2-氯-N-(2-甲氧基苄基)乙酰胺 | 81494-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-氯-N-(2-甲氧基苄基)乙酰胺
• 英文名称: 2-chloro-N-(2-methoxybenzyl)acetamide
• 英文别名: 2-chloro-N-[(2-methoxyphenyl)methyl]acetamide
• CAS: 81494-04-4
• 化学式: C₁₀H₁₂ClNO₂
• mdl: MFCD00752501
• 分子量: 213.664
• InChiKey: QUPFOFYYZHSFDJ-UHFFFAOYSA-N

物化性质

• 熔点：
  76-77 °C
• 沸点：
  392.1±32.0 °C(Predicted)
• 密度：
  1.186±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-氯-N-(2-甲氧基苄基)乙酰胺 在 盐酸羟胺 、 二甲基亚砜 、 sodium hydroxide 作用下， 反应 24.0h， 以41%的产率得到2-(hydroxyimino)-N-(2-methoxybenzyl)acetamide
  参考文献：
  名称：

  2-羟基烷酰胺肟的新合成

  摘要：

  在碱的存在下，α-卤代羧酸酰胺与3当量的盐酸羟胺的反应涉及形成卤原子的亲核取代产物，然后将其氧化成相应的肟。一锅转化可在各种非质子溶剂或80°C的乙醇中完成。二甲基亚砜作为溶剂可确保对氧化产物的最高选择性。N-取代的2-（羟基亚氨基）羧酸酰胺的产率为22-92％。

  DOI：

  10.1134/s1070428019040201
• 作为产物：
  描述：

  邻甲氧基苄胺 、 氯乙酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到2-氯-N-(2-甲氧基苄基)乙酰胺
  参考文献：
  名称：

  Probing Structural Requirements of Positive Allosteric Modulators of the M₄ Muscarinic Receptor

  摘要：

  The M, mAChR is implicated in several CNS disorders and possesses an allosteric binding site for which ligands modulating the affinity and/or efficacy of ACh may be exploited for selective receptor targeting. We report the synthesis of a focused library of putative M-4 PAMs derived from VU0152100 and VU10005. These compounds investigate the pharmacological effects of previously identified methoxy and fluoro substituents, providing useful estimates of affinity (K-B), cooperativity (alpha beta), and direct agonist properties (tau(B)).

  DOI：

  10.1021/jm401032k

文献信息

• A direct fixation of CO₂ for isotopic labelling of hydantoins using iodine–phosphine charge transfer complexes
  作者：John-Paul J. Bow、Valentina Adami、Agostino Marasco、Gaute Grønnevik、Dean A. Rivers、Guiseppe Alvaro、Patrick J. Riss

  DOI：10.1039/d2cc01754g

  日期：——

  Herein, we report a method for the isotopic labelling of hydantoins directly from CO2 by means of trimethyl-λ5-phosphine diiodide mediated carbonyl insertion. The method is suitable for 13C-labelling of diverse substrates and was implementated for 11C-labelling in PET-imaging facilities for the synthesis of radiotracers. Isolated yields of 90% and radiochemical yields of 89% were achieved for hydantoin

  在此，我们报道了一种通过三甲基-λ 5 -二碘化膦介导的羰基插入直接从 CO 2中同位素标记乙内酰脲的方法。该方法适用于不同底物的13 C-标记，并在 PET 成像设备中用于11 C-标记，用于合成放射性示踪剂。制剂中含有乙内酰脲的候选药物在 30 分钟内实现了 90% 的分离产率和 89% 的放射化学产率，具有高摩尔活性 (>400 MBq nmol -1 )。
• Novel N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides: synthesis, cytotoxicity, anticancer activity, COMPARE analysis and docking
  作者：Sergey I. Kovalenko、Inna S. Nosulenko、Alexey Yu. Voskoboynik、Galina G. Berest、Lyudmila N. Antipenko、Alexey N. Antipenko、Andrey M. Katsev

  DOI：10.1007/s00044-012-0257-x

  日期：2013.6

  The series of novel N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides were obtained by aminolysis of activated acids 1a-1d and by alkylation of potassium salts 2a-2d by N -aryl-2-chloroacetamies. The structures of compounds were determined by IR, H-1, C-13 NMR, LC- and EI-MS analyses. The results of cytotoxicity evaluation by bioluminescence inhibition of bacterium Photobacterium leiognathi Sh1 showed that compounds reveal moderate cytotoxicity. Screening of anticancer activity in vitro yielded the most active compounds 3t, 4b, 4f, 4l and 4n in micromolar concentrations with the GI(50) level (logGI(50) is from -7.57 to -4.05 for different cell lines, and logGI(50) mean graph midpoint varied from -5.30 to -4.50). Moreover, compound 4b had a distinctive selectivity against renal cancer, 4f-colon cancer and melanoma and 4l-renal cancer. The highest sensitivity to compound 4b showed renal cancer cell lines A498 (logGI(50) = -7.57). SAR-analysis was discussed, COMPARE analysis and docking was studied.The novel synthesis methods of the N-aryl(alkaryl)-2-[(3-R-2-oxo-2H-[1,2,4]triazino[2,3-c]quinazoline-6-yl)thio]acetamides are proposed. Anticancer activity and Photobacterium leiognathi Sh1 bioluminescence inhibition of synthesized compounds are discussed. SAR-analysis was discussed, and COMPARE analysis and docking was studied.
• SHAH, V. H.;PATEL, H. H.;PARIKH, A. R., J. INDIAN CHEM. SOC., 1982, 59, N 5, 678-680
  作者：SHAH, V. H.、PATEL, H. H.、PARIKH, A. R.

  DOI：——

  日期：——
• AOKI, KAMITI;ARABORI, XIDEHO;SATAKEH, KEHJGO;NIIKAVA, XIROEH
  作者：AOKI, KAMITI、ARABORI, XIDEHO、SATAKEH, KEHJGO、NIIKAVA, XIROEH

  DOI：——

  日期：——
• Probing Structural Requirements of Positive Allosteric Modulators of the M₄ Muscarinic Receptor
  作者：Tracey Huynh、Celine Valant、Ian T. Crosby、Patrick M. Sexton、Arthur Christopoulos、Ben Capuano

  DOI：10.1021/jm401032k

  日期：2013.10.24

  The M, mAChR is implicated in several CNS disorders and possesses an allosteric binding site for which ligands modulating the affinity and/or efficacy of ACh may be exploited for selective receptor targeting. We report the synthesis of a focused library of putative M-4 PAMs derived from VU0152100 and VU10005. These compounds investigate the pharmacological effects of previously identified methoxy and fluoro substituents, providing useful estimates of affinity (K-B), cooperativity (alpha beta), and direct agonist properties (tau(B)).