alpha-氯甲基-2-硝基-1H-咪唑-1-乙醇 | 13551-86-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: alpha-氯甲基-2-硝基-1H-咪唑-1-乙醇
• 英文名称: α-(chloromethyl)-2-nitro-1H-imidazole-1-ethanol
• 英文别名: 1-(chloromethyl)-2-(2-nitroimidazol-1-yl)ethanol；1-chloro-3-(2-nitro-1H-imidazol-1-yl)propan-2-ol；3-chloro-1-(2-nitro-1-imidazolyl)-2-propanol；1-chloro-3-(2-nitro-imidazol-1-yl)-propan-2-ol；1-(2-hydroxy-3-chloropropyl)-2-nitroimidazole；1-(2-nitro-1-imidazolyl)-3-chloro-2-propanol；alpha-(Chloromethyl)-2-nitroimidazole-1-ethanol；1-chloro-3-(2-nitroimidazol-1-yl)propan-2-ol
• CAS: 13551-86-5
• 化学式: C₆H₈ClN₃O₃
• 分子量: 205.601
• InChiKey: AANLIOPOVSJZLY-UHFFFAOYSA-N

物化性质

• 熔点：
  156-158 °C
• 沸点：
  439.8±55.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  83.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933290090

制备方法与用途

类别：有毒物质
毒性分级：高毒
急性毒性：口服-小鼠 LD50: 330 毫克/公斤；腹腔-小鼠 LD50: 158 毫克/公斤
可燃性危险特性：可燃，燃烧时分解生成有毒氯化物和氮氧化物气体
储运特性：库房应低温、通风且干燥，并与食品原料分开存放
灭火剂：水、二氧化碳、干粉、砂土

反应信息

• 作为反应物：
  描述：

  alpha-氯甲基-2-硝基-1H-咪唑-1-乙醇 以 乙酸乙酯 为溶剂， 反应 1.0h， 以300 mg的产率得到1-(2,3-环氧丙基)-2-硝基咪唑
  参考文献：
  名称：

  Probes for Imaging of Hypoxia

  摘要：

  检测缺氧细胞和组织的示范性探针具有以下结构。

  公开号：

  US20160151517A1
• 作为产物：
  描述：

  1-氯-3-(2-硝基-1H-咪唑-1-基)丙烷-2-酮 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以97%的产率得到alpha-氯甲基-2-硝基-1H-咪唑-1-乙醇
  参考文献：
  名称：

  Biocatalyzed synthesis of both enantiopure fluoromisonidazole antipodes

  摘要：

  Fluoromisonidazole (FMISO or F-MISO) is a radiotracer for positron emission tomography when F-18-labeled and is administrated in its racemic form. Herein, a straightforward synthesis of both enantiopure antipodes is proposed through a one-pot two-step microwave protocol to obtain a fluorinated ketone precursor followed by bioreduction using alcohol dehydrogenases from Rhodococcus ruber (ADH-A) or Lactobacillus brevis (LBADH). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.07.013

文献信息

• Hypoxia-selective, weakly basic 2-nitroimidazole delivery agents and methods of use thereof
  申请人：Lee David Y-W

  公开号：US20080102026A1

  公开（公告）日：2008-05-01

  The invention features a class of 2-nitroimidazole compounds with a secondary basic nitrogen atom and a linker bearing one or more therapeutic agents, cytotoxic agents, detectable labels, or chelating groups. In particular, the invention provides 2-nitroimidazole compounds containing a cluster of boron atoms for use in boron neutron capture therapy (BNCT). The 2-nitroimidazole compounds can be used to treat hypoxic conditions, including, e.g., cancer, inflammation, and ischemia. The weakly basic 2-nitroimidazole compounds target to hypoxic tissue and provide increased tissue concentration overall.

  这项发明涉及一类具有次生碱性氮原子和携带一个或多个治疗剂、细胞毒剂、可检测标签或螯合基团的2-硝基咪唑化合物。具体而言，该发明提供了含有硼原子簇的用于硼中子俘获疗法（BNCT）的2-硝基咪唑化合物。这些2-硝基咪唑化合物可用于治疗缺氧情况，包括癌症、炎症和缺血等病症。这些弱碱性的2-硝基咪唑化合物靶向于缺氧组织，并提供整体组织浓度的增加。
• Weakly basic 2-nitroimidazoles for the non-invasive detection of tissue hypoxia
  申请人：Raleigh James A.

