2-[(3-methoxybenzoyl)amino]benzoic acid methyl ester | 67836-50-4

• 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-methoxybenzoyl)amino]benzoic acid methyl ester
• 英文别名: Methyl 2-[(3-methoxybenzoyl)amino]benzoate
• CAS: 67836-50-4
• 化学式: C₁₆H₁₅NO₄
• mdl: MFCD00419123
• 分子量: 285.299
• InChiKey: JOSFHLUTLFZGFZ-UHFFFAOYSA-N

物化性质

• 沸点：
  372.1±27.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-[(3-methoxybenzoyl)amino]benzoic acid methyl ester 在 sodium hydroxide 、 氨 作用下， 以 甲醇 、 水 为溶剂， 生成 3'-甲氧基-2-苯基-4-喹唑啉酮
  参考文献：
  名称：

  作为新型PI3激酶p110alpha抑制剂的4-吗啉代-2-苯基喹唑啉及其相关衍生物的合成和生物学评估。

  摘要：

  制备了一系列的4-吗啉代-2-苯基喹唑啉及其相关衍生物，并将其评估为PI3激酶p110alpha的抑制剂。在这个系列中，噻吩并[3,2-d]嘧啶衍生物15e对p110alpha的抑制作用最强，IC（50）值为2.0 nM，并抑制A375黑色素瘤细胞的增殖，IC（50）值为50。 0.58微米 此外，发现15e对p110alpha的选择性高于其他PI3K同工型和蛋白激酶，这使其成为选择性PI3K p110alpha抑制剂的第一个实例。

  DOI：

  10.1016/j.bmc.2006.06.046
• 作为产物：
  描述：

  间甲氧基苯甲酰氯 、 邻氨基苯甲酸甲酯 在 三乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 2-[(3-methoxybenzoyl)amino]benzoic acid methyl ester
  参考文献：
  名称：

  Fungicidal Activity ofN-Benzoylanthranilates and Related Compounds

  摘要：

  甲基N-(取代苯甲酰基)邻氨基苯甲酸酯被发现对瓜类白粉病具有抑制活性，该病由单丝壳属的真菌引起。邻氨基苯甲酸和N-苯甲酰基对于这种类型的杀菌活性都是必不可少的。N-苯甲酰基的2位和4位取代不利于活性，除非是4-甲氧基。3位取代会以不同程度改变杀菌活性。通过对取代基参数的定量分析和回归分析表明，取代基的空间尺寸变化最能够解释活性的变化。

  DOI：

  10.1080/00021369.1980.10864289

文献信息

• Quinazolin-4-one derivatives
  申请人：Itai Akiko

  公开号：US20060229324A1

  公开（公告）日：2006-10-12

  A medicament having an inhibitory activity against hematopoietic prostaglandin D2 synthase, which comprises as an active ingredient a compound represented by the following general formula (I) or a salt thereof: wherein X represents a group represented by the formula —N═C(R 5 )— or the formula —NH—CH(R 5 )—, R 1 , R 2 , R 3 , and R 4 represent a hydrogen atom, a halogen atom, a C 1 to C 6 alkyl group, or a hydroxy group, R 5 represents a C 1 to C 6 alkyl group or a C 6 to C 10 aryl group, and R represents an amino group.

  一种具有对造血前列腺素D2合成酶抑制活性的药物，其包括以下一般式（I）所代表的化合物或其盐作为活性成分： 其中X代表由式—N═C(R5)—或式—NH—CH(R5)—所代表的基团，R1、R2、R3和R4代表氢原子、卤原子、C1到C6烷基或羟基，R5代表C1到C6烷基或C6到C10芳基，R代表氨基。
• Structure-activity relationships of fungicidal N-benzoylanthranilic esters.
  作者：Osamu KIRINO、Shigeo YAMAMOTO、Toshiro KATO

