N,N'-bis-(4-propoxy-phenyl)-thiourea | 42084-01-5

• 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: N,N'-bis-(4-propoxy-phenyl)-thiourea
• 英文别名: N,N'-Bis-(4-propoxy-phenyl)-thioharnstoff；N,N'--thioharnstoff；1,3-Bis(4-propoxyphenyl)thiourea
• CAS: 42084-01-5
• 化学式: C₁₉H₂₄N₂O₂S
• 分子量: 344.478
• InChiKey: MKKOMLHZQBUJMH-UHFFFAOYSA-N

物化性质

• 熔点：
  180-182 °C(Solv: ethanol (64-17-5))
• 沸点：
  470.1±55.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N'-bis-(4-propoxy-phenyl)-thiourea 在 乙酸酐 作用下， 生成 1-isothiocyanato-4-propoxy-benzene
  参考文献：
  名称：

  Buu-Hoi et al., Journal of the Chemical Society, 1955, p. 1581,1583

  摘要：

  DOI：
• 作为产物：
  描述：

  二硫化碳 、 对正丙氧基苯胺 在 sulfur 作用下， 以 乙醇 为溶剂， 以35%的产率得到N,N'-bis-(4-propoxy-phenyl)-thiourea
  参考文献：
  名称：

  Symmetrical and unsymmetrical analogues of isoxyl; active agents against Mycobacterium tuberculosis

  摘要：

  Symmetrical and unsymmetrical analogues of the antimycobacterial agent isoxyl-have been synthesized and tested against Mycobacterium tuberculosis H37Rv and Mycobacterium bovis BCG, some showing an increased bactericidal effect. In particular, compounds 1-(p-n-butylphenyl)-3-(4-propoxy-phenyl) thiourea (10) and 1-(p-n-butylphenyl)-3-(4-n-butoxy-phenyl) thiourea (11) showed an approximate 10-fold increase in in vitro potency compared to isoxyl, paralleled by increased inhibition of mycolic acid biosynthesis in M. bovis BCG. Interestingly, these isoxyl analogues showed relatively poor inhibition of oleate production, suggesting that the modifications have changed the spectrum of biological activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.095

文献信息

• Notes - Investigations in heterocycles. II. Unsymmetrical Ureas, Thioureas, and Related Thiazolines.
  作者：George deStevens、Heino Luts、Angelina Halamandaris

  DOI：10.1021/jo01095a620

  日期：1958.1
• Some Thiazolines and Thiazolidinones with Antituberculous Activity
  作者：R. H. Mizzoni、P. C. Eisman

  DOI：10.1021/ja01546a066

  日期：1958.7
• Bis-(substituted phenyl)-thioureas
  申请人：CIBA PHARM PROD INC

  公开号：US02703815A1

  公开（公告）日：1955-03-08
• Buu-Hoi et al., Journal of the Chemical Society, 1955, p. 1581,1583
  作者：Buu-Hoi et al.

  DOI：——

  日期：——
• Symmetrical and unsymmetrical analogues of isoxyl; active agents against Mycobacterium tuberculosis
  作者：Veemal Bhowruth、Alistair K. Brown、Robert C. Reynolds、Geoffrey D. Coxon、Simon P. Mackay、David E. Minnikin、Gurdyal S. Besra

  DOI：10.1016/j.bmcl.2006.06.095

  日期：2006.9

  Symmetrical and unsymmetrical analogues of the antimycobacterial agent isoxyl-have been synthesized and tested against Mycobacterium tuberculosis H37Rv and Mycobacterium bovis BCG, some showing an increased bactericidal effect. In particular, compounds 1-(p-n-butylphenyl)-3-(4-propoxy-phenyl) thiourea (10) and 1-(p-n-butylphenyl)-3-(4-n-butoxy-phenyl) thiourea (11) showed an approximate 10-fold increase in in vitro potency compared to isoxyl, paralleled by increased inhibition of mycolic acid biosynthesis in M. bovis BCG. Interestingly, these isoxyl analogues showed relatively poor inhibition of oleate production, suggesting that the modifications have changed the spectrum of biological activity. (c) 2006 Elsevier Ltd. All rights reserved.