[¹¹C]methyl bromide

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: [¹¹C]methyl bromide
• 英文别名: [11C]methyl bromide；bromo(111C)methane
• 化学式: CH₃Br
• 分子量: 93.9278
• InChiKey: GZUXJHMPEANEGY-BJUDXGSMSA-N

计算性质

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

反应信息

• 作为反应物：
  描述：

  [¹¹C]methyl bromide 在 NaI mixed with Carbograph-2 作用下， 生成 [11C]methyl iodide
  参考文献：
  名称：

  轻松合成碳 11 标记的基于胆固醇的阳离子脂质作为癌症基因传递成像的新潜在 PET 探针

  摘要：

  基于基因传递的基因治疗是治疗各种人类疾病（如癌症）的有前途的策略。阳离子脂质代表重要的合成基因递送系统之一。人们对使用生物医学成像技术正电子发射断层扫描 (PET) 进行基因治疗的成像非常感兴趣。碳 11 标记的基于胆固醇的阳离子脂质首先被设计和合成为新的潜在 PET 探针，用于癌症基因传递的成像。[(11)C-甲基]季胺目标示踪剂，N-[(11)C]甲基-N-[4-(cholest-5-en-3β-yloxycarbonyl)丁基]吡咯烷鎓碘化物([(11)C ]4a), N-[(11)C] 甲基-N'-[4-(cholest-5-en-3beta-yloxycarbonyl) 丁基] 咪唑鎓碘化物 ([(11)C]4b), N-[(11) )C]甲基-N-[4-(cholest-5-en-3β-yloxycarbonyl)丁基]哌啶鎓碘化物([(11)C]4c)，

  DOI：

  10.1016/j.steroids.2010.04.009
• 作为产物：
  描述：

  [11C]methane 在 溴 作用下， 生成 [¹¹C]methyl bromide
  参考文献：
  名称：

  Radiosynthesis of carbon-11-labeled camptothecin derivatives as potential positron emission tomography tracers for imaging of topoisomerase I in cancers

  摘要：

  Four carbon-11-labeled camptothecin derivatives, 9-[C-11]methoxy-20(S)-camptothecin ([C-11]5), 10-[C-11]methoxy-20(S)-camptothecin ([C-11]7), 9-nitro-10-[C-11]methoxy-20(S)-camptothecin ([C-11]9), and 9-[([C-11]trimethylamino)methyl]-10-hydroxy-20(S)-camptothecin ([C-11]11), have been synthesized as potential positron emission tomography tracers for imaging of topoisomerase I in cancers. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.05.108
• 作为试剂：
  描述：

  [11C]二氧化碳 、 silver trifluoromethanesulfonate 在 [11C]methane 、 [¹¹C]methyl bromide 作用下， 反应 0.18h， 生成 [11C]methyl triflate
  参考文献：
  名称：

  Synthesis of carbon-11-labeled aminoalkylindole derivatives as new candidates of cannabinoid receptor radioligands for PET imaging of alcohol abuse

  摘要：

  Carbon-11-labeled aminoalkylindole derivatives (1-butyl-7-[C-11] methoxy-1H-indol-3-yl)(naphthalene-1-yl)methanone ([C-11]3), 1-butyl-7-[C-11]methoxy-3-(naphthalene-1-ylmethyl)-1H-indole ([C-11]5), and 1-butyl-7-[C-11]methoxy-3-(naphthalene-2-yl)-1H-indole ([C-11]8) were prepared by O-[C-11]methylation of their corresponding precursors with [C-11]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [C-11]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/mu mol. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.10.097

文献信息

• Synthesis and preliminary biological evaluation of new carbon-11 labeled tetrahydroisoquinoline derivatives as SERM radioligands for PET imaging of ER expression in breast cancer
  作者：Mingzhang Gao、Min Wang、Kathy D. Miller、George W. Sledge、Qi-Huang Zheng

