phenyl (3-cyanophenyl)carbamate | 50699-53-1

• 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: phenyl (3-cyanophenyl)carbamate
• 英文别名: phenyl N-(3-cyanophenyl)carbamate
• CAS: 50699-53-1
• 化学式: C₁₄H₁₀N₂O₂
• mdl: MFCD11129076
• 分子量: 238.246
• InChiKey: FEGXRJLAYGXSEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  62.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  、 phenyl (3-cyanophenyl)carbamate 以 四氢呋喃 为溶剂， 生成 1-(((R/S)-2-trans)-2-(((R/S)-3-benzylpiperidin-1-yl)methyl)cyclohexyl)-3-(3-cyanophenyl)urea
  参考文献：
  名称：

  Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency

  摘要：

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.

  DOI：

  10.1021/jm049530m
• 作为产物：
  描述：

  氯甲酸苯酯 、 间氨基苯甲腈 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.17h， 生成 phenyl (3-cyanophenyl)carbamate
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Novel 1-[3-(1,8-Naphthyridin-2-yl)phenyl]-3-arylurea Derivatives

  摘要：

  2-氨基烟酸醛（1）与1-(3-硝基苯)乙酮（2）在哌啶存在下反应，形成2-(3-硝基苯)-1,8-萘啶（3）。化合物3与肼水合物还原后得到3-(1,8-萘啶-2-基)苯胺（4），随后与不同的芳基氨基甲酸酯缩合，生成1-[3-(1,8-萘啶-2-基)苯基]-3-芳基脲衍生物（6a-q）。所有化合物的结构通过红外光谱（IR）、核磁共振（NMR）和质谱数据得到了确认。此外，合成的新化合物还进行了抗菌活性评估。结果显示，测试的化合物对细菌细胞的生长具有抑制作用。

  DOI：

  10.14233/ajchem.2018.20972

文献信息

• [EN] NOVEL UREA DERIVATIVES AS TEC KINASE INHIBITORS AND USES THEREOF<br/>[FR] NOUVEAUX DÉRIVÉS D'URÉE EN TANT QU'INHIBITEURS DE KINASE TEC ET LEURS UTILISATIONS
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2013024427A1

  公开（公告）日：2013-02-21

  Provided are urea compounds of formula (I) as Tec kinase inhibitors, in particular ITK (interleukin-2 inducible tyrosine kinase) inhibitors. Also provided herein are processes for preparing compounds described herein, intermediates used in their synthesis, pharmaceutical compositions thereof, and methods for treating or preventing diseases, conditions and/or disorders mediated by ITK.

  提供的是式（I）的尿素化合物，作为Tec激酶抑制剂，特别是ITK（白细胞介素-2诱导酪氨酸激酶）抑制剂。本文还提供了制备所述化合物的方法、用于合成的中间体、药物组合物以及治疗或预防由ITK介导的疾病、状况和/或紊乱的方法。
• N-(3,5-二甲基金刚烷-1-基)-N’-取代苯基 脲类化合物及其制备方法和用途
  申请人：沈阳海诺威医药科技有限公司

  公开号：CN107417578B

  公开（公告）日：2020-02-07

  本发明属于药物化学技术领域，具体涉及N‑(3,5‑二甲基金刚烷‑1‑基)‑N'‑取代苯基脲类化合物及其制备方法和用途。该类化合物具有式Ⅰ所示结构，通过大鼠的新物体辨别实验、Y迷宫实验、定位航行和空间探索实验证明该类化合物可以提高模型大鼠的形象辨别记忆、工作学习记忆、空间学习记忆能力，具有良好的抗老年痴呆的效果。
• Discovery of 4-piperazinyl-2-aminopyrimidine derivatives as dual inhibitors of JAK2 and FLT3
  作者：Yingxiu Li、Tianyu Ye、Le Xu、Yuhong Dong、Yong Luo、Chu Wang、Yufei Han、Ke Chen、Mingze Qin、Yajing Liu、Yanfang Zhao

