5-碘-2-甲基-苯甲腈 | 52107-68-3

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-碘-2-甲基-苯甲腈
• 中文别名: 5-碘-2-甲基苯腈
• 英文名称: 5-iodo-2-methylbenzonitrile
• 英文别名: 5-iodo-2-methylcyanobenzene；5-Iod-2-methyl-benzonitril；5-Iod-2-methylbenzonitril
• CAS: 52107-68-3
• 化学式: C₈H₆IN
• 分子量: 243.047
• InChiKey: QPGQEWLZKVSLPK-UHFFFAOYSA-N

物化性质

• 熔点：
  72-73 °C
• 沸点：
  275.8±28.0 °C(Predicted)
• 密度：
  1.78±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  5-碘-2-甲基-苯甲腈 在 copper(l) iodide 、 正丁基锂 、 sodium azide 、 sodium ascorbate 、 N,N-二甲基乙二胺 、 二异丙胺 作用下， 以 正己烷 、 二乙二醇二甲醚 、 水 、 二甲基亚砜 为溶剂， 反应 5.5h， 生成 ethyl 1-amino-7-azido-3,3-dimethyl-3,4-dihydronaphthalene-2-carboxylate
  参考文献：
  名称：

  Development of tag-free photoprobes for studies aimed at identifying the target of novel Group A Streptococcus antivirulence agents

  摘要：

  We previously reported the identification and development of novel inhibitors of streptokinase (SK) expression by Group A Streptococcus (GAS), originating from a high throughput cell-based phenotypic screen. Although phenotypic screening is well-suited to identifying compounds that exert desired biological effects in potentially novel ways, it requires follow-up experiments to determine the macromolecular target(s) of active compounds. We therefore designed and synthesized several classes of chemical probes for target identification studies, guided by previously established structure-activity relationships. The probes were designed to first irreversibly photolabel target proteins in the intact bacteria, followed by cell lysis and click ligation with fluorescent tags to allow for visualization on SDS-PAGE gels. This stepwise, 'tag-free' approach allows for a significant reduction in molecular weight and polar surface area compared to full-length fluorescent or biotinylated probes, potentially enhancing membrane permeability and the maintenance of activity. Of the seven probes produced, the three most biologically active were employed in preliminary target identification trials. Despite the potent activity of these probes, specific labeling events were not conclusively observed due to a considerable degree of nonspecific protein binding. Nevertheless, the successful synthesis of potent biologically active probe molecules will serve as a starting point for initiating more sensitive methods of probe-based target identification. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.079
• 作为产物：
  描述：

  2-甲基-5-氨基苯腈 生成 5-碘-2-甲基-苯甲腈
  参考文献：
  名称：

  Gore,P.H. et al., Journal of the Chemical Society. Perkin transactions I, 1973, p. 2940 - 2948

  摘要：

  DOI：

文献信息

• [EN] SUCCINATE AND MALONATE SALT OF TRANS-4-(IR,3S)-6-CHLORO-3-PHENYLINDAN-1-YL)-1,2,2-TRIMETHYLPIPERAZINE AND THE USE AS A MEDICAMENT<br/>[FR] SEL DE SUCCINATE ET DE MALONATE DE TRANS-4-((1R,3S)-6-CHLORO-3-PHENYLINDAN-1-YL)-1,2,2-TRIMETHYLPIPERAZINE ET SON UTILISATION EN TANT QUE MEDICAMENT
  申请人：LUNDBECK & CO AS H

  公开号：WO2005016900A1

  公开（公告）日：2005-02-24

  4-((1R,3S)-6-Chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine hydrogen succinate or hadrogen malonat, pharmaceutical compositions containing these salts and the medical use thereof, including for the treatment of schizophrenia and other psychotic disorders. Also described are methods for the preparation of 4-((1R,3S)-6-Chloro-3-phenylindan-1-yl)-1,2,2-trimethylpiperazine and medical uses thereof.

  4-((1R,3S)-6-氯-3-苯基茚-1-基)-1,2,2-三甲基哌嗪氢丁二酸盐或氢丁二酸盐，含有这些盐的药物组合物及其医疗用途，包括用于治疗精神分裂症和其他精神疾病。还描述了制备4-((1R,3S)-6-氯-3-苯基茚-1-基)-1,2,2-三甲基哌嗪和其医疗用途的方法。
• High-Affinity Alkynyl Bisubstrate Inhibitors of Nicotinamide <i>N</i>-Methyltransferase (NNMT)
  作者：Rocco L. Policarpo、Ludovic Decultot、Elizabeth May、Petr Kuzmič、Samuel Carlson、Danny Huang、Vincent Chu、Brandon A. Wright、Saravanakumar Dhakshinamoorthy、Aimo Kannt、Shilpa Rani、Sreekanth Dittakavi、Joseph D. Panarese、Rachelle Gaudet、Matthew D. Shair

