4-(4-nitrobenzoyl)piperidine hydrochloride

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(4-nitrobenzoyl)piperidine hydrochloride
• 英文别名: 4-(4-nitrophenylcarbonyl)piperidine hydrochloride；(4-Nitrophenyl)(4-piperidinyl)ketone hydrochloride；(4-nitrophenyl)(piperidin-4-yl)methanone hydrochloride；(4-Nitro-phenyl)-piperidin-4-yl-methanone hydrochloride；(4-nitrophenyl)-piperidin-4-ylmethanone;hydrochloride
• 化学式: C₁₂H₁₄N₂O₃*ClH
• 分子量: 270.716
• InChiKey: WECADBRGHNQTCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.25
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  79.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-nitrobenzoyl)piperidine hydrochloride 在 氢溴酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 3-{2-[4-(4-硝基苯甲酰)-1-哌啶基]乙基}-2-硫代-2,3-二氢-4(1H)-喹唑啉酮
  参考文献：
  名称：

  Huang; Mathis, Journal of labelled compounds and radiopharmaceuticals, 1999, vol. 42, # SUPPL. 1, p. S406-S408

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯甲酰哌啶-4-羧酸 在 pi-allyl palladium chloride dimer 盐酸 、 氯化亚砜 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 为溶剂， 反应 40.0h， 生成 4-(4-nitrobenzoyl)piperidine hydrochloride
  参考文献：
  名称：

  Rapid synthesis of F-18 and H-2 dual-labeled altanserin, a metabolically resistant PET ligand for 5-HT2a receptors

  摘要：

  F-18 and H-2 dual-labeled altanserin (3, [F-18]d-ALT), a novel PET tracer for 5-HT2A receptors with metabolically resistant properties, was synthesized by [F-18]fluoride displacement of the corresponding deuterated nitro precursor in 32% yield (EOB) in 108 min with radiochemical purity 95% and specific activity >1000 mCi/mu mol (EOS). The key intermediate ethyl N-(2-chloroethyl-2,2-d(2))carbamate (7 was obtained by LiAlD4 reduction of a glycine ester (93%), chlorination and carbamoylation (79%). 4-(4-Nitrobenzoyl)piperidine (13) was synthesized (60%) by improving the published coupling reaction of p-nitrophenyltrimethylstannane (10), obtained from p-iodonitrobenzene and (CH3)(6)Sn-2 (94%), with 1-benzoylisonipecotic acid chloride (11) followed by acid hydrolysis. 13 was alkylated with 7 (82%), hydrolyzed and condensed with methyl o-isothiocyanatobenzoyate to provide with the precursor deuteronitmaltanserin (4, 75%).

  DOI：

  10.1002/(sici)1099-1344(199905)42:5<457::aid-jlcr206>3.0.co;2-0

文献信息

• Radiosynthesis and evaluation of a fluorine-18 labeled radioligand targeting vesicular acetylcholine transporter
  作者：Xuyi Yue、Zonghua Luo、Hui Liu、Kota Kaneshige、Stanley M. Parsons、Joel S. Perlmutter、Zhude Tu

  DOI：10.1016/j.bmcl.2018.09.030

  日期：2018.11

  radiolabeling precursor of (−)-[18F]VAT, a promising VAChT radiotracer with a logD value of 2.56. To evaluate (−)-5-OH-[18F]VAT as a radiotracer for VAChT, we performed in vitro binding assay to determine the potency of the minus enantiomer (−)-5-OH-VAT and plus enantiomer (+)-5-OH-VAT, indicating that (−)-5-OH-VAT is a more potent VAChT enantiomer. Radiosynthesis of (−)-5-OH-[18F]VAT was explored using three

