[18F]-4-fluorobenzoic acid chloride | 594847-99-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [18F]-4-fluorobenzoic acid chloride
• 英文别名: [18F]fluorobenzoyl chloride；4-(18F)fluoranylbenzoyl chloride
• CAS: 594847-99-1
• 化学式: C₇H₄ClFO
• 分子量: 157.561
• InChiKey: CZKLEJHVLCMVQR-RVRFMXCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  盐酸依达比星 、 [18F]-4-fluorobenzoic acid chloride 在 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 N-[(2S,3S,4S,6R)-6-[[(1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-2,4-dihydro-1H-tetracen-1-yl]oxy]-3-hydroxy-2-methyloxan-4-yl]-4-(18F)fluoranylbenzamide
  参考文献：
  名称：

  合成 18F-氟苯甲酸伊达比星衍生物作为预测化疗耐药性的新型潜在 PET 放射性示踪剂

  摘要：

  蒽环类药物是目前临床实践中使用最广泛的抗肿瘤药物之一。然而，在给予蒽环类药物后经常观察到导致无法根除肿瘤的化学抗性，并且还没有发现能够准确预测肿瘤对这些抗肿瘤药物的抗性的检测系统。我们试图制备一种 F-18 标记的伊达比星衍生物，一种 4-脱甲氧基-柔红霉素类似物，用于帮助评估体内对蒽环类药物的生理抗性。两种不同的合成途径需要制备关键中间体 [18F] 氟苯甲酸 ([18F]FBA)，以在其伯胺上用 F-18 标记伊达比星。第一种方法从 [18F]FBA 中分两步生成所需的 [18F] 氟苯甲酸酯伊达比星衍生物，而第二种策略包括通过在氰基膦酸二乙酯存在下用 [ 18 F] FBA 处理直接酰化伊达比星。尽管第一种方法产生较少的副产物，但它需要更多时间来获得 HPLC 纯化的放射性药物（100 分钟与 90 分钟），并导致放射化学产率较低（8-25% 与 25-39% 的衰减从起始氟化物校正）。版权所有

  DOI：

  10.1002/jlcr.990
• 作为产物：
  描述：

  4-[18F]氟苯甲酸 在 1,1-二氯甲醚 作用下， 反应 5.0h， 生成 [18F]-4-fluorobenzoic acid chloride
  参考文献：
  名称：

  合成 18F-氟苯甲酸伊达比星衍生物作为预测化疗耐药性的新型潜在 PET 放射性示踪剂

  摘要：

  蒽环类药物是目前临床实践中使用最广泛的抗肿瘤药物之一。然而，在给予蒽环类药物后经常观察到导致无法根除肿瘤的化学抗性，并且还没有发现能够准确预测肿瘤对这些抗肿瘤药物的抗性的检测系统。我们试图制备一种 F-18 标记的伊达比星衍生物，一种 4-脱甲氧基-柔红霉素类似物，用于帮助评估体内对蒽环类药物的生理抗性。两种不同的合成途径需要制备关键中间体 [18F] 氟苯甲酸 ([18F]FBA)，以在其伯胺上用 F-18 标记伊达比星。第一种方法从 [18F]FBA 中分两步生成所需的 [18F] 氟苯甲酸酯伊达比星衍生物，而第二种策略包括通过在氰基膦酸二乙酯存在下用 [ 18 F] FBA 处理直接酰化伊达比星。尽管第一种方法产生较少的副产物，但它需要更多时间来获得 HPLC 纯化的放射性药物（100 分钟与 90 分钟），并导致放射化学产率较低（8-25% 与 25-39% 的衰减从起始氟化物校正）。版权所有

  DOI：

  10.1002/jlcr.990

文献信息

• Synthesis ofL-[3,3,4,4,S-methyl-2H7]methionine for use as a substrate for the methionine loading test
  作者：Hiroshi Hasegawa、Yoshihiko Shinohara、Kazunori Tagoku、Takao Hashimoto

  DOI：10.1002/jlcr.428

  日期：2001.1

  Optically pure L-[3,3,4,4,S-methyl-2H7]methionine (L-[2H7]-methionine) for use as a substrate for the methionine loading test has been prepared. The racemic [2H7]methionine was prepared from DL-[3,3,4,4-2H4]methionine (DL-[2H4]methionine) by conversion of the S-CH3 group to a C2H3 group. The racemate was resolved by stereospecific hydrolysis of the N-acetylated derivative with acylase. After an intravenous administration of L-[2H7]methionine in a rat, the concentration of L-[2H7]methionine and the metabolites in plasma were determined by GC-MS-SIM. L-[2H4]Homocysteine and L-[2H4]methionine were detected in plasma at 30 min after dosing. These results show that L-[2H7]methionine was converted by de-methylation and subsequent re-methylation to form L-[2H4]methionine. Copyright © 2001 John Wiley & Sons, Ltd.

  已制备光学纯L-[3,3,4,4,S-甲基-2H7]蛋氨酸（L-[2H7]蛋氨酸），作为蛋氨酸负荷测试的底物。该外消旋体[2H7]蛋氨酸是通过将DL-[3,3,4,4-2H4]蛋氨酸（DL-[2H4]蛋氨酸）的S-CH3基团转化为C2H3基团制备的。通过与酰化酶的立体特异性水解，分离了外消旋混合物。在给大鼠静脉注射L-[2H7]蛋氨酸后，通过气相色谱-质谱-选择离子监测（GC-MS-SIM）测定了L-[2H7]蛋氨酸及其代谢物在血浆中的浓度。L-[2H4]同型半胱氨酸和L-[2H4]蛋氨酸在给药后30分钟时在血浆中被检测到。这些结果表明，L-[2H7]蛋氨酸通过去甲基化和随后的再甲基化转化为L-[2H4]蛋氨酸。版权所有 © 2001 John Wiley & Sons, Ltd.
• Development of Fluorine-18-Labeled 5-HT_1A Antagonists
  作者：Lixin Lang、Elaine Jagoda、Bernard Schmall、Bik-Kee Vuong、H. Richard Adams、David L. Nelson、Richard E. Carson、William C. Eckelman

