N-(2-chlorobenzoyl)anthranilic acid | 31408-56-7

• 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-chlorobenzoyl)anthranilic acid
• 英文别名: N-(2-Chlor-benzoyl)-anthranilsaeure；2-[(2-Chlorobenzoyl)amino]benzoic acid
• CAS: 31408-56-7
• 化学式: C₁₄H₁₀ClNO₃
• mdl: MFCD00585966
• 分子量: 275.691
• InChiKey: WLHKISBWQLYHFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 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：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-(2-chlorobenzoyl)anthranilic acid 在 乙酸酐 、 一水合肼 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 3-amino-2-(2-chlorophenyl)quinazolin-4(3H)-one
  参考文献：
  名称：

  Synthesis and characterization of quinazoline derivatives: search for hybrid molecule as diuretic and antihypertensive agents

  摘要：

  To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derived amino quinazolines and substituted benzene sulphonamides. All the synthesized compounds were evaluated for their diuretic (by Lipschitz et al. method), antihypertensive activity by non-invasive blood pressure (NIBP) using the tail-cuff method and anti-diabetic potential in rats. Six compounds showing significantly excellent activity were compared with metolazone, prazosin and diazoxide as standards. Compound N-[7-chloro-2-(4-methoxyphenyl)-4-oxoquinazolin-3(4H)-yl]-4 nitrobenzenesulfonamide (20) exhibited most potent of the series.

  DOI：

  10.3109/14756366.2013.845820
• 作为产物：
  描述：

  邻氯苯甲酰氯 在 sodium hydroxide 作用下， 以 吡啶 为溶剂， 生成 N-(2-chlorobenzoyl)anthranilic acid
  参考文献：
  名称：

  2-取代-4 H -3,1-苯并恶嗪-4-酮的合成

  摘要：

  邻氨基苯甲酸（1摩尔）在吡啶溶液中与苯甲酰氯（2摩尔）反应，以高收率得到2-苯基-4 H -3,1-苯并恶嗪-4-酮。与1摩尔。然而，得到了苯甲酰氯的苯并恶嗪酮和N-苯并氰基邻氨基苯甲酸的混合物。已经研究了反应的机理，并制备了各种2-取代的-4 H -3,1-苯并恶嗪-4-酮，并记录了它们的uv光谱。

  DOI：

  10.1039/j39680001593

文献信息

• Therapeutic and diagnostic ligand systems comprising transport molecule binding properties and medicaments containing the same
  申请人：——

  公开号：US20030185793A1

  公开（公告）日：2003-10-02

  The invention relates to transport molecule binding ligand compounds which comprise a therapeutically and/or diagnostically active substance and a carrier molecule-affine substance with a high association constant to the carrier molecule. The invention also relates to medicaments containing these ligand compounds and to diagnostic kits.

  这项发明涉及与载体分子结合的配体化合物，其包括具有治疗和/或诊断活性物质以及与载体分子具有高结合常数的载体分子亲和物质。该发明还涉及含有这些配体化合物的药物和诊断试剂盒。
• Traceless synthesis of 3H-quinazolin-4-ones via a combination of solid-phase and solution methodologies
  作者：Donogh J.R. O'Mahony、Viktor Krchňák

  DOI：10.1016/s0040-4039(01)02268-7

  日期：2002.2

  A solid-phase traceless synthesis of quinazolin-4-ones is described. An aldehyde functionalized resin was reductively aminated with primary amines, and the resin-bound secondary amine acylated with o-nitro-benzoic acids. The nitro group was reduced with tin(II) chloride, and the aniline acylated with acid anhydrides. Acidolytic cleavage afforded a diamide, which was cyclized in solution phase to the

  描述了喹唑啉-4-酮的固相无痕合成。将醛官能化的树脂用伯胺还原胺化，并将与树脂结合的仲胺用邻硝基苯甲酸酰化。硝基用氯化锡（II）还原，苯胺用酸酐酰化。酸解裂解得到二酰胺，将其在溶液相中环化为3 H-喹唑啉-4-酮，除去痕量的接头。
• Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae
  作者：Aymerick Eudes、Veronica Teixeira Benites、George Wang、Edward E. K. Baidoo、Taek Soon Lee、Jay D. Keasling、Dominique Loqué

  DOI：10.1371/journal.pone.0138972

  日期：——

  Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilates by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. This work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl-CoA- and benzoyl-CoA-utilizing transferases.

