N-[4-[(4-cyanophenyl)-sulfamoyl]phenyl]acetamide | 332943-26-7

• 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: N-[4-[(4-cyanophenyl)-sulfamoyl]phenyl]acetamide
• 英文别名: N-{4-[(4-cyanophenyl)sulfamoyl]phenyl}acetamide；4-[(N-acetyl-sulfanilyl)-amino]-benzonitrile；4-[(N-Acetyl-sulfanilyl)-amino]-benzonitril；N-Acetyl-sulfanilsaeure-(4-cyan-anilid)；N-[4-[(4-cyanophenyl)sulfamoyl]phenyl]acetamide
• CAS: 332943-26-7
• 化学式: C₁₅H₁₃N₃O₃S
• mdl: MFCD01134285
• 分子量: 315.353
• InChiKey: DKBKARWSUVAFMQ-UHFFFAOYSA-N

物化性质

• 熔点：
  252-253 °C
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-[(4-cyanophenyl)-sulfamoyl]phenyl]acetamide 在 sodium hydroxide 、 硫酸 作用下， 生成 3-((4-acetamidophenyl)sulfonamido)benzamide
  参考文献：
  名称：

  190.磺酰胺类。第一部分。根据酯氨解的一般理论，氨对磺酰氨基苯甲酸酯的作用

  摘要：

  DOI：

  10.1039/jr9450000732
• 作为产物：
  描述：

  4-sulfanilylamino-benzoic acid amide 在 sodium hydroxide 、 硫酸 作用下， 生成 N-[4-[(4-cyanophenyl)-sulfamoyl]phenyl]acetamide
  参考文献：
  名称：

  190.磺酰胺类。第一部分。根据酯氨解的一般理论，氨对磺酰氨基苯甲酸酯的作用

  摘要：

  DOI：

  10.1039/jr9450000732

文献信息

• Design, synthesis, and evaluation of substituted nicotinamide adenine dinucleotide (NAD+) synthetase inhibitors as potential antitubercular agents
  作者：Xu Wang、Yong-Mo Ahn、Adam G. Lentscher、Julia S. Lister、Robert C. Brothers、Malea M. Kneen、Barbara Gerratana、Helena I. Boshoff、Cynthia S. Dowd

  DOI：10.1016/j.bmcl.2017.08.012

  日期：2017.9

  value of 90 µM against Mtb NadE. Our modeling results show that these urea-sulfonamides potentially bind to the intramolecular ammonia tunnel, which transports ammonia from the glutaminase domain to the active site of the enzyme. This hypothesis is supported by data showing that, even when treated with potent inhibitors, NadE catalysis is restored when treated with exogenous ammonia. Most of these compounds

  烟酰胺腺嘌呤二核苷酸（NAD +）合成酶催化NAD +生物合成的最后一步。NAD +的消耗对活跃和休眠的结核分枝杆菌（Mtb）均具有杀菌作用。通过抑制Mtb的NAD +合成酶（NadE），我们期望消除NAD +的产生，这将导致生长和非复制Mtb的细胞死亡。已经研究了NadE抑制剂对各种病原体的抑制作用，但很少针对Mtb进行过测试。在这里，我们报道了先前由Brouillette等人报道的一系列脲磺酰胺的扩展。在对接研究的指导下，末端苯环上的取代基发生了变化，以了解该位置上取代基的结构-活性关系。测试化合物作为重组Mtb NadE和Mtb全细胞的抑制剂。尽管母体化合物对Mtb NadE的抑制作用非常弱（IC 50  = 1000 µM），但我们发现优化后的效价提高了10倍。用4-硝基取代母体化合物苯环上的3,4-二氯基团可得到4f，这是该系列化合物中最有效的，其IC 50为50Mtb NadE的90
• Development of (4-Cyanophenyl)glycine Derivatives as Reversible Inhibitors of Lysine Specific Demethylase 1
  作者：Daniel P. Mould、Cristina Alli、Ulf Bremberg、Sharon Cartic、Allan M. Jordan、Matthis Geitmann、Alba Maiques-Diaz、Alison E. McGonagle、Tim C. P. Somervaille、Gary J. Spencer、Fabrice Turlais、Donald Ogilvie

  DOI：10.1021/acs.jmedchem.7b00462

  日期：2017.10.12

  Inhibition of lysine specific demethylase 1 (LSD1) has been shown to induce the differentiation of leukemia stem cells in acute myeloid leukemia (AML). Irreversible inhibitors developed from the nonspecific inhibitor tranylcypromine have entered clinical trials; however, the development of effective reversible inhibitors has proved more challenging. Herein, we describe our efforts to identify reversible

