5-nitro-3H-benzo[c][1,2]dithiol-3-one | 1609395-17-6

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 5-nitro-3H-benzo[c][1,2]dithiol-3-one
• 英文别名: 5-Nitro-1,2-benzodithiol-3-one；5-nitro-1,2-benzodithiol-3-one
• CAS: 1609395-17-6
• 化学式: C₇H₃NO₃S₂
• 分子量: 213.238
• InChiKey: CIHZZWXQJMYZAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  60.21
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  在 sodium disulfide 作用下， 以 aq. phosphate buffer 、 乙腈 为溶剂， 反应 2.0h， 以89%的产率得到5-nitro-3H-benzo[c][1,2]dithiol-3-one
  参考文献：
  名称：

  Rational Design and Bioimaging Applications of Highly Selective Fluorescence Probes for Hydrogen Polysulfides

  摘要：

  Reactive sulfur species have received considerable attention due to their various biological functions. Among these molecules, hydrogen polysulfides (H2Sn, n > 1) are recently suggested to be the actual signaling molecules derived from hydrogen sulfide (H2S). Hydrogen polysulfides may also have their own biosynthetic pathways. The research on H2Sn is rapidly growing. However, the detection of H2Sn is still challenging. In this work we report a H2Sn-mediated benzodithiolone formation under mild conditions. Based on this reaction, specific fluorescent probes for H2Sn are prepared and evaluated. The probe DSP-3 shows good selectivity and sensitivity for H2Sn.

  DOI：

  10.1021/ja502968x

文献信息

• Real-time monitoring of a photoactivated hydrogen persulfide donor for biological entities
  作者：Amrita Chaudhuri、Yarra Venkatesh、Bikash Chandra Jena、Krishna Kalyani Behara、Mahitosh Mandal、N. D. Pradeep Singh

  DOI：10.1039/c9ob01982k

  日期：——

  Hydrogen persulfide (H2S2) plays an important role in sulfur-based redox signaling mechanisms. Herein, we developed a visible light activated ESIPT based H2S2 donor using a p-hydroxyphenacyl phototrigger. The unique feature of the designed H2S2 donor system is the ability to monitor the H2S2 release in real time through a non-invasive fluorescence color change approach, with the color changing from

  过硫化氢（H2S2）在基于硫的氧化还原信号机制中起重要作用。在本文中，我们开发了使用对羟基苯甲酰光触发的可见光活化的基于ESIPT的H2S2供体。设计的H2S2供体系统的独特功能是能够通过无创荧光变色方法实时监控H2S2释放，颜色从绿色变为蓝色。接下来，我们展示了使用基于荧光素的“开启”荧光探针对H2S2的检测和定量。此外，对设计的H2S2供体的体外研究表明，在MDA-MB-468细胞高度氧化的细胞环境中，可以实时监测H2S2的释放和细胞保护能力。
• Acyl Selenyl Sulfides as the Precursors for Reactive Sulfur Species (Hydrogen Sulfide, Polysulfide, and Selenyl Sulfide)
  作者：Akil Hamsath、Yingying Wang、Chun-tao Yang、Shi Xu、Danica Cañedo、Wei Chen、Ming Xian

  DOI：10.1021/acs.orglett.9b02021

  日期：2019.7.19

  Persulfides are receiving increased attention due to their links to hydrogen sulfide (H2S) and hydrogen polysulfide (H2Sn). Their close analogues selenyl sulfides (RSeSHs), however, have limited literature precedent, and their reactivity and possible role in biology are largely unknown. Here, we devised an acyl selenyl sulfide template to study RSeSH chemistry. Their stability and reactivity toward amines/thiols

  由于过硫化物与硫化氢（H 2 S）和多硫化氢（H 2 S n）的联系，因此受到越来越多的关注。然而，它们的紧密类似物硒烯硫化物（RSeSHs）的文献报道有限，而且它们的反应性和在生物学中的可能作用在很大程度上尚不清楚。在这里，我们设计了一个酰基硒基硫醚模板来研究RSeSH化学。研究了它们对胺/硫醇的稳定性和反应性。这些化合物可在不同条件下产生H 2 S或H 2 S 2，表明RSeSH是可能的中间体。
• Rational design of a lysosomal-targeted ratiometric two-photon fluorescent probe for imaging hydrogen polysulfides in live cells
  作者：Qingxin Han、Xuan Liu、Xuechuan Wang、Ruojun Yin、Huie Jiang、Jiaxi Ru、Weisheng Liu