  DOI：10.1021/acs.jmedchem.9b01238

  日期：2019.11.14

  structure-based rational design led to the development of potent and selective alkynyl bisubstrate inhibitors of NNMT. The reported nicotinamide–SAM conjugate (named NS1) features an alkyne as a key design element that closely mimics the linear, 180° transition state geometry found in the NNMT-catalyzed SAM → NAM methyl transfer reaction. NS1 was synthesized in 14 steps and found to be a high-affinity, subnanomolar

  烟酰胺N-甲基转移酶（NNMT）是一种使用辅因子S使烟酰胺（NAM）甲基化的代谢酶-腺苷甲硫氨酸（SAM）。NNMT过表达与糖尿病，肥胖症和各种癌症有关。在这项工作中，基于结构的合理设计导致了NNMT的有效和选择性炔基双底物抑制剂的发展。报道的烟酰胺-SAM共轭物（命名为NS1）以炔烃为主要设计元素，其紧密模拟NNMT催化的SAM→NAM甲基转移反应中发现的线性180°过渡态几何形状。NS1分14步合成，是一种高亲和力的亚纳摩尔级NNMT抑制剂。X射线共晶结构和SAR研究表明，炔基连接子具有跨过NNMT的甲基转移通道的能力，具有理想的形状互补性。这项工作中报道的化合物代表了迄今为止报道的最有效和选择性的NNMT抑制剂。
• A Pivotal Role of Chloride Ion on Nickel-Catalyzed Enantioselective Reductive Cross-Coupling to Perfluoroalkylated Boronate Esters
  作者：Dong Wang、Tao XU

  DOI：10.1021/acscatal.1c03265

  日期：2021.10.15

  The enantioselective construction of perfluoroalkyl-containing molecules is essential in materials science, agrochemistry, and medicinal chemistry. Herein, a nickel-catalyzed reductive cross-coupling was reported to generate chiral perfluoroalkylated boronate esters from the easily prepared perfluoroalkyl-substituted α-iodoboronates. The simple and mild conditions enable a broad range of aryl iodides

  含全氟烷基分子的对映选择性构建在材料科学、农业化学和药物化学中是必不可少的。在此，据报道，镍催化的还原交叉偶联可从易于制备的全氟烷基取代的 α-碘硼酸酯生成手性全氟烷基化硼酸酯。简单和温和的条件使广泛的芳基碘化物能够以良好的对映选择性提供产品。此外，与碘盐对底物活化的常见加速相比，系统研究了添加剂的影响，以揭示氯离子对镍还原的关键作用。
• Novel Propargyl-Linked Bisubstrate Analogues as Tight-Binding Inhibitors for Nicotinamide <i>N</i>-Methyltransferase
  作者：Dongxing Chen、Linjie Li、Krystal Diaz、Iredia D. Iyamu、Ravi Yadav、Nicholas Noinaj、Rong Huang

  DOI：10.1021/acs.jmedchem.9b01255

  日期：2019.12.12

  Nicotinamide N-methyltransferase (NNMT) catalyzes the methyl transfer from the cofactor S-adenosylmethionine to nicotinamide and other pyridine-containing compounds. NNMT is an important regulator for nicotinamide metabolism and methylation potential. Aberrant expression levels of NNMT have been implicated in cancer, metabolic, and neurodegenerative diseases, which makes NNMT a potential therapeutic

  烟酰胺N-甲基转移酶（NNMT）催化从辅因子S-腺苷甲硫氨酸到烟酰胺和其他含吡啶化合物的甲基转移。NNMT是烟酰胺代谢和甲基化潜力的重要调节剂。NNMT的异常表达水平与癌症，代谢和神经退行性疾病有关，这使NNMT成为潜在的治疗靶标。因此，有效的和选择性的NNMT抑制剂可作为研究NNMT在其介导疾病中的作用的有价值的工具。在这里，我们应用了一种合理的策略，通过新型的炔丙基接头设计并合成了紧密结合的双底物抑制剂LL320。LL320演示了K i值为1.6±0.3 nM，是迄今为止最有效的抑制剂。LL320的共晶结构证实了它与NNMT上底物和辅因子结合位点的相互作用。重要的是，这是使用炔丙基接头构建有效的甲基转移酶抑制剂的第一个例子，这将扩大我们对甲基转移过渡态的理解。
• Organometallic compound and organic light-emitting device including the same
  申请人：SAMSUNG ELECTRONICS CO., LTD.

  公开号：US10199584B2

  公开（公告）日：2019-02-05

  A silyl group-containing compound represented by Formula 1: wherein, in Formula 1, groups and variables are the same as described in the specification.

  由式 1 表示的含硅烷基化合物： 其中，在公式 1 中，组和变量与说明书中描述的相同。