anthraquinone-1-sulfenic acid | 75507-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: anthraquinone-1-sulfenic acid
• 英文别名: 1-anthraquinonesulfenic acid；fries acid；Fries' acid；9,10-dioxo-9,10-dihydro-anthracene-1-sulfenic acid；9,10-Dioxo-9,10-dihydro-anthracen-1-sulfensaeure；anthraquinone sulfenic acid；1-Hydroxysulfanylanthracene-9,10-dione
• CAS: 75507-58-3
• 化学式: C₁₄H₈O₃S
• 分子量: 256.282
• InChiKey: QFMLJHOMYRVHEJ-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: benzene (71-43-2))
• 沸点：
  517.5±60.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  79.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  anthraquinone-1-sulfenic acid 在 间氯过氧苯甲酸 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 1-蒽醌磺酸
  参考文献：
  名称：

  Equilibrium and kinetic studies of some reactions of 1-anthraquinonesulfenic acid and its methyl ester

  摘要：

  DOI：

  10.1021/jo00278a038
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 氢氧化钾 作用下， 生成 anthraquinone-1-sulfenic acid
  参考文献：
  名称：

  Dornow, Chemische Berichte, 1939, vol. 72, p. 568

  摘要：

  DOI：

文献信息

• Strained Cycloalkynes as New Protein Sulfenic Acid Traps
  作者：Thomas H. Poole、Julie A. Reisz、Weiling Zhao、Leslie B. Poole、Cristina M. Furdui、S. Bruce King

  DOI：10.1021/ja500364r

  日期：2014.4.30

  probes that form covalent adducts with cysteine-derived protein sulfenic acids. As a mechanistic alternative, the present study describes highly strained bicyclo[6.1.0]nonyne (BCN) derivatives as concerted traps of sulfenic acids. These strained cycloalkynes react efficiently with sulfenic acids in proteins and small molecules yielding stable alkenyl sulfoxide products at rates more than 100× greater

  蛋白质次磺酸是通过生物相关的活性氧与蛋白质硫醇反应形成的。亚磺酸的形成直接或通过蛋白质二硫键的后续形成调节酶和转录因子的功能。确定蛋白质次磺酸形成的位点、时间和条件对于理解细胞氧化还原调节仍然至关重要。目前捕获和分析次磺酸的方法包括使用二甲酮和其他亲核 1,3-二羰基探针，它们与半胱氨酸衍生的蛋白质次磺酸形成共价加合物。作为一种机械替代方法，本研究将高度应变的双环 [6.1.0] 壬炔 (BCN) 衍生物描述为次磺酸的协同陷阱。这些紧张的环炔烃与蛋白质和小分子中的次磺酸有效反应，以比 1,3-二羰基试剂高 100 倍以上的速率产生稳定的烯基亚砜产物，从而实现与生理硫化学的动力学竞争。与 1,3-二羰基试剂类似，BCN 化合物将次磺酸氧仿与硫醇、二硫化物、亚磺酸和 S-亚硝化形式的半胱氨酸区分开来，同时显示出可接受的细胞毒性特征。这些紧张的炔烃证明的提高的速率将它们鉴定为新的生物正交探针，应
• [EN] A METHOD FOR PREPARING SULFUR-CONTAINING COMPOUNDS<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE COMPOSÉS CONTENANT DU SOUFRE
  申请人：ROYAL COLLEGE OF SURGEONS IE

  公开号：WO2010066450A1

  公开（公告）日：2010-06-17

  The invention provides a method for preparing sulfur-containing compounds, the method comprising reacting a donor compound comprising at least one sulfur having at least one lone pair of electrons, with an acceptor compound; wherein the reaction occurs in the presence of an amine, optionally an amine catalyst, capable of activating the sulfur having at least one lone pair of electrons; and wherein the reaction occurs via the formation of an transient intermediate species, optionally a transient intermediate species, between the amine, optionally the amine catalyst and the donor compound; and wherein the donor compound is selected from the group consisting of a sulfurous acid, a sulfenic acid and a sulfinic acid or a salt, ester or amide of a sulfurous acid, a sulfenic acid and a sulfinic acid. The invention also provides sulfur-containing compounds of the formula: wherein R is selected from: (a) 1 -(4-Nitro-phenyl)-3-oxo-3-phenyl-propane; (b) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1 -phenyl-ethane; (c) 1-(4-Methoxy-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (d) 2-(3-Methyl-4-nitro-isoxazol-5-yl)-1-(4-nitro-phenyl)-ethane; (e) 1-(4-Fluoro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; (f) 1 -(4-Chloro-phenyl)-2-(3-methyl-4-nitro-isoxazol-5-yl)-ethane; and (g) 3-Oxo-cyclohexane. Finally, the invention provides use of chiral sulfur-containing compounds obtainable by the above-mentioned method or chiral sulfur-containing compounds as mentioned above for the resolution of racemic mixtures of amines.

