4-(甲基氨基)苯基硼酸 | 302348-49-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 4-(甲基氨基)苯基硼酸
• 英文名称: 4-(methylamino)phenylboronic acid
• 英文别名: [4-(methylamino)phenyl]boronic acid
• CAS: 302348-49-8
• 化学式: C₇H₁₀BNO₂
• 分子量: 150.973
• InChiKey: IDWLEJGVLKZNGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.59
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  52.5
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(甲基氨基)苯基硼酸 在 potassium fluoride 、 lithium hydroxide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 4-Bromo-3-(carboxymethoxy)-5-(4-{methyl[4-(trifluoromethyl)benzene]sulfonamido}phenyl)thiophene-2-carboxylic acid
  参考文献：
  名称：

  Monocyclic thiophenes as protein tyrosine phosphatase 1B inhibitors: Capturing interactions with Asp48

  摘要：

  A series of monocyclic thiophenes was designed and synthesized as PTP1B inhibitors. Guided by X-ray co-crystal structural information and computational modeling, rational design led to key interactions with Asp48 and improved inhibitory potency against PTP1B.

  DOI：

  10.1016/j.bmcl.2006.06.051

文献信息

• Synthesis and Cancer Stem Cell-Based Activity of Substituted 5-Morpholino-7<i>H</i>-thieno[3,2-<i>b</i>]pyran-7-ones Designed as Next Generation PI3K Inhibitors
  作者：Guillermo A. Morales、Joseph R. Garlich、Jingdong Su、Xiaodong Peng、Jessica Newblom、Kevin Weber、Donald L. Durden

  DOI：10.1021/jm301522m

  日期：2013.3.14

  has made PI3K a consensus target to inhibit as illustrated by more than 15 inhibitors now in clinical trials. Our previous work, built on the early pioneering multikinase inhibitor LY294002, resulted in the only PI3K vascular-targeted PI3K inhibitor prodrug, SF1126, which has now completed Phase I clinical trials. This inhibitor has properties that impart more in vivo activity than should be warranted

  磷脂酰肌醇-3-激酶（PI3K）通路在多种肿瘤中的失调使PI3K成为抑制的共识靶标，目前临床试验中已使用15种以上的抑制剂进行了说明。我们先前的工作是建立在早期的首创的多激酶抑制剂LY294002的基础上的，导致了唯一的PI3K血管靶向PI3K抑制剂前药SF1126，该药物现已完成I期临床试验。该抑制剂具有比其酶促效力应赋予的更多的体内活性，该酶促效力通常远低于其他临床阶段的PI3K抑制剂。我们着手探索保留了这些特性并同时展现出对PI3K更高效力的支架。这项工作导致发现了5-morpholino-7 H -thieno [3,2- b] pyran-7-one系统作为潜在的PI3K抑制剂新化合物类别的基础，对PI3K具有增强的效力。这些化合物的合成和基于癌症干细胞的活性在本文中报道。
• Simultaneous exploration of TBAF·3H 2 O as a base as well as a solvating agent for the palladium catalyzed Suzuki cross-coupling of 4-methyl-7-nonafluorobutylsulfonyloxy coumarins under microwave irradiation
  作者：M. Nibin Joy、Yadav D. Bodke、K.K. Abdul Khader、Ayyiliyath M. Sajith、Talavara Venkatesh、A.K. Ajeesh Kumar

  DOI：10.1016/j.jfluchem.2016.01.002

  日期：2016.2

  A concise, efficient and facile protocol for the synthesis of a variety of 4-methyl-7-aryl/heteroaryl coumarins has been developed by utilizing the palladium catalyzed Suzuki cross-coupling reaction of 4-methyl-7-nonafluorobutylsulfonyloxy coumarin with a wide range of electronically diverse boronic acids under microwave irradiation. In the presence of a suitable catalyst, ligand and base, the coupling

  通过利用钯催化的4-甲基-7-九氟丁基磺酰氧基香豆素与宽范围的钯催化的Suzuki交叉偶联反应，已开发出一种简捷，高效且简便的合成多种4-甲基-7-芳基/杂芳基香豆素的方案。微波辐射下各种电子硼酸的合成 在合适的催化剂，配体和碱的存在下，偶联反应顺利进行，以令人满意的至优异的产率得到联芳基。TBAF·3H 2的双重作用发现O作为溶剂以及溶剂，以及使用dppp作为具有适中咬合角（91°）的配体有助于反应成功。该优化条件的突出特征包括：反应时间短，产率高至优异以及对多种官能团的优异耐受性。
• Synthesis and biological evaluation of 4 arylcoumarin analogues as tubulin-targeting antitumor agents
  作者：Peggoty Mutai、Gilles Breuzard、Alessandra Pagano、Diane Allegro、Vincent Peyrot、Kelly Chibale

