N-(adamantan-1-yl)-2-bromoacetamide | 54059-81-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-(adamantan-1-yl)-2-bromoacetamide
• 英文别名: N-α-bromoacetyl amantadine；N-Adamantan-1-yl-2-bromo-acetamide；N-(1-adamantyl)-2-bromoacetamide
• CAS: 54059-81-3
• 化学式: C₁₂H₁₈BrNO
• mdl: MFCD18904289
• 分子量: 272.185
• InChiKey: PRIHBWFFGUPPOR-UHFFFAOYSA-N

物化性质

• 熔点：
  123-125 °C(Solv: hexane (110-54-3))
• 沸点：
  397.3±21.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.916
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  N-(adamantan-1-yl)-2-bromoacetamide 在 三乙酰氧基硼氢化钠 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 N-(adamantan-1-yl)-2-(4-(3,3-dimethylbutyl)-4,7-diazaspiro[2.5]octan-7-yl)acetamide
  参考文献：
  名称：

  Discovery of N-(1-adamantyl)-2-(4-alkylpiperazin-1-yl)acetamide derivatives as T-type calcium channel (Cav3.2) inhibitors

  摘要：

  Chemical evolution of a HTS-based fragment hit resulted in the identification of N-(1-adamantyl)-2-[4-(2-tetrahydropyran-4-ylethyl)piperazin-1-yl]acetamide, a novel, selective T-type calcium channel (Ca(v)3.2) inhibitor with in vivo antihypertensive effect in rats. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.092
• 作为产物：
  描述：

  金刚烷胺 以77%的产率得到N-(adamantan-1-yl)-2-bromoacetamide
  参考文献：
  名称：

  Acetamides and benzamides that are useful in treating sexual dysfunction

  摘要：

  本发明涉及使用式(I)的化合物治疗性功能障碍，以及含有式(I)化合物的组合物用于治疗性功能障碍。

  公开号：

  US20040029887A1

文献信息

• Synthesis of Amido-N-imidazolium Salts and their Applications as Ligands in Suzuki-Miyaura Reactions: Coupling of Hetero- aromatic Halides and the Synthesis of Milrinone and Irbesartan
  作者：Manian Rajesh Kumar、Kyungho Park、Sunwoo Lee

  DOI：10.1002/adsc.201000592

  日期：2010.12.17

  catalytic system based on palladium-amido-N-heterocyclic carbenes for Suzuki–Miyaura coupling reactions of heteroaryl bromides is described. A variety of sterically bulky, amido-N-imidazolium salts were synthesized in high yields from the corresponding anilines. This catalytic system effectively promoted Suzuki–Miyaura couplings of heteroaryl bromides and chlorides with a range of boronic acids to

  描述了基于钯-酰胺基-N-杂环卡宾的Suzuki-Miyaura杂芳基溴化物偶联反应的新催化体系。从相应的苯胺以高收率合成了各种空间庞大的酰胺基-N-咪唑鎓盐。该催化体系有效地促进了杂芳基溴化物和氯化物与一系列硼酸的Suzuki-Miyaura偶联，从而以高收率得到了相应的芳基化合物。随着取代基空间位阻的增加，产率增加。特别是，1-（2,6-二异丙基）-3- ñ - （2,4,6-三-叔-butylphenylacetamido）咪唑鎓溴化物（4BC）在2-溴吡啶和苯基硼酸的偶联反应中显示出850,000 TON。此外，药物化合物如米力农和厄贝沙坦是通过Suzuki-Miyaura偶联，使用体积庞大的酰胺基-N-咪唑鎓盐（4bc）作为配体合成的。
• New N -4 piperazinyl derivatives of norfloxacin: design, synthesis, and correlation of calculated physicochemical parameters with antibacterial activity
  作者：Gamal El-Din ABUO-RAHMA、Samar ABBAS、Mai SHOMAN、Ebtihal SAMIR、Rehab ABDEL-BAKY

  DOI：10.3906/kim-1706-16

  日期：——

  A group of $N-$4 piperazinyl derivatives of norfloxacin was synthesized and identified by different spectroscopic techniques. The $N-$4 piperazinyl substituent in target compounds 2a-2k, 3a-3c, and 4a and 4b was designed to have different electronic, steric, and physicochemical properties. The antibacterial activity of the newly synthesized compounds was evaluated against Pseudomonas aeruginosa, Escherichia coli, Klebsiella pneumoniae, and Staphylococcus aureus strains using norfloxacin as a reference. Results showed that most of the tested compounds had higher activity against E. coli and K. pneumoniae than norfloxacin, whereas only five derivatives were more active against P. aeruginosa. On the other hand, all derivatives were less active than norfloxacin against S. aureus. The biological activity of the target compounds, expressed in log MIC, is correlated with lipophilicity, polarizability, and topology parameters. Results showed that none of the calculated parameters could determine the biological activity. Consequently, the total volume of the molecule, bulkiness at C-7, electronic factors, and lipophilicity are important factors that should be considered in the design of new fluoroquinolones.

