N-benzyl-N’-isopropylurea | 71819-34-6

• 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: N-benzyl-N’-isopropylurea
• 英文别名: Urea, N-(1-methylethyl)-N'-(phenylmethyl)-；1-benzyl-3-propan-2-ylurea
• CAS: 71819-34-6
• 化学式: C₁₁H₁₆N₂O
• mdl: MFCD00027713
• 分子量: 192.261
• InChiKey: MCYFEMVPNDDDJK-UHFFFAOYSA-N

物化性质

• 沸点：
  377.2±21.0 °C(Predicted)
• 密度：
  1.028±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  41.1
• 氢给体数：
  2
• 氢受体数：
  1

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  N-benzyl-N’-isopropylurea 、 Actinoplanic acid A 以 四氢呋喃 为溶剂， 反应 96.0h， 生成 1-O,2-O-dibenzyl 3-O-[(E)-11-[(14E,18Z)-19-(4-ethyl-6-methyl-3,7-dioxo-7-phenylmethoxyheptyl)-12-hydroxy-11,13,15,17-tetramethyl-2,6-dioxo-4-phenylmethoxycarbonyl-1,7-dioxacycloicosa-14,18-dien-8-yl]-5-methylundec-6-en-2-yl] propane-1,2,3-tricarboxylate
  参考文献：
  名称：

  Structure, Chemistry, and Biology of Actinoplanic Acids: Potent Inhibitors of Ras Farnesyl-Protein Transferase

  摘要：

  The ras oncogene is found mutated in 50% of colon and 90% of pancreatic carcinomas. Farnesyl-protein transferase (FPTase) catalyzes farnesylation of the Ras protein, which is the essential step for the association of Ras with the plasma membrane, a critical requirement for Ras-mediated cell-transforming activity. Continued search for FPTase inhibitors led to the discovery of actinoplanic acid A and B, novel and potent inhibitors of the enzyme. We report here the details of the isolation, structure elucidation, chemistry, and biological activity of actinoplanic acid A and a significantly more active congener, actinoplanic acid B. Both of these compounds are highly functionalized 30-carbon chain length polyketides terminating with a carboxylic acid group. They are esterified with two units of carballylic acid. Actinoplanic acid A is cyclized into a macrocyclic bis-lactone, while the more potent acid B is acyclic. Both acids A and B inhibit farnesyl-protein transferase (FPTase) with IC50's of 230 and 50 nM and K-i values of 98 and 8 nM, respectively. The inhibition of FPTase by acids A and B is competitive with respect to farnesyl pyrophosphate (FPP) and uncompetitive with respect to Ras-CVIM, the peptide substrate.

  DOI：

  10.1021/jo00129a033
• 作为产物：
  描述：

  1-benzyl-3-isopropylthiourea 在 potassium dichloroiodate 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 以98%的产率得到N-benzyl-N’-isopropylurea
  参考文献：
  名称：

  二氯碘酸钾水溶液在尿素合成中的用途

  摘要：

  我们报告了一种直接和有效的反应方案，用于通过硫代脲与二氯碘酸钾水溶液（KICl 2）的处理来合成取代的脲。通过调节反应条件，带有活化的N-芳基取代基的硫脲可以进行选择性氧化或顺序氧化和碘化，在后一种情况下形成碘代芳基脲。

  DOI：

  10.1016/j.tetlet.2012.12.045

文献信息

• α-Haloalkyl Haloformates and Related Compounds 3.¹A Facile Synthesis of Symmetrical and Unsymmetrical Ureas<i>via</i>Chloromethyl Carbamates
  作者：Tamás Patonay、Erzsébet Patonay-Péli、László Zolnai、Ferenc Mogyoródi

  DOI：10.1080/00397919608004663

  日期：1996.11

  Abstract Chloromethyl carbamates were prepared by the reaction of chloromethyl chloroformates with amines and found to produce mono-, symmetrically or unsymmetrically di-and trisubstituted ureas including their N-hydroxy and N-alkoxy derivatives in moderate to good yield.

