2-氧代-2-[[4-(三氟甲基)苯基]氨基]乙酸 | 69066-42-8

• 物质功能分类: 有机原料 - 氨基化合物
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2-氧代-2-[[4-(三氟甲基)苯基]氨基]乙酸
• 中文别名: 特立氟胺杂质
• 英文名称: 2-oxo-2-[(4-trifluoromethylphenyl)amino]acetic acid
• 英文别名: N-(4-trifluoromethylphenyl)oxamic acid；4-Trifluoromethyloxanilic acid；2-Oxo-2-[[4-(trifluoromethyl)phenyl]amino]acetic Acid；2-oxo-2-[4-(trifluoromethyl)anilino]acetic acid
• CAS: 69066-42-8
• 化学式: C₉H₆F₃NO₃
• 分子量: 233.147
• InChiKey: WFZYVQMWEBADID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-(amino(piperidin-2-yl)methyl)-4-methylthiazol-5-yl)ethan-1-ol 、 2-氧代-2-[[4-(三氟甲基)苯基]氨基]乙酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 、 盐酸 作用下， 以39%的产率得到N¹-((5-(2-hydroxyethyl)-4-methylthiazol-2-yl)(piperidin-2-yl)methyl)-N²(4-(trifluoromethyl)phenyl)oxalamide dihydrochloride
  参考文献：
  名称：

  Design, Synthesis, and Antiviral Activity of Entry Inhibitors That Target the CD4-Binding Site of HIV-1

  摘要：

  The CD4 binding site on HIV-1 gp120 has been validated as a drug target to prevent HIV-1 entry to cells. Previously, we identified two small molecule inhibitors consisting of a 2,2,6,6-tetramethylpiperidine ring linked by an oxalamide to a p-halide-substituted phenyl group, which target this site, specifically, a cavity termed "Phe43 cavity". Here we use synthetic chemistry, functional assessment, and structure-based analysis to explore variants of each region of these inhibitors for improved antiviral properties. Alterations of the phenyl group and of the oxalamide linker indicated that these regions were close to optimal in the original lead compounds. Design of a series of compounds, where the tetramethylpiperidine ring was replaced with new scaffolds, led to improved antiviral activity. These new scaffolds provide insight into the surface chemistry at the entrance of the cavity and offer additional opportunities by which to optimize further these potential-next-generation therapeutics and microbicides against HIV-1.

  DOI：

  10.1021/jm3002247
• 作为产物：
  描述：

  2-氧代-2-[[4-(三氟甲基)苯基]氨基]乙酸乙酯 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以500 mg的产率得到2-氧代-2-[[4-(三氟甲基)苯基]氨基]乙酸
  参考文献：
  名称：

  [EN] OXALAMIDE HETEROBYCYCLIC COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY
  [FR] COMPOSÉS OXALAMIDE HÉTÉROBYCYCLIQUES ET COMPOSITIONS POUR LE TRAITEMENT D'AFFECTIONS ASSOCIÉES À UNE ACTIVITÉ DE STING

  摘要：

  本公开涉及化学实体（例如，化合物或药用盐，和/或水合物，和/或共晶，和/或化合物的药物组合），其抑制（例如，拮抗）干扰素基因激活器（STING）。所述化学实体可用于治疗条件、疾病或障碍，其中增加（例如，过度）STING激活（例如，STING信号传导）对主体（例如，人类）的病理和/或症状和/或疾病或障碍的进展有贡献。本公开还涉及含有相同化学实体的组合物，以及使用和制备这些组合物的方法。

  公开号：

  WO2021067805A1

文献信息

• Persulfate promoted tandem radical cyclization of ortho-cyanoarylacrylamides with oxamic acids for construction of carbamoyl quinoline-2,4-diones under metal-free conditions
  作者：Qing-Qing Han、Yuan-Yuan Sun、Shao-Hui Yang、Jing-Cheng Song、Zu-Li Wang

  DOI：10.1016/j.cclet.2021.04.019

  日期：2021.11

  An efficient and practical methods for the synthesis of carbamoyl quinoline-2,4-diones via the reaction of ortho-cyanoarylacrylamides with oxamic acids was described. This cyclic reaction could be performed efficiently under metal free conditions. Various products with functional groups could be obtained with moderate to high yields via radical mechanism.

