3-(4-Chloro-phenyl)-2-hydroperoxy-but-3-en-1-ol | 132533-13-2

• 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: 3-(4-Chloro-phenyl)-2-hydroperoxy-but-3-en-1-ol
• 英文别名: 3-(4-Chlorophenyl)-2-hydroperoxybut-3-en-1-ol
• CAS: 132533-13-2
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: NXTVDBDPRBUCTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 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：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-Chloro-phenyl)-2-hydroperoxy-but-3-en-1-ol 在 盐酸 、 sodium tetrahydroborate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.5h， 生成 3-[1-(4-Chlorophenyl)ethenyl]-1,2,5-trioxaspiro[5.5]undecan-9-ol
  参考文献：
  名称：

  Orally Active 1,2,4-Trioxanes:  Synthesis and Antimalarial Assessment of a New Series of 9-Functionalized 3-(1-Arylvinyl)-1,2,5-trioxaspiro[5.5]undecanes against Multi-Drug-Resistant Plasmodium yoelii nigeriensis in Mice

  摘要：

  Using easily accessible keto-trioxanes 7a-g as the starting materials, a series of new variously functionalized 1,2,4-trioxanes 10-36 have been prepared and evaluated for antimalarial activity against multi-drug-resistant Plasmodium yoelii nigeriensis in mice in the dose range of 24 mg/kg x 4 days to 96 mg/kg x 4 days by oral route. Trioxanes 10, 12, 14, 16, 18, 20, and 22 have shown promising antimalarial activity. Trioxanes 14 and 18, the two most active compounds of the series, provide 100% and 60% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively. In this model beta-arteether provides 100% and 20% protection at 48 mg/kg x 4 days and 24 mg/kg x 4 days, respectively.

  DOI：

  10.1021/jm051130r
• 作为产物：
  描述：

  (E)-3-(4-chlorophenyl)but-2-en-1-ol 在 氧气 、 亚甲兰 作用下， 以 乙腈 为溶剂， 反应 4.0h， 生成 3-(4-Chloro-phenyl)-2-hydroperoxy-but-3-en-1-ol
  参考文献：
  名称：

  AMINO-FUNCTIONALIZED 1,2,4-TRIOXANES USEFUL AS ANTIMALARIAL AGENTS AND PROCESS FOR PREPARATION THEREOF

  摘要：

  本发明涉及一种新型系列抗疟氨基功能化1,2,4-三氧杂环丁酮类似物，其化学式为4，其中Ar代表芳基，如苯基、4-联苯基、4-氯苯基、4-甲氧基苯基、4-甲基苯基，R代表苯基、4-甲氧基苯基、4-氯苯基、3,5-二氯苯基、4-乙酰氨基苯基、1-萘基、2-联苯基、4-联苯基、2-芴基、4-氟苯基、2-三氟甲基苯基、3-三氟甲基苯基和4-三氟甲基苯基等。

  公开号：

  US20060142378A1

文献信息

• Novel spiro-1,2,4-trioxanes
  申请人：Singh Chandan

  公开号：US20070191475A1

  公开（公告）日：2007-08-16

  The present invention relates to spiro 1,2,4-trioxanes of general formula 4. This invention more particularly relates to a process for the preparation of a series of spiro 1,2,4-trioxanes. Wherein, Ar represents aryl groups such as phenyl, 4-biphenyl, 4-chlorophenyl, 4-methoxyphenyl, 4-methylphenyl, 4-cyclohexylphenyl, 1-naphthyl, 2-naphthyl and the like and R represents hydrogen or the alkyl group such as methyl, ethyl and the like. Several of these compounds show high order of antimalarial activity against multidrug-resistant malaria in mice and thus hold promise as antimalarial agents against multidrug-resistant malaria.

  本发明涉及一般式4的螺环1,2,4-三氧杂环丙烷。该发明更具体地涉及一种制备一系列螺环1,2,4-三氧杂环丙烷的方法。其中，Ar代表芳基团，如苯基、4-联苯基、4-氯苯基、4-甲氧基苯基、4-甲基苯基、4-环己基苯基、1-萘基、2-萘基等，R代表氢或烷基，如甲基、乙基等。这些化合物中的几种显示出高度的抗疟活性，对多药耐药性疟疾在小鼠中具有作用，并因此有望作为抗多药耐药性疟疾的抗疟药物。
• WO2006/70381
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2007/77479
  申请人：——

  公开号：——

  公开（公告）日：——
• Singh, Chandan, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 2, p. 291
  作者：Singh, Chandan

  DOI：——

  日期：——
• Bile Acid-Based 1,2,4-Trioxanes: Synthesis and Antimalarial Assessment
  作者：Chandan Singh、Mohammad Hassam、Ved Prakash Verma、Ajit Shanker Singh、Niraj Krishna Naikade、Sunil K. Puri、Prakas R. Maulik、Ruchir Kant

  DOI：10.1021/jm301323k

  日期：2012.12.13

  A new series of bile acid-based trioxanes 23a-d, 24a-d, 25a-d, 26a, 26b, and 26d have been synthesized and assessed for their antimalarial activity against multidrug-resistant Plasmodium yoelii in Swiss mice by oral route. The antimalarial activity of these trioxanes showed a strong dependence on the side-chain length; shortening side-chain length lead to increase in activity. The antimalarial activity also showed even stronger dependence on the stereochemistry at C3 and C6 (C21 in Figure 5) of the trioxane moiety. Of the two diastereomers isolated of each of the trioxanes, more polar one was significantly more active than the less polar one. The more polar diastereomer of the trioxanes 26a, 26b, and 26d, were the most active compounds of the series. All these three trioxanes provided 100% protection at 24 mg/kg X 4 days. In this model beta-arteether provided 100% and 20% protection at 48 mg/kg X 4 days and 24 mg/kg X 4 days, respectively.