  赖氨酸特异性脱甲基酶1（LSD1）的抑制作用已显示出可诱导急性髓细胞性白血病（AML）中白血病干细胞的分化。由非特异性抑制剂tranylcypromine开发的不可逆抑制剂已进入临床试验。然而，事实证明开发有效的可逆抑制剂更具挑战性。本文中，我们描述了我们从高通量筛选和随后的计算机模拟方法中鉴定LSD1可逆抑制剂的努力。从通过生物化学和生物物理分析验证的单次点击（12）中，我们描述了我们从GSK-690（1）开发无环棚架的努力。对（4-氰基苯基）甘氨酰胺（例如29a）的进一步支架修饰导致化合物的开发32，具有ķ d 32纳米的值与EC 50 0.67μM的替代蜂窝生物标志物测定值。而且，该衍生物显示出与1观察到的hERG责任水平不同，代表了进一步开发的有希望的线索。
• Copper-Catalyzed Synthesis of Functionalized Aryl Sulfonamides from Sodium Sulfinates in Green Solvents
  作者：Long Yin Lam、King Hong Chan、Cong Ma

  DOI：10.1021/acs.joc.2c00777

  日期：2022.7.1

  industry. A one-step synthesis catalyzed by a copper salt was developed using stable solid commodity chemicals in sulfolane or, alternatively, in green solvents such as γ-valerolactone, iPrOAc, or nBuOAc with acetic acid. The method tolerated diverse functional groups commonly presented in current medicines and drug intermediates. The mechanistic study showed a radical coupling pathway between the sulfonyl

  官能化芳基磺酰胺是制药工业中的重要组成部分。使用稳定的固体商品化学品在环丁砜中或在绿色溶剂（如 γ-戊内酯、 i PrOAc 或n BuOAc 与乙酸）中开发了由铜盐催化的一步合成。该方法耐受当前药物和药物中间体中常见的多种官能团。机理研究表明，磺酰基和苯胺自由基之间的自由基偶联途径分别通过使用 K 2 S 2 O 8和铜催化剂。
• Midazolam premedication reduces propofol requirements for sedation during regional anesthesia
  作者：Masashi Nakagawa、Tadanori Mammoto、Ayako Hazama、Takashi Kita、Tetsuya Akamatsu、Noriko Kambara、Toshiko Sakai、Yoshihiko Kishi

  DOI：10.1007/bf03020731

  日期：2000.1

  Purpose: Propofol is often used for sedation during spinal anesthesia. We investigated the effects of midazolam premedication on the propofol requirements and incidence of complications during sedation.Methods: In a prospective randomized, controlled, and single-blinded study, 50 patients undergoing elective gynecological surgery were randomly divided into control and midazolam groups. Patients in the midazolam group received 2 mg midazolam im 30 min before arrival at the operation room. After spinal anesthesia was instituted with intrathecal injection of hyperbaric tetracaine, we provided sedation using continuous infusion of propofol, The level of sedation was controlled at a level between "eyes closed but reusable to command" and "eyes closed but reusable to mild physical stimulation" by adjusting the infusion rate. During sedation, the propofol requirements and complications were recorded and patients were asked, two hours after the end of operation, whether they remembered intraoperative events.Results: In the midazolam group, the loading dose, steady state infusion rate, and overall infusion rate of propofol were 0.74 mg.kg(-1), 2.86 mg.kg(-1).hr(-1), and 3.32 mg.kg(-1).hr(-1), respectively, which were about 17% lower than those in the control group (P < 0.05). Moreover, midazolam premedication reduced the incidence of intraoperative memory (P < 0.05), but had no effects on other complications.Conclusion: Midazolam premedication reduced propofol requirements and the incidence of intraoperative memory during sedation, These effects on sedation using propofol during spinal anesthesia are considered beneficial for patients.
• Sulfonamide Molecular Crystals: Thermodynamic and Structural Aspects
  作者：German L. Perlovich、Alex M. Ryzhakov、Valery V. Tkachev、Lars Kr. Hansen

  DOI：10.1021/cg1012389

  日期：2011.4.6

  The crystal structures of three sulfonamides with the structures C6H5-SO2NH-C6H5, C6H5-SO2NH-C6H4-R (R = 4-NO2), 4-NH2-C6H4-SO2NH-C6H4-R (R = 4-NO2; 4-CN) have been determined by X-ray diffraction. On the basis of our previous data and the obtained results, comparative analysis of crystal properties was performed: molecular conformational states, packing architecture, and hydrogen bond networks using graph set notations. Conformational flexibility of the bridge connecting two phenyl rings was studied and described by a correlation equation. Hydrogen bonds were grouped according to the frequency of hydrogen bond appearance within the definite graph set assignment. The strength of the T hydrogen bonds was evaluated. The influence of various molecular fragments on crystal lattice energy was analyzed. A correlation between melting points and fragmental molecular interactions in the crystal lattices was obtained. The thermodynamic aspects of the sulfonamide sublimation were studied by investigating the temperature dependence of vapor pressure using the transpiration method. A correlation between the Gibbs energy of the sublimation process and molecular H-bond acceptor factors was found. In addition, a regression equation was derived for describing the correlation between the sublimation entropy terms and crystal density data calculated from X-ray diffraction results. These dependencies allow us to predict sublimation thermodynamic parameters not knowing more than the molecular formula and crystal density.