6-fluorohex-1-yne | 373-16-0

• 分子结构分类: 有机化合物 - 乙炔化物
• 英文名称: 6-fluorohex-1-yne
• 英文别名: fluorohexyne；6-fluoro-hex-1-yne；6-Fluor-hex-1-in
• CAS: 373-16-0
• 化学式: C₆H₉F
• 分子量: 100.136
• InChiKey: YDUGWJMUYOGFLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  6-fluorohex-1-yne 在 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 四丁基氟化铵 、 sodium ascorbate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 N-succinimidyl 3-((1,2-bis(tert-butoxycarbonyl)guanidino)-methyl)-5-((4-(4-fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-benzoate
  参考文献：
  名称：

  N-Succinimidyl 3-((4-(4-[¹⁸F]fluorobutyl)-1H-1,2,3-triazol-1-yl)methyl)-5-(guanidinomethyl)benzoate ([¹⁸F]SFBTMGMB): a residualizing label for ¹⁸F-labeling of internalizing biomolecules

  摘要：

  一种纳米抗体5F7使用[¹⁸F]RL-I进行标记，这是一种残留性标记，保持了对HER2的亲和力和免疫反应性。

  DOI：

  10.1039/c5ob02258d
• 作为产物：
  描述：

  6-氯己炔 在 potassium fluoride 、 乙二醇 作用下， 生成 6-fluorohex-1-yne
  参考文献：
  名称：

  Toxic Fluorine Compounds. XVII.¹ Some 1-Fluoroalkanes, ι-Fluoroalkenes and ι-Fluoroalkynes

  摘要：

  DOI：

  10.1021/ja01566a079

文献信息

• TOXIC FLUORINE COMPOUNDS: XIX. ω-FLUOROALKYNES
  作者：F. L. M. Pattison、R. E. A. Dear

  DOI：10.1139/v63-380

  日期：1963.10.1

  Some ω-fluoroalkynes have been prepared and shown to be valuable intermediates in the synthesis of rare long-chain ω-fluoro compounds; successful representative reactions, in all of which the C—F bond remained intact, included Grignard reactions, partial and total catalytic hydrogenation, halogenation, and miscellaneous coupling reactions.

  一些 ω-氟炔已被制备出来，并被证明是合成稀有长链 ω-氟化合物的有价值的中间体；成功的代表性反应包括格氏反应、部分和全部催化氢化、卤化和杂项偶联反应，其中 C-F 键保持完整。
• ISATIN DERIVATIVES FOR USE AS IN VIVO IMAGING AGENTS
  申请人：Aboabye Eric Ofori

  公开号：US20110195024A1

  公开（公告）日：2011-08-11

  Isatin 5-sulfonamide derivatives, pharmaceutical compositions comprising the derivatives, their use as molecular imaging agents, their use for the diagnosis or treatment of diseases or disorders associated with dysregulation of apoptosis, methods for synthesizing the derivatives, methods for the molecular imaging of caspase activity and apoptosis, and methods of assessing the therapeutic effect of a test substance on caspase activity are disclosed.

  异吲哚啉-5-磺酰胺衍生物，包括这些衍生物的药物组合物，它们作为分子成像剂的用途，它们用于与凋亡失调相关的疾病或紊乱的诊断或治疗，合成这些衍生物的方法，用于测定caspase活性和凋亡的分子成像方法，以及评估试验物质对caspase活性的治疗效果的方法。
• Comparative Studies of Three Pairs of α- and γ-Conjugated Folic Acid Derivatives Labeled with Fluorine-18
  作者：Silvan D. Boss、Thomas Betzel、Cristina Müller、Cindy R. Fischer、Stephanie Haller、Josefine Reber、Viola Groehn、Roger Schibli、Simon M. Ametamey

  DOI：10.1021/acs.bioconjchem.5b00644

  日期：2016.1.20

  The folate receptor (FR) is upregulated in various epithelial cancer types (FR α-isoform), while healthy tissues show only restricted expression. FR-targeted imaging using folate radiopharmaceuticals is therefore a promising approach for the detection of FR-positive cancer tissue. Almost all folate-based radiopharmaceuticals have been prepared by conjugation at the γ-carboxylic functionality of the glutamate moiety of folic acid. In this work, three pairs of fluorinated α- and γ-conjugated folate derivatives were synthesized and their in vitro and in vivo properties compared. The syntheses of all six regioisomers were obtained in good chemical yields using a multistep synthetic approach including the highly selective Cu(I)-catalyzed 1,3-dipolar cycloaddition. The radiosyntheses of the α- and γ-conjugated 18F-labeled folate derivatives were accomplished in moderate to good radiochemical yields, high radiochemical purities (>95%), and specific activities ranging from 25 to 196 GBq/μmol. In vitro, all folate derivatives showed high binding affinity to the FR-α (IC50 = 1.4–2.2 nM). In vivo PET imaging and biodistribution studies in FR-positive KB tumor-bearing mice demonstrated similar FR-specific tumor uptake for both regioisomers of each pair of compounds. However, FR-unspecific liver uptake was significantly lower for the α-regioisomers compared to the corresponding γ-regioisomers. In contrast, kidney uptake was up to 50% lower for the γ-regioisomers than for the α-regioisomers. These results show that the site of conjugation in the glutamyl moiety of folic acid has a significant impact on the in vivo behavior of 18F-based radiofolates, but not on their in vitro FR-binding affinity. These findings may potentially stimulate new directions for the design of novel 18F-labeled folate-based radiotracers.

