1-[(2,4,6-Triisopropylphenyl)sulfonyl]piperazine | 420807-95-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[(2,4,6-Triisopropylphenyl)sulfonyl]piperazine
• 英文别名: 1-[2,4,6-tri(propan-2-yl)phenyl]sulfonylpiperazine
• CAS: 420807-95-0
• 化学式: C₁₉H₃₂N₂O₂S
• 分子量: 352.541
• InChiKey: PIWCYTFXNRMRDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[(2,4,6-Triisopropylphenyl)sulfonyl]piperazine 在 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成
  参考文献：
  名称：

  含磺酰哌嗪结构的1,3,4-噻二唑衍生物的合成、结构表征及生物活性

  摘要：

  为了开发新型细菌生物膜抑制剂，设计、合成了一系列含有磺酰哌嗪结构的1,3,4-噻二唑衍生物，并利用1 H 核磁共振（ 1 H NMR）、 13 C 核磁共振（ 13 C NMR）表征）和高分辨率质谱分析。同时，评估了它们的生物活性，并讨论了随之而来的构效关系。生物测定结果显示大多数化合物都表现出显着的抗菌功效。其中，化合物A 24在体外对米黄单胞菌表现出很强的功效，EC 50值为7.8 μg/mL。 oryzicola ( Xoc ) 病原体，超过了商业试剂噻二唑铜 (31.8 μg/mL) 和双甲噻唑 (43.3 μg/mL)。对其抗 Xoc 特性的机制研究表明，化合物 A 24通过增加细菌细胞膜的渗透性、抑制生物膜形成和细胞运动以及诱导细菌细胞形态变化来发挥作用。重要的是，体内试验表明其对水稻细菌性叶斑病具有优异的保护和治疗作用。此外，分子对接表明疏水效应和氢键相互作用是A 24与AvrRxo1-ORF1

  DOI：

  10.1002/cbdv.202400408
• 作为产物：
  描述：

  哌嗪 、 2,4,6-三异丙基苯磺酰氯 以 二氯甲烷 为溶剂， 生成 1-[(2,4,6-Triisopropylphenyl)sulfonyl]piperazine
  参考文献：
  名称：

  含磺酰哌嗪结构的1,3,4-噻二唑衍生物的合成、结构表征及生物活性

  摘要：

  为了开发新型细菌生物膜抑制剂，设计、合成了一系列含有磺酰哌嗪结构的1,3,4-噻二唑衍生物，并利用1 H 核磁共振（ 1 H NMR）、 13 C 核磁共振（ 13 C NMR）表征）和高分辨率质谱分析。同时，评估了它们的生物活性，并讨论了随之而来的构效关系。生物测定结果显示大多数化合物都表现出显着的抗菌功效。其中，化合物A 24在体外对米黄单胞菌表现出很强的功效，EC 50值为7.8 μg/mL。 oryzicola ( Xoc ) 病原体，超过了商业试剂噻二唑铜 (31.8 μg/mL) 和双甲噻唑 (43.3 μg/mL)。对其抗 Xoc 特性的机制研究表明，化合物 A 24通过增加细菌细胞膜的渗透性、抑制生物膜形成和细胞运动以及诱导细菌细胞形态变化来发挥作用。重要的是，体内试验表明其对水稻细菌性叶斑病具有优异的保护和治疗作用。此外，分子对接表明疏水效应和氢键相互作用是A 24与AvrRxo1-ORF1

  DOI：

  10.1002/cbdv.202400408

文献信息

• Synthesis and biological evaluation of novel indole derivatives containing sulfonamide scaffold as potential tubulin inhibitor
  作者：Ruo-Jun Man、Dan-Jie Tang、Xiao-Yuan Lu、Yong-Tao Duan、Xiang-Xiang Tao、Meng-Ru Yang、Le-Le Wang、Bao-Zhong Wang、Chen Xu、Hai-Liang Zhu

  DOI：10.1039/c6md00255b

  日期：——

  Microtubule-targeted drugs play a critical role in various types of cancer therapy worldwide. In our study, a series of novel indole derivatives containing a sulfonamide scaffold were designed, synthesized and biologically evaluated as potential tubulin polymerization inhibitors. Among them, compound 18 displayed the most potent inhibitory effect on antiproliferative activity against four types of

