9-[(3-fluoro-1-hydroxy-2-propoxy)methyl]guanine | 104495-35-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-[(3-fluoro-1-hydroxy-2-propoxy)methyl]guanine
• 英文别名: FHPG；2-amino-9-[[1-(fluoromethyl)-2-hydroxy-ethoxy]methyl]-1H-purin-6-one；2-amino-9-[(1-fluoro-3-hydroxypropan-2-yl)oxymethyl]-1H-purin-6-one
• CAS: 104495-35-4
• 化学式: C₉H₁₂FN₅O₃
• 分子量: 257.224
• InChiKey: NNQXQVNIWUIGQN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  鸟嘌呤 在 钯 吡啶 、 盐酸 、 甲醇 、 4-二甲氨基吡啶 、 硫酸氢铵 、 potassium fluoride 、 四丁基氟化铵 、 三乙胺 、 4,7,13,16,21,24-六氧-1,10-二氮双环[8.8.8]二十六烷 、 环己烯 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 9-[(3-fluoro-1-hydroxy-2-propoxy)methyl]guanine
  参考文献：
  名称：

  Preparation of tritium-labelled BIIL 260 of high specific radioactivity

  摘要：

  研究了多种合成高比放射性氚标记BIIL 260的方法。尝试通过与氚气的固相同位素交换以及与氚化水的同位素交换直接将氚引入BIIL 260，最终产品的比活性范围为2至7 Ci/mmol。然而，通过适当的BIIL 260合成片段进行固相和液相脱卤，然后通过化学合成将其转化为最终产品，得到的氚标记BIIL 260的比活性为25或71 Ci/mmol，这取决于在脱卤步骤中使用的前体和方法。版权 © 2002 John Wiley & Sons, Ltd.

  DOI：

  10.1002/jlcr.661

文献信息

• Synthesis and anti-herpes virus activity of acyclic 2'-deoxyguanosine analogs related to 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine
  作者：John C. Martin、Danny P. C. McGee、Gary A. Jeffrey、Doug W. Hobbs、Donald F. Smee、Thomas R. Matthews、Julian P. H. Verheyden

  DOI：10.1021/jm00158a011

  日期：1986.8

  Several "sugar" modified acyclic nucleoside analogues related to 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine (DHPG, 2) were synthesized and evaluated for antiviral activity. The preparation generally involved the condensation of the acetoxymethyl ether of alcohols 6c-g and 10-12a with diacetylguanine to give adducts 7c-g and 14-16, which were then deprotected to afford analogues 9c-g and 17-19. Alternatively

  合成了几种与9-[（1,3-二羟基-2-丙氧基）甲基]鸟嘌呤（DHPG，2）有关的“糖”修饰的无环核苷类似物，并评估了其抗病毒活性。制备通常涉及将醇6c-g和10-12a的乙酰氧基甲基醚与二乙酰鸟嘌呤缩合，得到加合物7c-g和14-16，然后将其脱保护得到类似物9c-g和17-19。或者，将醇12a和13a通过它们的甲苯磺酸酯12b和13b转化为碘化物，然后与鸟嘌呤的钠盐反应，得到脱保护后的类似物22和23。醛27上的醛醇-Cannizzaro交叉反应容易得到28，其脱保护得到类似物29。针对HSV-1的体外分析表明，所测试的所有化合物的活性均低于DHPG，尽管有几种是病毒胸苷激酶的良好底物。在小鼠脑炎模型中评估了更有前途的无环核苷9c，19和29，并证明在20 mg / kg的剂量下无法有效预防死亡。
• Compositions and Methods for Cellular Imaging and Therapy
  申请人：Yang J. David

  公开号：US20070248537A1

  公开（公告）日：2007-10-25

  The present invention relates generally to the fields of chemistry and radionuclide imaging. More particularly, it concerns compositions, kits and methods for imaging and therapy involving N 4 compounds and derivatives.

  本发明一般涉及化学和放射性核素成像领域。更具体地，涉及涉及N4化合物及其衍生物的成分、试剂盒和成像和治疗方法。
• Poly(peptide) as a chelator: methods of manufacture and uses
  申请人：Yang J. David

  公开号：US20060246005A1

  公开（公告）日：2006-11-02

  Novel compositions for imaging that include (a) a polypeptide that includes two or more consecutive amino acids that will function to non-covalently bind valent metal ions and (2) a valent metal ion chelated to at least one of the two consecutive amino acids, are disclosed. Also disclosed are methods of imaging using these novel compositions, such as methods of imaging a tumor within a subject. Methods of synthesizing an imaging agent and kits for preparing an imaging agent are also disclosed. Methods for determining the effectiveness of a candidate substance as an imaging agent that involve conjugating or chelating the candidate substance with a polypeptide that includes two or more consecutive amino acids that will function to non-covalently bind valent metal ions.

