γ(p-Chlorobenzoyl)nicotinic acid | 74975-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: γ(p-Chlorobenzoyl)nicotinic acid
• 英文别名: 4-(4-Chlorobenzoyl)nicotinic acid；4-(4-chlorobenzoyl)pyridine-3-carboxylic acid
• CAS: 74975-26-1
• 化学式: C₁₃H₈ClNO₃
• 分子量: 261.664
• InChiKey: KFYALDAYGFDWSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  γ(p-Chlorobenzoyl)nicotinic acid 在 硫酸 作用下， 反应 0.5h， 以33%的产率得到7-Chloro-2-azaanthraquinone
  参考文献：
  名称：

  Synthesis of 2-azaanthraquinone and its derivatives

  摘要：

  DOI：

  10.1007/bf00552781
• 作为产物：
  描述：

  吡啶-3,4-二甲酸酐 、 氯苯 在 aluminum (III) chloride 作用下， 反应 5.0h， 以15%的产率得到3-(4-氯苯甲酰基)异烟酸
  参考文献：
  名称：

  1,2,3,9b-Tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 2: Identification of BTA9881 as a preclinical candidate

  摘要：

  Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. 1,2,3,9b-Tetrahydro-5H-imidazo[2,1-a] isoindol-5-ones with general structure 1 were previously identified as promising inhibitors of RSV targeting the fusion glycoprotein. In particular, the introduction of a nitrogen at the 8-position of the tricyclic core yielded lead compounds 2 and 3. Extensive exploration of the R-2 group established that certain heterocyclic amides conferred potent RSV A& B activity and a good balance of physicochemical and pharmacokinetic properties. The antiviral activity was found to reside in a single enantiomer and compound 33a, (9bS)-9b-(4-chlorophenyl)-1(pyridin-3-ylcarbonyl)-1,2,3,9b-tetrahydro-5H-imidazo[10,20:1,2] pyrrolo[3,4-c] pyridin-5-one (known as BTA9881), was identified as a candidate for preclinical development. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.11.024

文献信息

• The discovery of 1,2,3,9b-tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 1
  作者：Silas Bond、Alistair G. Draffan、Jennifer E. Fenner、John Lambert、Chin Yu Lim、Bo Lin、Angela Luttick、Jeffrey P. Mitchell、Craig J. Morton、Roland H. Nearn、Vanessa Sanford、Pauline C. Stanislawski、Simon P. Tucker

  DOI：10.1016/j.bmcl.2014.11.018

  日期：2015.2

  Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. Compound 1a (9b-(4-chlorophenyl)-1-(4-fluorobenzoyl)-1,2,3,9b-tetrahydro-5H-imidazo[ 2,1-a]isoindol-5-one) was identified as an inhibitor of A and B strains of RSV targeting the fusion glycoprotein. SAR was developed by systematic exploration of the phenyl (R-1) and benzoyl (R-2) groups. Furthermore, introduction of a nitrogen at the 8-position of the tricyclic core resulted in active analogues with improved properties (aqueous solubility, protein binding and logD) and excellent rat pharmacokinetics (e. g., rat oral bioavailability of 89% for compound 17). (C) 2014 Elsevier Ltd. All rights reserved.
• ARTAMONOV A. A.; SHNEJDER T.; BARANOVA N. V., XIMIYA GETEROTSIKL. SOEDIN., 1980, HO 4, 514-518
  作者：ARTAMONOV A. A.、 SHNEJDER T.、 BARANOVA N. V.

  DOI：——

  日期：——
• Synthesis of 2-azaanthraquinone and its derivatives
  作者：A. A. Artamonov、T. Shneider、N. V. Baranova

  DOI：10.1007/bf00552781

  日期：1980.4
• 1,2,3,9b-Tetrahydro-5H-imidazo[2,1-a]isoindol-5-ones as a new class of respiratory syncytial virus (RSV) fusion inhibitors. Part 2: Identification of BTA9881 as a preclinical candidate
  作者：Silas Bond、Alistair G. Draffan、Jennifer E. Fenner、John Lambert、Chin Yu Lim、Bo Lin、Angela Luttick、Jeffrey P. Mitchell、Craig J. Morton、Roland H. Nearn、Vanessa Sanford、Kelly H. Anderson、Penelope A. Mayes、Simon P. Tucker

  DOI：10.1016/j.bmcl.2014.11.024

  日期：2015.2

  Respiratory syncytial virus (RSV) is a major cause of respiratory tract infections in infants, young children and adults. 1,2,3,9b-Tetrahydro-5H-imidazo[2,1-a] isoindol-5-ones with general structure 1 were previously identified as promising inhibitors of RSV targeting the fusion glycoprotein. In particular, the introduction of a nitrogen at the 8-position of the tricyclic core yielded lead compounds 2 and 3. Extensive exploration of the R-2 group established that certain heterocyclic amides conferred potent RSV A& B activity and a good balance of physicochemical and pharmacokinetic properties. The antiviral activity was found to reside in a single enantiomer and compound 33a, (9bS)-9b-(4-chlorophenyl)-1(pyridin-3-ylcarbonyl)-1,2,3,9b-tetrahydro-5H-imidazo[10,20:1,2] pyrrolo[3,4-c] pyridin-5-one (known as BTA9881), was identified as a candidate for preclinical development. (C) 2014 Elsevier Ltd. All rights reserved.