  以微管为靶标的药物在世界范围的各种癌症治疗中都起着关键作用。在我们的研究中，设计，合成了一系列含有磺酰胺支架的新型吲哚衍生物，并对其进行了生物学评估，以作为潜在的微管蛋白聚合抑制剂。其中，化合物18对四种类型的人类癌细胞系（IC 50值为0.24-0.59μM）和微管蛋白组装（IC 50 = 1.82μM）表现出最强的抑制作用。进一步的研究表明，化合物18是HeLa细胞凋亡的有效诱导剂，并可能在细胞周期的G2 / M期引起细胞停滞。分子对接和共聚焦显微镜分析结果表明该化合物18可以与微管蛋白的秋水仙碱结合位点紧密结合，并起微管蛋白聚合抑制剂的作用。还建立了3D-QSAR模型以提供更多信息，这些信息可用于设计具有更强微管蛋白抑制活性的新分子。
• Development of novel chromeno[4,3-c]pyrazol-4(2H)-one derivates bearing sulfonylpiperazine as antitumor inhibitors targeting PI3Kα
  作者：Yong Yin、Shao Sha、Xun Wu、She-Feng Wang、Fang Qiao、Zhong-Cheng Song、Hai-Liang Zhu

  DOI：10.1016/j.ejmech.2019.111630

  日期：2019.11

  PI3K signal pathway plays a vital role in cellular functions and becomes an attractive approach for cancer therapy. Herein, a new series of novel chromeno[4,3-c]pyrazol-4(2H)-one derivatives bearing sulfonylpiperazine based on the PI3K inhibitors and our previous research. They were screened for their PI3K inhibitory activities and anticancer effects in vitro. Biological studies indicated that compound 7m revealed the remarkable antiproliferative activity (IC50 ranging from 0.03 to 0.09 mu M) against four cancer cell lines (A549, Huh7, HL60 and HCT-116). Besides, compound 7m displayed a certain selective for PI3K alpha (IC50 = 0.009 mu M) over PI3K beta, gamma and delta, and meanwhile, it can remarkable decreased the expression level of p-Akt (Ser473) and p-S6K. In addition, compound 7m could not only induce HCT-116 cell arrest at G1 phase in a dose-dependent manner, but also induce cell apoptosis via upregulation of Bax and cleaved-caspase 3/9, and downregulation of Bcl-2. Besides, compound 7m can remarkably inhibit the growth of tumor in vivo. The above results suggested that compound 7m could be considered as a promising PI3K alpha inhibitor. (C) 2019 Elsevier Masson SAS. All rights reserved.
• Structure–Activity Relationship Studies on Isoindoline Inhibitors of Dipeptidyl Peptidases 8 and 9 (DPP8, DPP9): Is DPP8-Selectivity an Attainable Goal?
  作者：Sebastiaan Van Goethem、Veerle Matheeussen、Jurgen Joossens、Anne-Marie Lambeir、Xin Chen、Ingrid De Meester、Achiel Haemers、Koen Augustyns、Pieter Van der Veken

  DOI：10.1021/jm200383j

  日期：2011.8.25

  This work represents the first directed study to identify modification points in the topology of a representative DPP8/9-inhibitor, capable of rendering selectivity for DPP8 over DPP9. The availability of a DPP8-selective compound would be highly instrumental for studying and untwining the biological roles of DPP8 and DPP9 and for the disambiguation of biological effects of nonselective DPP-inhibitors that have mainly been ascribed to blocking of DPPIV's action. The cell-permeable DPP8/9-inhibitor 7 was selected as a lead and dissected into several substructures that were modified separately for evaluating their potential to contribute to selectivity. The obtained results, together with earlier work from our group, clearly narrow down the most probable DPP8-selectivity imparting modification points in DPP8/9 inhibitors to parts of space that are topologically equivalent to the piperazine ring system in 7. This information can be considered of high value for future design of compounds with maximal DPP8 selectivity.