N,N'-[磺酰基二(1,4-亚苯基)]二(氯乙酰胺) | 17328-16-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N,N'-[磺酰基二(1,4-亚苯基)]二(氯乙酰胺)
• 英文名称: 4,4′-bis(2-chloroacetamido)diphenylsulfone
• 英文别名: 2-chloro-N-{4-[4-(2-chloro-acetylamino)-benzenesulfonyl]-phenyl}-acetamide；N,N’-(sulfonyldi-4,1-phenylene)bis(2-chloroacetamide)；TC-E 5003；2-chloro-N-[4-[4-[(2-chloroacetyl)amino]phenyl]-sulfonylphenyl]acetamide；bis-[4-(2-chloro-acetylamino)-phenyl]-sulfone；Bis-[4-(2-chlor-acetylamino)-phenyl]-sulfon；bis[(p-chloroacetamido)phenyl]sulfone；Sulfone, bis((4-chloroacetylamino)phenyl)；2-chloro-N-[4-[4-[(2-chloroacetyl)amino]phenyl]sulfonylphenyl]acetamide
• CAS: 17328-16-4
• 化学式: C₁₆H₁₄Cl₂N₂O₄S
• 分子量: 401.27
• InChiKey: SHRCVZJKZJGIHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  191-192 °C
• 沸点：
  704.2±60.0 °C(Predicted)
• 密度：
  1.504±0.06 g/cm3(Predicted)
• 溶解度：
  溶于DMSO（高达50mg/ml）。

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  应存放在室温、干燥且密封的环境中。

制备方法与用途

TC-E 5003 是一种选择性的 PRMT1 抑制剂，其对 hPRMT1 的 IC50 值为 1.5 µM。TC-E 5003 在 TLR4 信号传导中表现出抗炎特性。

反应信息

• 作为反应物：
  描述：

  N,N'-[磺酰基二(1,4-亚苯基)]二(氯乙酰胺) 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-Azido-N-{4-[4-(2-azido-acetylamino)-benzenesulfonyl]-phenyl}-acetamide
  参考文献：
  名称：

  Size-Specific Ligands for RNA Hairpin Loops

  摘要：

  The targeting of one mRNA in the transcriptome requires small molecules that bind with substantial affinity and specificity. As such, compounds with specificity for individual RNA secondary structural motifs could be useful for targeting RNA. Described herein is the synthesis of a combinatorial library of 105 dimers of deoxystreptamine and the subsequent identification of compounds with specificity for specific RNA hairpin loop sizes, including tetraloops and octaloops. Such compounds will be useful for the perturbation of RNA function in vivo.

  DOI：

  10.1021/ja051685b
• 作为产物：
  描述：

  氯乙酰氯 、 氨苯砜 在 三乙胺 作用下， 以 丙酮 为溶剂， 以12.5%的产率得到N,N'-[磺酰基二(1,4-亚苯基)]二(氯乙酰胺)
  参考文献：
  名称：

  新型基于磺酰胺的Flt3抑制剂的设计与合成。

  摘要：

  背景技术Flt3是涉及不同白血病的致癌激酶。它与急性髓细胞性白血病（AML）最明显相关。Flt3特异性抑制剂在干扰AML方面显示出令人鼓舞的结果。方法使用两种在Flt3中复合的抑制剂，即quizartinib和F6M的晶体学结构，指导新的基于磺酰胺的Flt3抑制剂的合成。结果制备的化合物之一显示出低的微摩尔抗Flt3生物活性，并且有趣的是，其对相关的致癌激酶VEGFR2的低微摩尔生物活性。结论磺酰胺已成功地用作特权支架，用于合成新型的Flt3微摩尔效价抑制剂。

  DOI：

  10.2174/1573406415666190401144053

文献信息

• 2-Amino-4'(phenylsulfonyl) acetanilides
  申请人：American Cyanamid Company

  公开号：US04532349A1

  公开（公告）日：1985-07-30

  A method of modulating the immune response system in a warm-blooded animal by the administration of N-substituted-phenylthioanilines, N-substituted-phenylsulfinylanilines, and N-substituted-phenylsulfonylanilines, certain of which are new compounds.

  通过给温血动物施用N-取代苯硫基苯胺，N-取代苯亚砜基苯胺和N-取代苯砜基苯胺来调节免疫反应系统的方法，其中某些化合物是新化合物。
• Methods for production of functional beta cells
  申请人：Janssen Biotech, Inc.

  公开号：US10633635B2

  公开（公告）日：2020-04-28

  The invention provides for methods of differentiating pancreatic endocrine cells into pancreatic beta cells expressing PDX1, NKX6.1, MAFA, UCN3 and SLC2A. These pancreatic beta cells may be obtained by step-wise differentiation of pluripotent stem cells. The pancreatic beta cells exhibit glucose-dependent mitochondrial respiration and glucose-stimulated insulin secretion similar to islet cells.

  本发明提供了将胰腺内分泌细胞分化成表达PDX1、NKX6.1、MAFA、UCN3和SLC2A的胰腺β细胞的方法。这些胰腺β细胞可通过多能干细胞的逐步分化获得。胰岛β细胞表现出与胰岛细胞相似的葡萄糖依赖性线粒体呼吸和葡萄糖刺激的胰岛素分泌。
• Acyl derivatives of p-aminosulfonamides and dapsone as new inhibitors of the arginine methyltransferase hPRMT1
  作者：Elisabeth-Maria Bissinger、Ralf Heinke、Astrid Spannhoff、Adrien Eberlin、Eric Metzger、Vincent Cura、Pierre Hassenboehler、Jean Cavarelli、Roland Schüle、Mark T. Bedford、Wolfgang Sippl、Manfred Jung

  DOI：10.1016/j.bmc.2011.02.032

  日期：2011.6

  Arginine methylation is an epigenetic modification that receives increasing interest as it plays an important role in several diseases. This is especially true for hormone-dependent cancer, seeing that histone methylation by arginine methyltransferase I (PRMT1) is involved in the activation of sexual hormone receptors. Therefore, PRMT inhibitors are potential drugs and interesting tools for cell biology. A dapsone derivative called allantodapsone previously identified by our group served as a lead structure for inhibitor synthesis. Acylated derivatives of p-aminobenzenesulfonamides and the antilepra drug dapsone were identified as new inhibitors of PRMT1 by in vitro testing. The bis-chloroacetyl amide of dapsone selectively inhibited human PRMT1 in the low micromolar region and was selective for PRMT1 as compared to the arginine methyltransferase CARM1 and the lysine methyltransferase Set7/9. It showed anticancer activity on MCF7a and LNCaP cells and blocked androgen dependent transcription specifically in a reporter gene system. Likewise, a transcriptional block was also demonstrated in LNCaP cells using quantitative RT-PCR on the mRNA of androgen dependent genes. (C) 2011 Elsevier Ltd. All rights reserved.
• Deliwala et al., Proceedings - Indian Academy of Sciences, Section A, 1950, vol. 31, p. 21,22
  作者：Deliwala et al.

  DOI：——

  日期：——
• Rieckmann, Memorias do Instituto Butantan, 1952, vol. 24, p. 77,79
  作者：Rieckmann

  DOI：——

  日期：——