5-氯-2-甲酰氨基苯甲酸 | 26208-56-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 5-氯-2-甲酰氨基苯甲酸
• 英文名称: N-Formyl-5-chloranthranilsaeure
• 英文别名: 5-Chlor-N-formyl-anthranilsaeure；Benzoic acid, 5-chloro-2-(formylamino)-；5-chloro-2-formamidobenzoic acid
• CAS: 26208-56-0
• 化学式: C₈H₆ClNO₃
• 分子量: 199.594
• InChiKey: KMAABJINOGFJSU-UHFFFAOYSA-N

物化性质

• 熔点：
  205-207 °C
• 沸点：
  449.6±35.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• 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

反应信息

• 作为反应物：
  描述：

  5-氯-2-甲酰氨基苯甲酸 、 甲胺 在 吡啶 、 三氯化磷 作用下， 以 水 为溶剂， 反应 1.5h， 以52%的产率得到6-chloro-3-methylquinazolin-4(3H)-one
  参考文献：
  名称：

  4-Quinazolinones: synthesis and reduction of prostaglandin E2 production

  摘要：

  We synthesized and evaluated the anti-inflammatory activity of a series of 4-quinazolinone derivatives. Two approaches were used to yield the title compounds. A first group of quinazolinone derivatives was obtained by the appropriate substituted anthranilates. A second group of quinazolinone compounds was prepared through the benzoxazin-4-ones intermediate. The pharmacological results reveal that the synthesized derivatives exhibit a significant anti-inflammatory effect in an experimental ocular inflammation model. In fact, all the tested compounds lowered the prostaglandin E-2 (PGE(2)) production with respect to the control group (P < 0.05). The 3-cyclohexyl-6-chloro-quinazolin-4(3H)-one and 3-cyclohexyl-quinazolin-4(3H)-one derivatives were the most active compounds. These compounds significantly reduced PGE(2) levels even more than the reference drug tolmetin and significantly lower protein concentration and polymorphonuclear leukocytes number compared to the control group (P < 0.05). Therefore, these compounds may be useful to prevent ocular inflammatory reactions. (C) 1999 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(99)00102-0
• 作为产物：
  描述：

  原甲酸三乙酯 、 2-氨基-5-氯苯甲酸 在 silica gel supported sulfuric acid 作用下， 反应 0.2h， 以73%的产率得到5-氯-2-甲酰氨基苯甲酸
  参考文献：
  名称：

  硅胶上固定化硫酸对原甲酸三乙酯胺 N-甲酰化的催化性能

  摘要：

  在寻找方便、绿色和实用的催化方法以满足当前对有机合成的兴趣时，在硅胶上固定化硫酸的存在下，对各种胺的N-甲酰化进行了一种简单、绿色和高效的方案。H 2 SO 4 -SiO 2 )。所有反应均在回流的原甲酸三乙酯 (65 °C) 中进行。产品甲酰胺在 4 分钟至 2 小时内以高产率获得。目前的方法是有利的，因为它的反应时间短且产率高。该催化剂是可回收的，催化效率没有显着损失。

  DOI：

  10.3390/molecules27134213

文献信息

• 4-Quinazolinones: synthesis and reduction of prostaglandin E2 production
  作者：Natale Alfredo Santagati、Ennio Bousquet、Angelo Spadaro、Giuseppe Ronsisvalle

  DOI：10.1016/s0014-827x(99)00102-0

  日期：1999.11

  We synthesized and evaluated the anti-inflammatory activity of a series of 4-quinazolinone derivatives. Two approaches were used to yield the title compounds. A first group of quinazolinone derivatives was obtained by the appropriate substituted anthranilates. A second group of quinazolinone compounds was prepared through the benzoxazin-4-ones intermediate. The pharmacological results reveal that the synthesized derivatives exhibit a significant anti-inflammatory effect in an experimental ocular inflammation model. In fact, all the tested compounds lowered the prostaglandin E-2 (PGE(2)) production with respect to the control group (P < 0.05). The 3-cyclohexyl-6-chloro-quinazolin-4(3H)-one and 3-cyclohexyl-quinazolin-4(3H)-one derivatives were the most active compounds. These compounds significantly reduced PGE(2) levels even more than the reference drug tolmetin and significantly lower protein concentration and polymorphonuclear leukocytes number compared to the control group (P < 0.05). Therefore, these compounds may be useful to prevent ocular inflammatory reactions. (C) 1999 Elsevier Science S.A. All rights reserved.
• Catalytic Performance of Immobilized Sulfuric Acid on Silica Gel for N-Formylation of Amines with Triethyl Orthoformate
  作者：Sodeeq Aderotimi Salami、Xavier Siwe-Noundou、Rui W. M. Krause

  DOI：10.3390/molecules27134213

  日期：——

  In the search for convenient, green, and practical catalytic methods for the current interest in organic synthesis, a simple, green, and highly efficient protocol for N-formylation of various amines was carried out in the presence of immobilized sulfuric acid on silica gel (H2SO4–SiO2). All reactions were performed in refluxing triethyl orthoformate (65 °C). The product formamides were obtained with

  在寻找方便、绿色和实用的催化方法以满足当前对有机合成的兴趣时，在硅胶上固定化硫酸的存在下，对各种胺的N-甲酰化进行了一种简单、绿色和高效的方案。H 2 SO 4 -SiO 2 )。所有反应均在回流的原甲酸三乙酯 (65 °C) 中进行。产品甲酰胺在 4 分钟至 2 小时内以高产率获得。目前的方法是有利的，因为它的反应时间短且产率高。该催化剂是可回收的，催化效率没有显着损失。