3-(pyridin-2-yldisulfanyl)propyl 2-bromo-2-methylpropanoate | 817208-79-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 3-(pyridin-2-yldisulfanyl)propyl 2-bromo-2-methylpropanoate
• 英文别名: propyl-mercaptopyridine 2-bromoisobutyrate
• CAS: 817208-79-0
• 化学式: C₁₂H₁₆BrNO₂S₂
• 分子量: 350.301
• InChiKey: KOKKLHWCHXEEIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  425.2±43.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-溴-2-甲基丙酸 、 3-(pyridin-2-yldisulfanyl)propan-1-ol 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 3-(pyridin-2-yldisulfanyl)propyl 2-bromo-2-methylpropanoate
  参考文献：
  名称：

  Triblock Terpolymers Bearing a Redox-Cleavable Junction and a Photo-Cross-Linkable Block

  摘要：

  Two linear triblock terpolymers were synthesized and used to coat cotton textiles. These copolymers consist in sequence of a water-soluble poly(ethylene glycol) (PEG) block, a highly water- and oil-repellant poly[2-(perfluorooctyl)ethyl methacrylate] (PFOEMA) block, and a photo-cross-linkable poly(2-cinnamoyloxyethyl methacrylate) (PCEMA) block. The PEG block bonds to PFOEMA via a redox-cleavable disulfide junction (-S-2-). To prepare the copolymers, monomethoxy PEG (PEG-OH) was derivatized to yield a PEG chain bearing one terminal thiol group (PEG-SH). Atom transfer radical polymerization and deprotection chemistry were used to prepare Py-S-2-PFOEMA-b-PHEMA, where PHEMA and Py-S-2- denote poly(2-hydroxyethyl methacrylate) and a terminal pyridin-2-yldisulfanyl group, respectively. Reacting PEG-SH with Py-S-2-PFOEMA-b-PHEMA via a thiol disulfide exchange reaction yielded PEG-S-2-PFOEMA-b-PHEMA, and the cinnamation of the PHEMA block produced PEG-S-2-PFOEMA-b-PCEMA. PEG-S-2-PFOEMA-b-PCEMA dispersed in water and plasticized by a trace amount of dimethyl phthalate was then used to coat cotton textiles, and this coating was secured by photo-cross-linking the PCEMA domains. Treating the coating with dithiothreitol cleft the disulfide junction and thus the PEG block, revealing the hidden PFOEMA block and its water- and oil-repellant properties. Aqueous solutions of these copolymers could thus be applied onto a substrate to provide amphiphobic coatings.

  DOI：

  10.1021/ma501219h

文献信息

• Biomacromolecule Polymer Conjugates
  申请人：Maynard D. Heather

  公开号：US20070276088A1

  公开（公告）日：2007-11-29

  Chemical polymerization procedures initiated by, and proceeding from, a biomolecule, particularly a protein, for the formation of biomolecule-polymer conjugates, particularly protein-polymer conjugates, which have therapeutic uses, are intermediates for forming other materials or are usable in diagnostic sensors are disclosed. Polymerization can be initiated by a protein in the absence of additional initiation agents to form the protein-polymer conjugate. Alternatively, polymerization is initiated in the presence of an additional initiation agent that does not interact with the protein. Amino acids existing in the protein can serve as the sites for initiation of the polymerization or the protein can be modified to contain site(s) for initiation or protein with active sites can be prepared by recombinant methods, chemical ligation, solid-phase synthesis, or other techniques to generate site(s) for initiation.

  本发明揭示了由生物分子，特别是蛋白质，引发和进行的化学聚合程序，用于形成生物分子-聚合物共轭物，特别是蛋白质-聚合物共轭物，这些共轭物具有治疗用途，是形成其他材料的中间体或可用于诊断传感器。聚合可以在无需额外引发剂的情况下由蛋白质引发，形成蛋白质-聚合物共轭物。或者，在引发剂存在的情况下，可以引发聚合，该引发剂不与蛋白质相互作用。蛋白质中存在的氨基酸可以作为聚合的起始位点，或者可以修改蛋白质以包含起始位点，或者可以通过重组方法、化学连接、固相合成或其他技术制备具有活性位点的蛋白质，以生成起始位点。
• Multi-Functional Nano-Device
  申请人：McCarthy Patrick

  公开号：US20110286935A1

  公开（公告）日：2011-11-24

  A universal drug delivery platform for monoclonal antibody-based therapeutics is described. This universal platform resolves the problems of immunogenic response associated with the present monoclonal antibody based therapeutics by providing a multifunctional nano-device which comprises a well defined core/shell nano-structure that can function as a drug delivery platform linked to a monoclonal antibody through a single linking group.