  摘要 氨基甲酸氯甲酯是通过氯甲酸氯甲酯与胺反应制备的，并发现可以以中等至良好的收率生产单、对称或不对称双和三取代的脲，包括它们的 N-羟基和 N-烷氧基衍生物。
• [EN] INHIBITORS OF PROTEIN TYROSINE KINASE ACTIVITY<br/>[FR] INHIBITEURS D'ACTIVITÉ DE PROTÉINE TYROSINE KINASE
  申请人：METHYLGENE INC

  公开号：WO2009109035A1

  公开（公告）日：2009-09-11

  This invention relates to compounds that inhibit protein tyrosine kinase activity. In particular the invention relates to compounds that inhibit the protein tyrosine kinase activity of growth factor receptors, resulting in the inhibition of receptor signaling, for example, the inhibition of VEGF receptor signaling. The invention also provides compounds, compositions and methods for treating cell proliferative diseases and conditions and opthalmological diseases, disorders and conditions.

  本发明涉及抑制蛋白质酪氨酸激酶活性的化合物。特别是，本发明涉及抑制生长因子受体的蛋白质酪氨酸激酶活性的化合物，从而抑制受体信号传导，例如抑制VEGF受体信号传导。本发明还提供了用于治疗细胞增殖性疾病和状况以及眼科疾病、障碍和状况的化合物、组合物和方法。
• Highly Efficient Synthesis of Ureas and Carbamates from Amides by Iodosylbenzene-Induced Hofmann Rearrangement
  作者：Peng Liu、Zhiming Wang、Xianming Hu

  DOI：10.1002/ejoc.201101784

  日期：2012.4

  A simple and efficient method for the synthesis of 1,3-disubstituted ureas and carbamates from amides by using iodosylbenzene as the oxidant is described. Symmetric and asymmetric ureas and carbamates can be prepared by this procedure in up to 98 % yield. Ureidopeptides can also be prepared in good yield by this method.

  描述了一种使用碘代苯作为氧化剂从酰胺合成 1,3-二取代脲和氨基甲酸酯的简单有效的方法。对称和不对称尿素和氨基甲酸酯可以通过该程序以高达 98% 的产率制备。通过该方法也可以以良好的产率制备脲肽。
• Inhibitors of Protein Tyrosine Kinase Activity
  申请人：Raeppel Stëphane

  公开号：US20110257100A1

  公开（公告）日：2011-10-20

  This invention relates to compounds that inhibit protein tyrosine kinase activity. In particular the invention relates to compounds that inhibit the protein tyrosine kinase activity of growth factor receptors, resulting in the inhibition of receptor signaling, for example, the inhibition of VEGF receptor signaling. The invention also provides compounds, compositions and methods for treating cell proliferative diseases and conditions and ophthalmic diseases, disorders and conditions.

  本发明涉及抑制蛋白酪氨酸激酶活性的化合物。特别是，本发明涉及抑制生长因子受体的蛋白酪氨酸激酶活性的化合物，从而抑制受体信号传导，例如，抑制VEGF受体信号传导。本发明还提供了用于治疗细胞增殖性疾病和条件以及眼科疾病、障碍和条件的化合物、组合物和方法。
• Kinetics and Mechanism of the Aminolysis of Aryl N-Isopropyl Thiocarbamates in Acetonitrile
  作者：Hyuck-Keun Oh

  DOI：10.5012/bkcs.2011.32.11.4095

  日期：2011.11.20

  The aminolysis reactions of phenyl N-benzyl thiocarbamate with benzylamines in acetonitrile at are investigated. The reactions are first order in both the amine and the substrate. Under amine excess, pseudo-first coefficient () are obtained, plot of vs free amine concentration are linear. The signs of ( and with respect to the sustituent in the substrate and large value indicate that the reactions

  研究了苯硫代氨基甲酸苯酯与苄胺在乙腈中的氨解反应。胺和底物的反应都是一级反应。在胺过量的情况下，获得了伪第一系数 ()，对游离胺浓度的曲线是线性的。( 和相对于底物中的取代基和大值的符号表明反应进行一致的机制。涉及氘代苄胺亲核试剂的正常动力学同位素效应 (= 1.3 ~ 1.5) 表明氢键合的四中心型过渡态. 激活参数 , 和 , 与此过渡态结构一致。