2-imidazolylcarbonyloxyethyl disulfide | 877865-61-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-imidazolylcarbonyloxyethyl disulfide
• 英文别名: dithio-bis(ethyl 1H-imidazole-1-carboxylate)；2-[2-(Imidazole-1-carbonyloxy)ethyldisulfanyl]ethyl imidazole-1-carboxylate
• CAS: 877865-61-7
• 化学式: C₁₂H₁₄N₄O₄S₂
• 分子量: 342.4
• InChiKey: WMLXLTRMYZQNLJ-UHFFFAOYSA-N

物化性质

• 沸点：
  542.6±60.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  139
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-imidazolylcarbonyloxyethyl disulfide 、 加巴喷丁 在 碳酸氢钠 、 盐酸 作用下， 以 水 、 乙腈 为溶剂， 反应 72.0h， 以65%的产率得到2-[1-[[2-[2-[[1-(Carboxymethyl)cyclohexyl]methylcarbamoyloxy]ethyldisulfanyl]ethoxycarbonylamino]methyl]cyclohexyl]acetic acid
  参考文献：
  名称：

  Prodrugs containing novel bio-cleavable linkers

  摘要：

  本发明提供了公式(I)的化合物或其药用可接受的盐。本发明还提供了包含一个或多个公式I的化合物或其中间体以及一个或多个药用可接受的载体、车辆或稀释剂的药物组合物。本发明进一步提供了包括制备方法和使用方法在内的前药，包括释放一氧化氮的前药、双前药和相互前药，由公式I的化合物组成。

  公开号：

  US20060046967A1
• 作为产物：
  描述：

  2-羟乙基二硫化物 、 N,N'-羰基二咪唑 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-imidazolylcarbonyloxyethyl disulfide
  参考文献：
  名称：

  SYNTHESIS OF MORPHOLINO OLIGOMERS USING DOUBLY PROTECTED GUANINE MORPHOLINO SUBUNITS

  摘要：

  Morpholino化合物具有以下结构： 其中 R1选自由较低烷基、二(较低烷基)氨基和苯基组成的群体； R2选自由较低烷基、单环芳基甲基和单环(芳氧基)甲基组成的群体； R3选自由三芳基甲基和氢原子组成的群体；以及 Y选自由受保护或未受保护的羟基或氨基团；氯磷酰胺基团；以及与另一种morpholino化合物或morpholino寡聚体的环氮原子形成磷酰二胺酸酯键的群体。这类化合物包括双保护的morpholino鸟嘌呤（MoG）单体。还描述了它们在morpholino寡聚体合成中的用途。

  公开号：

  US20090131624A1

文献信息

• [EN] NANOPARTICLE, LIPOSOMES, POLYMERS, AGENTS AND PROTEINS MODIFIED WITH REVERSIBLE LINKERS<br/>[FR] NANOPARTICULES, LIPOSOMES, POLYMÈRES, AGENTS ET PROTÉINES MODIFIÉS AVEC DES LIEURS RÉVERSIBLES
  申请人：UNIV NORTH CAROLINA

  公开号：WO2012112689A1

  公开（公告）日：2012-08-23

  Pharmaceutical, chemical and biological agents containing a reversible disulfide linker are described. These agents can also be covalently bound or contained in delivery vehicles for delivering the agents to desired targets or areas. Also described are delivery vehicles which contain an agent having a reversible disulfide linker and to vehicles that are covalently linked to the agent containing a reversible disulfide linker. The modifications described herein can modify properties of the agents and vehicles, thereby providing desired solubility, stability, hydrophobicity and targeting while the reversibility of the linker can leave the agent to which it is attached free from residual chemical groups after being reduced.

  描述了含有可逆二硫键的药物、化学物质和生物制剂。这些制剂也可以共价结合或包含在传递载体中，以将制剂传递到所需的靶标或区域。还描述了含有可逆二硫键的制剂的传递载体，以及与含有可逆二硫键的制剂共价结合的载体。本文描述的修饰可以改变制剂和载体的性质，从而提供所需的溶解性、稳定性、疏水性和靶向性，而连接物的可逆性可以使其附着的制剂在还原后不受残留化学基团的影响。
• NANOPARTICLE, LIPOSOMES, POLYMERS, AGENTS AND PROTEINS MODIFIED WITH REVERSIBLE LINKERS
  申请人：DeSimone Joseph M.