  生物合成药物和生化产品提供了一种环保的替代传统化学合成的方法。这些替代方法需要设计代谢途径并鉴定具有适当活性的酶。肉桂酰、二氢肉桂酰和苯甲酰氨基酸酯是具有对人类健康有益活性的天然代谢物，目前对新衍生物的搜索正在扩大，以期发现具有增强生物活性的化合物。例如，在康乃馨（Dianthus caryophyllus）中的生物合成是由羟基肉桂酰/苯甲酰-CoA:氨基酸酯 N-羟基肉桂酰/苯甲酰转移酶（HCBT）催化的，该酶将羟基肉桂酰-CoA和苯甲酰-CoA与氨基酸酯结合在一起。我们最近展示了使用酵母（酿酒酵母，Saccharomyces cerevisiae）生物生产几种肉桂酰氨基酸酯的潜力，这得益于来自拟南芥（Arabidopsis thaliana）的4-香豆酰:CoA连接酶（4CL5）与HCBT的异源共表达。在这里，我们报告通过利用4CL5和HCBT的底物灵活性，在酵母中快速合成了超过160种肉桂酰、二氢肉桂酰和苯甲酰氨基酸酯，所用的原料包括天然和非天然肉桂酸、二氢肉桂酸、苯酸和氨基酸酯。我们的结果证明了在生物合成中利用酶的多能性，以在特定分子类别内实现高化学多样性。这项工作还指出，通过使用多用途的生物酶4CL5，以及特征化的肉桂酰-CoA和苯甲酰-CoA利用转移酶，可以实现多样且有价值的肉桂化、二氢肉桂化和苯甲化产品的组合生物合成潜力。
• Design, synthesis and antiproliferative activity of new amine, amino acid and dipeptide-coupled benzamides as potential sigma-1 receptor
  作者：Eman Youssef、Mohamed Abd El-Moneim、Walid Fathalla、Mohamed S. Nafie

  DOI：10.1007/s13738-020-01947-6

  日期：2020.10

  N-Alkyl-2-(substitutedbenzamido) benzamides and methyl 2-(2-(substitutedbenzamido) benzamido) alkanoates were prepared by either the reaction of amines or amino acid esters with benzoxazine derivatives or the DCC coupling of 2-substitutedbenzamido benzoic acid with amines or amino acid esters. Methyl 2-(2-(4-chlorobenzamido)benzamido alkanoates were used as the key intermediate for the preparation of dipeptide-coupled

  ñ通过胺或氨基酸酯与苯并恶嗪衍生物的反应，或2-取代的苯甲酰胺基苯甲酸与胺或氨基酸酯。以2-（2-（4-氯苯甲酰胺基）苯甲酰胺基甲基丙烯酸甲酯为主要中间体，通过叠氮化物和DCC偶联法制备了二肽偶联的苯甲酰胺，对所研究的化合物进行了计算机分子对接，作为人类σ1受体的激动剂。通过它们的结合能和配体-受体相互作用的分析以及对它们的理化性质和药物相似性得分的预测研究。针对乳腺癌MCF-7和肝A549癌细胞筛选对靶标具有最高结合亲和力的化合物，以测试其细胞毒性活性。化合物图11a，3a，8c，12a和13b显示了针对低IC 50值的被测化合物对MCF-7细胞系的有效细胞毒性活性，尤其是对于11a（5.3 µM，而标准药物5-FU 5.8 µM）。基于对这种命中候选物的鉴定，可以设计出具有抗癌活性的新的有效σ1受体。
• Ag-Catalyzed Practical Synthesis of <i>N</i>-Acyl Anthranilic Acids from Anthranils and Carboxylic Acids
  作者：Changshu Wu、Yang Gao、Yanping Huo、Xianwei Li、Qian Chen、Xiao-Qiang Hu

  DOI：10.1021/acs.joc.3c02586

  日期：2024.3.1

  A practical synthesis of valuable N-acyl anthranilic acids has been achieved via a silver-catalyzed imino-ketene generation from readily available anthranils and carboxylic acids. A wide range of carboxylic acids including sterically demanding aliphatic carboxylic acids, aromatic carboxylic acids, acrylic acids, and amino acids are compatible in this reaction. Moreover, this method can be used to modify

  通过银催化从容易获得的邻氨基苯甲酸和羧酸生成亚氨基乙烯酮，实现了有价值的N-酰基邻氨基苯甲酸的实际合成。多种羧酸，包括空间要求高的脂肪族羧酸、芳香族羧酸、丙烯酸和氨基酸，都适合该反应。此外，该方法还可用于修饰药物分子和天然产物，例如布洛芬、丙磺舒和乙酰甘氨酸。