2-乙酰氨基-6-氯苯甲酸甲酯 | 70625-65-9

• 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: 2-乙酰氨基-6-氯苯甲酸甲酯
• 英文名称: methyl 2-acetamido-6-chlorobenzoate
• 英文别名: 3'-Chloro-2'-methoxycarbonylacetanilid
• CAS: 70625-65-9
• 化学式: C₁₀H₁₀ClNO₃
• 分子量: 227.647
• InChiKey: CYKJEWDHYQONER-UHFFFAOYSA-N

物化性质

• 沸点：
  399.4±32.0 °C(Predicted)
• 密度：
  1.320±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙酰氨基-6-氯苯甲酸甲酯 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 25.0h， 生成 5-chloro-3-methyl-2,4(1H,3H)-quinazolinedione
  参考文献：
  名称：

  Linear and proximal benzo-separated alkylated xanthines as adenosine-receptor antagonists

  摘要：

  The linear and proximal benzo-separated derivatives of 8-phenyltheophylline, 1,3-diethyl-8-phenylxanthine, 1,3-dipropylxanthine, 1,3-dibutylxanthine, 3-isobutyl-1-methylxanthine, theophylline, caffeine, and isocaffeine have been synthesized and evaluated for affinity at the A1 and A2 adenosine receptors. Although structure-activity relationships in the benzo-separated series differed from the relationships in the simple xanthines, the most potent of the benzo-separated xanthines were about equal in affinity to the most potent of the corresponding xanthines. On the basis of the present results and the diverse structures reported in the literature as non-xanthine adenosine antagonists, it appears that the primary requirement for adenosine-receptor affinity in nonnucleosides is a flat, neutral, fused-ring heterocycle and that once this requirement is met there are numerous potential binding modes.

  DOI：

  10.1021/jm00130a004
• 作为产物：
  描述：

  3-氯-2-甲基苯胺 在 potassium permanganate 、 magnesium sulfate 作用下， 以 乙醚 为溶剂， 反应 2.5h， 生成 2-乙酰氨基-6-氯苯甲酸甲酯
  参考文献：
  名称：

  Linear and proximal benzo-separated alkylated xanthines as adenosine-receptor antagonists

  摘要：

  The linear and proximal benzo-separated derivatives of 8-phenyltheophylline, 1,3-diethyl-8-phenylxanthine, 1,3-dipropylxanthine, 1,3-dibutylxanthine, 3-isobutyl-1-methylxanthine, theophylline, caffeine, and isocaffeine have been synthesized and evaluated for affinity at the A1 and A2 adenosine receptors. Although structure-activity relationships in the benzo-separated series differed from the relationships in the simple xanthines, the most potent of the benzo-separated xanthines were about equal in affinity to the most potent of the corresponding xanthines. On the basis of the present results and the diverse structures reported in the literature as non-xanthine adenosine antagonists, it appears that the primary requirement for adenosine-receptor affinity in nonnucleosides is a flat, neutral, fused-ring heterocycle and that once this requirement is met there are numerous potential binding modes.

  DOI：

  10.1021/jm00130a004

文献信息

• Synthesis and Structure−Activity Relationships of 1,2,3,4-Tetrahydroquinoline-2,3,4-trione 3-Oximes:  Novel and Highly Potent Antagonists for NMDA Receptor Glycine Site
  作者：Sui Xiong Cai、Zhang-Lin Zhou、Jin-Cheng Huang、Edward R. Whittemore、Zizi O. Egbuwoku、Yixin Lü、Jon E. Hawkinson、Richard M. Woodward、Eckard Weber、John F. W. Keana

  DOI：10.1021/jm960214k

  日期：1996.1.1

  (QTOs) was synthesized and evaluated for antagonism of NMDA receptor glycine site. Glycine site affinity was determined using a [3H]DCKA binding assay in rat brain membranes and electrophysiologically in Xenopus oocytes expressing 1a/2C subunits of cloned rat NMDA receptors. Selected compounds were also assayed for antagonism of AMPA receptors in Xenopus oocytes expressing rat brain poly-(A)+RNA. QTOs