  公开号：US20140081012A1

  公开（公告）日：2014-03-20

  Pharmaceutical, chemical and biological agents containing a reversible disulfide linker are described. These agents can also be covalently bound or contained in delivery vehicles for delivering the agents to desired targets or areas. Also described are delivery vehicles which contain an agent having a reversible disulfide linker and to vehicles that are covalently linked to the agent containing a reversible disulfide linker. The modifications described herein can modify properties of the agents and vehicles, thereby providing desired solubility, stability, hydrophobicity and targeting while the reversibility of the linker can leave the agent to which it is attached free from residual chemical groups after being reduced.

  本文描述了含有可逆二硫键连接剂的制药、化学和生物制剂。这些制剂也可以共价结合或包含在传递载体中，以将制剂传递到所需的目标或区域。还描述了包含具有可逆二硫键连接剂的制剂的传递载体，以及与含有可逆二硫键连接剂的制剂共价链接的载体。本文所描述的修饰可以修改制剂和载体的性质，从而提供所需的溶解度、稳定性、疏水性和定向性，而连接剂的可逆性可以使其附着的制剂在还原后不留下残留的化学基团。
• Rendering Protein-Based Particles Transiently Insoluble for Therapeutic Applications
  作者：Jing Xu、Jin Wang、J. Christopher Luft、Shaomin Tian、Gary Owens、Ashish A. Pandya、Peter Berglund、Patrick Pohlhaus、Benjamin W. Maynor、Jonathan Smith、Bolyn Hubby、Mary E. Napier、Joseph M. DeSimone

  DOI：10.1021/ja302363r

  日期：2012.5.30

  Herein, we report the fabrication of protein (bovine serum albumin, BSA) particles which were rendered transiently insoluble using a novel, reductively labile disulfide-based cross-linker. After being cross-linked, the protein particles retain their integrity in aqueous solution and dissolve preferentially under a reducing environment. Our data demonstrates that cleavage of the cross-linker leaves no chemical residue on the reactive amino group. Delivery of a self-replicating RNA was achieved via the transiently insoluble PRINT protein particles. These protein particles can provide new opportunities for drug and gene delivery.
• Self-Immolative Polycations as Gene Delivery Vectors and Prodrugs Targeting Polyamine Metabolism in Cancer
  作者：Yu Zhu、Jing Li、Shrey Kanvinde、Zhiyi Lin、Stuart Hazeldine、Rakesh K. Singh、David Oupický

  DOI：10.1021/mp500469n

  日期：2015.2.2

  Polycations are explored as carriers to deliver therapeutic nucleic acids. Polycations are conventionally pharmacological inert with the sole function of delivering therapeutic cargo. This study reports synthesis of a self-immolative polycation (DSS-BEN) based on a polyamine analogue drug N-1,N-11-bisethylnorspermine (BENSpm). The polycation was designed to function dually as a gene delivery carrier and a prodrug targeting dysregulated polyamine metabolism in cancer. Using a combination of NMR and HPLC, we confirm that the self-immolative polycation undergoes intracellular degradation into the parent drug BENSpm. The released BENSpm depletes cellular levels of spermidine and spermine and upregulates polyamine catabolic enzymes spermine/spermidine N-1-acetyltransferase (SSAT) and spermine oxidase (SMO). The synthesized polycations form polyplexes with DNA and facilitate efficient transfection. Taking advantage of the ability of BENSpm to sensitize cancer cells to TNF alpha-induced apoptosis, we show that DSS-BEN enhances the cell killing activity of TNF alpha gene therapy. The reported findings validate DSS-BEN as a dual-function delivery system that can deliver a therapeutic gene and improve the outcome of gene therapy as a result of the intracellular degradation of DSS-BEN to BENSpm and the subsequent beneficial effect of BENSpm on dysregulated polyamine metabolism in cancer.
• [EN] REVERSIBLE FIXING REAGENTS AND METHODS OF USE THEREOF<br/>[FR] RÉACTIFS DE FIXATION RÉVERSIBLES ET LEURS MÉTHODES D'UTILISATION
  申请人：10X GENOMICS INC

  公开号：WO2021133845A1

  公开（公告）日：2021-07-01

  The present disclosure relates to compositions and methods for reversible fixation of biological samples using fixation reagents that form bis-carbamate crosslinks between amine-bearing moieties in biomolecules.