4-thiophenol | 100132-31-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯硫酚类
• 英文名称: 4-thiophenol
• 英文别名: 4-benzenethiol；2,2'-[(4-mercaptophenyl)imino]bisethanol；4-[N,N-bis(2-hydroxyethyl)amino]benzenethiol；2-[N-(2-hydroxyethyl)-4-sulfanylanilino]ethanol
• CAS: 100132-31-8
• 化学式: C₁₀H₁₅NO₂S
• 分子量: 213.301
• InChiKey: LSPQTRNZCCADCW-UHFFFAOYSA-N

物化性质

• 熔点：
  134 °C
• 沸点：
  422.0±40.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  44.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-thiophenol 在 盐酸 、 sodium azide 、 氯甲酸乙酯 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 、 sodium chloride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 25.17h， 生成
  参考文献：
  名称：

  DNA-directed alkylating agents. 3. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the length of the linker chain

  摘要：

  Four series of acridine-linked aniline mustards have been prepared and evaluated for in vitro cytotoxicity, in vivo antitumor activity, and DNA cross-linking ability. The anilines were attached to the DNA-intercalating acridine chromophores by link groups (-O-, -CH2-, -S-, and -SO2-) of widely varying electronic properties, providing four series of widely differing mustard reactivity where the alkyl chain linking the acridine and mustard moieties was varied from two to five carbons. Relationships were sought between chain length and biological properties. Within each series, increasing the chain length did not alter the reactivity of the alkylating moiety but did appear to position it differently on the DNA, since cross-linking ability (measured by agarose gel assay) altered with chain length, being maximal with the C4 analogue. The in vivo antitumor activities of the compounds depended to some extent on the reactivity of the mustard, with the least reactive SO2 compounds being inactive. However, DNA-targeting did appear to allow the use of less reactive mustards, since the S-linked acridine mustards showed significant activity whereas the parent S-mustard did not. Within each active series, the most active compound was the C4 homologue, suggesting some relationship between activity and extent of DNA alkylation.

  DOI：

  10.1021/jm00173a016
• 作为产物：
  描述：

  N,N-二羟乙基苯胺 在 lithium aluminium tetrahydride 、 溴 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 48.0h， 生成 4-thiophenol
  参考文献：
  名称：

  芳香族硫醇对蛋白质折叠过程中发生的硫醇-二硫键交换反应的影响。

  摘要：

  包含二硫键的蛋白质从变性蛋白质到天然蛋白质的折叠涉及许多硫醇-二硫键交换反应。这些反应中的许多反应都包含氧化还原缓冲液，该缓冲液是硫醇（RSH）和相应的二硫键（RSSR）的混合物。RSH的结构与其在体外折叠蛋白中的功效之间的关系仅在有限的范围内进行了研究。本文报道了脂族和尤其是芳族硫醇对蛋白质折叠期间发生的反应的影响。芳族硫醇可能特别有效，因为它们的硫醇pK（a）值和反应性与体内催化剂蛋白质二硫键异构酶（PDI）匹配。这项研究将芳香族硫醇的硫醇pK（a）值与其对小分子二硫键和蛋白质胰岛素的反应性相关联。测量了九种对位取代的芳族硫醇的硫醇pK（a）值；使用sigma（p-）值构建的Hammett图得出rho = -1.6 +/- 0.1。测定了芳香族和脂肪族硫醇与2-吡啶基二硫代乙醇（2-PDE）（一种小分子二硫化物）的反应性。芳族硫醇的反应性与pK（a）的关系图的斜率（β）为0.9。这些硫

  DOI：

  10.1021/jo015600a

文献信息

• Luciferase signal enhancing compositions
  申请人：Gene Stream Pty Ltd.

  公开号：EP2843411A1

  公开（公告）日：2015-03-04

  Reagents and compositions for use in reactions catalyzed by luciferase enzymes, in particular by a recombinant luciferase which is a non-secreted derivative of a luciferase that is secreted in its native form, in particular for use in luciferase-based gene reporter assays are described. The invention also provides methods and compositions for, inter alia, increasing the sensitivity and/or improving the kinetics of luciferase-catalysed reactions.

  本发明描述了用于荧光素酶催化反应的试剂和组合物，特别是用于重组荧光素酶催化反应的试剂和组合物，重组荧光素酶是以原生形式分泌的荧光素酶的非分泌衍生物，特别是用于基于荧光素酶的基因报告检测。本发明还提供了除其他外提高荧光素酶催化反应灵敏度和/或改善其动力学的方法和组合物。
• DNA-directed alkylating agents. 4. 4-Anilinoquinoline-based minor groove directed aniline mustards
  作者：G. Lance Gravatt、Bruce C. Baguley、William R. Wilson、William A. Denny

  DOI：10.1021/jm00109a005

  日期：1991.5

  A series of 4-anilinoquinoline-linked aniline mustards of widely varying mustard reactivity were prepared and evaluated for their antitumor activity. The compounds were designed as minor groove binding agents, where the aniline mustard ring is itself part of the DNA-binding ligand. While there was a general trend for cytotoxicity to correlate with mustard reactivity, this was much less pronounced than with untargeted mustards. The compounds were much more cytotoxic than the parent diols, and were at least 10-fold more cytotoxic than the corresponding aniline mustards themselves. Comparative cell line studies suggested that the mechanism of cytotoxicity varied with mustard reactivity. The most reactive mustards cross-linked DNA, while cell killing by the less reactive compounds appeared to be by the formation of bulky monoadducts. The compounds were active but not particularly dose-potent against P388 leukemia in vivo. The modest potency may be related to their poor aqueous solubility, since the more soluble methyl quaternary salts were equally active at much lower doses.
• VALU, KISIONE K.;GOURDIE, TRUDI A.;BORITZKI, THEODORE J.;GRAVATT, G. LANC+, J. MED. CHEM., 33,(1990) N1, C. 3014-3019
  作者：VALU, KISIONE K.、GOURDIE, TRUDI A.、BORITZKI, THEODORE J.、GRAVATT, G. LANC+

  DOI：——

  日期：——
• GRAVATT, G. LANCE;BAGULEY, BRUCE C.;WILSON, WILLIAM R.;DENNY, WILLIAM A., J. MED. CHEM., 34,(1991) N, C. 1552-1560
  作者：GRAVATT, G. LANCE、BAGULEY, BRUCE C.、WILSON, WILLIAM R.、DENNY, WILLIAM A.

  DOI：——

  日期：——
• LUCIFERASE SIGNAL ENHANCNG COMPOSITIONS
  申请人：Gene Stream Pty Ltd.

  公开号：EP2087132A1

  公开（公告）日：2009-08-12