  公开号：US20080085237A1

  公开（公告）日：2008-04-10

  The present invention incorporates weakly basic substituents (pKa about 8 or greater) such as pyrrolidine, piperidine, piperazine and azapane moieties in halogenated 2-nitromidazoles as a major improvement over prior art for the non-invasive detection of cellular hypoxia in normal and malignant tissues. The invention features the use of [18F] positron emission tomography, [19F] magnetic resonance spectroscopy, and [19F] magnetic resonance imaging. Improvements over prior art compounds are six-fold. 1) Salts of weakly basic reagents are highly water-soluble which facilitates administration. 2) Unreacted reagents are rapidly cleared from systemic circulation thereby decreasing background noise. 3) Reagents with weakly basic substituents are concentrated in tissue ˜3 fold above plasma levels thereby increasing binding intensity and enhancing signal detection. 4) Conjugate bases of weakly basic reagents have intermediate octanol-water partition coefficients that facilitate their penetration into all tissues including brain. 5) Cellular adducts of reagents containing weakly basic substituents are more stable than reagents of prior art. 6) Reagents with weakly basic substituents are effective for the detection of transient hypoxia in solid tissue.

  本发明将弱碱性取代基（pKa约为8或更高）如吡咯烷、哌啶、哌嗪和氮代环己烷基团引入卤代2-硝基咪唑中，作为对正常和恶性组织细胞缺氧的非侵入性检测的重大改进。该发明采用了[18F]正电子发射断层扫描、[19F]核磁共振波谱和[19F]核磁共振成像。与现有技术相比，改进了六倍。1）弱碱试剂的盐具有高水溶性，有利于给药。2）未反应的试剂会迅速从体循环中清除，从而减少背景噪音。3）含有弱碱性取代基的试剂在组织中的浓度约为血浆水平的3倍，从而增加结合强度并增强信号检测。4）弱碱性试剂的共轭碱具有中等的辛醇-水分配系数，有利于它们渗透到包括大脑在内的所有组织中。5）含有弱碱性取代基的试剂的细胞加合物比现有技术的试剂更稳定。6）含有弱碱性取代基的试剂对固体组织中瞬时缺氧的检测是有效的。
• Process for preparing chiral
  申请人：British Technoloyg Group Limited

  公开号：US05543527A1

  公开（公告）日：1996-08-06

  Chiral compounds useful as radiosensitizers or chemosensitizers having the formula ##STR1## wherein X is halogen or ##STR2## intermediates used to prepare these compounds, and a novel process to prepare these compounds are described.

  本文介绍了一种有用的手性化合物，可用作放射增敏剂或化学增敏剂，其化学式为##STR1##其中X是卤素或##STR2##用于制备这些化合物的中间体以及制备这些化合物的新方法。
• Derivatives of 2-nitro-imidazoles as hypoxic cell markers
  申请人：Natural Pharmacia International Inc.

  公开号：US05674693A1

  公开（公告）日：1997-10-07

  Derivatives of 2-nitro-imidazole, such as 1-(2-hydroxy-3-piperidinopropyl)-2-nitro-imidazole, are useful as hypoxic cell markers for immunochemical detection of hypoxia in tumor tissue.

  2-硝基咪唑的衍生物，例如1-(2-羟基-3-哌啶基丙基)-2-硝基咪唑，可用作低氧细胞标记物，在肿瘤组织中进行免疫化学检测，以便检测低氧状态。
• Metal complexes of N-heterocyclic carbenes as radiopharmaceuticals and antibiotics
  申请人：Youngs Wiley

  公开号：US20070021401A1

  公开（公告）日：2007-01-25

  A method for inhibiting microbial growth comprises administering an effective amount of a silver complex of a N-heterocyclic amine. A method for treating cancer cells or a method for imaging one or more tissues of a patient includes administering an effective amount of a complex of a N-heterocyclic amine and a radioactive metal. A method for treating urinary tract infections utilizing silver complexes of N-heterocyclic carbenes. N-heterocyclic carbenes of the present invention may be represented by the formula wherein Z is a heterocyclic group, and R 1 and R 2 are, independently or in combination, hydrogen or a C 1 -C 12 organic group selected from the group consisting of alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, aryl, arylalkyl, alkylaryl, heterocyclic, and alkoxy groups and substituted derivatives thereof.

  一种抑制微生物生长的方法包括给予有效量的N-杂环胺的银络合物。一种治疗癌细胞或成像患者一个或多个组织的方法包括给予有效量的N-杂环胺和放射性金属的络合物。一种利用N-杂环卡宾银络合物治疗尿路感染的方法。本发明的N-杂环卡宾可以用以下式表示，其中Z是杂环基，而R1和R2是独立或组合的氢或选择自烷基、环烷基、烯基、环烯基、炔基、芳基、芳基烷基、烷基芳基、杂环和烷氧基和其取代衍生物的C1-C12有机基。