4-(4-methoxyphenyl)-N-[(4-methylphenyl)methylideneamino]-1,3-thiazol-2-amine | 618064-93-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxyphenyl)-N-[(4-methylphenyl)methylideneamino]-1,3-thiazol-2-amine
• CAS: 618064-93-0
• 化学式: C₁₈H₁₇N₃OS
• 分子量: 323.418
• InChiKey: JMTIFRAYWPJLNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  74.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  对甲基苯甲醛 在 溶剂黄146 作用下， 以 乙醇 、 异丙醇 为溶剂， 生成 4-(4-methoxyphenyl)-N-[(4-methylphenyl)methylideneamino]-1,3-thiazol-2-amine
  参考文献：
  名称：

  Thiazole compounds with activity against Cryptococcus gattii and Cryptococcus neoformans in vitro

  摘要：

  Human cryptococcosis can occur as a primary or opportunistic infection and develop as an acute, subacute, or chronic, systemic infection involving different host organs. We evaluated the antifungal activity of thirteen compounds against Cryptococcus gattii and Cryptococcus neoformans in vitro, by assessing the toxicity of the compounds showing the greatest antifungal activity in VERO cells and murine macrophages. From these results, four compounds were considered promising for further studies because they displayed low cytotoxicity and significant antifungal activity. The heterocyclic compounds 1b, 1c, 1d, and 1m have antifungal activity levels between that of amphotericin B and fluconazole in vitro. The death curve of Cryptococcus spp. treated with these four compounds was similar to the curve obtained for amphotericin B, in that we observed a significant reduction in cell viability within the first 24 h of treatment. Additionally, we found that there was no effect when these compounds were combined with amphotericin and fluconazole, except for 1c, which antagonized the effect of amphotericin B against C. gattii, also reflected in the reduction of the post-antifungal effect (PAFE); however, this interaction did not alter the ergosterol content. The results shown in this paper reveal the discovery of novel thiazole compounds, which are easy to synthesize, and with potentially exhibit antifungal activity, and display low cytotoxicity in normal mammalian cells. These compounds can be used as prototypes for the design of new antifungal drugs against C gattii and C neoformans. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.07.032

文献信息

• Eco-Friendly One-Pot Synthesis of 2,4-Disubstituted Thiazoles by Grinding Under Catalyst- and Solvent-Free Conditions
  作者：Quansehng Ding、Dongjian Zhu、Huile Jin、Jiuxi Chen、Jinchang Ding、Huayue Wu

  DOI：10.1080/10426507.2010.492366

  日期：2011.1.31

  Abstract An efficient and facile synthesis of 2,4-disubstituted thiazoles is achieved by a one-pot reaction of aldehydes and α-bromoketones with thiosemicarbazide by grinding under catalyst- and solvent-free conditions. This method has notable advantages in terms of simple workup, neat conditions, high yield, reasonably rapid reaction rate, and environmental friendliness. Supplemental materials are

  摘要 通过醛和α-溴酮与氨基硫脲的一锅反应，在无催化剂和无溶剂的条件下研磨，实现了2,4-二取代噻唑的高效、简便合成。该方法具有后处理简单、条件整洁、收率高、反应速度合理、环境友好等显着优势。补充材料可用于本文。转至出版商在线版的磷、硫和硅及相关元素，查看免费的补充文件。图形概要
• Thiazole compounds with activity against Cryptococcus gattii and Cryptococcus neoformans in vitro
  作者：Nívea Pereira de Sá、Cleudiomar Inácio Lino、Nayara Cristina Fonseca、Beatriz Martins Borelli、Jonas Pereira Ramos、Elaine Maria Souza-Fagundes、Carlos Augusto Rosa、Daniel Assis Santos、Renata Barbosa de Oliveira、Susana Johann

  DOI：10.1016/j.ejmech.2015.07.032

  日期：2015.9

  Human cryptococcosis can occur as a primary or opportunistic infection and develop as an acute, subacute, or chronic, systemic infection involving different host organs. We evaluated the antifungal activity of thirteen compounds against Cryptococcus gattii and Cryptococcus neoformans in vitro, by assessing the toxicity of the compounds showing the greatest antifungal activity in VERO cells and murine macrophages. From these results, four compounds were considered promising for further studies because they displayed low cytotoxicity and significant antifungal activity. The heterocyclic compounds 1b, 1c, 1d, and 1m have antifungal activity levels between that of amphotericin B and fluconazole in vitro. The death curve of Cryptococcus spp. treated with these four compounds was similar to the curve obtained for amphotericin B, in that we observed a significant reduction in cell viability within the first 24 h of treatment. Additionally, we found that there was no effect when these compounds were combined with amphotericin and fluconazole, except for 1c, which antagonized the effect of amphotericin B against C. gattii, also reflected in the reduction of the post-antifungal effect (PAFE); however, this interaction did not alter the ergosterol content. The results shown in this paper reveal the discovery of novel thiazole compounds, which are easy to synthesize, and with potentially exhibit antifungal activity, and display low cytotoxicity in normal mammalian cells. These compounds can be used as prototypes for the design of new antifungal drugs against C gattii and C neoformans. (C) 2015 Elsevier Masson SAS. All rights reserved.