3-(4-cyclohexylphenyl)-1-hydroxy-but-3-en-2-hydroperoxide | 610781-37-8

• 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-cyclohexylphenyl)-1-hydroxy-but-3-en-2-hydroperoxide
• 英文别名: 3-(4-Cyclohexylphenyl)-2-hydroperoxybut-3-en-1-ol
• CAS: 610781-37-8
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: WFHGBOWLAAUSPR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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-cyclohexylphenyl)-1-hydroxy-but-3-en-2-hydroperoxide 在 盐酸 、 sodium hydride 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 19.5h， 生成 2-{3-[1-(4-cyclohexyl-phenyl)-vinyl]-1,2,5-trioxa-spiro[5.5]undec-9-ylidene}-propionic acid ethyl ester
  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：

  3-(4-cyclohexylphenyl)-2-butenol 在 chlorophyll a 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 3-(4-cyclohexylphenyl)-1-hydroxy-but-3-en-2-hydroperoxide
  参考文献：
  名称：

  利用叶绿素选择性 PET 和 EnT 催化合成 N-烷基化喹啉-2(1H)-酮、异喹啉-1(2H)-酮和 1,2,4-三恶烷

  摘要：

  分别通过选择性光诱导电子转移（PET）和能量转移（EnT）实现了喹啉-2（1 H ）-酮、异喹啉-1（2 H ）-酮和1,2,4-三恶烷的光催化合成，由叶绿素在可见光照射下产生。喹啉-2(1 H )-酮、异喹啉-1(2 H )-酮和1,2,4-三恶烷是具有生物活性的支架，其遵循温和反应方案的合成受到高度追捧。这项工作展示了叶绿素的不同光催化作用，即喹啉或异喹啉的电子转移以及以烯丙醇为底物的能量转移，在绿色反应条件下提供有氧氧化。机理研究证实，催化循环遵循电子转移途径来进行N-烷基（异）喹啉鎓盐的氧化。此外，该方法为(N)-杂环的有机转化提供了一种环境友好、简单的反应策略。

  DOI：

  10.1039/d1ob01865e

文献信息

• [EN] NOVEL SUBSTITUTED 1,2,4-TRIOXANES USEFUL AS ANTIMALARIAL AGENTS AND A PROCESS FOR THE PREPARATION THEREOF<br/>[FR] NOUVEAUX 1,2,4-TRIOXANES SUBSTITUES UTILISES COMME ANTIPALUDIQUES ET PROCEDE DE PREPARATION DE CES ANTIPALUDIQUES
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2003082852A1

  公开（公告）日：2003-10-09

  In the present invention relates to a novel series of antimalarial 1,2,4-trioxanes analogues of general formula (7), wherein R represents cycloalkyl groups selected from the groups consisting of cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl or aryl groups selected from phenyl, 4-bromophenyl and 4-chlorophenyl, R1 and R2 represent hydrogen, alkyl group selected from methyl, ethyl, propyl and decyl, aryl selected from phenyl or parts of a cyclic systems such as cyclopentane, cyclohexane, substituted cyclohexane, cycloheptane bicyclo(2.2.1)heptane, adamantane and its preparation thereof; several of these novel compounds show promising antimalarial activity against multidrug resistant malaria in mice.

  本发明涉及一种新的抗疟疾1,2,4-三氧杂环己烷类似物的一般式(7)，其中R代表从环戊基、环己基、环庚基和环辛基中选择的环烷基或从苯基、4-溴苯基和4-氯苯基中选择的芳基，R1和R2代表氢、从甲基、乙基、丙基和癸基中选择的烷基，从苯基中选择的芳基或环戊烷、环己烷、取代环己烷、环庚烷、双环[2.2.1]庚烷、金刚烷等环系统的部分；这些新化合物中的一些显示出对小鼠多药耐药疟疾具有很好的抗疟活性。
• Substituted 1,2,4-trioxanes useful as antimalarial agents and a process for the preparation thereof
  申请人：——

  公开号：US20040053991A1

  公开（公告）日：2004-03-18

  In the present invention relates to a novel series of antimalarial 1,2,4-trioxanes analogues of general formula 7, 1 wherein R represents cycloalkyl groups selected from the groups consisting of cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl or aryl groups selected from phenyl, 4-bromophenyl and 4-chlorophenyl, R 1 and R 2 represent hydrogen, alkyl group selected from methyl, ethyl, propyl and decyl, aryl selected from phenyl or parts of a cyclic systems such as cyclopentane, cyclohexane, substituted cyclohexane, cycloheptane bicyclo(2.2.1)heptane, adamantane and its preparation thereof; several of these novel compounds show promising antimalarial activity against multidrug resistant malaria in mice.

  本发明涉及一种新型系列抗疟疾1,2,4-三氧杂环己烷类似物，其一般式为7,1，其中R代表从环戊基、环己基、环庚基和环辛基中选择的环烷基或从苯基、4-溴苯基和4-氯苯基中选择的芳基，R1和R2代表氢、从甲基、乙基、丙基和癸基中选择的烷基，从苯基中选择的芳基或从环戊烷、环己烷、取代环己烷、环庚烷、双环[2.2.1]庚烷、金刚烷等环系统的部分；这些新型化合物中的一些显示出对小鼠多药耐药疟疾具有很好的抗疟活性。
• 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。
• Design, Synthesis, Structure‐Activity Relationship and Docking Studies of Novel Functionalized Arylvinyl‐1,2,4‐Trioxanes as Potent Antiplasmodial as well as Anticancer Agents
  作者：Mohit K. Tiwari、Paolo Coghi、Prakhar Agrawal、Bharti Rajesh K. Shyamlal、Li Jun Yang、Lalit Yadav、Yuzhong Peng、Richa Sharma、Dharmendra K. Yadav、Dinkar Sahal、Vincent Kam Wai Wong、Sandeep Chaudhary

  DOI：10.1002/cmdc.202000045

  日期：2020.7.3

  against A549 lung cancer cell lines. In silico docking studies of the most active anticancer compounds, 8 l and 8 m , against EGFR were found to validate the wet lab results. In summary, a new series of functionalized aryl‐vinyl‐1,2,4‐trioxanes (8 a –p ) has been shown to display dual potency as promising antiplasmodial and anticancer agents.

  制备了一系列新的合成的功能化芳基乙烯基1,2,4-三恶烷（8 a – p），并使用SYBR green-I评估了它们对恶性疟原虫耐氯喹Pf INDO菌株的体外抗疟原虫活性。荧光测定。与氯喹（IC）相比，化合物8 g（IC 50 = 0.051μM; SI = 589.41）和8 m（IC 50 = 0.059μM ; SI = 55.93）分别显示出更强的抗血浆活性11倍和> 9倍50 = 0.546μM； SI = 36.63）。不同的计算机对许多靶蛋白的对接研究表明，活性最高的芳基乙烯基1,2,4-三恶烷（8 g和8 m）显示出二氢叶酸还原酶（DHFR）的结合亲和力与氯喹和青蒿琥酯的亲和力相当。在体外的细胞毒性潜力8 - p也针对人肺（A549）和肝（HepG2细胞）肿瘤细胞系评价与永生化的正常肺（BEAS-2B）和肝（LO2）细胞系一起。筛选后，得到五种衍生物。8 a，8 h，8 l，8
• WO2007/77479
  申请人：——

  公开号：——

  公开（公告）日：——