161-162 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• 沸点：
  563.5±50.0 °C(Predicted)
• 密度：
  1.199±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-[2-((triphenylmethyl)thio)ethyl]chloroacetamide 在 N-羟基丁二酰亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 乙腈 为溶剂， 反应 96.0h， 生成 trimethyl-γ-L-glutamyl-L-glutamyl-7,10-diaza-9-oxo-7-[2-(triphenylmethyl)thioethyl]-12-[(triphenylmethyl)-thio]dodecanamide
  参考文献：
  名称：

  PRECURSOR USED FOR LABELING HEPATORCYTE RECEPTOR AND CONTAINING TRISACCHARIDE AND DIAMIDE DEMERCAPTIDE LIGAND, METHOD FOR PREPARING THE SAME, RADIOTRACER AND PHARMACEUTICAL COMPOSITION OF THE SAME

  摘要：

  一种用于标记肝细胞受体并应用于用于肝癌成像或药物组合物的放射示踪剂的前体被揭示。该前体是一种双功能化合物。双功能基团包括三糖结构和二酰胺二巯基（N2S2）配体。三糖具有高亲和力，能与肝细胞表面的非糖蛋白受体（ASGPR）结合，而N2S2配体与放射性同位素反应形成中性络合物。因此，前体停留在肝细胞表面，提供放射同位素标记或治疗肝癌的效果。

  公开号：

  US20140031533A1
• 作为产物：
  描述：

  三苯基甲醇 在 三乙胺 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 6.0h， 生成 N-[2-((triphenylmethyl)thio)ethyl]chloroacetamide
  参考文献：
  名称：

  PRECURSOR USED FOR LABELING HEPATORCYTE RECEPTOR AND CONTAINING TRISACCHARIDE AND DIAMIDE DEMERCAPTIDE LIGAND, METHOD FOR PREPARING THE SAME, RADIOTRACER AND PHARMACEUTICAL COMPOSITION OF THE SAME

  摘要：

  一种用于标记肝细胞受体并应用于用于肝癌成像或药物组合物的放射示踪剂的前体被揭示。该前体是一种双功能化合物。双功能基团包括三糖结构和二酰胺二巯基（N2S2）配体。三糖具有高亲和力，能与肝细胞表面的非糖蛋白受体（ASGPR）结合，而N2S2配体与放射性同位素反应形成中性络合物。因此，前体停留在肝细胞表面，提供放射同位素标记或治疗肝癌的效果。

  公开号：

  US20140031533A1

文献信息

• H3LMN COMPOUND USED AS RADIOACTIVE AGENT FOR TREATMENT OF LIVER CANCER AND MANUFACTURING METHOD THEREOF
  申请人：Liu Show-Wen

  公开号：US20110065904A1

  公开（公告）日：2011-03-17

  H 3 LMN series compounds used as radioactive agents for treatment of liver cancer and a manufacturing method thereof are revealed. 2-thioethylamine hydrochloride is reacted with triphenylmethanol for protection of thiol to obtain 2-[(triphenylmethyl)thio]ethylamine. Then obtain N-[2-((triphenylmethyl)thio)ethyl]chloroacetamide by a transamidation reaction between 2-[(triphenylmethyl)thio]ethylamine and chloroactyl chloride. Next produce a amine-amide-thiol ligand-N-[2-((triphenylmethyl)thio)ethyl][2-((triphenylmethyl)thio)ethylamino]acetamide by a substitution reaction of N-[2-((triphenylmethyl)thio)ethyl]chloroacetamide and 2-[(triphenylmethyl)thio]ethylamine. After respective reaction with 1-bromotetradecane, 1-bromohexadecane and ethyl 16-bromohexadecanoate, H 3 LMN series compounds are obtained. These amine-amide-dithiols quadridentate ligands can react with MO 3+ (M=Tc or Re) to produce electrically neutral complexes. The complexes have high lipophilicity, allowing them soluble in lipiodol to be applied to radiation therapy for liver cancer.

  LMN系列化合物被用作治疗肝癌的放射性药剂，以及其制造方法被揭示。2-硫乙胺盐酸盐与三苯甲醇反应以保护硫醇，得到2-[(三苯甲基)硫基]乙胺。然后通过2-[(三苯甲基)硫基]乙胺与氯乙酰氯之间的转酰胺反应获得N-[2-((三苯甲基)硫基)乙基]氯乙酰胺。接下来通过N-[2-((三苯甲基)硫基)乙基]氯乙酰胺和2-[(三苯甲基)硫基]乙胺的取代反应产生一种胺-酰胺-硫醇配体-N-[2-((三苯甲基)硫基)乙基][2-((三苯甲基)硫基)乙胺基]乙酰胺。在分别与1-溴四十二烷、1-溴十六烷和乙基-16-溴十六烷酸酯反应后，得到H3LMN系列化合物。这些胺-酰胺-二硫醇四齿配体可以与MO3+(M=Tc或Re)反应，产生电中性络合物。这些络合物具有高脂溶性，使它们可溶于碘油，用于肝癌的放射治疗。
• BIFUNCTIONAL COMPOUND WITH MONOSACCHARIDE AND N2S2 LIGAND, AND PREPARATION AND USE THEREOF
  申请人：LIU SHOW-WEN

  公开号：US20120009669A1

  公开（公告）日：2012-01-12

  A bifunctional compound with a monosaccharide and a N 2 S 2 ligand, and more particularly, a bifunctional compound with a N 2 S 2 ligand and aminohexylacetyl galactosamine (ah-GalNAc 4 ) is provided. A method for preparing the bifunctional compound with a monosaccharide and a N 2 S 2 ligand is also provided, including activating a carboxyl group in an organic ligand, reacting the activated carboxyl group with a galactopyranoside through amidation, and then hydrolyzing. The bifunctional compound of the present invention is widely useful in nuclear medicine for preparation of liver imaging agents for assisting in correct diagnosis of diseases.

