2-氨基-4-甲氧基-N-甲基苯甲酰胺 | 104775-67-9

• 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: 2-氨基-4-甲氧基-N-甲基苯甲酰胺
• 英文名称: 2-amino-4-methoxy-N-methylbenzamide
• CAS: 104775-67-9
• 化学式: C₉H₁₂N₂O₂
• 分子量: 180.206
• InChiKey: VLTOORIWKFQMCO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基-4-甲氧基-N-甲基苯甲酰胺 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 N,N-二异丙基乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 2-Chloro-7-methoxy-3-methyl-4(3H)-quinazolinone
  参考文献：
  名称：

  Identification and optimization of a new series of anti-tubercular quinazolinones

  摘要：

  A high throughput phenotypic screening against Mycobacterium smegmatis led us to the discovery of a new class of bacteriostatic, highly hydrophobic antitubercular quinazolinones that potently inhibited the in vitro growth of either extracellular or intramacrophagic M. tuberculosis (Mtb), via modulation of an unidentified but yet novel target. Optimization of the initial hit compound culminated in the identification of potent but poorly soluble Mtb growth inhibitors, three of which were progressed to in vivo efficacy studies. Despite nanomolar in vitro potency and attractive PK properties, none of these compounds was convincingly potent in our in vivo mouse tuberculosis models. This lack of efficacy may be linked to the poor drug-likeness of the test molecules and/or to the properties of the target.[GRAPHICS](C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.09.043
• 作为产物：
  描述：

  4-methoxy-N-methyl-2-nitrobenzamide 生成 2-氨基-4-甲氧基-N-甲基苯甲酰胺
  参考文献：
  名称：

  MIKI, TOSAKU;ASANO, AKIXIDEH;XOSOKAMI, TORU

  摘要：

  DOI：

文献信息

• [EN] PYRIDINE COMPOUNDS<br/>[FR] COMPOSÉS PYRIDINES
  申请人：ASTRAZENECA AB

  公开号：WO2009153589A1

  公开（公告）日：2009-12-23

  The present invention relates to compounds that inhibit of focal adhesion kinase function, processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment in warm-blooded animals such as humans of diseases such as cancer.

  本发明涉及抑制细胞焦点粘附激酶功能的化合物，其制备方法，含有其作为活性成分的药物组合物，以及它们作为药物的用途，以及用于制造用于治疗温血动物（如人类）癌症等疾病的药物。
• Two-Directional Approach for the Rapid Synthesis of 2,4-Bis-Aminoaryl Pyridine Derivatives
  作者：Rémy Morgentin、Bernard Barlaam、Kevin Foote、Lorraine Hassall、Janet Hawkins、Clifford D. Jones、Antoine Le Griffon、Aurelien Peru、Patrick Plé

  DOI：10.1080/00397911.2010.520403

  日期：2012.1.1

  pyridine compounds from a common starting material. The C-4/C-2 approach uses palladium-mediated coupling reactions to sequentially functionalize C-4 and then C-2. An alternative C-2/C-4 route uses a regioselective SNAr reaction to first substitute at C-2 then subsequently at C-4 by a palladium-mediated reaction. Both approaches have been used successfully to provide a range of 2,4-bis-aminoaryl pyridine

  摘要 我们同时开发了两种不同的方法，以从常见的起始材料中快速获取 2,4-双氨基芳基吡啶化合物。C-4/C-2 方法使用钯介导的偶联反应依次功能化 C-4，然后是 C-2。另一种 C-2/C-4 路线使用区域选择性 SNAr 反应，首先在 C-2 处取代，然后在 C-4 处通过钯介导的反应进行取代。两种方法均已成功用于提供一系列 2,4-双-氨基芳基吡啶化合物。图形概要
• Development of novel 2-[4-(aminoalkoxy)phenyl]-4(3H)-quinazolinone derivatives as potent and selective histamine H3 receptor inverse agonists
  作者：Takashi Mizutani、Tsuyoshi Nagase、Sayaka Ito、Yasuhisa Miyamoto、Takeshi Tanaka、Norihiro Takenaga、Shigeru Tokita、Nagaaki Sato

  DOI：10.1016/j.bmcl.2008.10.034

  日期：2008.12

  Novel 2-[4-(aminoalkoxy)phenyl]-4(3H)-quinazolinone derivatives were identified as potent human H(3) receptor inverse agonists. After systematic modification of lead 5a, the potent and selective analog 5r was identified. Elimination of hERG K(+) channel and human alpha(1A)-adrenoceptor activities is the main focus of the present study.

  新型2- [4-（氨基烷氧基）苯基] -4（3H）-喹唑啉酮衍生物被确定为有效的人H（3）受体反向激动剂。在对铅5a进行系统修饰后，鉴定出了有效且选择性的类似物5r。消除hERG K（+）通道和人类alpha（1A）-肾上腺素受体活性是本研究的主要重点。
• Palladium-Catalyzed Oxidative Three-Component Coupling of Anthranilamides with Isocyanides and Arylboronic Acids: Access to 2,3-Disubstituted Quinazolinones
  作者：Chun Qian、Kui Liu、Shou-Wei Tao、Fang-Ling Zhang、Yong-Ming Zhu、Shi-Lin Yang

  DOI：10.1021/acs.joc.8b01218

  日期：2018.8.17

  A novel palladium-catalyzed oxidative three-component coupling of easily accessible N-substituted anthranilamides with isocyanides and arylboronic acids is achieved. This protocol offers an alternative approach toward 2,3-disubstituted quinazolinones with a wide substrate scope and good functional group tolerance.

  实现了易于获得的N-取代邻氨基苯甲酰胺与异氰化物和芳基硼​​酸的新型钯催化的氧化三组分偶联。该协议为具有较宽的底物范围和良好的官能团耐受性的2，3-二取代的喹唑啉酮提供了另一种方法。
• Synthesis of 2-aryl quinazolinones <i>via</i> iron-catalyzed cross-dehydrogenative coupling (CDC) between N–H and C–H bonds
  作者：Yoonkyung Jang、Seok Beom Lee、Junhwa Hong、Simin Chun、Jeeyeon Lee、Suckchang Hong

  DOI：10.1039/d0ob00866d

  日期：——

  describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C–H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination–aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated

  在这里，我们描述了通过甲基芳烃和邻氨基苯甲酰胺之间的交叉脱氢偶联直接合成喹唑啉酮。苄sp。的C-H官能化3碳被二-实现吨丁基过氧化物在空气下，和随后的胺化需氧氧化过程完成环过程。铁催化了整个反应过程，在反应条件下可耐受各种官能团，提供了31种使用甲基芳烃衍生物的2-芳基喹唑啉酮实例，收率为57–95％。合成潜力已通过含芳基杂环的额外合成得到证明。