4-氯-2-苯基噻吩并[3,2-d]嘧啶 | 214417-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 中文名称: 4-氯-2-苯基噻吩并[3,2-d]嘧啶
• 英文名称: 4-chloro-2-phenylthieno[3,2-d]pyrimidine
• 英文别名: 4-chloro-2-phenyl-thieno[3,2-d]pyrimidine
• CAS: 214417-22-8
• 化学式: C₁₂H₇ClN₂S
• 分子量: 246.72
• InChiKey: CXDKDIMCVLMEDW-UHFFFAOYSA-N

物化性质

• 熔点：
  118-119 °C
• 沸点：
  299.1±22.0 °C(Predicted)
• 密度：
  1.396±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  4-氯-2-苯基噻吩并[3,2-d]嘧啶 在 2,2,6,6-四甲基哌啶 、 正丁基锂 、 CdCl₂*TMEDA 、 碘 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以70%的产率得到4-chloro-6-iodo-2-phenylthieno[3,2-d]pyrimidine
  参考文献：
  名称：

  Direct metallation of thienopyrimidines using a mixed lithium–cadmium base and antitumor activity of functionalized derivatives

  摘要：

  一系列噻吩并[2,3-d]和噻吩并[3,2-d]嘧啶类化合物已通过去质子-镉化-捕获序列作为关键步骤轻松合成。其中一些合成的化合物被筛选出具有抗癌（细胞毒性）活性，而(S)-2-(6-碘-2-苯基噻吩并[2,3-d]嘧啶-4-基氨基)-3-苯基丙酸显示出对肝、人乳腺癌和宫颈癌细胞系具有显著活性。

  DOI：

  10.1039/b915274a
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 吡啶 、 ammonium hydroxide 、 三氯氧磷 作用下， 反应 2.5h， 生成 4-氯-2-苯基噻吩并[3,2-d]嘧啶
  参考文献：
  名称：

  Design, Synthesis, and Biological Activities of New Thieno[3,2-d]pyrimidines as Selective Type 4 Phosphodiesterase Inhibitors

  摘要：

  A common pharmacophore for compounds structurally related to nitraquazone has been derived. Using this pharmacophore, new structures have been designed, synthesized, and evaluated for their inhibitory potencies against cyclic adenosine 5'-monophosphate (cAMP) specific phosphodiesterase (PDE 4). From these compounds, 4-benzylamino-2-butylthieno[3,2-d]-pyrimidine (4) was selected for optimization. The effects of changes to the lipophilic groups and the amino linkage on the PDE 4 activity have been investigated. As a result, some potent PDE 4 inhibitors, selective with respect to PDE 3, have been identified. A selected group of compounds have been further evaluated for their ability to displace [H-3]rolipram from its binding site and also to potentiate isoprenaline-induced cAMP accumulation in isolated guinea pig eosinophils. Of these, 2-butyl-4-cyclohexylaminothieno[3,2-d]pyrimidine (33) has an interesting profile, with an important improvement in PDE 4/[H-3]rolipram ratio with respect to reference drugs, and good activity in cAMP potentiation, consistent with efficient cell penetration.

  DOI：

  10.1021/jm981012m

文献信息

• N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20070099877A1

  公开（公告）日：2007-05-03

  Disclosed are N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar and R 1 -R 4 are defined herein. The present invention relates to the discovery that compounds having Formulae I-II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  揭示了N-芳基噻吩吡嘧啶-4-胺及其类似物，由以下的式子I-II表示：其中Ar和R1-R4在此有所定义。本发明涉及发现具有式子I-II的化合物是半胱氨酸蛋白酶的激活剂和凋亡诱导剂。因此，本发明的半胱氨酸蛋白酶激活剂和凋亡诱导剂可用于诱导在各种临床病况中发生细胞死亡，这些病况中存在细胞不受控制的生长和异常细胞的扩散。
• N-alkyl-N-aryl-thienopyrimidin-4-amines and analogs as activators of caspases and inducers of apoptosis and the use thereof
  申请人：Cai Xiong Sui

  公开号：US20070213305A1

  公开（公告）日：2007-09-13

  Disclosed are N-alkyl-N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar, R 1 -R 4 and R 10 are defined herein. The present invention relates to the discovery that compounds having Formulae I-II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及公开的N-烷基-N-芳基噻唑嘧啶-4-胺及其类似物，其由式I-II表示：其中Ar、R1-R4和R10如本文所定义。本发明关于发现具有式I-II的化合物是caspase的激活剂和凋亡诱导剂。因此，本发明的caspase激活剂和凋亡诱导剂可用于在多种临床情况下诱导细胞死亡，其中发生异常细胞的不受控制的生长和扩散。
• Discovery of 4-anilino-N-methylthieno[3,2-d]pyrimidines and 4-anilino-N-methylthieno[2,3-d]pyrimidines as potent apoptosis inducers
  作者：William Kemnitzer、Nilantha Sirisoma、Chris May、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmcl.2009.04.145

  日期：2009.7

  We report the discovery of N-((benzo[d][1,3]dioxol-5-yl)methyl)-6-phenylthieno[3,2-d] pyrimidin-4-amine (2a) as an apoptosis inducer using our proprietary cell-and caspase-based ASAP HTS assay, and SAR study of HTS hit 2a which led to the discovery of 4-anilino-N-methylthieno[3,2-d] pyrimidines and 4-anilino-N-methylthieno[2,3-d] pyrimidines as potent apoptosis inducers. Compounds 5d and 5e were the most potent with EC50 values of 0.008 and 0.004 mu M in T47D human breast cancer cells, respectively. Compound 5d was found to be highly active in the MX-1 breast cancer model. Functionally, compounds 5d and 5e both induced apoptosis through inhibition of tubulin polymerization. (C) 2009 Elsevier Ltd. All rights reserved.
• WO2008/92860
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] N-ARYL-THIENOPYRIMIDIN-4-AMINES AND ANALOGS AS ACTIVATORS OF CASPASES AND INDUCERS OF APOPTOSIS AND THE USE THEREOF<br/>[FR] N-ARYL-THIENOPYRIMIDIN-4-AMINES ET ANALOGUES EN TANT QU'ACTIVATEURS DE CASPASES ET INDUCTEURS D'APOPTOSE ET UTILISATION ASSOCIEE
  申请人：CYTOVIA INC

  公开号：WO2007056215A2

  公开（公告）日：2007-05-18

  (EN) Disclosed are N-aryl-thienopyrimidin-4-amines and analogs thereof, represented by the Formulae I-II: wherein Ar and R1-R4 are defined herein. The present invention relates to the discovery that compounds having Formulae I-II are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention may be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.(FR) L'invention concerne des N-aryl-thiénopyrimidin-4-amines et des analogues de celles-ci, représentés par les formules I et II, dans lesquelles Ar et R1-R4 sont tels que définis dans la description. La présente invention concerne également la découverte que les composés représentés par les formule I et II sont des activateurs de caspases et des inducteurs d'apoptose. Par conséquent, les activateurs de caspases et inducteurs d'apoptose de l'invention peuvent être utilisés afin d'induire la mort cellulaire dans divers états cliniques dans lesquels apparaissent une croissance et une propagation incontrôlées de cellules anormales.