methyl 2-(4-chlorobenzamido)benzoate | 37619-18-4

• 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: methyl 2-(4-chlorobenzamido)benzoate
• 英文别名: 2-(4-chloro-benzoylamino)-benzoic acid methyl ester；2-(4-Chlor-benzamino)-benzoesaeure-methylester；methyl 2-[(4-chlorobenzoyl)amino]benzoate
• CAS: 37619-18-4
• 化学式: C₁₅H₁₂ClNO₃
• mdl: MFCD00088004
• 分子量: 289.718
• InChiKey: ZYEPFICGIPSSPH-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C
• 沸点：
  361.4±27.0 °C(Predicted)
• 密度：
  1.328±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 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：
  55.4
• 氢给体数：
  1
• 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：

  methyl 2-(4-chlorobenzamido)benzoate 在 ammonium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 生成 2-(4-chlorophenyl)-4(3H)-quinazolinone
  参考文献：
  名称：

  Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors

  摘要：

  The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.067
• 作为产物：
  描述：

  4-氯苯甲酰氯 、 邻氨基苯甲酸甲酯 以 二氯甲烷 为溶剂， 反应 20.0h， 以72%的产率得到methyl 2-(4-chlorobenzamido)benzoate
  参考文献：
  名称：

  新型谷氨酰胺连接的2,3-二取代喹唑啉酮衍生物的合成作为有效的抗微生物剂和抗氧化剂

  摘要：

  从邻氨基苯甲酸甲酯和不同的取代酸和酰氯合成了一系列新颖的谷氨酰胺连接的2，3-二取代的喹唑啉酮共轭物。化合物5a – l的制备得率很高。使用纸盘扩散技术，筛选了所有化合物对革兰氏阳性和革兰氏阴性细菌的抗菌活性以及对白色念珠菌和黄曲霉的抗真菌活性。还通过琼脂条纹稀释法确定化合物的最小抑制浓度。发现化合物5b表现出最有效的体外抗微生物活性。当测试其抗氧化活性时，化合物5i和5l显示出有效的自由基清除活性，而化合物5g对2,2-二苯基-1-吡啶并肼基，羟基，一氧化氮和超氧化物自由基清除测定具有中等作用。这些结果表明，三种喹唑啉酮类似物（5g，5i和5l）可被视为有用的模板，可用于将来开发以获得更有效的抗氧化剂。

  DOI：

  10.1007/s00044-012-0269-6

文献信息

• 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。
• 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.
• Papadopoulos, Eleftherios P.; Torres, Catherine D., Heterocycles, 1982, vol. 19, # 6, p. 1039 - 1042
  作者：Papadopoulos, Eleftherios P.、Torres, Catherine D.

  DOI：——

  日期：——
• Legrand,L., Bulletin de la Societe Chimique de France, 1960, p. 337 - 343
  作者：Legrand,L.

  DOI：——

  日期：——
• PAPADOPOULOS, E. P.;TORRES, C. D., HETEROCYCLES, 1982, 19, N 6, 1039-1042
  作者：PAPADOPOULOS, E. P.、TORRES, C. D.

  DOI：——

  日期：——