3-(3-phenylselenoureido)benzenesulfonamide

• 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: 3-(3-phenylselenoureido)benzenesulfonamide
• 化学式: C₁₃H₁₃N₃O₂SSe
• 分子量: 354.291
• InChiKey: ZNJCOPMXQMVMNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.11
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.22
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  1-异苯甲腈 在 selenium 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 3-(3-phenylselenoureido)benzenesulfonamide
  参考文献：
  名称：

  Discovery of New Selenoureido Analogues of 4-(4-Fluorophenylureido)benzenesulfonamide as Carbonic Anhydrase Inhibitors

  摘要：

  A series of benzenesulfonamides bearing selenourea moieties was obtained considering the ureido-sulfonamide SLC-0111, in Phase I clinical trials as antitumor agent, as a lead molecule. All compounds showed interesting inhibition potencies against the physiologically relevant human (h) carbonic anhydrase (hCAs, EC 4.2.1.1) isoforms I, II, IV, and IX. The most flexible analogues in the series 14-19 showed low nanomolar inhibition constants against hCA I, II, and IX. We assessed selected compounds on the in vitro antioxidant properties and binding modes and evaluated ex vivo human prostate (PC3), breast (MDA-MB-231), and colon-rectal (HT-29) cancer cell lines both in normoxic and hypoxic conditions.

  DOI：

  10.1021/acsmedchemlett.7b00280

文献信息

• Structural Insights into <i>Schistosoma mansoni</i> Carbonic Anhydrase (SmCA) Inhibition by Selenoureido-Substituted Benzenesulfonamides
  作者：Andrea Angeli、Marta Ferraroni、Akram A. Da’dara、Silvia Selleri、Mariana Pinteala、Fabrizio Carta、Patrick J. Skelly、Claudiu T. Supuran

  DOI：10.1021/acs.jmedchem.1c00840

  日期：2021.7.22

  anhydrase from the worm Schistosoma mansoni (SmCA) is considered a new anti-parasitic target because suppressing its expression interferes with schistosome metabolism and virulence. Here, we present the inhibition profiles of selenoureido compounds on recombinant SmCA and resolution of the first X-ray crystal structures of SmCA in adduct with a selection of such inhibitors. The key molecular features

  曼氏血吸虫的外皮碳酸酐酶(SmCA) 被认为是一种新的抗寄生虫靶点，因为抑制其表达会干扰血吸虫代谢和毒力。在这里，我们展示了硒脲基化合物对重组 SmCA 的抑制特性，以及在选择此类抑制剂的情况下，SmCA 在加合物中的第一个 X 射线晶体结构的分辨率。获得了这些化合物与 SmCA 加合物的关键分子特征，并与人类同种型 hCA II 进行了比较，以了解负责酶亲和力和选择性的主要结构因素。鉴定出比人类酶更特异性地抑制血吸虫的化合物。结果扩展了该领域的现有知识，并为在不久的将来开发更有效的抗寄生虫药铺平了道路。
• Seleno Containing Compounds as Potent and Selective Antifungal Agents
  作者：Andrea Angeli、Alice Velluzzi、Silvia Selleri、Clemente Capasso、Costanza Spadini、Mattia Iannarelli、Clotilde S. Cabassi、Fabrizio Carta、Claudiu T. Supuran

  DOI：10.1021/acsinfecdis.2c00250

  日期：2022.9.9

  sulfur and oxygen. In addition, such compounds showed excellent selectivity against Malassezia pachydermatis over its related genus strains Malassezia furfur and Malassezia globosa. Safe cytotoxicity profiles on bovine kidney cells (MDBK) and human HaCat cells, as well as the shallow hemolytic activity on defibrinated sheep blood, allowed us to consider these compounds as up-and-coming novel antifungals

  由于耐药现象和人畜共患病，真菌促进的感染正在成为严重的全球健康紧急情况。这项工作研究了带有酰基/硒脲基部分和伯/仲磺酰胺基团的化合物作为新型抗真菌剂，通过生物体定向硒毒性和抑制新出现的治疗靶点碳酸酐酶（CAs；EC 4.2.1.1）发挥作用。报告的数据清楚地表明，相对于标准护理药物，含硒支架显示出明显的抗真菌活性，当硫属元素被其同源等排元素硫和氧取代时，这种活性被抑制。此外，相对于其相关的糠秕马拉色菌属菌株，此类化合物对厚皮马拉色菌表现出优异的选择性和球形马拉色菌。对牛肾细胞 (MDBK) 和人类 HaCat 细胞的安全细胞毒性特征，以及对脱纤维绵羊血的浅层溶血活性，使我们能够将这些化合物视为有前途的新型抗真菌剂。
• Discovery of New Selenoureido Analogues of 4-(4-Fluorophenylureido)benzenesulfonamide as Carbonic Anhydrase Inhibitors
  作者：Andrea Angeli、Damiano Tanini、Thomas S. Peat、Lorenzo Di Cesare Mannelli、Gianluca Bartolucci、Antonella Capperucci、Carla Ghelardini、Claudiu T. Supuran、Fabrizio Carta

  DOI：10.1021/acsmedchemlett.7b00280

  日期：2017.9.14

  A series of benzenesulfonamides bearing selenourea moieties was obtained considering the ureido-sulfonamide SLC-0111, in Phase I clinical trials as antitumor agent, as a lead molecule. All compounds showed interesting inhibition potencies against the physiologically relevant human (h) carbonic anhydrase (hCAs, EC 4.2.1.1) isoforms I, II, IV, and IX. The most flexible analogues in the series 14-19 showed low nanomolar inhibition constants against hCA I, II, and IX. We assessed selected compounds on the in vitro antioxidant properties and binding modes and evaluated ex vivo human prostate (PC3), breast (MDA-MB-231), and colon-rectal (HT-29) cancer cell lines both in normoxic and hypoxic conditions.