2-(4-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one | 60442-59-3

• 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
• 英文名称: 2-(4-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
• 英文别名: 2-(4-methoxyphenyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one；2-(4-methoxy-phenyl)-5,6,7,8-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one；2-(4-methoxyphenyl)-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one；2-(4-methoxyphenyl)-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one
• CAS: 60442-59-3
• 化学式: C₁₇H₁₆N₂O₂S
• mdl: MFCD00773594
• 分子量: 312.392
• InChiKey: MXYYHEJTMJMGSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  78.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one 在 三氯氧磷 作用下， 生成 4-chloro-2-(4-methoxy-phenyl)-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-d]pyrimidine
  参考文献：
  名称：

  神奇的鸟枪法抗炎药物治疗：合成新型噻吩嘧啶单体/异二聚体作为具有强效抗氧化活性的双重 COX-2 和 15-LOX 抑制剂

  摘要：

  新出现的证据表明，炎症和氧化应激在各种疾病中相互交织。我们推测神奇的霰弹枪方法对这些疾病的潜在影响，以试图减轻当前 NSAID 的缺点。因此，我们合理设计并合成了新的四氢苯并[4,5]噻吩并[2,3-d]嘧啶单体/异二聚体作为具有强大抗氧化活性的双选择性 COX-2/15-LOX 抑制剂。合成的化合物接受了多种体外生物测定的攻击。关于单体系列，化合物 5k 发挥最高的 COX-2 抑制活性 （IC50 = 0.068 μM，SI = 160.441），而化合物 5i 表现出最高的 15-LOX 抑制活性 （IC50 = 1.97 μM）。异二聚体 11 超过最活跃的单体成员，成为整个研究中最有效和最具选择性的成员 （COX-2 IC50 = 0.065 μM，SI = 173.846,15-LOX IC50 = 1.86 μM）。异二聚体设计的灵感来自于 COX-2 亚型的伴侣单体之间的串

  DOI：

  10.1016/j.ejmech.2023.115724
• 作为产物：
  描述：

  2-(4-methoxy-benzoylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carbonitrile 生成 2-(4-methoxyphenyl)-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  杂环化合物。V.2,4-二取代的噻吩并嘧啶†

  摘要：

  DOI：

  10.1002/jhet.5570130346

文献信息

• ZnO-CeO2 nanocomposite: efficient catalyst for the preparation of thieno[2,3-d]pyrimidin-4(3H)-one derivatives
  作者：Farzaneh Ghayour、Mohammad Reza Mohammad Shafiee、Majid Ghashang

  DOI：10.1515/mgmc-2017-0038

  日期：2018.4.13

  mean particle size of the nanocomposite determined by dynamic light scattering technique was 58 nm. The catalytic activity of ZnO-CeO2 nanocomposite was examined on the synthesis of thieno[2,3-d]pyrimidin-4(3H)-one derivatives. In all cases, the products were obtained in good to excellent yields.

  摘要 采用共沉淀法制备氧化锌-氧化铈(ZnO-CeO2)纳米复合材料，并通过X射线衍射(XRD)、场发射扫描电子显微镜(FE-SEM)和粒度分布分析对其进行表征。XRD图显示氧化铈的立方相作为主要相。FE-SEM 图像显示了样品中氧化锌和氧化铈的均匀性分布。通过动态光散射技术测定的纳米复合材料的平均粒径为 58 nm。ZnO- 纳米复合材料的催化活性在噻吩并[2,3-d]嘧啶-4(3H)-one 衍生物的合成中进行了检测。在所有情况下，产品都以良好到极好的收率获得。
• Three possible products from the reactions of gewald's amide with aromatic aldehydes
  作者：Sergey G. Dzhavakhishvili、Nikolay Yu. Gorobets、Vladimir I. Musatov、Sergey M. Desenko、Boris V. Paponov