  DOI：10.1016/j.dyepig.2019.107877

  日期：2020.2

  transducer. But fluorescent probes for rapid, sensitive, and selective detecting of H2Sn are still lacking, above all the lysosomal-targeted ones. In this work, by integrating the alkylmorpholine group and 2-fluoro-5-nitrobenzoyl- group into the molecular structure of 1,8-naphthalimide based fluorophore, a new lysosome-targetable ratiometric two-photon fluorescent probe for H2Sn has been designed and synthesized

  多硫化氢（H 2 S n，n> 1）在与H 2 S相关的生理功能和病理过程中起着重要作用，H 2 S 2被认为是新发现的强信号转导者。但是，仍然缺乏用于快速，灵敏和选择性检测H 2 S n的荧光探针，尤其是针对溶酶体的探针。在这项工作中，通过将烷基吗啉基团和2-氟-5-硝基苯甲酰基团整合到基于1,8-萘二甲酰亚胺的荧光团的分子结构中，一种用于H 2 S n的新型溶酶体靶向比例式双光子荧光探针已经设计和合成。探针表现出良好的稳定性，响应时间短（5分钟），高的选择性和灵敏度（LOD = 10纳米），线性范围宽（0-25μM），可佩双光子吸收截面（Φ最大 = 324 GM），良好的膜渗透性和生物相容性，以及溶酶体靶向能力。此外，这项工作为溶酶体H 2 S n的检测和成像提供了一种有前途的方法，因此有可能在H 2 S n相关的生物学和病理学研究中应用。
• Visualization of hydrogen polysulfides in living cells and in vivo via a near-infrared fluorescent probe
  作者：Xiaoqing Wang、Qian Sun、Liming Zhao、Shuwen Gong、Li Xu

  DOI：10.1007/s00775-019-01718-6

  日期：2019.10

  Hydrogen polysulfides (H2Sn, n > 1), as the oxidized forms of H2S, have attracted increasing attention these years due to their involvement in signaling transduction and cytoprotective processes. It is necessary to detect H2Sn in living systems for the study of their functions. In this work, we report a BODIPY-based near-infrared emitting fluorescence probe NIR-PHS1, with "turn-on" response, rapid

  作为硫化氢的氧化形式，多硫化氢（H2Sn，n> 1）由于近年来参与信号转导和细胞保护过程而受到越来越多的关注。有必要在生命系统中检测 ，以研究其功能。在这项工作中，我们报告了基于BODIPY的近红外发射荧光探针NIR-PHS1，具有“开启”响应，快速响应速率（在10分钟内），出色的选择性和出色的灵敏度（检测限= 12 nM）响应朝向 。该探针已成功应用于可视化活细胞中的内源性 。此外，它可用于活小鼠中 的近红外体内成像。因此，NIR-PHS1可能是研究 在生命系统中的生物学作用的潜在成像工具。
• An isophorone-based far-red emitting ratiometric fluorescent probe for selective sensing and imaging of polysulfides
  作者：Liming Zhao、Qian Sun、Chuanzhi Sun、Changli Zhang、Wenzeng Duan、Shuwen Gong、Zhipeng Liu

  DOI：10.1039/c8tb01813h

  日期：——

  Therefore, accurate detection of H2Sn levels in living systems is of great significance. In this study, we report an isophorone-based far-red emitting fluorescent probe (RPHS1) for selective ratiometric sensing and imaging of H2Sn. RPHS1 shows specific ratiometric response towards H2Sn with fast reaction rate and low detection limit in aqueous media. Furthermore, confocal fluorescence microscopy experiments

  最近的研究表明，作为活性硫物种家族和H 2 S的氧化形式的成员，多硫化氢（H 2 S n）在生理和病理过程中起着重要的作用。因此，准确检测生命系统中H 2 S n的含量具有重要意义。在这项研究中，我们报告了基于异佛尔酮的远红光发射荧光探针（RPHS1），用于H 2 S n的选择性比率传感和成像。RPHS1显示出对H 2 S n的特定比例响应反应速度快，在水性介质中的检出限低。此外，共聚焦荧光显微镜实验表明，RPHS1可用于活细胞中的H 2 S n成像。