2-p-tolylthiazol-4(5H)-one | 722465-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-p-tolylthiazol-4(5H)-one
• 英文别名: 2-(4-methylphenyl)thiazol-4-one；2-(4-Methylphenyl)-4(5H)-thiazolone；2-(4-methylphenyl)-1,3-thiazol-4-one
• CAS: 722465-90-9
• 化学式: C₁₀H₉NOS
• 分子量: 191.254
• InChiKey: CZSFUVWCMTVCIR-UHFFFAOYSA-N

物化性质

• 沸点：
  313.0±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  54.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-p-tolylthiazol-4(5H)-one 、 对甲氧基苯乙酮 在 ammonium acetate 作用下， 以 甲苯 为溶剂， 反应 0.75h， 以56%的产率得到(Z)-5-(1-(4-methoxyphenyl)ethylidene)-2-p-tolylthiazol-4(5H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors

  摘要：

  A class of 5-lipoxygenase (5-LO) inhibitors characterized by a central 5-benzylidene-2-phenyl-thiazolinone scaffold was synthesized as a new series of molecular modifications and extensions of a previously reported series. Compounds were tested in a cell-based and a cell-free assay and furthermore evaluated for their influence on cell viability. The presented substituted thiazolinone scaffold turned out to be essential for both the 5-LO inhibitory activity and the non-cytotoxic profile. With (Z)-5-(4-methoxybenzylidene)-2-(naphthalen-2-yl)-5H-thiazol-4-one (2k, ST1237), a potent, direct, non-cytotoxic 5-LO inhibitor with IC50 of 0.08 mu M and 0.12 mu M (cell-free assay and intact cells), we present a promising lead optimization and development for further investigations as novel anti-inflammatory drug. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.003
• 作为产物：
  描述：

  巯基乙酸 、 对甲苯腈 以 乙醇 为溶剂， 反应 1.0h， 生成 2-p-tolylthiazol-4(5H)-one
  参考文献：
  名称：

  Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors

  摘要：

  A class of 5-lipoxygenase (5-LO) inhibitors characterized by a central 5-benzylidene-2-phenyl-thiazolinone scaffold was synthesized as a new series of molecular modifications and extensions of a previously reported series. Compounds were tested in a cell-based and a cell-free assay and furthermore evaluated for their influence on cell viability. The presented substituted thiazolinone scaffold turned out to be essential for both the 5-LO inhibitory activity and the non-cytotoxic profile. With (Z)-5-(4-methoxybenzylidene)-2-(naphthalen-2-yl)-5H-thiazol-4-one (2k, ST1237), a potent, direct, non-cytotoxic 5-LO inhibitor with IC50 of 0.08 mu M and 0.12 mu M (cell-free assay and intact cells), we present a promising lead optimization and development for further investigations as novel anti-inflammatory drug. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.04.003

文献信息

• Enantioselective Construction of Spiro Thiazol-4-one Derivatives with Multiple Stereocenters via an Organocatalyzed Multicomponent Cascade Reaction
  作者：Yuanyuan Xiao、Rongrong Jiang、Youming Wang、Zhenghong Zhou

  DOI：10.1002/adsc.201800086

  日期：2018.5.16

  We have developed an organocatalyzed asymmetric three‐component reaction of thiazol‐4‐ones, acrolein and nitroolefins, which provides an efficient approach to access optically active spiro thiazol‐4‐ones. Under the catalysis of a bifunctional squaramide derived from L‐tert‐leucine, the reactions of a wide range of thiazol‐4‐ones, acrolein and nitroolefins took place smoothly to generate the corresponding

  我们已经开发了噻唑-4-酮，丙烯醛和硝基烯烃的有机催化不对称三组分反应，这提供了一种有效的途径来获得旋光性螺噻唑-4-酮。在衍生自L-叔亮氨酸的双功能方酸酰胺的催化下，各种噻唑-4-酮，丙烯醛和硝基烯烃的反应顺利进行，生成了相应的螺噻唑酮衍生物，该衍生物带有四个连续的立体异构中心，收率高，产率高。对映选择性水平。以一对可分离的差向异构体的形式获得标题手性螺噻唑酮，其通过两次迈克尔加成，随后的亨利过程形成。
• Enantioselective construction of novel chiral spirooxindoles incorporating a thiazole nucleus
  作者：L.-Y. Cui、Y.-M. Wang、Z.-H. Zhou

