4-氯-7-(4-甲氧基-苯基)-5-苯基-7H-吡咯并[2,3-D]嘧啶 | 220835-25-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 4-氯-7-(4-甲氧基-苯基)-5-苯基-7H-吡咯并[2,3-D]嘧啶
• 英文名称: 4-chloro-7-(4-methoxyphenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine
• 英文别名: 4-Chloro-7-(4-methoxy-phenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine；4-chloro-7-(4-methoxyphenyl)-5-phenylpyrrolo[2,3-d]pyrimidine
• CAS: 220835-25-6
• 化学式: C₁₉H₁₄ClN₃O
• 分子量: 335.793
• InChiKey: ODBFVJIVUPXYGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-氯-7-(4-甲氧基-苯基)-5-苯基-7H-吡咯并[2,3-D]嘧啶 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 7-(4-methoxyphenyl)-9-phenyl-7H-pyrrolo[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine-3-thione
  参考文献：
  名称：

  Evaluation of the anti-inflammatory activity of some pyrrolo[2,3-d]pyrimidine derivatives

  摘要：

  A series of novel pyrrolo[2,3-d]pyrimidine and fused pyrrolo[2,3-d]pyrimidine derivatives were synthesized and their structures were characterized by elemental analysis, H-1 NMR, IR, and mass spectroscopy. Their in vivo anti-inflammatory activities were evaluated, and the results indicated that some of the title compounds compounds showed significant activities. These compounds are 2b ((7-(4-Methoxyphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-hydrazine), 7b (4-(2-(Benzyl)hydrazinyl)-7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d] pyrimidine), 7d (4-(2-(Benzyl)hydrazinyl)-7-(4-methoxyphenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine), and 9b (4-(3,5-Dimethyl-4H-pyrazol-1-yl)-7-(4-Methoxyphenyl)-5,6-diphenyl-4,7dihydro-3H-pyrrolo[2,3-d]pyrimidine).

  DOI：

  10.1007/s00044-012-0217-5
• 作为产物：
  描述：

  2-氨基-1-(4-甲氧基苯基)-4-苯基吡咯-3-腈 在 三氯氧磷 作用下， 反应 27.0h， 生成 4-氯-7-(4-甲氧基-苯基)-5-苯基-7H-吡咯并[2,3-D]嘧啶
  参考文献：
  名称：

  7 H-四唑并[1,5- c ]吡咯并[3,2- e ]嘧啶的合成及其对4-氨基吡咯并[2,3- d ]嘧啶的还原环裂解

  摘要：

  通过4-肼基-5,7的重氮化反应合成了一些新的7,9-二取代的7 H -1,2,3,4-四唑并[1,5- c ]吡咯并[3,2- e ]嘧啶5二取代-7 ħ吡咯并[2,3- d ]嘧啶4通过肼解得到的4-氯-5,7-二取代- 7 ħ吡咯并[2,3- d ]嘧啶3或经由之间的取代反应3和叠氮化钠。5,7-二取代-7 H-吡咯并[2,3- d ]嘧啶-4（3 H）-ones 2通过将2-氨基-3-氰基-1,4-二取代的吡咯1与甲酸进行环缩合反应制得三氯甲烷，用氯氧化氯进行氯化，得到3。已经报道了通过5的还原环裂解合成4-氨基-5，7-二取代的7 H-吡咯并[2，3- d ]嘧啶6的新途径。

  DOI：

  10.1002/jhet.5570350609

文献信息

• Synthesis of 7<i>H</i>-tetrazolo[1,5-<i>c</i>]pyrrolo[3,2-<i>e</i>]pyrimidines and their reductive ring cleavage to 4-aminopyrrolo[2,3-<i>d</i>]pyrimidines
  作者：Chaitanya G. Dave、Rina D. Shah

