3,4-bis(butylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione | 40428-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3,4-bis(butylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione
• 英文别名: 3,4-dibutylthiomaleimide；2,3-Bis-(n-butylmercapto)-maleinimid；3,4-bis-butylsulfanyl-pyrrole-2,5-dione；3,4-Bis(butylsulfanyl)pyrrole-2,5-dione
• CAS: 40428-09-9
• 化学式: C₁₂H₁₉NO₂S₂
• 分子量: 273.42
• InChiKey: RVHHRIDCCNMZBU-UHFFFAOYSA-N

物化性质

• 沸点：
  384.0±42.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-bis(butylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione 在 三乙基硼 、 三乙胺 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 25.5h， 生成 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-{14-[3,4-bis(butylthio)-2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl]-3,6,9,12-tetraoxatetradecylthio}tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  通过光诱导和 BEt3 引发的硫点击反应将生物活性分子与荧光二硫代马来酰亚胺结合

  摘要：

  研究了自由基硫醇 - 烯加成的两种形式、在 2,2-二甲氧基-2-苯基苯乙酮存在下的光诱导反应和使用三乙基硼烷作为引发剂的无紫外线氢硫醇化反应，用于荧光的共轭。二硫代马来酰亚胺转化为生物活性化合物。制备带有乙烯基醚官能团的二硫代马来酰亚胺衍生物作为烯烃伙伴。这与一系列硫醇结合使用，包括硫糖、卡托普利、N-乙酰基-L-半胱氨酸和 2-磺基乙硫醇钠。Et3B 引发的方法优于光诱导反应，因为它最大限度地减少了敏感马来酰亚胺基团的分解。乙烯基醚衍生物和加成产物在四氢呋喃中发出绿光。这些化合物都显示出几乎相同的吸收和发射光谱，证明硫醇的结构对分子马来酰亚胺部分的荧光性质没有影响。氢硫醇化产物显示出相对较高的量子产率。

  DOI：

  10.1002/ejoc.201501116
• 作为产物：
  描述：

  3,4-二溴-1H-吡咯-2,5-二酮 、 丁硫醇 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 3,4-bis(butylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  亲脂性替考拉宁假糖苷配基衍生物作为新型抗流感病毒药物的构效关系研究

  摘要：

  评价了六种系列的半合成亲脂糖肽抗生素衍生物对甲型和乙型流感病毒的体外活性。通过使用多种缀合方法，通过将一个或两个侧链偶联至糖肽核心的N-末端来制备新的替考拉宁假糖苷配基衍生的脂糖肽。通过将双烷硫基马来酰亚胺直接或通过不同长度的连接基连接到糖肽上，合成了带有两个亲脂基团的三个系列衍生物。通过点击化学，直接或通过四甘醇接头将单烷基/芳基链引入相同位置，即可获得第四和第五系列化合物。第六类半合成衍生物是通过磺酰化的方式获得的。N末端。在测试的42种亲脂性替考拉宁假糖苷配基衍生物中，约有一半显示出对A和B型流感病毒的广泛活性，其中一些具有合理的或没有细胞毒性。侧链长度和亲脂性的微小差异似乎对抗病毒活性和细胞毒性具有重大影响。还发现了几种脂糖肽对人冠状病毒具有活性。

  DOI：

  10.1016/j.ejmech.2018.08.058

文献信息

• Conjugation-Induced Fluorescent Labeling of Proteins and Polymers Using Dithiomaleimides
  作者：Mathew P. Robin、Paul Wilson、Anne B. Mabire、Jenny K. Kiviaho、Jeffery E. Raymond、David M. Haddleton、Rachel K. O’Reilly

  DOI：10.1021/ja3105494

  日期：2013.2.27

  Dithiomaleimides (DTMs) with alkyl substituents are shown to be a novel class of highly emissive fluorophores. Variable solubility and further functionalization can easily be tailored through the choice of N and S substituents. Inclusion of a DTM unit into a ROP/RAFT initiator or insertion into the disulfide bond of salmon calcitonin (sCT) demonstrates the utility for fluorescent labeling of polymers and proteins. Simultaneous PEGylation and fluorescent labeling of sCT is also demonstrated, using the DTM unit as both a linker and a fluorophore. It is anticipated that DTMs will offer an attractive alternative to commonly used bulky, planar fluorophores.
• New Functional Handle for Use as a Self-Reporting Contrast and Delivery Agent in Nanomedicine
  作者：Mathew P. Robin、Anne B. Mabire、Joanne C. Damborsky、Elizabeth S. Thom、Ursula H. Winzer-Serhan、Jeffery E. Raymond、Rachel K. O’Reilly

  DOI：10.1021/ja403587c

  日期：2013.6.26

  The synthesis and photophysical characterization of a chromophore-bridged block copolymer system is presented. This system is based on a dithiomaleimide (DTM) functional group as a highly emissive functionality which can readily be incorporated into polymeric scaffolds. A key advantage of this new reporter group is its versatile chemistry, ease of further functionalization, and notably small size, which allows for ready incorporation without affecting or disrupting the self-assembly process critical to the formation of core shell polymeric contrast and drug delivery agents. We demonstrate the potential of this functionality with a diblock system which has been shown to be appropriate for micellization and, when in the micellar state, does not self quench The block copolymer is shown to be significantly more emissive than the lone dye, with a concentration independent emission and anisotropy profile from 1.5 mM to 0.15 mu M. An emission lifetime and anisotropy decay comparison of the block copolymer to its micelle displays that time-domain fluorescence lifetime imaging (FLIM) is able to rapidly resolve differences in the supramolecular state of this block dye block polymer system. Furthermore, the ability to resolve these differences in the supramolecular state means that the DTM micelles are capable of self reporting when disassembly occurs, simply by monitoring with FLIM. We demonstrate the great potential for in vitro applications that this system provides: by using :FLIM to Observe micelle disassembly in different vascular components of rat hippocampal tissue. In total this system represents a new class of in chain emitter which is appropriate for application in quantitative imaging and the tracking of particle degradation/disassembly events in biological environments.