  DOI：10.1039/c6ra14178a

  日期：——

  Asymmetric cascade Michael/cyclization reaction between 2-substituted thiazol-4-ones and 2-(2-oxoindolin-3-ylidene)malononitriles was investigated using a series of chiral bifunctional hydrogen-bonding organocatalysts. Good yields (up to 91%) and excellent enantioselectivities (up to 98% ee) were achieved by using a (1R,2R)-1,2-diphenylethane-1,2-diamine derived thiourea catalyst. This method provides an

  使用一系列手性双功能氢键有机催化剂研究了2-取代的噻唑-4-酮与2-（2-氧代吲哚-3-亚甲基）丙二腈之间的不对称级联迈克尔/环化反应。通过使用（1 R，2 R）-1,2-二苯乙烷-1,2-二胺衍生的硫脲催化剂，可以获得良好的收率（最高91％）和出色的对映选择性（最高98％ee）。该方法提供了一种优雅的合成途径，可用于获得具有潜在生物活性的新型噻唑融合螺硫醇。
• Development and evaluation of ST-1829 based on 5-benzylidene-2-phenylthiazolones as promising agent for anti-leukotriene therapy
  作者：Andreas P. Lill、Carmen B. Rödl、Dieter Steinhilber、Holger Stark、Bettina Hofmann

  DOI：10.1016/j.ejmech.2014.10.054

  日期：2015.1

  Different inflammatory diseases and allergic reactions are mediated by leukotrienes, which arise from the oxygenation of arachidonic acid catalyzed by 5-lipoxygenase (5-LO). One promising approach for an effective anti-leukotriene therapy is the inhibition of this key enzyme. This study presents the synthesis and development of a potent and direct 5-LO inhibitor based on the well characterized 5-benzylidene-2-phenylthiazolone C06, whose further pharmacological investigation was precluded due to its low solubility. Through optimization of C06, evaluation of structure activity relationships including profound assessment of the thiazolone core and consideration of the solubility, the 5-benzyl-2-phenyl-4-hydroxythiazoles represented by 46 (ST-1829, 5-(4-chlorobenzyl)-2-p-tolylthiazol-4-ol) were developed. Compound 46 showed an improved 5-LO inhibitory activity in cell-based (IC50 values 0.14 mu M) and cell-free assays (IC50 values 0.03 mu M) as well as a prominent enhanced solubility. Furthermore, it kept its promising inhibitory potency in the presence of blood serum, excluding excessive binding to serum proteins. These facts combined with the non-cytotoxic profile mark a major step towards an effective anti-inflammatory therapy. (C) 2014 Elsevier Masson SAS. All rights reserved.
• Synthesis and biological evaluation of a class of 5-benzylidene-2-phenyl-thiazolinones as potent 5-lipoxygenase inhibitors
  作者：Sebastian Barzen、Carmen B. Rödl、Andreas Lill、Dieter Steinhilber、Holger Stark、Bettina Hofmann

  DOI：10.1016/j.bmc.2012.04.003

  日期：2012.6

  A class of 5-lipoxygenase (5-LO) inhibitors characterized by a central 5-benzylidene-2-phenyl-thiazolinone scaffold was synthesized as a new series of molecular modifications and extensions of a previously reported series. Compounds were tested in a cell-based and a cell-free assay and furthermore evaluated for their influence on cell viability. The presented substituted thiazolinone scaffold turned out to be essential for both the 5-LO inhibitory activity and the non-cytotoxic profile. With (Z)-5-(4-methoxybenzylidene)-2-(naphthalen-2-yl)-5H-thiazol-4-one (2k, ST1237), a potent, direct, non-cytotoxic 5-LO inhibitor with IC50 of 0.08 mu M and 0.12 mu M (cell-free assay and intact cells), we present a promising lead optimization and development for further investigations as novel anti-inflammatory drug. (C) 2012 Elsevier Ltd. All rights reserved.