1-phenyl-3-(prop-2-yn-1-yl)urea | 101871-81-2

• 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: 1-phenyl-3-(prop-2-yn-1-yl)urea
• 英文别名: 1-Phenyl-3-prop-2-yn-1-ylurea；1-phenyl-3-prop-2-ynylurea
• CAS: 101871-81-2
• 化学式: C₁₀H₁₀N₂O
• mdl: MFCD11756585
• 分子量: 174.202
• InChiKey: LPMOFOYPMBQANL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-(prop-2-yn-1-yl)urea 在 sodium methylate 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 5-methyl-1-phenyl-1,3-dihydro-imidazol-2-one
  参考文献：
  名称：

  Imidazole derivatives, preparation and therapeutic application thereof

  摘要：

  化合物式（I）的化合物，制备化合物式（I）的方法，它们的药物组成物，以及治疗与M3肌动蛋白和/或S-HT4 5-羟色胺受体相关的疾病的方法。

  公开号：

  US06200991B1
• 作为产物：
  描述：

  苯甲酰基叠氮化物 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 1-phenyl-3-(prop-2-yn-1-yl)urea
  参考文献：
  名称：

  Novel VEGFR-2 kinase inhibitors identified by the back-to-front approach

  摘要：

  We report a novel VEGFR-2 inhibitor, developed by the back-to-front approach. Docking experiments indicated that the 3-chloromethylphenylurea motif of the lead compound occupied the back pocket of VEGFR-2 kinase. An attempt was made to enhance the binding affinity of 1 by expanding the structure to access the front pocket using a triazole linker. A library of 1,4-(disubstituted)-1H-1,2,3-triazoles were screened in silico, and one compound (VH02) was identified with an IC50 against VEGFR-2 of 0.56 mu M. VH02 showed antiangiogenic effects, inhibiting tube formation in HUVEC cells (EA.hy926) at 0.3 mu M, 13 times lower than its cytotoxic dose. These enzymatic and cellular activities suggest that VH02 has potential as a lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.042

文献信息

• METHODS AND COMPOUNDS FOR RESTORING MUTANT p53 FUNCTION
  申请人：PMV Pharmaceuticals, Inc.

  公开号：US20170240525A1

  公开（公告）日：2017-08-24

  Mutations in oncogenes and tumor suppressors contribute to the development and progression of cancer. The present disclosure describes compounds and methods to recover wild-type function to p53 mutants. The compounds of the present invention can bind to mutant p53 and restore the ability of the p53 mutant to bind DNA and activate downstream effectors involved in tumor suppression. The disclosed compounds can be used to reduce the progression of cancers that contain a p53 mutation.

  癌基因和肿瘤抑制基因的突变促成了癌症的发展和进展。本公开披露描述了一种化合物和方法，用于恢复p53突变体的野生型功能。本发明的化合物可以结合突变型p53，并恢复p53突变体结合DNA并激活参与肿瘤抑制的下游效应子的能力。所披露的化合物可用于减少含有p53突变的癌症的进展。
• Electrophile-Mediated Reactions of Functionalized Propargylic Substrates
  作者：Aurelija Urbanaitė、Mantas Jonušis、Rita Bukšnaitienė、Simonas Balkaitis、Inga Čikotienė

  DOI：10.1002/ejoc.201501063

  日期：2015.11

  compounds have been studied. This investigation has led to the development of a mild, economic, and effective method for the synthesis of functionalized 4H-1,3-oxazines, 4H-1,3-thiazines, 4,5-dihydrothiazoles, and α-substituted enones. The structure of the propargylic substrate and the nature of electrophile influence both the outcome and regioselectivity of processes.

  已经研究了一系列 N-和 O-炔丙基化合物的无金属卤素、硫属元素或氧代碳鎓离子介导的炔-羰基或炔-硫代转化。该研究开发了一种温和、经济且有效的合成功能化 4H-1,3-恶嗪、4H-1,3-噻嗪、4,5-二氢噻唑和 α-取代烯酮的方法。炔丙基底物的结构和亲电试剂的性质影响过程的结果和区域选择性。
• A three-component, Zn(OTf)₂-mediated entry into trisubstituted 2-aminoimidazoles
  作者：Alexei Lukin、Anna Bakholdina、Anna Kryukova、Alexander Sapegin、Mikhail Krasavin

  DOI：10.3762/bjoc.15.103

  日期：——

  Zn(OTf)2-mediated cyclocondensation with a primary amine yielded trisubstituted 2-aminoimidazoles. These findings are in contrast to the previously reported base-promoted unimolecular cyclization of propargylureas (leading to 2-imidazolones) and extend the range of Lewis acid-catalyzed azole syntheses based on N-carbonyl propargylamines.

  三组分反应涉及原位生成炔丙基脲，随后与伯胺进行Zn（OTf）2介导的环缩合，生成三取代的2-氨基咪唑。这些发现与先前报道的炔丙基脲的碱促进的单分子环化（导致2-咪唑酮）相反，并且扩展了基于N-羰基炔丙基胺的路易斯酸催化的唑合成的范围。
• [EN] 5-MEMBERED HETEROARYL COMPOUNDS CONTAINING A HYDROXAMATE MOIETY AND THEIR USE<br/>[FR] COMPOSÉS HÉTÉROARYLES À 5 CHAÎNONS CONTENANT UNE FRACTION HYDROXAMATE ET LEUR UTILISATION
  申请人：UNIV LILLE

  公开号：WO2020148403A1

  公开（公告）日：2020-07-23

  The present invention is directed to 5-membered heteroaryl compounds containing a hydroxamate moiety of Formula I, pharmaceutically acceptable salts or solvates thereof, and their use as sensitizers for chemotherapy of malignant tumors.

  本发明涉及含有Formula I的羟肟基团的5-成员杂芳化合物，其药用可接受盐或溶剂，以及它们作为恶性肿瘤化疗的增敏剂的用途。
• 2,2,2-Trifluroenthanol promoted synthesis of unsymmetrical ureas from dioxazolones and amines via tandem lossen rearrangement/condensation process
  作者：Jian Li、Wang He、Pan Lei、Jiacheng Song、Jiyou Huo、Hongbo Wei、Hongjin Bai、Weiqing Xie

  DOI：10.1080/00397911.2021.1983605

  日期：2021.12.2

  (TFE) promoted synthesis of unsymmetric ureas was described. This approach enabled the construction of a variety of ureas from the readily prepared and easy-to-handle dioxazolones and amines via tandem Lossen rearrangement/condensation process. The reaction featured mild conditions for the urea synthesis under metal-free conditions, which was successively applied in the scale-up synthesis of herbicides

  摘要 描述了 2,2,2-三氟乙醇 (TFE) 促进不对称尿素的合成。这种方法能够通过串联洛森重排/缩合过程从易于制备且易于处理的二恶唑酮和胺中构建各种尿素。该反应具有在无金属条件下合成尿素的温和条件，该反应先后应用于除草剂Monuro和Isoproturon的放大合成。