  合成了一组$N$-4哌嗪基诺氟沙星衍生物，并通过不同的光谱技术进行鉴定。目标化合物2a-2k、3a-3c、4a和4b中的$N$-4哌嗪基取代基被设计为具有不同的电子、立体和物理化学性质。评估了新合成化合物对铜绿假单胞菌、大肠杆菌、肺炎克雷伯菌和金黄色葡萄球菌菌株的抗菌活性，以诺氟沙星为参照。结果显示，大多数被测化合物对大肠杆菌和肺炎克雷伯菌的活性高于诺氟沙星，而只有五种衍生物对铜绿假单胞菌的活性更高。另一方面，所有衍生物对金黄色葡萄球菌的活性都低于诺氟沙星。目标化合物的生物活性（以对数最低抑菌浓度表示）与亲脂性、极化率和拓扑参数相关。结果表明，计算的参数均不能确定生物活性。因此，分子的总体积、C-7处的体积、电子因素和亲脂性是设计新型氟喹诺酮时应考虑的重要因素。
• Design, synthesis and evaluation of novel ¹⁹F magnetic resonance sensitive protein tyrosine phosphatase inhibitors
  作者：Yu Li、Guiquan Xia、Qi Guo、Li Wu、Shizhen Chen、Zhigang Yang、Wei Wang、Zhong-Yin Zhang、Xin Zhou、Zhong-Xing Jiang

  DOI：10.1039/c6md00277c

  日期：——

  Fluorine is a highly attractive element for both medicinal chemistry and imaging technologies. To facilitate protein tyrosine phosphatase (PTP)-targeted drug discovery and imaging-guided PTP research on fluorine, several highly potent and 19F MR sensitive PTP inhibitors were discovered through a structure-based focused library strategy.

  氟对于药物化学和成像技术都是极具吸引力的元素。为了促进针对蛋白质酪氨酸磷酸酶（PTP）的药物发现和对氟的成像指导PTP研究，通过基于结构的聚焦文库策略发现了几种高效和19 F MR敏感的PTP抑制剂。
• Discovery of a Small-Molecule Inhibitor of Interleukin 15: Pharmacophore-Based Virtual Screening and Hit Optimization
  作者：Agnès Quéméner、Mike Maillasson、Laurence Arzel、Benoit Sicard、Romy Vomiandry、Erwan Mortier、Didier Dubreuil、Yannick Jacques、Jacques Lebreton、Monique Mathé-Allainmat

  DOI：10.1021/acs.jmedchem.7b00485

  日期：2017.7.27

  approaches targeting IL-15. This study is an original approach aimed at discovering small-molecule inhibitors impeding IL-15/IL-15R interaction. A pharmacophore and docking-based virtual screening of compound libraries led to the selection of 240 high-scoring compounds, 36 of which were found to bind IL-15, to inhibit the binding of IL-15 to the IL-2Rβ chain or the proliferation of IL-15-dependent cells or

  白介素（IL）-15是一种多效细胞因子，在结构上接近IL-2，并与之共享IL-2β和γ受体（R）亚基。通过促进NK，NK-T和CD8 + T细胞的活化和增殖，IL-15在先天和适应性免疫中起着重要的作用。而且，高水平的IL-15表达与炎性和自身免疫性疾病的关联导致了针对IL-15的各种拮抗方法的发展。这项研究是旨在发现阻碍IL-15 / IL-15R相互作用的小分子抑制剂的原始方法。对化合物库进行药效学和基于对接的虚拟筛选导致选择了240种高得分化合物，其中36种被发现与IL-15结合，从而抑制IL-15与IL-2Rβ链的结合或增殖IL-15依赖性细胞或两者兼有。
• Amide-Based <i>Cinchona</i> Alkaloids as Phase-Transfer Catalysts: Synthesis and Potential Application
  作者：Maciej Majdecki、Patryk Niedbala、Janusz Jurczak

  DOI：10.1021/acs.orglett.9b03065

  日期：2019.10.4

  easily and efficiently from inexpensive and commercially available substrates. We tested this class of alkaloids in the alkylation of glycine derivative, carried out under phase-transfer catalyst conditions. The presented hybrid catalysts offer both high reaction yields (up to 97%) and high enantioselectivities of the obtained product (up to 94% ee).

  本文中，我们以季铵盐的形式提供了金鸡纳生物碱的简单酰胺衍生物的文库。所获得的衍生物可以很容易和有效地从廉价的和可商购的基质中产生。我们在相转移催化剂条件下进行的甘氨酸衍生物烷基化反应中测试了这类生物碱。所提出的杂化催化剂提供了高的反应产率（高达97％）和所获得的产物的高的对映选择性（高达94％的ee）。