  本文描述了一种单克隆抗体治疗的通用药物传递平台。这个通用平台通过提供一个多功能纳米器件来解决目前单克隆抗体治疗所涉及的免疫原性反应问题，该纳米器件包括一个明确定义的核/壳纳米结构，可以通过单个连接基团连接到单克隆抗体，作为药物传递平台。
• [EN] BIOMACROMOLECULE POLYMER CONJUGATES<br/>[FR] CONJUGUES POLYMERES BIOMACROMOLECULAIRES
  申请人：UNIV CALIFORNIA

  公开号：WO2005039641A3

  公开（公告）日：2006-05-26
• Cysteine-Reactive Polymers Synthesized by Atom Transfer Radical Polymerization for Conjugation to Proteins
  作者：Debora Bontempo、Karina L. Heredia、Benjamin A. Fish、Heather D. Maynard

  DOI：10.1021/ja045063m

  日期：2004.12.1

  In this communication we report a strategy for the synthesis of semitelechelic polymers reactive to cysteines. An initiator modified with a pyridyl disulfide was prepared and used for the CuBr/2,2'-bipyridine-mediated atom transfer radical polymerization (ATRP) of 2-hydroxyethyl methacrylate. Polydispersity indices (M(w)/M(n)) of the polymers with different molecular weights were 1.25 or less. The pyridyl disulfide end group was preserved during the polymerization and allowed direct conjugation of the polymer to cysteine residues of bovine serum albumin. The described method provides a general way for the preparation of protein-polymer conjugates through a reversible disulfide bond without the need for postsynthesis modification of the polymers.
• Triblock Terpolymers Bearing a Redox-Cleavable Junction and a Photo-Cross-Linkable Block
  作者：Muhammad Rabnawaz、Guojun Liu

  DOI：10.1021/ma501219h

  日期：2014.8.12

  Two linear triblock terpolymers were synthesized and used to coat cotton textiles. These copolymers consist in sequence of a water-soluble poly(ethylene glycol) (PEG) block, a highly water- and oil-repellant poly[2-(perfluorooctyl)ethyl methacrylate] (PFOEMA) block, and a photo-cross-linkable poly(2-cinnamoyloxyethyl methacrylate) (PCEMA) block. The PEG block bonds to PFOEMA via a redox-cleavable disulfide junction (-S-2-). To prepare the copolymers, monomethoxy PEG (PEG-OH) was derivatized to yield a PEG chain bearing one terminal thiol group (PEG-SH). Atom transfer radical polymerization and deprotection chemistry were used to prepare Py-S-2-PFOEMA-b-PHEMA, where PHEMA and Py-S-2- denote poly(2-hydroxyethyl methacrylate) and a terminal pyridin-2-yldisulfanyl group, respectively. Reacting PEG-SH with Py-S-2-PFOEMA-b-PHEMA via a thiol disulfide exchange reaction yielded PEG-S-2-PFOEMA-b-PHEMA, and the cinnamation of the PHEMA block produced PEG-S-2-PFOEMA-b-PCEMA. PEG-S-2-PFOEMA-b-PCEMA dispersed in water and plasticized by a trace amount of dimethyl phthalate was then used to coat cotton textiles, and this coating was secured by photo-cross-linking the PCEMA domains. Treating the coating with dithiothreitol cleft the disulfide junction and thus the PEG block, revealing the hidden PFOEMA block and its water- and oil-repellant properties. Aqueous solutions of these copolymers could thus be applied onto a substrate to provide amphiphobic coatings.