4-oxo-2-thioxo-6-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidine-5-carbonitrile | 877460-86-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-oxo-2-thioxo-6-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
• 英文别名: 4-oxo-2-sulfanylidene-6-[3-(trifluoromethyl)phenyl]-1H-pyrimidine-5-carbonitrile
• CAS: 877460-86-1
• 化学式: C₁₂H₆F₃N₃OS
• 分子量: 297.26
• InChiKey: AZLPIXSPESQXBT-UHFFFAOYSA-N

物化性质

• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-oxo-2-thioxo-6-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 、 3-甲基苄溴 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 2-(m-tolylmethylsulfanyl)-6-oxo-4-[3-(trifluoromethyl)phenyl]-1H-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Parallel synthesis of 5-cyano-6-aryl-2-thiouracil derivatives as inhibitors for hepatitis C viral NS5B RNA-dependent RNA polymerase

  摘要：

  From random screening of our compound libraries, we identified it hit compound with an IC50 of 27 mu M against hepatitis C viral NS5B RNA-dependent RNA polymerase. By using a parallel synthetic strategy, a series of its derivatives were synthesized. From their anti-HCV activity screening, compounds with single digital 3.8 micromolar activity were obtained. (c) 2005 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2005.10.001
• 作为产物：
  描述：

  3-三氟甲基苯甲醛 、 硫脲 、 氰乙酸乙酯 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以56%的产率得到4-oxo-2-thioxo-6-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  作为BACE1抑制剂的2-取代硫代N-（4-取代噻唑/ 1 H-咪唑-2-基）乙酰胺：合成，生物学评估和对接研究

  摘要：

  在这项工作中，开发了一系列2-取代-硫基-N-（4-取代-噻唑/ 1H-咪唑-2-基）乙酰胺衍生物作为β-分泌酶（BACE-1）抑制剂。在对接研究的支持下，设计了一个小的衍生物库，对其进行了合成并在体外进行了生物学评估。另外，所选择的化合物以对BACE-1的亲和力（K D），血脑屏障（BBB）的通透性和细胞毒性进行测试。研究表明，最强的类似物41（IC 50  =  4.6μM）具有较高的预测BBB通透性和较低的细胞毒性，可作为进一步优化的良好先导结构。

  DOI：

  10.1016/j.ejmech.2017.06.020

文献信息

• 具有β-分泌酶抑制功能的化合物，制备该化合 物的方法及其用途
  申请人：北京大学

  公开号：CN104860937B

  公开（公告）日：2018-02-06

  本发明公开了具有β分泌酶抑制功能的化合物，制备该化合物的方法及其用途。本发明化合物，结构如式I、式II或式II所示。式I结构中，X为S或NH；R1选自氢、硝基；R2、R4相同或不同，各自分别选自氢、卤素、硝基、取代芳基；R3选自氢、硝基、氨基、1到4个碳的直链、支链烷基及取代烷基、1到4个碳的烷氨基或烷氧基、1到4个碳的烷酰胺基；R分别位于苯环的2位或3位或4位，选自氢、1到4个碳的直链、支链烷基及取代烷基、1到4个碳的烷氨基或烷氧基，1到4个碳的烷酰胺基。式II结构中，R选自不同取代芳基。式III结构中，R选自氢、氰基。实验证明，本发明的化合物具有较好的β分泌酶抑制活性，作为β分泌酶抑制剂将具有广阔的应用价值。
• 2-Thiopyrimidinones as therapeutic agents
  申请人：Sikorski A. James

  公开号：US20060100226A1

  公开（公告）日：2006-05-11

  The present invention provides compounds of Formulas I-VII, or pharmaceutically acceptable derivatives thereof, wherein the compounds are as defined in the specification. These compounds are inhibitors of protein kinases, particularly inhibitors of MEKK protein kinases. The invention also provides pharmaceutically acceptable compositions comprising the compounds of the invention and methods of utilizing those compounds and compositions in the treatment of various protein kinase mediated disorders, such as inflammatory disorders.

