3,4-bis(phenylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione | 32774-53-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,4-bis(phenylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione
• 英文别名: 3,4-dithiophenolmaleimide；3,4-bis-phenylsulfanyl-pyrrole-2,5-dione；dithiophenolmaleimide；2,3-Bis-(phenylmercapto)-maleinimid；Bis(phenylsulfanyl)maleimide；3,4-bis(phenylsulfanyl)pyrrole-2,5-dione
• CAS: 32774-53-1
• 化学式: C₁₆H₁₁NO₂S₂
• 分子量: 313.401
• InChiKey: FOZQRPUQSWGWSE-UHFFFAOYSA-N

物化性质

• 熔点：
  123-126 °C
• 沸点：
  462.0±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 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(phenylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione 在 N-甲基吗啉 、 三乙胺 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 4.5h， 生成 N-benzyl-3,4-dithiophenolmaleimide
  参考文献：
  名称：

  A mild synthesis of N-functionalised bromomaleimides, thiomaleimides and bromopyridazinediones

  摘要：

  Bromomaleimides are useful building blocks in synthesis and powerful reagents for the selective chemical modification of proteins. A mild new synthesis of these reagents is described, along with the convenient transferability of the approach to dithiomaleimides and bromopyridazinediones. (c) 2013 The Authors. Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.088
• 作为产物：
  描述：

  3,4-二溴-1H-吡咯-2,5-二酮 、 苯硫酚 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 12.0h， 以84.1%的产率得到3,4-bis(phenylsulfanyl)-2,5-dihydro-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Highly efficient disulfide bridging polymers for bioconjugates from radical-compatible dithiophenol maleimides

  摘要：

  本文介绍了通过活自由基聚合直接合成二噻吩酚马来酰亚胺功能聚合物的方法，无需进行保护基化学反应。合成的聚合物在等摩尔量使用时，可成功用作鲑鱼降钙素的二硫桥接剂，无需传统上与肽生物共轭相关的复杂纯化策略。

  DOI：

  10.1039/c2cc30259d

文献信息

• Reversible covalent linkage of functional molecules
  申请人：Smith Mark

  公开号：US09295729B2

  公开（公告）日：2016-03-29

  The present invention relates to the use of a compound containing a moiety of formula (I) as a reagent for linking a compound of formula R1—H which comprises a first functional moiety of formula F1 to a second functional moiety of formula F2 wherein X, X′, Y, R1, F1 and F2 are as defined herein. The present invention also provides related processes and products. The present invention is useful for creating functional conjugate compounds, and specifically conjugates in which at least one of the constituent molecules carries a thiol group.

  本发明涉及使用含有式(I)的基团的化合物作为将具有式F1的第一功能基团的化合物R1-H与具有式F2的第二功能基团连接的试剂 其中X、X'、Y、R1、F1和F2如本文所定义。本发明还提供相关的工艺和产品。本发明适用于制备功能共轭化合物，特别是至少一种组分分子携带硫醇基团的共轭物。
• [EN] VIA CYCLOADDITION BILATERALLY FUNCTIONALIZED ANTIBODIES<br/>[FR] ANTICORPS FONCTIONNALISÉS BILATÉRALEMENT PAR CYCLOADDITION
  申请人：SYNAFFIX BV

  公开号：WO2021144314A1

  公开（公告）日：2021-07-22

  The present invention provides antibody-payload conjugates having a payload-to-antibody ratio of 1. The antibody-payload conjugate is according to structure (1): formula (1), wherein: - a, b, c and d are each independently 0 or 1; - e is an integer in the range of 0 - 10; - L1, L2 and L3 are linkers; - D is a payload; - BM is a branching moiety; - Su is a monosaccharide; - G is a monosaccharide moiety; - GlcNAc is an N-acetylglucosamine moiety; - Fuc is a fucose moiety; - Z are connecting groups. The invention further provides a method for preparing the antibody-payload conjugate according to the invention, an intermediate compound in that preparation method, and medical uses of the antibody-payload conjugate according to the invention.

  本发明提供了一种抗体-有效载荷偶联物，其有效载荷与抗体的比例为1。所述抗体-有效载荷偶联物如结构(1)所示：公式(1)，其中：- a、b、c和d每个独立地为0或1；- e是0至10之间的整数；- L1、L2和L3是连接臂；- D是有效载荷；- BM是分支基团；- Su是单糖；- G是单糖基团；- GlcNAc是N-乙酰葡萄糖胺基团；- Fuc是岩藻糖基团；- Z是连接基团。本发明还提供了根据本发明制备抗体-有效载荷偶联物的方法、该制备方法中的中间化合物，以及根据本发明的抗体-有效载荷偶联物的医疗用途。
• Di-substituted maleic amide linker for antibody drug conjugating and preparation method and use thereof
  申请人：Mabwell (shanghai) Bioscience Co., Ltd.

  公开号：US10987430B2

  公开（公告）日：2021-04-27

  Provided in the present invention are a di-substituted maleic amide linker conjugated to an antibody and a preparation method and use thereof. In particular, the present invention conjugates a strongly cytotoxic active substance to a biomacromolecule through a class of new linkers. The class of linkers can selectively act simultaneously with disulphide chains, so as to greatly improve the substance homogeneity of a conjugate. The conjugate prepared by the linker of the present invention has a high inhibitory activity on a cell strain expressing the corresponding antigen. Also provided is a method for preparing the above-mentioned conjugate and the use.

  本发明提供了一种二取代马来酰胺连接物与抗体结合的制备方法及其用途。具体而言，本发明通过一类新连接物将一种强烈细胞毒活性物质与生物大分子结合。这类连接物可以与二硫键同时选择性地作用，从而极大地提高结合物质的均一性。本发明连接物制备的结合物对表达相应抗原的细胞株具有高抑制活性。还提供了制备上述结合物的方法和用途。
• Reduction-responsive dithiomaleimide-based nanomedicine with high drug loading and FRET-indicated drug release
  作者：Hua Wang、Ming Xu、Menghua Xiong、Jianjun Cheng

  DOI：10.1039/c5cc00148j

  日期：——

  We developed a dithiomaleimide-based nanomedicine with high drug loading, GSH-responsiveness, and FRET-indicated drug release.

  我们开发了一种基于二硫代马来酰亚胺的纳米药物，具有高药物载荷、对谷胱甘肽的响应性和荧光共振能量转移指示的药物释放。
• Antibody-Drug Conjugates, Compositions and Methods of Use
  申请人：Igenica Biotherapeutics, Inc.

  公开号：US20140363454A1

  公开（公告）日：2014-12-11

  Antibody-cytotoxin antibody-drug conjugates and related compounds, such as linker-cytotoxin conjugates and the linkers used to make them, tubulysin analogs, and intermediates in their synthesis; compositions; and methods, including methods of treating cancers.

  抗体-细胞毒素抗体药物偶联物及相关化合物，如连接剂-细胞毒素偶联物和用于制备它们的连接剂，管芽菌素类似物和其合成中间体；组合物；以及方法，包括治疗癌症的方法。