2-(3-benzylureido)benzoic acid | 728911-05-5

• 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: 2-(3-benzylureido)benzoic acid
• 英文别名: N-benzylcarbamoyl-anthranilic acid；N-Benzylcarbamoyl-anthranilsaeure；2-(benzylcarbamoylamino)benzoic acid
• CAS: 728911-05-5
• 化学式: C₁₅H₁₄N₂O₃
• 分子量: 270.288
• InChiKey: QCLRLHJAKXQKSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(3-benzylureido)benzoic acid 在 三光气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 生成 3-benzylquinazoline-2,4-dione
  参考文献：
  名称：

  Synthesis and evaluation of highly selective quinazoline-2,4-dione ligands for sphingosine-1-phosphate receptor 2

  摘要：

  新的喹唑啉-2,4-二酮类似物被开发为鞘氨醇1磷酸受体2配体。[¹¹C]2i 在外周组织疾病中作为正电子发射断层扫描探针具有巨大潜力。

  DOI：

  10.1039/d1md00357g
• 作为产物：
  描述：

  邻氨基苯甲酸 在 iron(III) chloride 、 三乙胺 作用下， 以 乙醚 、 1,2-二氯乙烷 为溶剂， 反应 6.0h， 生成 2-(3-benzylureido)benzoic acid
  参考文献：
  名称：

  Iron(iii) catalysed synthesis of unsymmetrical di and trisubstituted ureas – a variation of classical Ritter reaction

  摘要：

  介绍了利用经典Ritter反应合成非对称二取代和三取代脲类化合物的方法，该反应由FeCl3催化。该方案具有重要意义，因为其前体易于获得，反应条件温和，而且在对能够形成稳定碳正离子中间体的醇进行烷基化时，即使是空间位阻较大的基团也能适用。

  DOI：

  10.1039/c2ob06916d

文献信息

• Mechanochemical Synthesis of Substituted 4H-3,1-Benzoxazin-4-ones, 2-Aminobenzoxazin-4-ones, and 2-Amino-4H-3,1-benzothiazin-4-ones Mediated by 2,4,6-Trichloro-1,3,5-triazine and Triphenylphosphine
  作者：Mookda Pattarawarapan、Sirawit Wet-osot、Dolnapa Yamano、Wong Phakhodee

  DOI：10.1055/s-0036-1588125

  日期：——

  A mild and convenient approach for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-ones, 2-aminobenzoxazin-4-ones, and 2-amino-4H-3,1-benzothiazin-4-ones under solvent-assisted grinding is reported. In the presence of 2,4,6-trichloro-1,3,5-triazine and catalytic triphenylphosphine, cyclodehydration of N-substituted anthranilic acid derivatives proceeded rapidly within minutes at room temperature

  在溶剂下合成 2-取代 4H-3,1-benzoxazin-4-ones、2-aminobenzoxazin-4-ones 和 2-amino-4H-3,1-benzothiazin-4-ones 的温和而方便的方法-辅助研磨被报道。在 2,4,6-三氯-1,3,5-三嗪和催化三苯基膦的存在下，N-取代邻氨基苯甲酸衍生物的环脱水在室温下在几分钟内迅速进行。通过使用最少量的溶剂和廉价的试剂，产品也以良好到极好的收率获得。
• Efficient preparation of 3-substituted quinazolinediones directly from anthranilic acids and isocyanates
  作者：Natalie Koay、Louis-Charles Campeau

  DOI：10.1002/jhet.551

  日期：2011.3

  An efficient and practical synthesis of 3‐substituted quinazolinediones is described. The protocol uses readily available isocyanates and anthranilic acids as precursors in a one‐pot operation and has been demonstrated on >50 g scale. Isolation of the products via filtration directly from the reaction media is facile, affording high‐purity material. This procedure was then applied to the synthesis

  描述了一种高效，实用的3-取代喹唑啉二酮的合成方法。该协议在一口操作中使用了现成的异氰酸酯和邻氨基苯甲酸作为前体，并已证明> 50 g规模。通过过滤直接从反应介质中分离产物很容易，从而提供了高纯度的物质。然后将该程序应用于Zenarestat的合成。J.杂环化​​学。（2011）。
• Aromatic 2-(Thio)ureidocarboxylic Acids As a New Family of Modulators of Multidrug Resistance-Associated Protein 1: Synthesis, Biological Evaluation, and Structure−Activity Relationships
  作者：Hans-Georg Häcker、Stefan Leyers、Jeanette Wiendlocha、Michael Gütschow、Michael Wiese

  DOI：10.1021/jm900688v

  日期：2009.8.13

  Four series of aromatic carboxylic acids were prepared with a urea or thiourea moiety at the neighboring position to the carboxyl group and benzene or thiophene as aromatic scaffold. Using a calcein AM assay, these compounds were evaluated as inhibitors of multidrug resistance-associated protein I (MRP1) and selected compounds were examined toward P-glycoprotein (P-gp) as well as breast cancer resistance protein (BCRP) to assess selectivity for MRP1. Two 2-thioureidobenzo[b]-thiophene-3-carboxylic acids (48, 49) were identified as particularly potent inhibitors of MRP1, with IC50 values of around 1 mu M. The structural features of this new family or nontoxic MRP1 inhibitors include a (thio)urea disubstituted with preferentially two alkyl groups at the terminal nitrogen and an additional fused aromatic ring.
• Inhibition of cathepsin G by 4H-3,1-benzoxazin-4-ones
  作者：Michael Gütschow、Ulf Neumann

  DOI：10.1016/s0968-0896(97)00128-4

  日期：1997.10

  A series of 4H-3,1-benzoxazin-4-ones is reported that inhibit the serine proteases human cathepsin G and bovine chymotrypsin. The synthesis and kinetic parameters of the alkaline hydrolysis is described. These compounds act as acyl-enzyme inhibitors of both enzymes. The reaction of cathepsin G with 2-benzylamino-4H-3,1-benzoxazin-4-one (20) was studied in detail. A partition in deacylation of the initially formed acyl-enzyme was observed, leading to the formation of 2-(3-benzylureido)benzoic acid (26) and 3-benzylquinazoline-2,4-(1H,3H)-dione (27). A 6-methyl substitution strongly increased the acylation rate of both proteases. Introduction of an aryl moiety into the 2-substituent led to compounds with K-i values towards cathepsin G in the nanomolar range. Their inhibitory potency is stronger than that of other synthetic inhibitors of cathepsin G. (C) 1997 Elsevier Science Ltd.
• Isatoic Anhydride. III. Reactions with Primary and Secondary Amines
  作者：Roger P. Staiger、E. C. Wagner

  DOI：10.1021/jo50016a024

  日期：1953.10