  DOI：10.1016/j.ejmech.2019.111590

  日期：2019.11

  Hybridization strategy is an effective strategy to obtain multi-target inhibitors in drug design. In this study, we assembled the pharmacophores of momelotinib and tandutinib to get a series of 4-piperazinyl-2-aminopyrimidine derivatives. All compounds were tested for the inhibition of JAK2 and FLT3 enzymes, of which, compounds with potent enzyme activities were assayed for antiproliferative activities against three cancer cell lines (HEL, MV4-11, and HL60). The structure-activity relationship studies were conducted through variations in two regions, the "A" phenyl ring and "B" phenyl ring. Compound 14j showed the most balanced in vitro inhibitory activity against JAK2 and FLT3 (JAK2 IC50 = 27 nM, FLT3 IC50 = 30 nM), and it also showed potent inhibition against the above tested cell lines. In the cellular context, 14j strongly induced apoptosis by arresting cell cycle in the G(1)/S phase, and was selected as a promising JAK2/FLT3 dual inhibitor. (C) 2019 Elsevier Masson SAS. All rights reserved.
• [EN] UREA DERIVATIVES WHICH CAN BE USED TO TREAT CANCER<br/>[FR] DÉRIVÉS D'URÉE POUVANT ÊTRE UTILISÉS POUR TRAITER LE CANCER
  申请人：[en]SCORPION THERAPEUTICS, INC.

  公开号：WO2022265993A1

  公开（公告）日：2022-12-22

  This disclosure provides compounds of Formula (I), Formula (II), and pharmaceutically acceptable salts thereof, that inhibit phosphatidylinositol 4,5-bisphosphate 3-kinase (PI3K) isoform alpha (PI3Ka). These chemical entities are useful, e.g., for treating a condition, disease or disorder in which increased (e.g., excessive) PI3Ka activation 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 provides compositions containing the same as well as methods of using and making the same.
• Discovery of CC Chemokine Receptor-3 (CCR3) Antagonists with Picomolar Potency
  作者：George V. De Lucca、Ui Tae Kim、Brian J. Vargo、John V. Duncia、Joseph B. Santella、Daniel S. Gardner、Changsheng Zheng、Ann Liauw、Zhang Wang、George Emmett、Dean A. Wacker、Patricia K. Welch、Maryanne Covington、Nicole C. Stowell、Eric A. Wadman、Anuk M. Das、Paul Davies、Swamy Yeleswaram、Danielle M. Graden、Kimberly A. Solomon、Robert C. Newton、George L. Trainor、Carl P. Decicco、Soo. S. Ko

  DOI：10.1021/jm049530m

  日期：2005.3.1

  Starting with our previously described(20) class of CC chemokine receptor-3 (CCR3) antagonist, we improved the potency by replacing the phenyl linker of 1 with a cyclohexyl linker and by replacing the 4-benzylpiperidine with a 3-benzylpiperidine. The resulting compound, 32, is a potent and selective antagonist of CCR3. SAR studies showed that the 3-acetylphenyl urea of 32 could be replaced with heterocyclic ureas or heterocyclic-substituted phenyl ureas and still maintain the potency (inhibition of eotaxin-induced chemotaxis) of this class of compounds in the low-picomolar range (IC50 = 10-60 pM), representing some of the most potent CCR3 antagonists reported to date. The potency of 32 for mouse CCR3 (chemotaxis IC50 = 41 nM) and its oral bioavailability in mice (20% F) were adequate to assess the efficacy in animal models of allergic airway inflammation. Oral administration of 32 reduced eosinophil recruitment into the lungs in a dose-dependent manner in these animal models. On the basis of its overall potency, selectivity, efficacy, and safety profile, the benzenesulfonate salt of 32, designated DPC168, entered phase 1 clinical trials.