  揭示了用于成像的新颖组合物，包括（a）包含两个或更多连续氨基酸的多肽，这些氨基酸将起到非共价结合价态金属离子的作用，以及（2）与这两个连续氨基酸中的至少一个螯合的价态金属离子。还公开了使用这些新颖组合物进行成像的方法，例如成像主体内的肿瘤的成像方法。还公开了合成成像剂的方法和用于制备成像剂的试剂盒。还公开了用于确定候选物质作为成像剂有效性的方法，该方法涉及将候选物质与包含两个或更多连续氨基酸的多肽结合或螯合，这些氨基酸将起到非共价结合价态金属离子的作用。
• Ethylenedicysteine (EC)-drug conjugates, compositions and methods for tissue specific disease imaging
  申请人：Board of Regents, The University of Texas System

  公开号：US20040166058A1

  公开（公告）日：2004-08-26

  The invention provides, in a general sense, a new labeling strategy employing compounds that are are N 2 S 2 chelates conjugated to a targeting ligand, wherein the targeting ligand is a disease cell cycle targeting compound, a tumor angiogenesis targeting ligand, a tumor apoptosis targeting ligand, a disease receptor targeting ligand, amifostine, angiostatin, monoclonal antibody C225, monoclonal antibody CD31, monoclonal antibody CD40, capecitabine, COX-2, deoxycytidine, fullerene, herceptin, human serum albumin, lactose, leuteinizing hormone, pyridoxal, quinazoline, thalidomide, transferrin, or trimethyl lysine. The present invention also pertains to kits employing the compounds of interest, and methods of assessing the pharmacology of an agent of interest using the present compounds.

  该发明提供了一种新的标记策略，采用将N2S2螯合物与靶向配体结合的化合物，其中靶向配体是疾病细胞周期靶向化合物、肿瘤血管生成靶向配体、肿瘤凋亡靶向配体、疾病受体靶向配体、氨基磷酸酯、抗血管生成素、单克隆抗体C225、单克隆抗体CD31、单克隆抗体CD40、卡培他滨、COX-2、脱氧胞苷、富勒烯、赫塞汀、人血清白蛋白、乳糖、黄体生成激素、吡ridoxal、喹唑啉、沙利度胺、转铁蛋白或三甲基赖氨酸。本发明还涉及使用感兴趣的化合物的试剂盒，以及利用本发明化合物评估感兴趣药剂的药理学方法。
• N2S2 chelate-targeting ligand conjugates
  申请人：Yang J. David

  公开号：US20050129619A1

  公开（公告）日：2005-06-16

  The invention provides, in a general sense, a new labeling strategy employing compounds that are are N 2 S 2 chelates conjugated to a targeting ligand, wherein the targeting ligand is a disease cell cycle targeting compound, a tumor angiogenesis targeting ligand, a tumor apoptosis targeting ligand, a disease receptor targeting ligand, amifostine, angiostatin, monoclonal antibody C225, monoclonal antibody CD31, monoclonal antibody CD40, capecitabine, a COX-2 inhibitor, deoxycytidine, fullerene, herceptin, human serum albumin, lactose, leuteinizing hormone, pyridoxal, quinazoline, thalidomide, transferrin, or trimethyl lysine. The present invention also pertains to kits employing the compounds of interest, and methods of assessing the pharmacology of an agent of interest using the present compounds.

  该发明提供了一种新的标记策略，使用N2S2螯合物与靶向配体结合，其中靶向配体是疾病细胞周期靶向化合物、肿瘤血管生成靶向配体、肿瘤凋亡靶向配体、疾病受体靶向配体、氨磷汀、血管生成抑制素、单克隆抗体C225、单克隆抗体CD31、单克隆抗体CD40、卡培他滨、COX-2抑制剂、脱氧胞苷、富勒烯、赫塞汀、人血清白蛋白、乳糖、黄体生成激素、吡哆醛、喹唑啉、沙利度胺、转铁蛋白或三甲基赖氨酸。本发明还涉及使用感兴趣的化合物的试剂盒，以及使用本发明化合物评估感兴趣药物的药理学方法。