6-Methyl-2-p-tolylsulfanyl-quinoline-3-carbaldehyde | 1376342-17-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6-Methyl-2-p-tolylsulfanyl-quinoline-3-carbaldehyde
• 英文别名: 6-methyl-2-(4-methylphenyl)sulfanylquinoline-3-carbaldehyde
• CAS: 1376342-17-4
• 化学式: C₁₈H₁₅NOS
• 分子量: 293.389
• InChiKey: HTNVODVHAPXYFK-UHFFFAOYSA-N

物化性质

• 沸点：
  465.4±45.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  55.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Methyl-2-p-tolylsulfanyl-quinoline-3-carbaldehyde 、 4-羟基苯甲酰肼 在 nickel(II) nitrate hexahydrate 作用下， 以 甲醇 为溶剂， 以90%的产率得到(E)-4-hydroxy-N'-((6-methyl-2-(p-tolylthio)quinolin-3-yl)methylene)benzohydrazide
  参考文献：
  名称：

  Schiff’s base derivatives bearing 2-thiophenoxyquinoline nucleus as new antibacterial agents

  摘要：

  A series of new Schiff's base derivatives 4a-x bearing 2-thiophenoxyquinoline nucleus have been designed and synthesized by reaction of 2-thiophenoxyquinoline-3-carbaldehydes 2a-d with various benzohydrazides 3a-f in the presence of Ni(NO3)(2)center dot 6H(2)O as a catalyst. In vitro antibacterial screening was carried out against two Gram-positive bacteria (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and two Gram-negative bacteria (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525). Of the compounds studied, compound 4e showed chief activity (MIC = 3.13 mu g/mL) against S. aureus, and compounds 4p, 4k, and 4w were found to possess effective antibacterial activity against employed strains compared with standards used. The structures of Schiff's base derivatives were established by using various spectroscopic methods. A crystal structure of compound 4k has been determined by X-ray diffraction analysis.

  DOI：

  10.1007/s00044-013-0655-8
• 作为产物：
  描述：

  4-甲基乙酰苯胺 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6-Methyl-2-p-tolylsulfanyl-quinoline-3-carbaldehyde
  参考文献：
  名称：

  Synthesis of N-arylquinolone derivatives bearing 2-thiophenoxyquinolines and their antimicrobial evaluation

  摘要：

  A new series of 2-thiophenoxyquinolines based trifluoromethyl substituted N-aryl quinolone derivatives 8a-f and 9a-f have been synthesized via a one-pot multicomponent reaction. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains. Compounds 8c, 9c and 9e exhibited comparable antimicrobial activity to first line drugs. (C) 2014 Manish P. Patel. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2014.04.002

文献信息

• Synthesis and Antimicrobial Evaluation of New Pyrano[4,3-b]pyran and Pyrano[3,2-c]chromene Derivatives Bearing a 2-Thiophenoxyquinoline Nucleus
  作者：Jigar A. Makawana、Manish P. Patel、Ranjan G. Patel

  DOI：10.1002/ardp.201100203

  日期：2012.4

  A new series of pyrano[4,3‐b]pyran 4a–i and pyrano[3,2‐c]chromene 6a–r derivatives bearing a 2‐thiophenoxyquinoline nucleus were synthesized by reaction of 2‐(4‐(un)‐substituted thiophenoxy)quinoline‐3‐carbaldehydes 2a–i with 6‐methyl‐4‐hydroxypyran‐2‐one 3 and 4‐hydroxy‐6‐(un)‐substituted‐2H‐chromen‐2‐one 5a–b respectively and malononitrile at room temperature in the presence of KOH as a basic catalyst

  通过 2-(4-(un)- 反应合成了一系列带有 2-噻吩氧基喹啉核的吡喃并[4,3-b]吡喃 4a-i 和吡并[3,2-c]色烯 6a-r 衍生物取代的噻吩氧基)喹啉-3-甲醛 2a-i 分别与 6-甲基-4-羟基吡喃-2-one 3 和 4-羟基-6-(un)-取代的-2H-色胺-2-one 5a-b 和丙二腈在室温下，在 KOH 作为碱性催化剂存在下。使用肉汤对三种革兰氏阳性菌（肺炎链球菌、枯草芽孢杆菌、破伤风梭菌）、三种革兰氏阴性菌（伤寒沙门氏菌、大肠杆菌、霍乱弧菌）和两种真菌（白色念珠菌、烟曲霉）进行了筛选微量稀释 MIC（最低抑菌浓度）法。经过抗菌素筛选，
• Synthesis and in vitro antimicrobial evaluation of novel 2-amino-6-(phenylthio)-4-(2-(phenylthio)quinolin-3-yl)pyridine-3,5-dicarbonitriles
  作者：Mehul B. Kanani、Manish P. Patel

  DOI：10.1007/s00044-012-0292-7

  日期：2013.6

  A new series of 2-thiophenoxyquinoline-based penta-substituted pyridine derivatives, 6(a–r), has been synthesized by base-catalyzed cyclocondensation reaction through multi-component reaction (MCR) approach. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains, specifically three Gram-positive bacteria (Streptococcus pneumoniae

  通过多组分反应（MCR）的碱催化环缩合反应合成了一系列新的基于2-硫代苯氧基喹啉的五取代吡啶衍生物。6（a - r）。研究了合成化合物对代表性病原菌的体外抗菌活性，特别是三种革兰氏阳性菌（肺炎链球菌，枯草芽孢杆菌，破伤风梭菌），三种革兰氏阴性菌（大肠杆菌，鼠伤寒沙门氏菌，霍乱弧菌）和两种真菌（黑曲霉，白色念珠菌。）。发现大多数化合物与标准药物具有同等效力或更有效。
• Schiff’s base derivatives bearing 2-thiophenoxyquinoline nucleus as new antibacterial agents
  作者：Jigar A. Makawana、Chetan B. Sangani、Shashikant B. Teraiya、Hai-Liang Zhu

  DOI：10.1007/s00044-013-0655-8

  日期：2014.1

  A series of new Schiff's base derivatives 4a-x bearing 2-thiophenoxyquinoline nucleus have been designed and synthesized by reaction of 2-thiophenoxyquinoline-3-carbaldehydes 2a-d with various benzohydrazides 3a-f in the presence of Ni(NO3)(2)center dot 6H(2)O as a catalyst. In vitro antibacterial screening was carried out against two Gram-positive bacteria (Bacillus subtilis ATCC 6633 and Staphylococcus aureus ATCC 6538) and two Gram-negative bacteria (Escherichia coli ATCC 35218 and Pseudomonas aeruginosa ATCC 13525). Of the compounds studied, compound 4e showed chief activity (MIC = 3.13 mu g/mL) against S. aureus, and compounds 4p, 4k, and 4w were found to possess effective antibacterial activity against employed strains compared with standards used. The structures of Schiff's base derivatives were established by using various spectroscopic methods. A crystal structure of compound 4k has been determined by X-ray diffraction analysis.
• Synthesis of N-arylquinolone derivatives bearing 2-thiophenoxyquinolines and their antimicrobial evaluation
  作者：Mehul B. Kanani、Manish P. Patel

  DOI：10.1016/j.cclet.2014.04.002

  日期：2014.7

  A new series of 2-thiophenoxyquinolines based trifluoromethyl substituted N-aryl quinolone derivatives 8a-f and 9a-f have been synthesized via a one-pot multicomponent reaction. In vitro antimicrobial activity of the synthesized compounds was investigated against a representative panel of pathogenic strains. Compounds 8c, 9c and 9e exhibited comparable antimicrobial activity to first line drugs. (C) 2014 Manish P. Patel. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.