  DOI：10.1002/jhet.5570450243

  日期：2008.3

  Transformations of 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (Gewald's amide) in the reactions with aromatic aldehydes were studied. Efficient methods for synthesis of three possible types of products: 2-aryl-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3H)-one, 2-(1-arylmethylidene-amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide and 2-aryl-2,3,5,6,7,8-hexahydro[1]benzo-thieno[2

  研究了2-氨基-4,5,6,7-四氢苯并[ b ]噻吩-3-羧酰胺（Gewald's amide）在与芳族醛的反应中的转化。合成三种可能类型产物的有效方法：2-芳基-5,6,7,8-四氢[1]苯并噻吩并[2,3 - d ]嘧啶-4（3 H）-one，2-（1-芳基亚甲基-氨基）-4,5,6,7-四氢苯并[ b ]噻吩-3-羧酰胺和2-芳基-2,3,5,6,7,8-六氢[1]苯并噻吩并[2,3 - d ]嘧啶-4（1 ħ） -酮衍生物被开发出来。通过过滤可以容易地分离所有产物，具有非常好的总产率。还研究了这些化合物的相互转化。
• Thienopyrimidine derivatives exert their anticancer efficacy via apoptosis induction, oxidative stress and mitotic catastrophe
  作者：Haneen Amawi、Chandrabose Karthikeyan、Rekha Pathak、Noor Hussein、Ryann Christman、Robert Robey、Charles R. Ashby、Piyush Trivedi、Ashim Malhotra、Amit K. Tiwari

  DOI：10.1016/j.ejmech.2017.07.028

  日期：2017.9

  In this study, a series of 13 structural variants of thieno[2,3d]pyrimidine derivatives (6a-6m) were synthesized and screened for cytotoxicity in a panel of colorectal, ovarian, and brain cancer cell lines. The selectivity of the compounds was assessed by determining the cytotoxicity in normal epithelial cell line (CHO). The most potent compound, 6j, was efficacious (with IC50 range of 0.6-1.2 mu M) in colon (HCT116 and HCT15), brain (LN-229 and GBM-10) and ovarian (A2780 and OV2008) cancer cell lines. In contrast, in the normal cell line (CHO), the IC50 values for 6j were 14 +/- 1.3 mu M. Compound 6j significantly inhibited the clonogenic potential of HCT116, OV2008 and A2780 cell lines in concentration dependent (0.5 - 4 mu M) manner. Also, 6j induced 1) formation of reactive oxygen species; 2) apoptosis and 3) mitotic catastrophe in HCT116 and OV2008 cells (IC50 = 0.5-2 mu M). Furthermore, apoptosis was the predominant mechanism of death in A2780 cells. The cytotoxicity of 6j in wild type HCT116 cells was similar to that in HCT116 cells lacking the apoptotic genes for Bax, Bak, or Bak and Bax, indicating that 6j induces mitotic catastrophe as alternative mechanism of death when when certain apoptotic proteins are absent. In summary, this study has identified a lead molecule, 6j, that selectively induces oxidative stress, apoptosis and mitotic catastrophe in specific cancer (colon and ovarian) cell lines. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Design, synthesis, and biological evaluation of new thieno[2,3-<i>d</i>] pyrimidine derivatives as targeted therapy for PI3K with molecular modelling study
  作者：Fatma M. Elmenier、Deena S. Lasheen、Khaled A. M. Abouzid

  DOI：10.1080/14756366.2021.2010729

  日期：2022.12.31
• Inhibition of tumor cell proliferation by thieno[2,3-d]pyrimidin-4(1H)-one-based analogs
  作者：Yanong D. Wang、Steven Johnson、Dennis Powell、John P. McGinnis、Miriam Miranda、Sridhar K. Rabindran

  DOI：10.1016/j.bmcl.2005.05.127

  日期：2005.8

  On the basis of a screening lead from an assay using a pair of p21 isogenic cell lines (p21-proficient cells and p21-deficient cells) to identify chemoselective agents, a series of novel thieno[2,3-d]pyrimidin-4(1H)-one-based analogs was prepared. Some analogs inhibited the growth of human colon tumor cells. (c) 2005 Elsevier Ltd. All rights reserved.