(R)-(+)-2-chloromethyl-1-methylpiperidine | 868542-16-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R)-(+)-2-chloromethyl-1-methylpiperidine
• 英文别名: (2R)-2-(chloromethyl)-1-methylpiperidine
• CAS: 868542-16-9
• 化学式: C₇H₁₄ClN
• mdl: MFCD09800596
• 分子量: 147.648
• InChiKey: FGMRHGUEOYXVMX-SSDOTTSWSA-N

物化性质

• 沸点：
  183.8±13.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-chloromethyl-1-methylpiperidine 在 三氯化铝 、 sodium hydride 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 AM2233
  参考文献：
  名称：

  Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor

  摘要：

  A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochemical and imaging studies. 2-iodophenyl-[1-(l-methylpiperidin2-ylmethyl)]-1H-indol-3-yllmethanone (8, AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated 8, (R)-8, and (S)-8 were prepared by radioiododestannylation of the tributyltin analogues in high yields, radiochemical purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [I-131](R)-8 as radioligand, racemic 8 exhibited a K-i value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiographic experiments with mouse brain sections, the distribution of radioiodinated 8 was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [I-131](S)-8 and none occurred with the (R)-enantiomer [I-131] (R)-8 in sections from CB1 receptor knockout mice. Radioiodinated 8 thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors.

  DOI：

  10.1021/jm050135l
• 作为产物：
  描述：

  D-哌啶-2-甲酸 在 lithium aluminium tetrahydride 、 甲酸 、 氯化亚砜 、 乙酰氯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 46.0h， 生成 (R)-(+)-2-chloromethyl-1-methylpiperidine
  参考文献：
  名称：

  Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor

  摘要：

  A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochemical and imaging studies. 2-iodophenyl-[1-(l-methylpiperidin2-ylmethyl)]-1H-indol-3-yllmethanone (8, AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated 8, (R)-8, and (S)-8 were prepared by radioiododestannylation of the tributyltin analogues in high yields, radiochemical purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [I-131](R)-8 as radioligand, racemic 8 exhibited a K-i value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiographic experiments with mouse brain sections, the distribution of radioiodinated 8 was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [I-131](S)-8 and none occurred with the (R)-enantiomer [I-131] (R)-8 in sections from CB1 receptor knockout mice. Radioiodinated 8 thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors.

  DOI：

  10.1021/jm050135l

文献信息

• Synthesis and Biological Evaluation of C-17-Amino-Substituted Pyrazole-Fused Betulinic Acid Derivatives as Novel Agents for Osteoarthritis Treatment
  作者：Jie Wang、Wenhui Wei、Xiaofei Zhang、Shiqi Cao、Bintao Hu、Yang Ye、Min Jiang、Tianqi Wang、Jianping Zuo、Shijun He、Chunhao Yang

  DOI：10.1021/acs.jmedchem.1c01019

  日期：2021.9.23

  A series of pyrazole-fused betulinic acid (BA) derivatives were designed and synthesized by replacing the carboxyl group at C-17 with aliphatic amine, amide, and urea groups. The suppressive effects of the compounds on osteoclast (OC) formation and inflammatory cytokine production were evaluated on murine macrophages, RAW264.7 cells, conditioned with receptor activator for nuclear factor-κB ligand

  通过用脂肪胺、酰胺和脲基团取代C-17位的羧基，设计并合成了一系列吡唑稠合桦木酸（BA）衍生物。在用核因子-κB 配体受体激活剂 (RANKL)/巨噬细胞集落刺激因子 (M-CSF) 调节的小鼠巨噬细胞 RAW264.7 细胞上评估了这些化合物对破骨细胞 (OC) 形成和炎症细胞因子产生的抑制作用或脂多糖（LPS）。结果表明，与桦木酸相比，这些化合物中的大多数都表现出显着的抑制效力。化合物25表现出显着的抑制OC分化的活性，IC 50值为1.86 μM。同时，化合物25对RAW264.7细胞的IL-1β分泌表现出最有希望的抑制作用，进一步发现在单碘乙酸钠（MIA）诱导的骨关节炎大鼠模型中具有治疗作用。在 MIA 诱发的大鼠中观察到剂量依赖性益处，化合物25治疗后关节疼痛得到改善，软骨损伤和骨变化减少。
• Potent Cannabinergic Indole Analogues as Radioiodinatable Brain Imaging Agents for the CB1 Cannabinoid Receptor
  作者：Hongfeng Deng、Andrew N. Gifford、Alexander M. Zvonok、Guangjian Cui、Xiuyan Li、Pusheng Fan、Jeffrey R. Deschamps、Judith L. Flippen-Anderson、S. John Gatley、Alexandros Makriyannis

  DOI：10.1021/jm050135l

  日期：2005.10.1

  A series of novel aminoalkylindoles was synthesized in an effort to develop compounds that are potent agonists at the CB1 cannabinoid receptor and that are also easily labeled with radioisotopes of iodine for biochemical and imaging studies. 2-iodophenyl-[1-(l-methylpiperidin2-ylmethyl)]-1H-indol-3-yllmethanone (8, AM2233) had a very high affinity for the rat CB1 receptor, with most of the affinity residing with the (R)-enantiomer. Radioiodinated 8, (R)-8, and (S)-8 were prepared by radioiododestannylation of the tributyltin analogues in high yields, radiochemical purities, and specific radioactivities. In a mouse hippocampal membrane preparation with [I-131](R)-8 as radioligand, racemic 8 exhibited a K-i value of 0.2 nM compared with 1.6 nM for WIN55212-2. In autoradiographic experiments with mouse brain sections, the distribution of radioiodinated 8 was consistent with that of brain CB1 receptors. Again, very little specific binding was seen with the (S)-enantiomer [I-131](S)-8 and none occurred with the (R)-enantiomer [I-131] (R)-8 in sections from CB1 receptor knockout mice. Radioiodinated 8 thus appears to be a suitable radioligand for studies of CB1 cannabinoid receptors.