2-(3-nitrophenyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one | 142354-85-6

• 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-(3-nitrophenyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one
• 英文别名: 2-(3-nitrophenyl)-5,6,7,8-tetrahydro-3H-[1]benzothiolo[2,3-d]pyrimidin-4-one
• CAS: 142354-85-6
• 化学式: C₁₆H₁₃N₃O₃S
• 分子量: 327.364
• InChiKey: PGKKSSRLXTZLGF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(3-nitrophenyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one 在 三氯氧磷 作用下， 反应 6.0h， 生成
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new thieno[2,3-d] pyrimidine derivatives as targeted therapy for PI3K with molecular modelling study

  摘要：

  DOI：

  10.1080/14756366.2021.2010729
• 作为产物：
  描述：

  环己酮 在 吗啉 、 盐酸 、 sulfur 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-(3-nitrophenyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of new thieno[2,3-d] pyrimidine derivatives as targeted therapy for PI3K with molecular modelling study

  摘要：

  DOI：

  10.1080/14756366.2021.2010729

文献信息

• Synthesis and bioevaluation of new vascular-targeting and anti-angiogenic thieno[2,3-d]pyrimidin-4(3H)-ones
  作者：Madeleine Gold、Leonhard Köhler、Clarissa Lanzloth、Ion Andronache、Shrikant Anant、Prasad Dandawate、Bernhard Biersack、Rainer Schobert

  DOI：10.1016/j.ejmech.2020.112060

  日期：2020.3

  A series of forty-six 5,6-annulated 2-arylthieno [2,3-d]pyrimidin-4(3H)-ones were prepared as potentially pleiotropic anticancer drugs with variance in the tubulin-binding trimethoxyphenyl motif at C-2 of a thieno [2,3-d]pyrimidine fragment, enlarged by additional rings of different size and substitution. By assessing their cytotoxicity against various cancer cells, their influence on the polymerization

  制备了一系列四十六种5,6-环化的2-芳基噻吩并[2,3-d]嘧啶-4（3H）-作为潜在的多效抗癌药物，在C-2的C-2处微管蛋白结合的三甲氧基苯基基序有所不同。噻吩并[2,3-d]嘧啶片段，通过不同大小和取代的附加环扩大。通过评估它们对各种癌细胞的细胞毒性，它们对纯净微管蛋白聚合以及微管和F-肌动蛋白细胞骨架动力学的影响，以及它们在体外和体内的血管破坏和抗血管生成活性，确定了结构-活性关系。这表明3-碘-4,5-二甲氧基苯基取代的噻吩并嘧啶2e作为有希望的抗癌药物有待进一步研究。2020 Elsevier Ltd.保留所有权利。
• 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.
• [EN] ANTI-VIRAL AGENTS THAT ACTIVATE RNASE L<br/>[FR] AGENTS ANTI-VIRAUX QUI ACTIVENT L'ARNSE L
  申请人：CLEVELAND CLINIC FOUNDATION

  公开号：WO2007127212A2

  公开（公告）日：2007-11-08

  [EN] RNase L Activators and methods of using the same are disclosed herein.
  [FR] L'invention concerne des activateurs d'ARNse L et des méthodes pour les utiliser.