  该发明提供了一种制备含硫化合物的方法，该方法包括将包含至少一个硫原子且至少一个孤对电子的给体化合物与受体化合物反应；其中，在胺的存在下进行反应，可选地，在能够激活至少一个硫原子具有至少一个孤对电子的胺的存在下进行反应；反应通过形成瞬态中间体物种进行，可选地，通过胺、可选地胺催化剂和给体化合物之间的瞬态中间体物种进行反应；给体化合物选自包括亚硫酸、亚硫酸和亚砜酸或亚硫酸、亚硫酸和亚砜酸的盐、酯或酰胺的群；该发明还提供了符合以下公式的含硫化合物：其中R选自：(a) 1-(4-硝基苯基)-3-氧代-3-苯基-丙烷；(b) 2-(3-甲基-4-硝基异噁唑-5-基)-1-苯基-乙烷；(c) 1-(4-甲氧基苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(d) 2-(3-甲基-4-硝基异噁唑-5-基)-1-(4-硝基苯基)-乙烷；(e) 1-(4-氟苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；(f) 1-(4-氯苯基)-2-(3-甲基-4-硝基异噁唑-5-基)-乙烷；和(g) 3-氧代环己烷。最后，该发明提供了通过上述方法获得的手性含硫化合物或上述提到的手性含硫化合物用于分离胺的外消旋混合物。
• [EN] BORONIC AND BORINIC ACID COMPOUNDS AS INHIBITORS OF SULFENIC ACID-CONTAINING PROTEINS<br/>[FR] COMPOSÉS ACIDE BORONIQUE ET BORINIQUE EN TANT QU'INHIBITEURS DE PROTÉINES CONTENANT UN ACIDE SULFÉNIQUE
  申请人：PENN STATE RES FOUND

  公开号：WO2014084944A1

  公开（公告）日：2014-06-05

  A boronic or borinic acid compound is used to inhibit the activity of a sulfenic acid-containing protein. Thus, a biologically-active sulfenic acid-containing protein is contacted with an activity-inhibiting effective amount of a boronic or borinic acid compound of Formula (I) or a salt, hydrate or solvate thereof, whose components are disclosed within, and that contact is maintained for a time sufficient to inhibit the biological activity of the protein.

  硼酸或硼酸酯化合物被用于抑制含有砜酸的蛋白质的活性。因此，与一定量的化合物(I)的硼酸或硼酸酯或其盐、水合物或溶剂化合物接触，其中其组分在其中披露，并且此接触维持足够长的时间以抑制蛋白质的生物活性。
• Aromatic sulfenates for type I phototherapy
  申请人：MALLINCKRODT INC.

  公开号：US20030158127A1

  公开（公告）日：2003-08-21

  The present invention discloses novel sulfenate derivatives and their bioconjugates for phototherapy of tumors and other lesions. The sulfenates of the present invention are designed to absorb low-energy ultraviolet, visible, or near-infrared (NIR) region of the electromagnetic spectrum. The phototherapeutic effect is caused by direct interaction of free radicals, the reactive intermediate produced upon photofragmentation of the sulfenate moiety, with the tissue of interest.

  本发明公开了用于肿瘤和其他病变光疗的新型亚磺酸盐衍生物及其生物结合剂。本发明的亚硫酸盐可吸收电磁波谱中的低能量紫外线、可见光或近红外（NIR）区域。光疗效果是由自由基（亚磺酸盐分子光碎裂时产生的活性中间体）与相关组织的直接相互作用引起的。
• Capturing a Sulfenic Acid with Arylboronic Acids and Benzoxaborole
  作者：C. Tony Liu、Stephen J. Benkovic

  DOI：10.1021/ja407628a

  日期：2013.10.2

  Post-translational redox generation of cysteine-sulfenic acids (Cys-SOH) functions as an important reversible regulatory mechanism for many biological functions, such as signal transduction, balancing cellular redox states, catalysis, and gene transcription. Herein we show that arylboronic acid's and cyclic benzoxaboroles can form adducts with sulfenic acids in aqueous medium and that these boron based compounds can potentially be used to trap biologically significant sulfenic acids. As proof of principle we demonstrate that a benzoxaborole can inhibit the enzyme activity of an iron-containing nitrile hydratase, which requires a catalytic alpha Cys114-SOH in the active site The nature of the adduct and the effect of the boronic acid's pK(a)(B) on the stability constant of the adduct are discussed within.