1-[4-(methylthio)phenyl]-2-propanone | 88356-92-7

• 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: 1-[4-(methylthio)phenyl]-2-propanone
• 英文别名: 1-(4-methylsulfanylphenyl)propan-2-one；1-(4-(methylthio)phenyl)propan-2-one；deamino-oxo-4-methylthioamphetamine；4-Methylthiophenyl acetone；1-[4-(Methylsulfanyl)phenyl]propan-2-one
• CAS: 88356-92-7
• 化学式: C₁₀H₁₂OS
• mdl: MFCD11553500
• 分子量: 180.271
• InChiKey: RYFZDEIJXAESAA-UHFFFAOYSA-N

物化性质

• 沸点：
  105-115 °C(Press: 0.05-0.3 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)
• 保留指数：
  1335

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[4-(methylthio)phenyl]-2-propanone 在 镍 sodium hydroxide 、 氢气 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 20.0h， 生成 N-(6-Hydroxy-4'-methylsulfanyl-biphenyl-3-yl)-acetamide
  参考文献：
  名称：

  Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N.omega.-oxides

  摘要：

  A series of 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl] [1,1'-biphenyl]-2-ols and N omega-oxides was prepared from the substituted 1-phenyl-2-propanones proceeding through the 5-nitro[1,1'-biphenyl]-2-ols, the corresponding amino, and acetamido derivatives to the N-[5-[(alkylamino)methyl]-6-hydroxy[1,1'-biphenyl]-3-yl]acetamides and final condensation with 4,7-dichloroquinoline or the N-oxide. In a quantitative structure-activity relationship study first run on 28 and later expanded to 40 substituted phenyl analogues and their N omega-oxides, increasing antimalarial potency vs. Plasmodium berghei in mice was found to be correlated with decreasing size (sigma MR) and electron donation (sigma sigma) of the phenyl ring substituents. A significant correlation with N omega-oxidation could not be demonstrated. Initial high activity against P. berghei infections in mice led to expanded studies that demonstrated in addition excellent activity against resistant strains of parasite, activity in primate models, and pharmacokinetic properties apparently allowing protection against infection for extended periods of time even after oral administration. Such properties encourage the clinical trial of a member of this class in man.

  DOI：

  10.1021/jm00156a009
• 作为产物：
  描述：

  1-(4-methylthiophenyl)-2-nitro-1-propene 在 甲酸 、 硫酸 、 C₁₉H₂₆ClIrN₃O⁽¹⁺⁾*Cl^(1-) 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 以34 %的产率得到1-[4-(methylthio)phenyl]-2-propanone
  参考文献：
  名称：

  铱催化和 pH 依赖性硝基烯烃还原成酮

  摘要：

  开发了α,β-二取代硝基烯烃向酮的高度化学选择性转化。与酸相容的铱催化剂是转化的关键。在 2500 S/C比率下，硝基烯烃很容易转化为酮，分离产率高达 72%。提出了一种新的机制模式，涉及将硝基烯烃还原为亚硝基烯烃和N -烯基羟胺。这种转化已准备好放大到克级合成。pH值在控制化学选择性方面起着不可或缺的作用。

  DOI：

  10.3390/molecules27227822

文献信息

• Substituted isoxazoles for the treatment of inflammation
  申请人：G.D. Searle & Co.

  公开号：EP1223167A3

  公开（公告）日：2002-08-07

  A class of substituted isoxazolyl compounds is described for use in treating inflammation and inflammation-related disorders. Compounds of particular interest are defined by Formula (III) wherein R7 is selected from hydroxyl, lower alkyl, carboxyl, halo, lower carboxylalkyl, lower alkoxycarbonylalkyl, lower alkoxyalkyl, lower carboxyalkoxyalkyl, lower haloalkyl, lower haloalkylsulfonyloxy, lower hydroxyalkyl, lower aryl (hydroxylalkyl), lower carboxyaryloxyalkyl, lower alkoxycarbonylaryloxyalkyl, lower cycloalkyl, lower cycloalkylalkyl, and lower aralkyl; and wherein R8 is one or more radicals independently selected from hydrido, lower alkylsulfinyl, lower alkyl, cyano, carboxyl, lower alkoxycarbonyl, lower haloalkyl, hydroxyl, lower hydroxyalkyl, lower haloalkoxy, amino, lower alkylamino, lower arylamino, lower aminoalkyl, nitro, halo, lower alkoxy, aminosulfonyl, and lower alkylthio; or a pharmaceutically-acceptable salt thereof.