  DOI：10.1271/bbb1961.44.2149

  日期：——

  The antifungal activity of 37 N-(methoxy-substituted benzoyl)anthranilic esters was tested on the powdery mildew of barley caused by Erysiphe graminis by the pot test. Among the methyl N-(methoxy-substituted benzoyl)anthranilates tested, 3, 4-dimethoxybenzoyl derivative exhibited the highest activity. The variation in fungicidal activity of N-(3, 4-dimethoxy-benzoyl)anthranilic esters was shown to be related with variation in hydrophobicity and the electronic property of the alcohol moiety of the ester. The branching at the α-position of the alcohol moiety of the ester was detrimental to the activity.

  37种N-(甲氧基取代的苯甲酰)蒽醌酯的抗真菌活性通过盆栽试验在由小麦白粉病（Erysiphe graminis）引起的大麦粉状霉菌上进行了测试。在测试的甲基N-(甲氧基取代的苯甲酰)蒽醌酯中，3,4-二甲氧基苯甲酰衍生物表现出最高的活性。N-(3,4-二甲氧基苯甲酰)蒽醌酯的杀真菌活性的变化被证明与酯的醇基的疏水性和电子性质的变化相关。醇基在α位的支链对活性是有害的。
• 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。
• The evaluation and structure–activity relationships of 2-benzoylaminobenzoic esters and their analogues as anti-inflammatory and anti-platelet aggregation agents
  作者：Pei-Wen Hsieh、Tsong-Long Hwang、Chin-Chung Wu、Shin-Zan Chiang、Chung-I Wu、Yang-Chang Wu

  DOI：10.1016/j.bmcl.2006.12.038

  日期：2007.3

  Forty-seven 2-benzoylaminobenzoic esters were synthesized and evaluated in anti-platelet aggregation, inhibition of superoxide anion generation, and inhibition of neutrophil elastase release assays. Most 2-benzoylamino-4-chlorobenzoic acid derivatives showed selective inhibitory effects on arachidonic acid (AA)-induced platelet aggregation. Among them, compounds 615 and 7b exhibited more potent inhibitory effects (ca. 200-fold) than aspirin. Additionally, compounds 1a and 5a showed strong inhibitory effects on neutrophil superoxide generation with IC50 values of 0.65 and 0.17 mu M, respectively. However, compounds 6d and 6e exhibited dual inhibitory effects on platelet aggregation and neutrophil elastase (NE) release; therefore, these two compounds may be new leads for development as anti-inflammatory and anti-platelet aggregatory agents. (c) 2006 Elsevier Ltd. All rights reserved.
• Fungicidal Activity of<i>N</i>-Benzoylanthranilates and Related Compounds
  作者：Osamu Kirino、Shigeo Yamamoto、Toshiro Kato

  DOI：10.1080/00021369.1980.10864289

  日期：1980.9

  Methyl N-(substituted benzoyl)anthranilates were found to possess inhibitory activity against the powdery mildew of cucumber caused by Sphaerotheca fuliginea. Both the anthranilate and the N-benzoyl moieties were essential for this type of fungicidal activity. Substitution at the 2- and 4-positions of the N-benzoyl group was unfavorable to the activity except for the 4-methoxy group. Substitution at the 3-position varied the fungicidal activity to various extents. The variation in the activity of 3-substituted derivatives was analyzed quantitatively with substituent parameters and regression analysis indicating that the variation in the steric dimension of substituents was most responsible for the activity.

  甲基N-(取代苯甲酰基)邻氨基苯甲酸酯被发现对瓜类白粉病具有抑制活性，该病由单丝壳属的真菌引起。邻氨基苯甲酸和N-苯甲酰基对于这种类型的杀菌活性都是必不可少的。N-苯甲酰基的2位和4位取代不利于活性，除非是4-甲氧基。3位取代会以不同程度改变杀菌活性。通过对取代基参数的定量分析和回归分析表明，取代基的空间尺寸变化最能够解释活性的变化。