  DOI：10.1016/j.ejmech.2008.01.001

  日期：2008.10

  receptor-based breast cancer imaging agents for diagnostic use in biomedical imaging technique positron emission tomography (PET). Tetrahydroisoquinoline derivatives are a class of selective estrogen receptor modulators (SERMs) with high binding affinity and specificity exhibiting up to 50 folds for ERalpha over ERbeta. New carbon-11 labeled tetrahydroisoquinoline derivatives, [11C]methyl 1-(2-(4-(2-(4-f

  雌激素受体（ERs）是治疗乳腺癌和开发基于受体的乳腺癌显像剂的诱人靶标，可用于生物医学成像技术正电子发射断层扫描（PET）的诊断。四氢异喹啉衍生物是一类选择性雌激素受体调节剂（SERM），具有较高的结合亲和力和特异性，相对于ERbeta，其对ERalpha的表达高达50倍。新的碳11标记的四氢异喹啉衍生物，[11C]甲基1-（2-（4-（2-（4-氟苯基）-6-羟基-1-甲基-1,2,3,4-四氢异喹啉-1-基）苯氧基）乙基）哌啶-4-羧酸酯（[11C] 10a）和[11C]甲基1-（2-（4-（2-（4-（4-氯苯基）-6-羟基-1-甲基-1,2）首先设计，合成和评估了3,4-四氢异喹啉-1-基）苯氧基）乙基）哌啶-4-羧酸酯（[11C] 10b）。使用[11C] CH3OTf通过对其相应前体进行O- [11C]甲基化来制备目标示踪剂，并通过固相萃取（SPE）纯化程序进行分离，以40-6
• Synthesis of new carbon-11-labeled 7-aroyl-aminoindoline-1-sulfonamides as potential PET agents for imaging of tubulin polymerization in cancers
  作者：Min Wang、Mingzhang Gao、Kathy D. Miller、George W. Sledge、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1002/jlcr.1462

  日期：2008.1

  The tubulin polymerization is an attractive target for anticancer therapy and in the development of cancer imaging agents for use in biomedical imaging technique positron emission tomography (PET). 7-Aroyl-aminoindoline-1-sulfonamides are a novel class of potent antitublin agents. Carbon-11-labeled 7-aroyl-aminoindoline-1-sulfonamides have been synthesized as new potential PET agents for imaging of tubulin polymerization in cancers. The target tracers were prepared by O-[11C]methylation of their corresponding precursors using [11C]CH3OTf and isolated by a simplified solid-phase extraction purification procedure in 40–55% radiochemical yields based on [11C]CO2 and decay corrected to the end of bombardment (EOB), 15–20 min overall synthesis time from EOB, >98% radiochemical purity, and 74–111 GBq/µmol specific activity at the end of synthesis. Copyright © 2008 John Wiley & Sons, Ltd.

  微管蛋白聚合是抗癌治疗和用于生物医学成像技术正电子发射断层扫描（PET）的癌症成像剂开发的一个有吸引力的靶点。7-芳酰基-氨基喃啶-1-磺酰胺是一种新型的有效抗微管蛋白药物。已合成碳-11标记的7-芳酰基-氨基喃啶-1-磺酰胺，作为用于成像癌症中微管蛋白聚合的新潜在PET试剂。通过使用[11C]CH3OTf对其相应前体进行O-[11C]甲基化，制备了目标示踪剂，并通过简化的固相提取纯化程序分离，辐射化学产率为40-55%（基于[11C]CO2），并经衰变校正至轰击结束（EOB），从EOB起总体合成时间为15-20分钟，辐射化学纯度超过98%，合成结束时特定活度为74-111 GBq/µmol。版权 © 2008 John Wiley & Sons, Ltd.
• Synthesis and preliminary biological evaluation of radiolabeled 5-BDBD analogs as new candidate PET radioligands for P2X4 receptor
  作者：Min Wang、Mingzhang Gao、Jill A. Meyer、Jonathan S. Peters、Hamideh Zarrinmayeh、Paul R. Territo、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.bmc.2017.05.031