  提供了一种具有单糖和N2S2配体的双功能化合物，更具体地说，提供了一种具有N2S2配体和氨基己酰半乳糖胺（ah-GalNAc4）的双功能化合物。还提供了一种制备具有单糖和N2S2配体的双功能化合物的方法，包括激活有机配体中的羧基，通过酰胺化将激活的羧基与半乳糖苷反应，然后水解。本发明的双功能化合物在核医学中广泛用于制备肝脏成像剂，以帮助正确诊断疾病。
• Bifunctional compound and method for manufacturing the same
  申请人：ATOMIC ENERGY COUNCIL-INSTITUTE OF NUCLEAR ENERGY RESEARCH

  公开号：US09227931B1

  公开（公告）日：2016-01-05

  A bifunctional compound and a method for manufacturing the same are revealed. The structural formula of the compound includes two main functional groups. One functional group is a diamide dithiolate (N2S2) ligand able to bind with radioisotopes. The other functional group is polybasic carboxylic acid that binds to biochemical substances. Based on properties of the above two functional groups, the compound of the present invention can be used for preparation of radiopharmaceuticals such as radiotracter for disease diagnosis or radioactive therapeutic agent for disease treatment.

  揭示了一种双功能化合物及其制备方法。该化合物的结构式包括两个主要功能基团。一个功能基团是能够与放射性同位素结合的二酰胺二硫醇配体（N2S2）。另一个功能基团是能够与生化物质结合的多碱性羧酸。基于上述两个功能基团的性质，本发明的化合物可用于制备放射性药物，如用于疾病诊断的放射示踪剂或用于疾病治疗的放射性治疗剂。
• Compound containing carboxylate ester and N2S2 ligand bi-functional groups and manufacturing method thereof
  申请人：LIU Show-Wen

  公开号：US20100056804A1

  公开（公告）日：2010-03-04

  A compound containing carboxylate ester and N2S2 ligand bi-functional groups and a manufacturing method thereof are disclosed. The S in the N2S2 ligand of the compound containing carboxylate ester and N2S2 ligand bi-functional groups includes a protective group so as to avoid to be oxidized and easy storage. In a complex reaction, the protective group is automatically released As to the active carboxylate ester, it is for reacting with compounds having amino groups such as amines, amino acids, peptides, or protein etc while the N2S2 ligand is for bonding with technetium or rhenium so as to form neutral complex. The compound containing carboxylate ester and N2S2 ligand bi-functional groups is applied to radiopharmaceuticals such as contrast agents for tissues and target agents.

  揭示了一种含有羧酸酯和N2S2配体双功能基团的化合物及其制备方法。所述化合物中N2S2配体中的S包含有保护基团，以避免氧化并便于储存。在复杂反应中，保护基团会自动释放，使活性羧酸酯可以与具有氨基的化合物（如胺、氨基酸、肽或蛋白质等）反应，而N2S2配体则与锝或铼结合，形成中性配合物。含有羧酸酯和N2S2配体双功能基团的化合物应用于放射性药物，如组织对比剂和靶向药物。
• Precursor used for labeling hepatorcyte receptor and containing trisaccharide and diamide demercaptide ligand, method for preparing the same, radiotracer and pharmaceutical composition of the same
  申请人：Liu Show-Wen

  公开号：US09150602B2

  公开（公告）日：2015-10-06

  A precursor used for labeling hepatocyte receptors and applied to radiotracers for imaging or pharmaceutical compositions for liver cancers is revealed. The precursor is a bifunctional compound. The bifunctional group includes a trisaccharide structure and a diamide dimercaptide (N2S2) ligand. The trisaccharide has high affinity to asialoglycoprotein receptors (ASGPR) on surfaces of hepatocytes while N2S2 ligand reacts with radioisotopes to form neutral complexes. Thus the precursor stays on surfaces of hepatocytes to provide radioisotope labeling or treatment effect of liver cancers.

  揭示了一种用于标记肝细胞受体并应用于放射性示踪剂或治疗肝癌的制药组合物的前体。该前体是一种双功能化合物。双功能基团包括三糖结构和二酰胺二硫醇（N2S2）配体。三糖具有高亲和力，可与肝细胞表面的非酰化糖蛋白受体（ASGPR）结合，而N2S2配体与放射性同位素反应形成中性配合物。因此，该前体停留在肝细胞表面，以提供肝细胞的放射性同位素标记或治疗肝癌的效果。