  水泡乙酰胆碱转运蛋白（VAChT）是一种可靠的生物标记物，用于评估与患者认知障碍相关的脑内胆碱能神经元的丢失。5- Hydrotetralin化合物（±）-5-OH-VAT是有效的（ķ我 = 4.64±0.32 nM）的和选择性的中VAChT（> 1800倍和398倍为σ 1和σ 2，分别受体）具有良好的亲水性（LogD = 1.78），而（-）-5-OH-VAT最初是（-）-[ 18 F] VAT的放射性标记前体，这是有希望的VAChT放射性示踪剂，logD值为2.56。为了评估（-）-5-OH- [ 18 F] VAT作为VAChT的放射性示踪剂，我们执行了体外结合测定法来测定负对映异构体（-）-5-OH-VAT和正对映异构体（+）-5-OH-VAT的效力，表明（-）-5-OH-VAT是更有效的VAChT对映体。使用三种策略探索了（-）-5-OH- [ 18 F] VAT的放射性合成。（-）-5-OH-
• Synthesis, evaluation and metabolic studies of radiotracers containing a 4-(4-[18F]-fluorobenzyl)piperidin-1-yl moiety for the PET imaging of NR2B NMDA receptors
  作者：Romain Labas、Gwénaëlle Gilbert、Olivier Nicole、Martine Dhilly、Ahmed Abbas、Olivier Tirel、Alain Buisson、Joël Henry、Louisa Barré、Danièle Debruyne、Franck Sobrio

  DOI：10.1016/j.ejmech.2011.03.013

  日期：2011.6

  In this study, novel specific PET radioligands containing the 4-(4-fluorobenzyl)piperidine moiety and selectively antagonistic for the NR2B subunit containing NMDA receptors were developed. Two antagonists, RGH-896 (1a) and 4-(4-fluorobenzyl)piperidinyl-1-methyl-2-benzimidazol-5-ol (2a), belonging to two different structural families, were radiolabeled by an aromatic nucleophilic radiofluorination followed by a reduction of the para-position carbonyl function. Radiotracers [F-18]1a, [F-18]2a or the pattern 4-(4-[(18)[F]-fluorobenzyl)piperidine ([(18)[F]6) demonstrated an identical in vivo behavior with high accumulation of radioactivity in bone and cartilage which would suggest a radiodefluorination of the radiotracers. The identification of metabolites from 6 by LC-MS-MS confirmed the significant degree of defluorination as a result of the in vivo hydroxylation in the benzyl ring. In conclusion, [(18)[F]1a or [(18)[F]2a are not suitable for imaging the NR2B NMDA receptors due to their poor brain penetration. We also argue for a cautious use of the radiolabeled pattern, 4-(4-[(18)[F]-fluorobenzyl)piperidine, to develop PET radiotracers.(C) 2011 Elsevier Masson SAS. All rights reserved.
• Radiosynthesis of [18F]N-(4-phenylbutyl)-4-(4-fluorobenzoyl)piperidine for studying serotonin 5-HT2a receptors
  作者：Kenji Hashimoto、Kentaro Hatano、Yoshio Minabe、Masaomi Iyo、Masahiko Taniguchi、Osamu Hoshino、Yojiro Sakiyama、Yasuhiro Kawasumi

  DOI：10.1002/(sici)1099-1344(1998100)41:10<941::aid-jlcr151>3.0.co;2-6

  日期：1998.10

  N-(4-Phenylbutyl)-4-(4-fluorobenzoyl)pipe [4-PBFBP] shows highly selective binding to serotonin 5-HT2A receptors with high affinity. In this study, we prepared [F-18]4-PBFBP for in vivo study of 5-HT2A receptors in the brain using positron emission tomography (PET). Nucleophilic aromatic displacement of N-(4-phenylbutyl)-4-(4-nitrobenzoyl)piperidine by no carrier added [F-18]fluoride which was solubilized by Kryptofix 222 in DMSO produced [F-18]4-PBFBP with high specific radioactivity. The product was purified by reversed phase preparative HPLC and was extracted from the collected eluate by SEP-PAK(R) C18 cartridge prior to formulation. The radiochemical yield of the final product was 15 +/- 1.8 % (mean +/- S.D. of three experiments) with decay correction and the specific activity was 113 +/- 27 GBq/mu mol (mean +/- S.D. of three experiments) at E.O.S. after a total preparation time of about 160 min. The radiochemical purity of [F-18]4-PBFBP was more than 99%. The regional distribution of [F-18]4-PBFBP in mouse brain was also examined.
• Monclus, Michel; Luxen, Andre, Organic Preparations and Procedures International, 1992, vol. 24, # 6, p. 692 - 694
  作者：Monclus, Michel、Luxen, Andre

  DOI：——

  日期：——
• CROUZEL, C.;VENET, M.;IRIE, T.;SANZ, G.;BOULLAIS, C., J. LABELL. COMPOUNDS AND RADIOPHARM., 25,(1988) N 4, 403-414
  作者：CROUZEL, C.、VENET, M.、IRIE, T.、SANZ, G.、BOULLAIS, C.

  DOI：——

  日期：——