7-Chlorotetrazolo[1,5-a]quinoline-4-carbaldehyde | 1186031-69-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7-Chlorotetrazolo[1,5-a]quinoline-4-carbaldehyde
• 英文别名: 7-chlorotetrazolo[1,5-a]quinoline-4-carbaldehyde
• CAS: 1186031-69-5
• 化学式: C₁₀H₅ClN₄O
• 分子量: 232.629
• InChiKey: FXHVFDJAXHVZTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-Chlorotetrazolo[1,5-a]quinoline-4-carbaldehyde 、 4-溴邻苯二胺 在 对甲苯磺酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.07h， 以73%的产率得到4-(5-bromo-1H-benzo[d]imidazol-2-yl)-7-chlorotetrazolo[1,5-a]quinoline
  参考文献：
  名称：

  Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity

  摘要：

  Keeping the objective to build up a new structural class of potent antimicrobials, a series of some new 4-Benzimidazol-2-yl tetrazolo[1,5-a]quinoline derivatives has been synthesized by reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde and o-phenylenediamine in the presence of an organocatalyst p-TsOH under the influence of microwave irradiation. The identity of all the compounds has been established by H-1 NMR, C-13 NMR, FTIR, and elemental analysis. The synthesized compounds were subjected to in vitro antimicrobial screening against a representative panel of pathogenic strains including three Gram-positive bacteria (Bacillus subtilis, Clostridium tetani, and Streptococcus pneumoniae) and three Gram-negative bacteria (Escherichia coli, Salmonella typhi, and Vibrio cholerae) as well as two fungal organisms (Aspergillus fumigatus and Candida albicans) by employing broth microdilution method. Of the compounds studied, compound 5e demonstrated significant activity against a Gram-positive bacteria Bacillus subtilis.

  DOI：

  10.1007/s00044-010-9388-0
• 作为产物：
  描述：

  2,6-二氯喹啉-3-甲醛 在 sodium azide 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 7-Chlorotetrazolo[1,5-a]quinoline-4-carbaldehyde
  参考文献：
  名称：

  分子碘催化合成基于四唑并[1,5- a ]-喹啉的咪唑类作为新型抗菌剂和抗结核剂

  摘要：

  一系列一些新的四唑并[1,5-的一个]喹啉基于四取代咪唑衍生物6A -升已通过的四唑的反应[1,5-合成一个]喹啉-4-甲醛3A - d，苯偶酰4，芳族胺5a – c和乙酸铵在碘存在下通过一锅多组分反应（MCR）方法。筛选所有衍生物的抗微生物和抗结核活性，其结果值得进一步研究。

  DOI：

  10.1016/j.cclet.2012.11.007

文献信息

• Design, synthesis and molecular modeling of biquinoline–pyridine hybrids as a new class of potential EGFR and HER-2 kinase inhibitors
  作者：Chetan B. Sangani、Jigar A. Makawana、Yong-Tao Duan、Yong Yin、Shashikant B. Teraiya、Nilesh J. Thumar、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2014.07.094

  日期：2014.9

  A new series of biquinoline-pyridine hybrids were designed and synthesized by a base-catalyzed cyclocondensation through one-pot multicomponent reaction. All compounds were tested for in vitro anticancer activities against two cancer cell lines A549 (adenocarcinomic human alveolar basal epithelial) and Hep G2 (liver cancer). Enzyme inhibitory activities of all compounds were carried out against EGFR and HER-2 kinase. Of the compounds studied, majority of the compounds showed effective anticancer activity against used cancer cell lines. Compound 9i (IC50 = 0.09 mu M) against EGFR and (IC50 = 0.2 mu M) against HER-2 kinase displayed the most potent inhibitory activity as compared to other member of the series. In the molecular modelling study, compound 9i was bound in to the active pocket of EGFR with four hydrogen bonds and two pi-cation interactions having minimum binding energy Delta G(b) = -54.4 kcal/mol. (C) 2014 Elsevier Ltd. All rights reserved.
• Molecular iodine catalyzed synthesis of tetrazolo[1,5-a]-quinoline based imidazoles as a new class of antimicrobial and antituberculosis agents
  作者：Divyesh C. Mungra、Harshad G. Kathrotiya、Niraj K. Ladani、Manish P. Patel、Ranjan G. Patel

  DOI：10.1016/j.cclet.2012.11.007

  日期：2012.12

  A series of some new tetrazolo[1,5-a]quinoline based tetrasubstituted imidazole derivatives 6a–l have been synthesized by a reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde 3a–d, benzil 4, aromatic amine 5a–c and ammonium acetate in the presence of iodine through one-pot multi-component reaction (MCR) approach. All the derivatives were screened for antimicrobial and antituberculosis activities

  一系列一些新的四唑并[1,5-的一个]喹啉基于四取代咪唑衍生物6A -升已通过的四唑的反应[1,5-合成一个]喹啉-4-甲醛3A - d，苯偶酰4，芳族胺5a – c和乙酸铵在碘存在下通过一锅多组分反应（MCR）方法。筛选所有衍生物的抗微生物和抗结核活性，其结果值得进一步研究。
• Microwave-assisted synthesis of some new tetrazolo[1,5-a]quinoline-based benzimidazoles catalyzed by p-TsOH and investigation of their antimicrobial activity
  作者：Divyesh C. Mungra、Manish P. Patel、Ranjan G. Patel

  DOI：10.1007/s00044-010-9388-0

  日期：2011.7

  Keeping the objective to build up a new structural class of potent antimicrobials, a series of some new 4-Benzimidazol-2-yl tetrazolo[1,5-a]quinoline derivatives has been synthesized by reaction of tetrazolo[1,5-a]quinoline-4-carbaldehyde and o-phenylenediamine in the presence of an organocatalyst p-TsOH under the influence of microwave irradiation. The identity of all the compounds has been established by H-1 NMR, C-13 NMR, FTIR, and elemental analysis. The synthesized compounds were subjected to in vitro antimicrobial screening against a representative panel of pathogenic strains including three Gram-positive bacteria (Bacillus subtilis, Clostridium tetani, and Streptococcus pneumoniae) and three Gram-negative bacteria (Escherichia coli, Salmonella typhi, and Vibrio cholerae) as well as two fungal organisms (Aspergillus fumigatus and Candida albicans) by employing broth microdilution method. Of the compounds studied, compound 5e demonstrated significant activity against a Gram-positive bacteria Bacillus subtilis.