  DOI：10.1021/jm980456f

  日期：1999.5.1

  We have synthesized five fluorinated derivatives of WAY 100635, N-2-[4-(2-methoxyphenyl)piperazino]ethyl)-N-(2-pyridyl)cyclohexanecarboxamide (4a), using various acids in place of the cyclohexanecarboxylic acid (CHCA, 2a) in the reaction scheme. The five acids are 4-fluorobenzoic acid (FB, 2b), 4-fluoro-3-methylbenzoic acid (MeFB, 2c), trans-4-fluorocyclohexanecarboxylic acid (FC, 2d), 4-(fluoromethyl)benzoic acid (FMeB, 2e), and 3-nitro-4-(fluoromethyl)benzoic acid (NFMeB, 2f) (see Scheme 1). These compounds were radiolabeled with fluorine-18, and their biological properties were evaluated in rats and compared with those of [C-11]carbonyl WAY 100635 ([carbonyl-C-11]4a), [Carbonyl-C-11]4a cleared the brain with a biological half-life averaging 41 min. The metabolite-corrected blood radioactivity had a half-life of 29 min. [F-18]FCWAY ([F-18]4d) gave half-lives and intercepts comparable to [carbonyl-C-11]4a in the brain, but the blood clearance was faster. [F-18]FBWAY ([F-18]4b) showed an early rapid net efflux from the whole brain, clearing with a biological half-life of 35 min. The metabolite-corrected blood half-life was 41 min. The comparable whole brain and blood half-lives for Me[F-18]FBWAY ([F-18]4c) were 16 and 18 min, respectively. For each compound, the corresponding carboxylic acid was identified as a major metabolite in blood. Fluoride was also found after injection of [F-18]4d. However, for all compounds there was a good correlation (R > 0.97) between the differential uptake ratio (DUR, (%ID/g) x body weight (g)/100) in individual rat brain regions at 30 min after injection and the concentration of receptors as determined by in vitro quantitative autoradiography in rat. Specific binding ratios [region of interest (ROI)/ cerebellum-1] in control studies for cortex (Ctx) and hippocampus (H) were higher for [carbonyl-C-11]4a and [F-18]4d compared to [F-18]4b and [F-18]4c. [F-18]4d has similar pharmacokinetic properties and comparable specific binding ratios to [carbonyl-11C]4a. Fifty nanomoles of 4a blocked only 30% of the specific binding of [F-18]4d, while complete blockade was obtained from co-injection of 200 nmol of 4a (H/Cb-1 from 17.2 to 0.6). [F-18]4b and [F-18]4c showed lower specific binding ratios than [carbonyl-C-11]4a and [F-18]4d. [F-18]4c was superior to [F-18]4b since its specific binding was more readily blocked by 4a. These studies suggest that [F-18]4c should be a useful compound to assess dynamic changes in serotonin levels while [F-18]4d, with its high contrast and F-18 label, should provide better statistics and quantification for static measurement of 5-HT1A receptor distribution.
• Kiesewetter, Dale O.; Eckelman, William C., Journal of labelled compounds and radiopharmaceuticals, 2001, vol. 44, p. S903 - S905
  作者：Kiesewetter, Dale O.、Eckelman, William C.

  DOI：——

  日期：——
• Shiue C.-Y., Shiue G. G., Zhuang Z. P., Kung M.-P., Kung H. F., J. Nucl. Med, 35 (1994) N 5, Suppl., S 252
  作者：Shiue C.-Y., Shiue G. G., Zhuang Z. P., Kung M.-P., Kung H. F.

  DOI：——

  日期：——
• Synthesis of an18F-fluorobenzoate idarubicin derivative as new potential PET radiotracer to predict chemotherapy resistance
  作者：Yann Seimbille、Johannes Czernin、Michael E. Phelps、Daniel H. S. Silverman

  DOI：10.1002/jlcr.990

  日期：2005.10.15

  accurately predict tumor resistance to those antitumor agents. We sought to prepare an F-18 labeled derivative of idarubicin, a 4-demethoxy-daunorubicin analogue, to use in helping to assess physiologic resistance to anthracyclines in vivo. Two different synthetic pathways, which required the preparation of the key intermediate [18F]fluorobenzoic acid ([18F]FBA), are advanced to label idarubicin with F-18

  蒽环类药物是目前临床实践中使用最广泛的抗肿瘤药物之一。然而，在给予蒽环类药物后经常观察到导致无法根除肿瘤的化学抗性，并且还没有发现能够准确预测肿瘤对这些抗肿瘤药物的抗性的检测系统。我们试图制备一种 F-18 标记的伊达比星衍生物，一种 4-脱甲氧基-柔红霉素类似物，用于帮助评估体内对蒽环类药物的生理抗性。两种不同的合成途径需要制备关键中间体 [18F] 氟苯甲酸 ([18F]FBA)，以在其伯胺上用 F-18 标记伊达比星。第一种方法从 [18F]FBA 中分两步生成所需的 [18F] 氟苯甲酸酯伊达比星衍生物，而第二种策略包括通过在氰基膦酸二乙酯存在下用 [ 18 F] FBA 处理直接酰化伊达比星。尽管第一种方法产生较少的副产物，但它需要更多时间来获得 HPLC 纯化的放射性药物（100 分钟与 90 分钟），并导致放射化学产率较低（8-25% 与 25-39% 的衰减从起始氟化物校正）。版权所有