N-(2-carbamoylphenyl)picolinamide | 157979-82-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-carbamoylphenyl)picolinamide
• 英文别名: N-(2-carbamoylphenyl)pyridine-2-carboxamide
• CAS: 157979-82-3
• 化学式: C₁₃H₁₁N₃O₂
• 分子量: 241.249
• InChiKey: CFWBWWGTYFKZGU-UHFFFAOYSA-N

物化性质

• 熔点：
  219-221 °C
• 沸点：
  374.0±22.0 °C(predicted)
• 密度：
  1.338±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-carbamoylphenyl)picolinamide 在 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 2-吡啶-2-基-1H-喹唑啉-4-酮
  参考文献：
  名称：

  Discovery of Potent Cyclic GMP Phosphodiesterase Inhibitors. 2-Pyridyl- and 2-Imidazolylquinazolines Possessing Cyclic GMP Phosphodiesterase and Thromboxane Synthesis Inhibitory Activities

  摘要：

  Moderate cyclic GMP phosphodiesterase (cGMP-PDE, PDE V) inhibitor 2-phenyl-4-anilino-quinazoline (1) was identified utilizing MultiCASE assisted drug design (MCADD) technology. Modification of compound 1 was conducted at the 2-, 4-, and 6-positions of the quinazoline ring for enhancement of cGMP-PDE inhibitory activity. The 6-substituted 2-(imidazol-1-yl)-quinazolines are 1000 times more potent in in vitro PDE V enzyme assay than the well-known inhibitor zaprinast. The 6-substituted derivatives of 2-(3-pyridyl)quinazoline 84 and 2-(imidazol-1-yl)quinazoline 86 exhibited more than 1000-fold selectivity for PDE V over the other four PDE isozymes. In addition, cGMP-PDE inhibitors 64, 65, and 73 were found to have an additional property of thromboxane synthesis inhibitory activity.

  DOI：

  10.1021/jm00018a014
• 作为产物：
  描述：

  o-[N-(α-picolyl)amino]acetophenone 在 sodium azide 、 氧气 、 copper diacetate 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 以85%的产率得到N-(2-carbamoylphenyl)picolinamide
  参考文献：
  名称：

  铜催化的吡啶甲酰胺指示的C（CO）-C（烷基）键裂解使酮转化为酰胺

  摘要：

  描述了铜催化的C（CO）-C（烷基）键的化学选择性裂解，导致含N的方向性基团的螯合助剂形成C-N键。廉价的乙酸铜（II）可作为转化的方便催化剂。该方法突出了新兴的在有机合成中将未活化的烷基酮转化为酰胺的策略，并为CC键断裂提供了新的策略。

  DOI：

  10.1039/c7ob01636k

文献信息

• Discovery of Potent Cyclic GMP Phosphodiesterase Inhibitors. 2-Pyridyl- and 2-Imidazolylquinazolines Possessing Cyclic GMP Phosphodiesterase and Thromboxane Synthesis Inhibitory Activities
  作者：Sung J. Lee、Yoshitaka Konishi、Dingwei T. Yu、Tamara A. Miskowski、Christopher M. Riviello、Orest T. Macina、Manton R. Frierson、Kigen Kondo、Masafumi Sugitani

  DOI：10.1021/jm00018a014

  日期：1995.9

  Moderate cyclic GMP phosphodiesterase (cGMP-PDE, PDE V) inhibitor 2-phenyl-4-anilino-quinazoline (1) was identified utilizing MultiCASE assisted drug design (MCADD) technology. Modification of compound 1 was conducted at the 2-, 4-, and 6-positions of the quinazoline ring for enhancement of cGMP-PDE inhibitory activity. The 6-substituted 2-(imidazol-1-yl)-quinazolines are 1000 times more potent in in vitro PDE V enzyme assay than the well-known inhibitor zaprinast. The 6-substituted derivatives of 2-(3-pyridyl)quinazoline 84 and 2-(imidazol-1-yl)quinazoline 86 exhibited more than 1000-fold selectivity for PDE V over the other four PDE isozymes. In addition, cGMP-PDE inhibitors 64, 65, and 73 were found to have an additional property of thromboxane synthesis inhibitory activity.
• Copper-catalyzed transformation of ketones to amides via C(CO)–C(alkyl) bond cleavage directed by picolinamide
  作者：Haojie Ma、Xiaoqiang Zhou、Zhenzhen Zhan、Daidong Wei、Chong Shi、Xingxing Liu、Guosheng Huang

  DOI：10.1039/c7ob01636k

  日期：——

  cleavage of the C(CO)–C(alkyl) bond leading to C–N bond formation with a chelation-assist from N-containing directing groups is described. Inexpensive Cu(II)-acetate serves as a convenient catalyst for the transformation. This method highlights the emerging strategy to transform unactivated alkyl ketones into amides in organic synthesis and provides a new strategy for C–C bond cleavage.

  描述了铜催化的C（CO）-C（烷基）键的化学选择性裂解，导致含N的方向性基团的螯合助剂形成C-N键。廉价的乙酸铜（II）可作为转化的方便催化剂。该方法突出了新兴的在有机合成中将未活化的烷基酮转化为酰胺的策略，并为CC键断裂提供了新的策略。
• Collaborative Virtual Screening Identifies a 2-Aryl-4-aminoquinazoline Series with Efficacy in an <i>In Vivo</i> Model of <i>Trypanosoma cruzi</i> Infection
  作者：Taisuke Tawaraishi、Atsuko Ochida、Yuichiro Akao、Sachiko Itono、Masahiro Kamaura、Thamina Akther、Mitsuyuki Shimada、Stacie Canan、Sanjoy Chowdhury、Yafeng Cao、Kevin Condroski、Ola Engkvist、Amanda Francisco、Sunil Ghosh、Rina Kaki、John M. Kelly、Chiaki Kimura、Thierry Kogej、Kazuya Nagaoka、Akira Naito、Garry Pairaudeau、Constantin Radu、Ieuan Roberts、David Shum、Nao-aki Watanabe、Huanxu Xie、Shuji Yonezawa、Osamu Yoshida、Ryu Yoshida、Charles Mowbray、Benjamin Perry

  DOI：10.1021/acs.jmedchem.2c00775

  日期：2023.1.26