嘧啶异氰酸 | 72975-49-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 嘧啶异氰酸
• 中文别名: 2-异氰酸嘧啶酯
• 英文名称: 2-Isocyanatopyrimidine
• 英文别名: pyrimidinyl isocyanate
• CAS: 72975-49-6
• 化学式: C₅H₃N₃O
• 分子量: 121.098
• InChiKey: NDQSFGFRMPGVLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-苯基-4-甲基-1-戊炔-3醇 、 嘧啶异氰酸 在 三乙胺 作用下， 以 甲苯 为溶剂， 反应 36.0h， 生成 4-methyl-1-phenylpent-1-yn-3-yl pyrimidin-2-ylcarbamate
  参考文献：
  名称：

  咪唑键合的N-杂芳族化合物通过C-N键形成的自由基级联反应的电化学合成

  摘要：

  我们已开发出一种通过杂芳基胺与束缚的内部炔烃的区域特异性电化学（3 + 2）环化反应制备各种咪唑并合的N-杂芳族化合物的统一策略。电合成采用新型的四芳基肼作为催化剂，具有广泛的底物范围，并且不需要过渡金属催化剂和氧化剂。

  DOI：

  10.1002/anie.201711876
• 作为产物：
  描述：

  Pyrimidine-2-carbonyl azide 以 甲苯 为溶剂， 反应 1.0h， 生成 嘧啶异氰酸
  参考文献：
  名称：

  Novel Tetrahydropyrido[1,2-a]isoindolone Derivatives (Valmerins): Potent Cyclin-Dependent Kinase/Glycogen Synthase Kinase 3 Inhibitors with Antiproliferative Activities and Antitumor Effects in Human Tumor Xenografts

  摘要：

  The development of CDK and GSK3 inhibitors has been regarded as a potential therapeutic approach, and a substantial number-of-diverse structures have been reported to inhibit CDKs and GSK-3 beta. in recent years. Only a few molecules have gone through or are currently undergoing clinical trials as CDK and GSK inhibitors. In this paper, we prepared valmerins, a new family containing the tetrahydropyrido[1,2-a]isoindone core. The fused heterocycle was prepared with a straightforward synthesis that was functionalized by a (het)arylurea. Twelve valmerins inhibited the CDK5 and GSK3 with an IC50 < 100 nM. A semiquantitative kinase scoring was realized, and a cellular screening was done. At the end of study, we investigated the in vivo potency of one valmerin. Mice exhibited good tolerance to our lead, which proved its efficacy and clearly blocked tumor growth. Valmerins appear also as good candidates: for further development as anticancer agents.

  DOI：

  10.1021/jm3008536

文献信息

• Asymmetric Indoline Synthesis via Intramolecular Aza-Michael Addition Mediated by Bifunctional Organocatalysts
  作者：Ryota Miyaji、Keisuke Asano、Seijiro Matsubara

  DOI：10.1021/ol401538b

  日期：2013.7.19

  A novel method for the asymmetric synthesis of 2-substituted indolines, employing bifunctional amino(thio)urea catalysts, was developed. The reaction proceeded via an intramolecular aza-Michael addition mediated by activation through hydrogen bonding. The catalytic process was shown to be highly versatile and applicable to a wide range of substrates due to the flexible catalytic mechanism utilizing a noncovalent interaction.
• Novel Tetrahydropyrido[1,2-<i>a</i>]isoindolone Derivatives (Valmerins): Potent Cyclin-Dependent Kinase/Glycogen Synthase Kinase 3 Inhibitors with Antiproliferative Activities and Antitumor Effects in Human Tumor Xenografts
  作者：Rajâa Boulahjar、Aziz Ouach、Chiurato Matteo、Stephane Bourg、Myriam Ravache、Rémy le Guével、Séverine Marionneau、Thibauld Oullier、Olivier Lozach、Laurent Meijer、Christiane Guguen-Guillouzo、Saïd Lazar、Mohamed Akssira、Yves Troin、Gérald Guillaumet、Sylvain Routier

  DOI：10.1021/jm3008536

  日期：2012.11.26

  The development of CDK and GSK3 inhibitors has been regarded as a potential therapeutic approach, and a substantial number-of-diverse structures have been reported to inhibit CDKs and GSK-3 beta. in recent years. Only a few molecules have gone through or are currently undergoing clinical trials as CDK and GSK inhibitors. In this paper, we prepared valmerins, a new family containing the tetrahydropyrido[1,2-a]isoindone core. The fused heterocycle was prepared with a straightforward synthesis that was functionalized by a (het)arylurea. Twelve valmerins inhibited the CDK5 and GSK3 with an IC50 < 100 nM. A semiquantitative kinase scoring was realized, and a cellular screening was done. At the end of study, we investigated the in vivo potency of one valmerin. Mice exhibited good tolerance to our lead, which proved its efficacy and clearly blocked tumor growth. Valmerins appear also as good candidates: for further development as anticancer agents.
• Electrochemical Synthesis of Imidazo-Fused N-Heteroaromatic Compounds through a C−N Bond-Forming Radical Cascade
  作者：Zhong-Wei Hou、Zhong-Yi Mao、Yared Yohannes Melcamu、Xin Lu、Hai-Chao Xu

  DOI：10.1002/anie.201711876

  日期：2018.2.5

  We have developed a unified strategy for preparing a variety of imidazo‐fused N‐heteroaromatic compounds through regiospecific electrochemical (3+2) annulation reaction of heteroarylamines with tethered internal alkynes. The electrosynthesis employs a novel tetraarylhydrazine as the catalyst, has a broad substrate scope, and obviates the need for transition‐metal catalysts and oxidizing reagents.

  我们已开发出一种通过杂芳基胺与束缚的内部炔烃的区域特异性电化学（3 + 2）环化反应制备各种咪唑并合的N-杂芳族化合物的统一策略。电合成采用新型的四芳基肼作为催化剂，具有广泛的底物范围，并且不需要过渡金属催化剂和氧化剂。