((4-(trifluoromethyl)benzyl)sulfanyl)acetic acid

• 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: ((4-(trifluoromethyl)benzyl)sulfanyl)acetic acid
• 英文别名: 2-[[4-(Trifluoromethyl)phenyl]methylsulfanyl]acetic acid
• 化学式: C₁₀H₉F₃O₂S
• mdl: MFCD11647313
• 分子量: 250.241
• InChiKey: CEIMPCSXDNARHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  62.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((4-(trifluoromethyl)benzyl)sulfanyl)acetic acid 在 双氧水 作用下， 以 甲醇 、 水 为溶剂， 以81%的产率得到((4-(trifluoromethyl)benzyl)sulfinyl)acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of (E)-3,4-Dihydroxystyryl Aralkyl Sulfones and Sulfoxides as Novel Multifunctional Neuroprotective Agents

  摘要：

  Novel (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides were designed and synthesized as new analogues of 1, which showed interesting multifunctional neuroprotective effects, including antioxidative and antineuroinflammatory properties. Specifically, target compounds display excellent potency in scavenging reactive free radicals and demonstrate potent effects against various kinds of toxicities, including H2O2, 6-hydroxydopamine, and lipopolysaccharide in different types of neuronal cells. The antioxidative properties of the target compounds are more potent than that of 1, and the antineuroinflammatory properties are less strong than that of 1. According to the parallel artificial membrane permeation assay for the blood brain barrier, target compounds possess greater blood brain barrier (BBB) permeability than 1. In short, due to improvement of the antioxidative effect, stability, and BBB permeability, (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides can thus be considered as potential multifunctional neuroprotective agents and serve as new lead candidates in the treatment of neurodegenerative diseases.

  DOI：

  10.1021/jm500258v
• 作为产物：
  描述：

  巯基乙酸 、 1-溴-三氟对二甲苯 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以88%的产率得到((4-(trifluoromethyl)benzyl)sulfanyl)acetic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of (E)-3,4-Dihydroxystyryl Aralkyl Sulfones and Sulfoxides as Novel Multifunctional Neuroprotective Agents

  摘要：

  Novel (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides were designed and synthesized as new analogues of 1, which showed interesting multifunctional neuroprotective effects, including antioxidative and antineuroinflammatory properties. Specifically, target compounds display excellent potency in scavenging reactive free radicals and demonstrate potent effects against various kinds of toxicities, including H2O2, 6-hydroxydopamine, and lipopolysaccharide in different types of neuronal cells. The antioxidative properties of the target compounds are more potent than that of 1, and the antineuroinflammatory properties are less strong than that of 1. According to the parallel artificial membrane permeation assay for the blood brain barrier, target compounds possess greater blood brain barrier (BBB) permeability than 1. In short, due to improvement of the antioxidative effect, stability, and BBB permeability, (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides can thus be considered as potential multifunctional neuroprotective agents and serve as new lead candidates in the treatment of neurodegenerative diseases.

  DOI：

  10.1021/jm500258v

文献信息

• Synthesis, characterization, and radioprotective activity of α,β-unsaturated aryl sulfone analogs and their Tempol conjugates
  作者：Nan Zhou、Tian Feng、Xin Shen、Jiahui Cui、Rangxin Wu、Libin Wang、Siwang Wang、Shengyong Zhang、Hui Chen

  DOI：10.1039/c7md00017k

  日期：——

  Some novel α,β-unsaturated aromatic sulfone analogs (5a–5m) and their Tempol conjugates (6a–6e) have been synthetically prepared, characterized and evaluated for their radioprotective activity under γ-ray radiation. The Tempol conjugates were characterized by X-ray single crystal diffraction. In vitro studies showed that 5a, 5b and 6b had superior activities to Ex-Rad pre-treated before 5 Gy irradiation

  已经合成了一些新颖的α，β-不饱和芳族砜类似物（5a-5m）和它们的Tempol共轭物（6a-6e），表征并评估了它们在γ射线辐射下的辐射防护活性。Tempol共轭物通过X射线单晶衍射进行表征。体外研究表明，5a，5b和6b的活性优于5Gy辐照前的Ex-Rad，5a，6a和6b的活性比5Gy辐照后的Ex-Rad更好，而5a，6a和6b同时显示出预防和缓解作用，表明将α，β-不饱和芳族砜与Tempol氮氧化物结合使用的优势。在化合物处理的细胞中，p53和磷酸化p53的水平均显着低于未处理的辐照细胞。缀合物提供改善的放射防护能力，这是治疗方案中的优点。
• 砜类氮氧自由基作为辐射防护剂的应用
  申请人：中国人民解放军第四军医大学

  公开号：CN104817488B

  公开（公告）日：2018-04-24

  本发明公开了结构通式（I）所示的砜类氮氧自由基及其作为辐射防护剂的应用，其中，R1不存在或为卤素、C1‑C3的烷基、C1‑C3的烷氧基或‑CF3；R2为氢、卤素、C1‑C3的烷基、C1‑C3的烷氧基或‑ 。本发明兼具自由基淬灭和保护DNA等生物活性分子、抑制细胞凋亡的作用。（1）。
• Potent, non-thiol inhibitors of farnesyltransferase
  作者：Michael J. Breslin、S.Jane deSolms、Elizabeth A. Giuliani、Gerald E. Stokker、Samuel L. Graham、David L. Pompliano、Scott D. Mosser、Kelly A. Hamilton、John H. Hutchinson

  DOI：10.1016/s0960-894x(98)00586-1

  日期：1998.12

  The structure-activity relationship of a series of non-thiol CaaX analogs, which are inhibitors of farnesyltransferase, is described. These inhibitors contain a substituted phenyl group at the N terminus, which may occupy a novel binding domain on the Ras protein. (C) 1998 Elsevier Science Ltd. All rights reserved.
• INHIBITORS OF FARNESYL-PROTEIN TRANSFERASE
  申请人：Merck & Co., Inc.

  公开号：EP0783318A1

  公开（公告）日：1997-07-16
• EP0783318A4
  申请人：——

  公开号：EP0783318A4

  公开（公告）日：1999-10-20