  日期：2017.7

  desmethylated precursors with [11C]CH3OTf through N-[11C]methylation and isolated by HPLC combined with SPE in 30–50% decay corrected radiochemical yields with 370–1110 GBq/µmol specific activity at EOB. 5-(3-[18F]Fluorophenyl)-1,3-dihydro-2H-benzofuro[3,2-e][1,4]diazepin-2-one ([18F]F-5-BDBD, [18F]5a) and 5-(3-(2-[18F]fluoroethoxy)phenyl)-1,3-dihydro-2H-benzofuro[3,2-e][1,4]diazepin-2-one ([18F]FE-5-BDBD

  P2X4受体已成为治疗和PET成像的神经炎症和相关的脑部疾病（例如阿尔茨海默氏病）的有趣分子靶标。这项研究报告了新的候选PET P2X4受体放射性配体的首次设计，合成，放射性标记和生物学评估，使用5-BDBD（一种特定的P2X4受体拮抗剂）作为支架。5-（3-羟基苯基）-1- [ 11 C]甲基-1,3-二氢-2 H-苯并呋喃[3,2- e ] [1,4]二氮杂-2--2-（N- [ 11 C] Me-5-BDBD类似物，[ 11 C] 9）和5-（3-溴苯基）-1- [ 11 C]甲基-1,3-二氢-2 H-苯并呋喃[3,2- e ] [1， 4] diazepin-2-one（N- [ 11 C] Me-5-BDBD，[ 11 C] 8c）是由其相应的具有[ 11 C] CH 3 OTf的脱甲基前体通过N- [ 11 C]甲基化制备的，并通过HPLC与SPE组合在30中分离在EOB处，
• A new high-yield synthetic route to PET CB1 radioligands [11C]OMAR and its analogs
  作者：Mingzhang Gao、Min Wang、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2012.04.030

  日期：2012.6

  OMAR analogs reference standards and their corresponding desmethylated precursors were synthesized from substituted anilines either in 4 and 5 steps with 27–32% and 24–31% yield, or in 3 and 4 steps with 21–30% and 19–28% yield, respectively. [11C]OMAR and its analog radioligands were prepared from their desmethylated precursors with [11C]CH3OTf through O-[11C]methylation and isolated by HPLC combined

  OMAR类似物参考标准品及其相应的去甲基化前体是由取代的苯胺分4步和5步合成的，产率为27–32％和24–31％，或分3步和4步合成的，产率为21–30％和19–28％，分别。[ 11 C] OMAR及其类似物放射性配体由具有[ 11 C] CH 3 OTf的脱甲基前体通过O- [ 11 C]甲基化制备，并通过HPLC结合固相萃取（SPE）在50-65％的放射化学中进行分离产生基于[ 11 C] CO 2的化合物，并将其衰减校正为轰击结束（EOB），在EOB处的比活为370–740 GBq /μmol。
• [11C]Enzastaurin, the first design and radiosynthesis of a new potential PET agent for imaging of protein kinase C
  作者：Min Wang、Lu Xu、Mingzhang Gao、Kathy D. Miller、George W. Sledge、Qi-Huang Zheng

  DOI：10.1016/j.bmcl.2011.01.100

  日期：2011.3

  Enzastaurin (LY317615) is a potent and selective protein kinase C (PKC) inhibitor with an IC50 value of similar to 6 nM. [C-11] Enzastaurin (3-(1-[C-11] methyl-1H-indol-3-yl)-4-[1-[1-(2-pyridinylmethyl)-4-piperidinyl]-1H- indol-3-yl]-1H-pyrrole-2,5-dione), a new potential PET agent for imaging of PKC, was first designed and synthesized in 20-25% decay corrected radiochemical yield and 370-555 GBq/mu mol specific activity at end of bombardment (EOB). The synthetic strategy was to prepare a carbon-11-labeled maleic anhydride intermediate followed by the conversion to maleimide. (C) 2011 Elsevier Ltd. All rights reserved.