  合成了一系列的1,2,3,4-四氢喹啉-2,3,4-三酮3-肟（QTO），并评估了其对NMDA受体甘氨酸位点的拮抗作用。使用[3H] DCKA结合测定法在大鼠脑膜中和在表达克隆的大鼠NMDA受体1a / 2C亚基的非洲爪蟾卵母细胞中通过电生理学测定甘氨酸位点亲和力。还分析了所选化合物对表达大鼠脑聚-（A）+ RNA的爪蟾卵母细胞中AMPA受体的拮抗作用。通过将2，4-喹啉二醇亚硝化来制备QTO。结构活性研究表明，在5、6和7位上的取代会增加效力，而在8位上的取代会导致效力降低。在评估的衍生工具中，有5,6，7-trichloro-QTO是最有效的拮抗剂，在[3H] DCKA结合试验中，IC50为7 nM，非洲爪蟾卵母细胞中表达的NMDA受体的Kb为1-2 nM。在电生理测定中，5,6,7-Trichloro-QTO对AMPA受体的Kb也为180 nM。将QTO的SAR与1,4-二氢喹喔啉-2
• Chemistry of salicylic acid and anthranilic acid. I. Reduction of methyl salicylate, methyl anthranilate and their derivatives with sodium borohydride.
  作者：HIROYUKI ASAKAWA、YOSHIYO FUKUSHIMA、EIKO IMAMIYA、YUTAKA KAWAMATSU

  DOI：10.1248/cpb.27.522

  日期：——

  The ester derivatives of salicylic acid and some kinds of anthranilic acid were reduced to corresponding alcohols with sodium borohydride. The reduction behavior of 4-oxo-1, 3-benzodioxanes (IXa-b), 1, 2-dihydro-4-oxo-3, 1-benzoxazines (XIIa-c, e, k) and 4-oxo-3, 1-benzoxazines (XVd-j) were also investigated. These results may be explained in terms of the contribution of the electronic structure of carbonyl group or the neighbouring participation of hydroxyl or amino group.

  水杨酸的酯衍生物和某些类型的氨基苯酸用硼氢钠还原为相应的醇。还研究了4-氧-1,3-苯并二恶烷（IXa-b）、1,2-二氢-4-氧-3,1-苯并噁嗪（XIIa-c, e, k）和4-氧-3,1-苯并噁嗪（XVd-j）的还原行为。这些结果可以通过碳酰基的电子结构贡献或羟基或氨基的邻近参与来解释。
• Inhibition of cyclic nucleotide phosphodiesterases from pig coronary artery by benzo-separated analogs of 3-isobutyl-1-methylxanthine
  作者：Stewart W. Schneller、Augusto C. Ibay、Elizabeth A. Martinson、Jack N. Wells

  DOI：10.1021/jm00156a013

  日期：1986.6

  The linear and proximal benzo-separated analogues of 7-benzyl-3-isobutyl-1-methylxanthine, 3-isobutyl-1,8-dimethylxanthine, 3-isobutyl-8-tert-butyl-1-methylxanthine, 3-isobutyl-8-(methoxymethyl)-1-methylxanthine , and 1-isoamyl-3-isobutylxanthine have been prepared and assayed as inhibitors of the peak I and peak II forms of cyclic nucleotide phosphodiesterase from pig coronary artery. Most of the benzo analogues were less effective inhibitors of these phosphodiesterases when compared to 3-isobutyl-1-methylxanthine (IBMX) even though the active sites of both enzyme forms tolerated the stretched-out xanthines. Indeed, the linear benzo-separated analogue of 7-benzyl-IBMX was a more potent inhibitor of peak I activity than was IBMX.
• Linear and proximal benzo-separated alkylated xanthines as adenosine-receptor antagonists
  作者：Stewart W. Schneller、Augusto C. Ibay、William J. Christ、Robert F. Bruns

  DOI：10.1021/jm00130a004

  日期：1989.10

  The linear and proximal benzo-separated derivatives of 8-phenyltheophylline, 1,3-diethyl-8-phenylxanthine, 1,3-dipropylxanthine, 1,3-dibutylxanthine, 3-isobutyl-1-methylxanthine, theophylline, caffeine, and isocaffeine have been synthesized and evaluated for affinity at the A1 and A2 adenosine receptors. Although structure-activity relationships in the benzo-separated series differed from the relationships in the simple xanthines, the most potent of the benzo-separated xanthines were about equal in affinity to the most potent of the corresponding xanthines. On the basis of the present results and the diverse structures reported in the literature as non-xanthine adenosine antagonists, it appears that the primary requirement for adenosine-receptor affinity in nonnucleosides is a flat, neutral, fused-ring heterocycle and that once this requirement is met there are numerous potential binding modes.