  DOI：10.1016/j.bmc.2017.01.035

  日期：2017.3

  The synthesis of twenty-six 4-arylcoumarin analogues of combretastatin A-4 (CA-4) led to the identification of two new compounds (25 and 26) with strong cytotoxic activity. Both compounds had a high cytotoxic effect on a CA-4-resistant colon adenocarcinoma cell line (HT29D4). The compounds affected cell cycle progression characterized by a mitotic block. The activity of these compounds against microtubules

  康布雷他汀A-4（CA-4）的26种4-芳基香豆素类似物的合成导致鉴定出两种具有强细胞毒活性的新化合物（25和26）。两种化合物均对耐CA-4的结肠腺癌细胞系（HT29D4）具有很高的细胞毒性作用。该化合物影响以有丝分裂阻滞为特征的细胞周期进程。检查了这些化合物在体外和细胞中对微管的活性，发现这两种化合物在体外均能有效抑制通过亚化学计量模式（如CA-4）形成微管。通过免疫荧光，观察到两种化合物均诱导强烈的微管网络破坏。我们的结果为开发针对CA-4耐药癌细胞的新型有效抗微管蛋白分子提供了有力的实验基础。
• 2-(6-Phenyl-1H-indazol-3-yl)-1H-benzo[d]imidazoles: Design and synthesis of a potent and isoform selective PKC-ζ inhibitor
  作者：John I. Trujillo、James R. Kiefer、Wei Huang、Atli Thorarensen、Li Xing、Nicole L. Caspers、Jacqueline E. Day、Karl J. Mathis、Kuniko K. Kretzmer、Beverley A. Reitz、Robin A. Weinberg、Roderick A. Stegeman、Ann Wrightstone、Lori Christine、Robert Compton、Xiong Li

  DOI：10.1016/j.bmcl.2008.11.105

  日期：2009.2

  The inhibition of PKC-zeta has been proposed to be a potential drug target for immune and inflammatory diseases. A series of 2-(6-phenyl-1H indazol-3-yl)-1H-benzo[d]imidazoles with initial high crossover to CDK-2 has been optimized to afford potent and selective inhibitors of protein kinase c-zeta (PKC-zeta). The determination of the crystal structures of key inhibitor:CDK-2 complexes informed the design and analysis of the series. The most selective and potent analog was identified by variation of the aryl substituent at the 6-position of the indazole template to give a 4-NH(2) derivative. The analog displays good selectivity over other PKC isoforms (alpha, betaII, gamma, delta, epsilon, mu, theta, eta and iota/lambda) and CDK-2, however it displays marginal selectivity against a panel of other kinases (37 profiled).
• Parallel Chemistry Approach to Identify Novel Nuclear Receptor Ligands Based on the GW0742 Scaffold
  作者：Kelly A. Teske、Ganesha Rai、Premchendar Nandhikonda、Preetpal S. Sidhu、Belaynesh Feleke、Anton Simeonov、Adam Yasgar、Ajit Jadhav、David J. Maloney、Leggy A. Arnold

  DOI：10.1021/acscombsci.7b00066

  日期：2017.10.9

  We describe the parallel synthesis of novel analogs of GW0742, a peroxisome proliferator-activated receptor delta (PPAR delta) agonist For that purpose, modified reaction conditions were applied, such as a solid-phase palladium-catalyzed Suzuki coupling. In addition, tetrazole-based compounds were generated as a bioisostere for carboxylic acid-containing ligand GW0742. The new compounds were investigated for their ability to activate PPAR delta mediated transcription and their cross-reactivity with the vitamin D receptor (VDR), another member of the nuclear receptor superfamily. We identified many potent PPAR delta agonists that were less toxic than GW0742, where similar to 65 of the compounds synthesized exhibited partial PPAR delta activity (23-98%) with EC50 values ranging from 0.007-18.2 mu M. Some ligands, such as compound 32, were more potent inhibitors of VDR-mediated transcription with significantly reduced PPAR delta activity than GW0742, however, none of the ligands were completely selective for VDR inhibition over PPAR delta activation of transcription.