4-hydroxy-5-methyl-3-propylthiophen-2(5H)-one | 677722-91-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4-hydroxy-5-methyl-3-propylthiophen-2(5H)-one
• 英文别名: 3-hydroxy-2-methyl-4-propyl-2H-thiophen-5-one
• CAS: 677722-91-7
• 化学式: C₈H₁₂O₂S
• 分子量: 172.248
• InChiKey: VJPMXKXALLLPNY-UHFFFAOYSA-N

物化性质

• 熔点：
  49-50 °C
• 沸点：
  288.8±40.0 °C(Predicted)
• 密度：
  1.187±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-hydroxy-5-methyl-3-propylthiophen-2(5H)-one 在 盐酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 4-Hydroxy-5-(6-hydroxy-hexyl)-5-methyl-3-propyl-5H-thiophen-2-one
  参考文献：
  名称：

  Analogues of Thiolactomycin as Potential Antimalarial Agents

  摘要：

  Analogues of the natural antibiotic thiolactomycin (TLM), an inhibitor of the condensing reactions of type II fatty acid synthase, were synthesized and evaluated for their ability to inhibit the growth of the malaria parasite Plasmodium falciparum. Alkylation of the C4 hydroxyl group led to the most significant increase in growth inhibition (over a 100-fold increase in activity compared to TLM). To investigate the mode of action, the P. falciparum KASIII enzyme was produced for inhibitor assay. A number of TLM derivatives were identified that showed improved inhibition of this enzyme compared to TLM. Structure-activity relationships for enzyme inhibition were identified for some series of TLM analogues, and these also showed weak correlation with inhibition of parasite growth, but this did not hold for other series. On the basis of the lack of a clear correlation between inhibition of pfKASIII activity and parasite growth, we conclude that pfKASIII is not the primary target of TLM analogues. Some of the analogues also inhibited the growth of the parasitic protozoa Trypanosoma cruzi, T. brucei, and Leishmania donovani.

  DOI：

  10.1021/jm049067d
• 作为产物：
  描述：

  4-Acetylsulfanyl-3-oxo-2-propyl-pentanoic acid methyl ester 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 4-hydroxy-5-methyl-3-propylthiophen-2(5H)-one
  参考文献：
  名称：

  一些硫内酯衍生物的合成、抗疟评价和分子对接研究

  摘要：

  摘要 在本研究中，新型硫内酯衍生物的设计、合成和表征采用各种分析技术，如红外、 1 H NMR、 13 C NMR、质谱数据和元素分析。评估了所有合成化合物对恶性疟原虫 Dd2 和 3d7 菌株的体外抗疟活性。所有合成的化合物也进行了与 pf KASI/II 酶的分子对接研究，以分析它们在酶活性位点的结合方向。发现化合物 5d、5e 和 5i 对 Dd2 菌株和 3D7 菌株的 IC 50 最有效，IC 50 范围分别为 0.09-0.19 μM 和 0.03-0.04 μM，并且它们与活性物质的残基显示出良好的结合亲和力pf KASI/II 的站点。

  DOI：

  10.1016/j.molstruc.2016.12.095

文献信息

• Analogues of thiolactomycin as potential anti-malarial and anti-trypanosomal agents
  作者：S Jones

  DOI：10.1016/j.bmc.2003.11.023

  日期：2004.2.15

  A series of analogues of the naturally occurring antibiotic thiolactomycin (TLM) have been synthesised and evaluated for their ability to inhibit the growth of the malaria parasite, Plasmodium falciparum. Thiolactomycin is an inhibitor of Type II fatty acid synthase which is found in plants and most prokaryotes, but not an inhibitor of Type I fatty acid synthase in mammals. A number of the analogues showed inhibition equal to or greater than TLM. The introduction of hydrophobic alkyl groups at the C3 and C5 positions of the thiolactone ring lead to increased inhibition, the best showing a fourteenfold increase in activity over TLM. In addition, some of the analogues showed activity when assayed against the parasitic protozoa, Trypanosoma cruzi and Trypanosoma brucei. (C) 2003 Elsevier Ltd. All rights reserved.
• AQUEOUS COMPOSITION COMPRISING A COMPOUND OF THIOLACTONE TYPE AND A SILICONE AND PROCESS FOR TREATING KERATIN MATERIALS WITH THE COMPOSITION
  申请人：L'Oreal

  公开号：US20200030215A1

  公开（公告）日：2020-01-30

  The present invention relates to a composition comprising: (a) one more compound(s) of thiolactone type, and (b) one or more silicones.
• COMPOSITION COMPRISING A COMPOUND OF THIOLACTONE TYPE AND A PARTICULAR SOLVENT AND PROCESS FOR TREATING KERATIN MATERIALS WITH THE COMPOSITION
  申请人：L'Oreal

  公开号：US20200031796A1

  公开（公告）日：2020-01-30

  The present invention relates to a composition comprising: (a) at least one compound of thiolactone type, and (b) one or more solvents, which may be identical or different, chosen from polar (non-)protic organic solvents; the pH of said composition being less than or equal to 7.