N-(2-carbamoylphenyl)quinoline-2-carboxamide | 262590-33-0

• 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)quinoline-2-carboxamide
• CAS: 262590-33-0
• 化学式: C₁₇H₁₃N₃O₂
• 分子量: 291.309
• InChiKey: VYYZIAKXTBFCAB-UHFFFAOYSA-N

物化性质

• 熔点：
  269-271 °C(Solv: methanol (67-56-1))
• 沸点：
  453.8±25.0 °C(Predicted)
• 密度：
  1.359±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• 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)quinoline-2-carboxamide 在 sodium hydroxide 、 mesityllithium 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 乙醇 、 水 、 正戊烷 为溶剂， 反应 1.41h， 生成 色氨酸A
  参考文献：
  名称：

  Regioselective Quinazolinone-Directed Ortho Lithiation of Quinazolinoylquinoline:  Practical Synthesis of Naturally Occurring Human DNA Topoisomerase I Poison Luotonin A and Luotonins B and E

  摘要：

  A regioselective quinazolinone-directed ortho lithiation on an adjacent quinoline moiety has been used as a key step for a short, efficient, and practical synthesis of the human DNA topoisomerase I poison luotonin A and luotonins B and E. The quinazolinoylquinoline 5 on treatment with in situ-generated nonnucleophilic mesityllithium furnished the desired dilithiated intermediate 6, which on treatment with formaldehyde followed by Mitsunobu ring closure reaction gave luotonin A (1a) in very good yield. The reaction of dilithiated intermediate 6 with DMF directly furnished luotonin B (1b) in 81% yield. Luotonin B (1b) on methylation with p-TSA/methanol gave luotonin E (1c) in 82% yield.

  DOI：

  10.1021/jo040153v
• 作为产物：
  描述：

  N-(2-acetylphenyl)quinoline-2-carboxamide 在 sodium azide 、 氧气 、 copper diacetate 、 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 以76%的产率得到N-(2-carbamoylphenyl)quinoline-2-carboxamide
  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

• Total Synthesis of the Fumiquinazoline Alkaloids:  Solution-Phase Studies¹
  作者：Haishan Wang、A. Ganesan

  DOI：10.1021/jo9914364

  日期：2000.2.1

  Biomimetic total syntheses of glyantrypine, fumiquinazoline F, fumiquinazoline G, and fiscalin B were achieved in four steps from tryptophan methyl ester. In the key step, the anthranilamide residue in a linear tripeptide is dehydrated to a benzoxazine by reaction with triphenylphosphine, iodine, and a tertiary amine. The benzoxazines subsequently undergo rearrangement to the natural products via an amidine

  从色氨酸甲酯通过四个步骤实现了仿生的喹硫平，氟喹唑啉F，氟喹唑啉G和紫杉醇B的仿生总合成。在关键步骤中，线性三肽中的邻氨基苯甲酰胺残基通过与三苯基膦，碘和叔胺反应而脱水成苯并恶嗪。苯并恶嗪随后经由an中间体经历重排成天然产物。该脱水恶嗪至喹唑啉的路线适用于广泛的N-酰基蒽酰胺，包括空间受阻的情况。
• [EN] STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY<br/>[FR] INHIBITEURS DE GLUCOSYLE TRANSFÉRASE DE STREPTOCOCCUS MUTANS POUR LA THÉRAPIE DES CARIES DENTAIRES
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2019195430A1

  公开（公告）日：2019-10-10

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.

  本发明涉及通过抑制葡萄糖基转移酶(Gtf)来抑制链球菌生物膜形成的方法。提供了用于抑制链球菌生物膜形成的化合物、组合物和方法，以及用于预防、抑制和/或治疗龋齿形成的方法，以及用于识别能够预防、抑制和/或治疗龋齿形成的化合物的方法。
• Discovery of Potent Inhibitors of <i>Streptococcus mutans</i> Biofilm with Antivirulence Activity
  作者：Bhavitavya Nijampatnam、Parmanand Ahirwar、Piyasuda Pukkanasut、Holly Womack、Luke Casals、Hua Zhang、Xia Cai、Suzanne M. Michalek、Hui Wu、Sadanandan E. Velu

  DOI：10.1021/acsmedchemlett.0c00373

  日期：2021.1.14
• STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY
  申请人：UAB Research Foundation

  公开号：US20210115007A1

  公开（公告）日：2021-04-22

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.
• Regioselective Quinazolinone-Directed Ortho Lithiation of Quinazolinoylquinoline:  Practical Synthesis of Naturally Occurring Human DNA Topoisomerase I Poison Luotonin A and Luotonins B and E
  作者：Santosh B. Mhaske、Narshinha P. Argade

  DOI：10.1021/jo040153v

  日期：2004.6.1

  A regioselective quinazolinone-directed ortho lithiation on an adjacent quinoline moiety has been used as a key step for a short, efficient, and practical synthesis of the human DNA topoisomerase I poison luotonin A and luotonins B and E. The quinazolinoylquinoline 5 on treatment with in situ-generated nonnucleophilic mesityllithium furnished the desired dilithiated intermediate 6, which on treatment with formaldehyde followed by Mitsunobu ring closure reaction gave luotonin A (1a) in very good yield. The reaction of dilithiated intermediate 6 with DMF directly furnished luotonin B (1b) in 81% yield. Luotonin B (1b) on methylation with p-TSA/methanol gave luotonin E (1c) in 82% yield.