  本发明提供了I-VII式化合物或其药学上可接受的衍生物，其中所述化合物如规范中所定义。这些化合物是蛋白激酶的抑制剂，特别是MEKK蛋白激酶的抑制剂。本发明还提供了包含本发明化合物的药学上可接受的组合物以及利用这些化合物和组合物治疗各种蛋白激酶介导的疾病的方法，例如炎症性疾病。
• [EN] PROCESSES FOR THE PREPARATION OF SUBSTITUTED THIOCHROMAN DERIVATIVES<br/>[FR] PROCEDES DE PREPARATION DE DERIVES DE THIOCHROMANE SUBSTITUES
  申请人：RANBAXY LAB LTD

  公开号：WO2006040644A2

  公开（公告）日：2006-04-20

  The invention relates to processes for the preparation of substituted thiochroman derivatives of Formula (I), wherein R2 is hydrogen or lower alkyl; R1 is hydrogen, halogen, a leaving group or a group of Formula (II), wherein A is phenyl or heteroaryl selected from the group consisting of pyridynyl, thienyl, furyl, pyridazinyl, pyrimidinyl, pyrazinyl, thiazolyl or oxazolyl; n is an integer having a value between 0 to 5; and B is hydrogen, -COOH or its pharmaceutically acceptable salt, ester or amide thereof, -CH2oH or its ether or ester derivative thereof, -CHO or and acetal derivative thereof, or -COR3 or ketal derivative thereof, wherein R3 is C1-5 alkyl, cycloalkyl or alkenyl. More particularly, it relates to a process for the preparation of tazarotene of Formula (III). The Invention also relates to a novel polymrophic form of tazarotene designated as Form A of tazarotene and process for producing it. The invention also relates to pharmaceutical compositions that include the Form A of tazarotene and use of said composition for treating stable plaque psoriasis and facial acne vulgaris.
• 2-Substituted-thio- N -(4-substituted-thiazol/1 H -imidazol-2-yl)acetamides as BACE1 inhibitors: Synthesis, biological evaluation and docking studies
  作者：Gang Yan、Lina Hao、Yan Niu、Wenjie Huang、Wei Wang、Fengrong Xu、Lei Liang、Chao Wang、Hongwei Jin、Ping Xu

  DOI：10.1016/j.ejmech.2017.06.020

  日期：2017.9

  In this work, a series of 2-substituted-thio-N-(4-substituted-thiazol/1H-imidazol-2-yl)acetamide derivatives were developed as β-secretase (BACE-1) inhibitors. Supported by docking study, a small library of derivatives were designed, synthesized and biologically evaluated in vitro. In addition, the selected compounds were tested with affinity (KD) towards BACE-1, blood brain barrier (BBB) permeability

  在这项工作中，开发了一系列2-取代-硫基-N-（4-取代-噻唑/ 1H-咪唑-2-基）乙酰胺衍生物作为β-分泌酶（BACE-1）抑制剂。在对接研究的支持下，设计了一个小的衍生物库，对其进行了合成并在体外进行了生物学评估。另外，所选择的化合物以对BACE-1的亲和力（K D），血脑屏障（BBB）的通透性和细胞毒性进行测试。研究表明，最强的类似物41（IC 50  =  4.6μM）具有较高的预测BBB通透性和较低的细胞毒性，可作为进一步优化的良好先导结构。
• Parallel synthesis of 5-cyano-6-aryl-2-thiouracil derivatives as inhibitors for hepatitis C viral NS5B RNA-dependent RNA polymerase
  作者：Yili Ding、Jean-Luc Girardet、Kenneth L. Smith、Gary Larson、Brett Prigaro、Jim Z. Wu、Nanhua Yao

  DOI：10.1016/j.bioorg.2005.10.001

  日期：2006.2

  From random screening of our compound libraries, we identified it hit compound with an IC50 of 27 mu M against hepatitis C viral NS5B RNA-dependent RNA polymerase. By using a parallel synthetic strategy, a series of its derivatives were synthesized. From their anti-HCV activity screening, compounds with single digital 3.8 micromolar activity were obtained. (c) 2005 Elsevier Inc. All rights reserved.