2-(1-phenoxypropan-2-ylidene)thiosemicarbazide | 25976-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(1-phenoxypropan-2-ylidene)thiosemicarbazide
• 英文别名: Phenoxy-aceton-thiosemicarbazon；phenoxy-acetone thiosemicarbazone；[(E)-(1-methyl-2-phenoxy-ethylidene)amino]thiourea；[(E)-1-phenoxypropan-2-ylideneamino]thiourea
• CAS: 25976-74-3
• 化学式: C₁₀H₁₃N₃OS
• 分子量: 223.299
• InChiKey: STZXVFVALYCLRE-XYOKQWHBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  91.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1-phenoxypropan-2-ylidene)thiosemicarbazide 在 劳森试剂 、 sodium acetate 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 反应 38.0h， 生成 5-ethyl-2-[(2E)-2-(1-phenoxypropan-2-ylidene)hydrazinyl]-1,3-thiazole-4-thione
  参考文献：
  名称：

  Structural Investigation of Anti-Trypanosoma cruzi 2-Iminothiazolidin-4-ones Allows the Identification of Agents with Efficacy in Infected Mice

  摘要：

  We modified the thiazolidinic ring at positions N3, C4, and C5, yielding compounds 6-24. Compounds with a phenyl at position N3, 15-19, 22-24, exhibited better inhibitory properties for cruzain and against the parasite than 2-iminothiazolidin-4-one S. We were able to identify one high-efficacy trypanocidal compound, 2-minothiazolidin-4-one 18, which inhibited the activity of cruzain and the proliferation of epirnastigotes and was cidal for trypomastigotes but was not toxic for splenocytes. Having located some of the structural determinants of the trypanocidal properties, we subsequently wished to determine if the exchange of the thiazolidine for a thiazole ring leaves the functional properties unaffected. We therefore tested thiazoles 26-45 and observed that they did not inhibit cruzain, but they exhibited trypanocidal effects. Parasite development was severely impaired when treated with 18, thus reinforcing the notion that this class of heterocycles can lead to useful cidal agents for Chagas disease.

  DOI：

  10.1021/jm301518v
• 作为产物：
  描述：

  苯酚 在 potassium carbonate 、 溶剂黄146 作用下， 以 乙醇 、 丁酮 为溶剂， 反应 2.5h， 生成 2-(1-phenoxypropan-2-ylidene)thiosemicarbazide
  参考文献：
  名称：

  Structural Investigation of Anti-Trypanosoma cruzi 2-Iminothiazolidin-4-ones Allows the Identification of Agents with Efficacy in Infected Mice

  摘要：

  We modified the thiazolidinic ring at positions N3, C4, and C5, yielding compounds 6-24. Compounds with a phenyl at position N3, 15-19, 22-24, exhibited better inhibitory properties for cruzain and against the parasite than 2-iminothiazolidin-4-one S. We were able to identify one high-efficacy trypanocidal compound, 2-minothiazolidin-4-one 18, which inhibited the activity of cruzain and the proliferation of epirnastigotes and was cidal for trypomastigotes but was not toxic for splenocytes. Having located some of the structural determinants of the trypanocidal properties, we subsequently wished to determine if the exchange of the thiazolidine for a thiazole ring leaves the functional properties unaffected. We therefore tested thiazoles 26-45 and observed that they did not inhibit cruzain, but they exhibited trypanocidal effects. Parasite development was severely impaired when treated with 18, thus reinforcing the notion that this class of heterocycles can lead to useful cidal agents for Chagas disease.

  DOI：

  10.1021/jm301518v

文献信息

• Environmental controls of NDVI and sheep production in the Tierra del Fuego steppe of Argentina
  作者：Gabriela Posse、Ana María Cingolani

  DOI：10.2307/1479004

  日期：2000.12

  Abstract. We analysed vegetation dynamics in Tierra del Fuego steppes using Normalized Difference Vegetation Index (NDVI) data provided by advanced very high‐resolution radiometer (AVHRR) on board the National Oceanic and Atmospheric Administration (NOAA) polar satellite. Our objective, at a regional scale, was to analyse the spatial variability of NDVI dynamics in relation to parent material and geographic location, representing the fertility and climate gradients respectively; at a local scale, it was to analyse the inter‐annual variability associated with climate and its relation with sheep production indices. The general pattern of NDVI dynamics was analysed with Principal Component Analysis. We found that the geographic location was more important than landscape type in explaining NDVI dynamics despite the fact that the variation in landscape type reflects a fertility gradient strongly associated with floristic composition and secondary productivity.Discriminant Analysis was performed to identify the variables that better distinguish geographic units. The Northern region (with the lowest precipitation and the highest temperatures) had lower NDVI values over the year. In the Central region, NDVI reached the highest value of the season, surpassing both other regions. The Southern region (the coldest and moistest) had its growth pattern displaced towards the summer. For the Central region we analysed 10 years of monthly NDVI data with PCA. We found that precipitation from August to December and winter temperature are the most important determinants of overall NDVI values. Lamb production was correlated with spring and early summer NDVI values. Sheep mortality is affected by low NDVI values in late summer and high annual amplitude. Satellite information allowed us to characterize the vegetation dynamics of three ecological areas across the Fuegian steppe.
• ANTINEOPLASTIC COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：CENTRO DE INGENIERIA GENETICA Y BIOTECNOLOGIA

  公开号：EP1892245B1

  公开（公告）日：2015-07-29
• Structural Investigation of Anti-<i>Trypanosoma cruzi</i> 2-Iminothiazolidin-4-ones Allows the Identification of Agents with Efficacy in Infected Mice
  作者：Diogo Rodrigo Magalhaes Moreira、Salvana Priscylla Manso Costa、Marcelo Zaldini Hernandes、Marcelo Montenegro Rabello、Gevanio Bezerra de Oliveira Filho、Cristiane Moutinho Lagos de Melo、Lucas Ferreira da Rocha、Carlos Alberto de Simone、Rafaela Salgado Ferreira、Jordana Rodrigues Barbosa Fradico、Cássio Santana Meira、Elisalva Teixeira Guimarães、Rajendra Mohan Srivastava、Valéria Rêgo Alves Pereira、Milena Botelho Pereira Soares、Ana Cristina Lima Leite

  DOI：10.1021/jm301518v

  日期：2012.12.27

  We modified the thiazolidinic ring at positions N3, C4, and C5, yielding compounds 6-24. Compounds with a phenyl at position N3, 15-19, 22-24, exhibited better inhibitory properties for cruzain and against the parasite than 2-iminothiazolidin-4-one S. We were able to identify one high-efficacy trypanocidal compound, 2-minothiazolidin-4-one 18, which inhibited the activity of cruzain and the proliferation of epirnastigotes and was cidal for trypomastigotes but was not toxic for splenocytes. Having located some of the structural determinants of the trypanocidal properties, we subsequently wished to determine if the exchange of the thiazolidine for a thiazole ring leaves the functional properties unaffected. We therefore tested thiazoles 26-45 and observed that they did not inhibit cruzain, but they exhibited trypanocidal effects. Parasite development was severely impaired when treated with 18, thus reinforcing the notion that this class of heterocycles can lead to useful cidal agents for Chagas disease.