  DOI：10.1002/jhet.5570350609

  日期：1998.11

  9-disubstituted 7H-1,2,3,4-tetrazolo[1,5-c]pyrrolo[3,2-e]pyrimidines 5 have been synthesized either by diazotization of 4-hydrazino-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 4 obtained by hydrazinolysis of 4-chloro-5,7-disubstituted-7H-pyrrolo[2,3-d]pyrimidines 3 or via a substitution reaction between 3 and sodium azide. 5,7-Disubstituted-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-ones 2 were obtained by cyclocondensation

  通过4-肼基-5,7的重氮化反应合成了一些新的7,9-二取代的7 H -1,2,3,4-四唑并[1,5- c ]吡咯并[3,2- e ]嘧啶5二取代-7 ħ吡咯并[2,3- d ]嘧啶4通过肼解得到的4-氯-5,7-二取代- 7 ħ吡咯并[2,3- d ]嘧啶3或经由之间的取代反应3和叠氮化钠。5,7-二取代-7 H-吡咯并[2,3- d ]嘧啶-4（3 H）-ones 2通过将2-氨基-3-氰基-1,4-二取代的吡咯1与甲酸进行环缩合反应制得三氯甲烷，用氯氧化氯进行氯化，得到3。已经报道了通过5的还原环裂解合成4-氨基-5，7-二取代的7 H-吡咯并[2，3- d ]嘧啶6的新途径。
• Augustine, Cicily; Agrawal, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 8, p. 1653 - 1658
  作者：Augustine, Cicily、Agrawal

  DOI：——

  日期：——
• Evaluation of the anti-inflammatory activity of some pyrrolo[2,3-d]pyrimidine derivatives
  作者：Mosaad S. Mohamed、Rehab Kamel、Rania H. Abd El-hameed

  DOI：10.1007/s00044-012-0217-5

  日期：2013.5

  A series of novel pyrrolo[2,3-d]pyrimidine and fused pyrrolo[2,3-d]pyrimidine derivatives were synthesized and their structures were characterized by elemental analysis, H-1 NMR, IR, and mass spectroscopy. Their in vivo anti-inflammatory activities were evaluated, and the results indicated that some of the title compounds compounds showed significant activities. These compounds are 2b ((7-(4-Methoxyphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-hydrazine), 7b (4-(2-(Benzyl)hydrazinyl)-7-(4-methoxyphenyl)-5,6-diphenyl-7H-pyrrolo[2,3-d] pyrimidine), 7d (4-(2-(Benzyl)hydrazinyl)-7-(4-methoxyphenyl)-5-phenyl-7H-pyrrolo[2,3-d]pyrimidine), and 9b (4-(3,5-Dimethyl-4H-pyrazol-1-yl)-7-(4-Methoxyphenyl)-5,6-diphenyl-4,7dihydro-3H-pyrrolo[2,3-d]pyrimidine).
• Synthesis and kinetic testing of new inhibitors for a metallo-β-lactamase from Klebsiella pneumonia and Pseudomonas aeruginosa
  作者：Mosaad S. Mohamed、Waleed M. Hussein、Ross P. McGeary、Peter Vella、Gerhard Schenk、Rania H. Abd El-hameed

  DOI：10.1016/j.ejmech.2011.10.030

  日期：2011.12

  There are currently no clinically useful inhibitors against metallo-beta-lactamases (MBLs), enzymes that confer resistance against a broad spectrum of commonly used antibiotics and that are produced by an increasing number of bacterial pathogens. New pyrrole derivatives were synthesized and assayed for their inhibitory effect on the catalytic activity of the IMP-1 MBL from Pseudomonas aeruginosa and Klebsiella pneumoniae. Six compounds tested (3a-3c, 5, 7 and 8) show micromolar inhibition constants (K-i values range from similar to 10 to 30 mu M). In silico docking was employed to investigate the binding mode of the strongest inhibitor, 3b, in the active site of IMP-1. Implications for further improvements of binding efficiency and specificity are discussed. (C) 2011 Elsevier Masson SAS. All rights reserved.