  描述了一种通过邻-氰基芳基丙烯酰胺与草酸反应合成氨基甲酰基喹啉-2,4-二酮的有效且实用的方法。这种循环反应可以在无金属条件下有效地进行。通过自由基机理，可以以中高产率获得各种带有官能团的产物。
• [EN] OXALAMIDE HETEROBYCYCLIC COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH STING ACTIVITY<br/>[FR] COMPOSÉS OXALAMIDE HÉTÉROBYCYCLIQUES ET COMPOSITIONS POUR LE TRAITEMENT D'AFFECTIONS ASSOCIÉES À UNE ACTIVITÉ DE STING
  申请人：IFM DUE INC

  公开号：WO2021067805A1

  公开（公告）日：2021-04-08

  This disclosure features chemical entities (e.g., a compound or a pharmaceutically acceptable salt, and/or hydrate, and/or cocrystal, and/or drug combination of the compound) that inhibit (e.g., antagonize) Stimulator of Interferon Genes (STING). Said chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) STING activation (e.g., STING signaling) contributes to the pathology and/or symptoms and/or progression of the condition, disease or disorder (e.g., cancer) in a subject (e.g., a human). This disclosure also features compositions containing the same as well as methods of using and making the same.

  本公开涉及化学实体（例如，化合物或药用盐，和/或水合物，和/或共晶，和/或化合物的药物组合），其抑制（例如，拮抗）干扰素基因激活器（STING）。所述化学实体可用于治疗条件、疾病或障碍，其中增加（例如，过度）STING激活（例如，STING信号传导）对主体（例如，人类）的病理和/或症状和/或疾病或障碍的进展有贡献。本公开还涉及含有相同化学实体的组合物，以及使用和制备这些组合物的方法。
• Metal-Free Synthesis of Carbamoylated Chroman-4-Ones via Cascade Radical Annulation of 2-(Allyloxy)arylaldehydes with Oxamic Acids
  作者：Long-Yong Xie、Sha Peng、Li-Hua Yang、Xiao-Wen Liu

  DOI：10.3390/molecules27207049

  日期：——

  An efficient and straightforward approach for the synthesis of carbamoylated chroman-4-ones has been well-developed. The reaction is triggered through the generation of carbamoyl radicals from oxamic acids under metal-free conditions, which subsequently undergoes decarboxylative radical cascade cyclization on 2-(allyloxy)arylaldehydes to afford various amide-containing chroman-4-one scaffolds with

  一种用于合成氨基甲酰化 chroman-4-ones 的有效且直接的方法已得到很好的开发。该反应是通过在无金属条件下由草酸生成氨基甲酰基自由基引发的，随后在 2-(烯丙氧基)芳醛上进行脱羧自由基级联环化，得到各种具有高官能团耐受性的含酰胺 chroman-4-one 支架和广泛的底物范围。
• Persulfate-Promoted Carbamoylation/Cyclization of Alkenes: Synthesis of Amide-Containing Quinazolinones
  作者：Jia-Jun Tang、Meng-Yang Zhao、Ying-Jun Lin、Li-Hua Yang、Long-Yong Xie

  DOI：10.3390/molecules29050997

  日期：——

  The incorporation of amide groups into biologically active molecules has been proven to be an efficient strategy for drug design and discovery. In this study, we present a simple and practical method for the synthesis of amide-containing quinazolin-4(3H)-ones under transition-metal-free conditions. This is achieved through a carbamoyl-radical-triggered cascade cyclization of N3-alkenyl-tethered quinazolinones

  将酰胺基团掺入生物活性分子已被证明是药物设计和发现的有效策略。在这项研究中，我们提出了一种在无过渡金属条件下合成含酰胺的喹唑啉-4(3H)-酮的简单实用的方法。这是通过氨基甲酰基自由基触发的 N3-烯基连接的喹唑啉酮级联环化来实现的。值得注意的是，氨基甲酰基自由基是在 (NH4)2S2O8 存在下草酰胺酸的氧化脱羧过程中原位产生的。
• Minisci‐Type Carbamoylation of Azauracils with Oxamic Acids
  作者：Changduo Pan、Dongdong Chen、Miao Zeng、Haoyang Tian、Jin‐Tao Yu

  DOI：10.1002/ejoc.202301177

  日期：2024.2.19

  A Minisci‐type carbamoylation of azauracils was developed to afford 6‐carbamoyl azauracils in yields up to 94 %. In this transformation, oxamic acids were employed as the carbamoyl radical sources under metal‐free conditions. It features high atom economy, good functional group compatibility and convenient operation.

  摘要 研究人员开发了一种偶氮嘧啶的迷你型氨基甲酰化技术，可获得 6-氨基甲酰偶氮嘧啶，收率高达 94%。在这一转化过程中，氨基甲酰基来源是在无金属条件下使用的草酸。它具有原子经济性高、官能团兼容性好和操作方便等特点。