  描述了一类取代的异氧氮杂环化合物，用于治疗炎症和与炎症相关的疾病。特别感兴趣的化合物由公式（III）定义，其中R7从羟基，低烷基，羧基，卤素，低羧基烷基，低烷氧羰基烷基，低烷氧基烷基，低羧氧基烷氧基，低卤代烷基，低卤代烷基磺酰氧基，低羟基烷基，低芳基（羟基烷基），低羧基芳氧基烷基，低烷氧羰基芳氧基烷基，低环烷基，低环烷基烷基和低芳基烷基中选择；R8是一个或多个基团，独立地从氢化物，低烷基亚砜基，低烷基，氰基，羧基，低烷氧羰基，低卤代烷基，羟基，低羟基烷基，低卤代氧基，氨基，低烷基氨基，低芳基氨基，低氨基烷基，硝基，卤素，低烷氧基，氨基磺酰基和低烷硫基中独立选择；或其药学上可接受的盐。
• Isoxazole compounds as cyclooxygenase inhibitors
  申请人：G. D. Searle & Co.

  公开号：US05859257A1

  公开（公告）日：1999-01-12

  A class of substituted isoxazolyl compounds is described for use in treating cyclooxygenase-2 related disorders. Compounds of particular interest are defined by Formula I ##STR1## wherein R.sup.1, R.sup.2, and R.sup.3, are described in the specification.

  所述一类取代异噁唑基化合物用于治疗与环氧合酶-2相关的疾病。特别感兴趣的化合物由下式I定义：其中R.sup.1、R.sup.2和R.sup.3在说明书中有描述。
• Development of a Robust and Practical Process for the Darzens Condensation and α,β-Epoxide Rearrangement: Scope and Limitations of the Methodology
  作者：Fabrice Gallou、Jeremy Zimbron、Manuela Seeger-Weibel、Hans Hirt

  DOI：10.1055/s-2008-1067002

  日期：2008.4

  benzaldehydes and subsequent α,β-epoxy rearrangement is reported. The process developed is both amenable to large scale and parallel synthesis. While electron-poor benzaldehydes gave mixtures of aryl ketones and 2-substituted aryl ketones in mediocre to low yields, electron-rich benzaldehydes were found to react in high yields with complete regioselectivity to form 2-substituted aryl ketones.

  报道了取代苯甲醛的 Darzens 缩合和随后的 α,β-环氧重排的实用且稳健的过程。所开发的工艺既适用于大规模合成，也适用于平行合成。虽然贫电子苯甲醛以中等至低产率产生芳基酮和 2-取代芳基酮的混合物，但发现富电子苯甲醛以高产率反应形成 2-取代芳基酮，具有完全的区域选择性。
• [EN] 5-PHENYLTHIAZOLE DERIVATIVES AND THEIR USE AS P13 KINASE INHIBITORS<br/>[FR] DERIVES DE 5-PHENYLTHIAZOLE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PI3 KINASE
  申请人：NOVARTIS AG

  公开号：WO2004078754A1

  公开（公告）日：2004-09-16

  Compounds of formula (I) in free or salt form, wherein R1, R2, R3, Wand R5 have the meanings as indicated in the specification, are useful for treating diseases mediated by phosphatidylinositol 3-kinase. Pharmaceutical compositions that contain the compounds and processes for preparing the compounds are also described.

  式（I）中的化合物以自由形式或盐形式存在，其中R1、R2、R3、W和R5的含义如规范中所示，用于治疗由磷脂酰肌醇3-激酶介导的疾病。还描述了含有这些化合物的药物组合物和制备这些化合物的方法。
• Synthesis and in vitro toxicity of 4-MTA, its characteristic clandestine synthesis byproducts and related sulfur substituted α-alkylthioamphetamines
  作者：Suzanne M. Cloonan、John J. Keating、Desmond Corrigan、John E. O’Brien、Pierce V. Kavanagh、D. Clive Williams、Mary J. Meegan

  DOI：10.1016/j.bmc.2010.04.022

  日期：2010.6.1

  drugs often contain byproducts of uncontrolled, illegal clandestine synthetic processes. We report the isolation and structural identification of a number of novel pyridines, dihydropyridone and N,N-di(1-aryl-2-propyl) amines as route-specific byproducts associated with clandestine synthesis of 4-MTA and related amphetamines. We report the in vitro cytotoxicity of 4-MTA, its synthesis byproducts together

  4-甲硫基苯丙胺（4-MTA）被认为是一种3,4-亚甲二氧基甲基苯丙胺（MDMA）滥用药物。这种苯丙胺类药物通常含有不受控制的非法秘密合成过程的副产物。我们报告了许多新型吡啶，二氢吡啶酮和N，N的分离和结构鉴定-二（1-芳基-2-丙基）胺是与4-MTA和相关苯丙胺的秘密合成有关的途径特定的副产物。我们报告了4-MTA的体外细胞毒性，其合成副产物与一些结构相关的硫取代的α-烷基苯乙胺在过度表达人单胺转运蛋白的细胞系以及主要神经元细胞系模型和多巴胺能神经母细胞瘤细胞系中。在药理定义的浓度范围内，发现4-MTA以及许多其他与结构相关的苯丙胺衍生物和合成杂质对这些细胞具有细胞毒性，这表明4-MTA在体外是细胞毒性剂，因此可能具有神经毒性剂的潜力。体内。