4-Hydroxy-2-butanone thiosemicarbazone | 13349-19-4

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-Hydroxy-2-butanone thiosemicarbazone
• 英文别名: [(E)-4-hydroxybutan-2-ylideneamino]thiourea
• CAS: 13349-19-4
• 化学式: C₅H₁₁N₃OS
• 分子量: 161.228
• InChiKey: YVSVACHPRHKOBL-QPJJXVBHSA-N

物化性质

• 熔点：
  142-145 °C
• 沸点：
  305.5±44.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  103
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  4-Hydroxy-2-butanone thiosemicarbazone 、 alpha-溴-4-甲氧基苯乙酮 以 异丙醇 为溶剂， 以88%的产率得到(E)-3-[2-(4-(4-methoxyphenyl)thiazol-2-yl)hydrazono]butan-1-ol
  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
• 作为产物：
  描述：

  4-羟基-2-丁酮 、 氨基硫脲 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 4-Hydroxy-2-butanone thiosemicarbazone
  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

• Computer-aided molecular design, synthesis and evaluation of antifungal activity of heterocyclic compounds
  作者：Nereu Junio Cândido Oliveira、Iasmin Natália Santos Teixeira、Philipe Oliveira Fernandes、Gabriel Corrêa Veríssimo、Aline Dias Valério、Carolina Paula de Souza Moreira、Túlio Resende Freitas、Anna Clara Ventura Fonseca、Adriano de Paula Sabino、Susana Johann、Vinicius Gonçalves Maltarollo、Renata Barbosa de Oliveira

  DOI：10.1016/j.molstruc.2022.133573

  日期：2022.11

  perspective, heterocyclic compounds namely thiazolylhydrazones, furan, tetrazole, triazole and thiadiazoline derivatives were synthesized and tested in vitro against seven clinical importance Cryptococcus and Candida species. In this study, virtual screening techniques were applied using a scaffold-hopping database, FDA approved drugs and a ZINC subset. Some of the compounds evaluated showed promising

  免疫功能低下患者真菌感染的门诊并发症和抗菌药物耐药机制的发展表明需要开发新的抗真菌药物。从这个角度来看，合成了杂环化合物，即噻唑基腙、呋喃、四唑、三唑和噻二唑啉衍生物，并在体外针对七种具有临床重要性的隐球菌和念珠菌进行了测试。在这项研究中，使用支架跳跃数据库、FDA 批准的药物和 ZINC 子集应用虚拟筛选技术。一些评估的化合物显示出对白色念珠菌、光滑念珠菌、克氏念珠菌、近平滑念珠菌、热带念珠菌、新生念珠菌和C. gatti，显示最小抑制浓度 (MIC) 值在 0.12-250 µM 范围内。