  叶酸受体（FR）在各种上皮癌（FR α-异构体）中上调，而在健康组织中只显示有限的表达。因此，使用叶酸放射性药物进行 FR 靶向成像是检测 FR 阳性癌症组织的一种很有前景的方法。几乎所有基于叶酸的放射性药物都是通过在叶酸谷氨酸分子的γ-羧基官能团上进行共轭制备的。在这项工作中，合成了三对氟化α-和γ-共轭叶酸衍生物，并比较了它们的体外和体内特性。采用多步合成方法，包括高选择性的 Cu（I）催化 1,3-二极环化反应，以良好的化学收率合成了所有六种区域异构体。α-和γ-共轭的 18F 标记叶酸衍生物的放射合成具有中等至良好的放射化学收率、较高的放射化学纯度（>95%）和 25 至 196 GBq/μmol 的比活度。在体外，所有叶酸衍生物都显示出与 FR-α 的高结合亲和力（IC50 = 1.4-2.2 nM）。在 FR 阳性 KB 肿瘤小鼠体内进行的 PET 成像和生物分布研究表明，每对化合物的两种区域异构体都有类似的 FR 特异性肿瘤摄取。然而，与相应的γ-区域异构体相比，α-区域异构体对FR-非特异性肝脏摄取量明显较低。相反，肾脏对γ-雷焦异构体的摄取量比对α-雷焦异构体的摄取量低 50%。这些结果表明，叶酸谷酰胺酰基中的共轭部位对 18F 放射性叶酸盐的体内行为有重大影响，但对其体外 FR 结合亲和力没有影响。这些发现有可能为设计新型 18F 标记叶酸类放射性示踪剂提供新的方向。
• [EN] PROSTHETIC COMPOUNDS FOR LABELING INTERNALIZING BIOMOLECULES<br/>[FR] COMPOSÉS PROTHÉTIQUES POUR LE MARQUAGE DE BIOMOLÉCULES D'INTERNALISATION
  申请人：UNIV DUKE

  公开号：WO2014179715A1

  公开（公告）日：2014-11-06

  Prosthetic compounds are disclosed that are effective for radiolabeling biomolecules with 18F. Representative biomolecules include antibodies (e.g., monoclonal antibodies (mAbs) and nanobodies (sdAbs)), antibody fragments, and peptides that may have an affinity for particular types of cells, such as cancer cells. The prosthetic compounds effectively address the art-recognized difficulties associated with the retention of radioactivity within the targeted cells, due to internalization of the biomolecule, followed by proteolytic degradation. Representative prosthetic compounds include (i) a succinimidyloxycarbonyl moiety, (ii) a radioactive moiety bearing 18F, and (iii) a charged moiety, i.e., a moiety that is charged under the physiological conditions of the internal cell environment.

  本发明公开了一种用于18F标记生物分子的假体化合物。代表性的生物分子包括抗体（例如单克隆抗体（mAbs）和纳米抗体（sdAbs）），抗体片段和可能具有亲和力的肽，例如对特定类型的细胞（如癌细胞）具有亲和力的肽。这些假体化合物有效地解决了与靶向细胞内部化和蛋白酶降解导致的放射性保留困难有关的技术难题。代表性的假体化合物包括（i）琥珀酰亚氧羰基基团，（ii）带有18F放射性基团，以及（iii）带电基团，即在内部细胞环境的生理条件下带电的基团。
• Isatin derivatives for use as in vivo imaging agents
  申请人：Aboagye Eric Ofori

  公开号：US08961930B2

  公开（公告）日：2015-02-24

  Isatin 5-sulfonamide derivatives, pharmaceutical compositions comprising the derivatives, their use as molecular imaging agents, their use for the diagnosis or treatment of diseases or disorders associated with dysregulation of apoptosis, methods for synthesizing the derivatives, methods for the molecular imaging of caspase activity and apoptosis, and methods of assessing the therapeutic effect of a test substance on caspase activity are disclosed.

  本发明公开了5-磺酰胺基异喹啉衍生物、包含该衍生物的制药组合物、其作为分子成像剂的应用、其用于诊断或治疗与细胞凋亡失调相关的疾病或疾病的方法、合成该衍生物的方法、测定caspase活性和细胞凋亡的分子成像方法以及评估测试物质对caspase活性的治疗效果的方法。