3-(4-chlorophenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]-pyrimidin-4-one | 111423-08-6

• 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: 3-(4-chlorophenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]-pyrimidin-4-one
• 英文别名: 3-(4-chlorophenyl)-2-thioxo-5,6,7,8-tetrahydro-1H-benzo[4,5]thieno[2,3-d]pyrimidine-4-one；3-(4-chlorophenyl)-2-thioxo-2,3,5,6,7,8-hexahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4(1H)-one；3-(4-chlorophenyl)-2-sulfanylidene-5,6,7,8-tetrahydro-1H-[1]benzothiolo[2,3-d]pyrimidin-4-one
• CAS: 111423-08-6
• 化学式: C₁₆H₁₃ClN₂OS₂
• mdl: MFCD01850672
• 分子量: 348.877
• InChiKey: OQFXKSADQKBXRA-UHFFFAOYSA-N

物化性质

• 熔点：
  289-292 °C(Solv: ethanol (64-17-5))
• 沸点：
  556.7±60.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 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：
  92.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(4-chlorophenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]-pyrimidin-4-one 在 吡啶 、 一水合肼 作用下， 反应 15.0h， 以75%的产率得到3-(4-chlorophenyl)-2-hydrazino-5,6,7,8-tetrahydrobenzo(b)thiophene[2,3-d]pyrimidine-4(3H)-one
  参考文献：
  名称：

  Synthesis of Some Thienopyrimidine Derivatives

  摘要：

  硫代噻吩嘧啶酮、烷硫基和芳烷硫噻吩嘧啶酮、噻吩嘧啶酮、噻吩嘧啶、噻吩嘧啶二酮及噻吩三唑嘧啶酮通过2-氨基-3-羧乙氧基-4,5-二取代噻吩和2-氨基-3-氰基-4,5-二取代噻吩与不同试剂的反应制备得到。

  DOI：

  10.3390/11070498
• 作为产物：
  描述：

  4-imino-2-thioxo-1,2,5,6,7,8-tetrahydro-4H-benzo(b)thieno(2,3-d)(1,3)thiazine 在 氢氧化钾 作用下， 反应 3.0h， 生成 3-(4-chlorophenyl)-2-thioxo-2,3,5,6,7,8-hexahydro-1H-benzo[4,5]thieno[2,3-d]-pyrimidin-4-one
  参考文献：
  名称：

  Sukumaran, P.; Rajasekharan, K. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 642 - 646

  摘要：

  DOI：

文献信息

• Synthesis, Characterization and Biological Studies of Some Novel Thieno[2,3-d]pyrimidines
  作者：Khulud M. Al-Taisan、Hassan M. A. Al-Hazimi、Shar S. Al-Shihry

  DOI：10.3390/molecules15063932

  日期：——

  Several 2-unsubstituted thieno[2,3-d]pyrimidines have been prepared from 2-aminothiophene-3-carboxylic acid esters and their carbonitrile analogs. Some triazolo-thienopyrimidine and 2-thioxothienopyrimidine representatives have also been synthesized using thermal and microwave (MW) irradiation techniques. Structures of the prepared compounds were elucidated on the basis of IR, NMR, 2D NMR and mass

  已经从 2-氨基噻吩-3-羧酸酯及其腈类似物制备了几种 2-未取代的噻吩并 [2,3-d] 嘧啶。一些三唑并噻吩并嘧啶和 2-硫代噻吩并嘧啶的代表也已使用热和微波 (MW) 辐射技术合成。基于红外、核磁共振、二维核磁共振和质谱数据阐明了所制备化合物的结构。还检查了一些选定的合成化合物的生物活性。
• Facile Synthesis of 2-Alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-<i>d</i>]pyrimidin-4(3<i>H</i>)-ones
  作者：Xiao-Hua Zeng、Min Liu、Ming-Wu Ding、Hong-Wu He

  DOI：10.1080/00397910903097294

  日期：2010.4.26

  aza-Wittig reaction of iminophosphorane 1 with CS2, reacted with amine to give 2-thioxo-2,3,5,6,7,8-hexahydrobenzothieno[2,3-d]pyrimidin-4(1H)-ones 4 in the presence of sodium ethoxide. S-Alkylation of 4 produced 2-alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidin-4(3H)-ones 5 in good yields.

  异硫氰酸酯 2，由亚氨基正膦 1 与 CS2 的氮杂-Wittig 反应获得，与胺反应得到 2-thioxo-2,3,5,6,7,8-六氢苯并噻吩并[2,3-d]嘧啶-4(1H) -ones 4 在乙醇钠的存在下。4 的 S-烷基化以良好的产率产生 2-烷硫基-5,6,7,8-四氢苯并噻吩并[2,3-d]嘧啶-4(3H)-ones 5。
• Novel antiproliferative agents bearing substituted thieno[2,3-d]pyrimidine scaffold as dual VEGFR-2 and BRAF kinases inhibitors and apoptosis inducers; design, synthesis and molecular docking
  作者：Rasha A. Hassan、Mohammed I.A. Hamed、Amr M. Abdou、Yara El-Dash

  DOI：10.1016/j.bioorg.2022.105861

  日期：2022.8

  was greatly reduced resulting in significantly disrupted wound healing patterns after treatment with compounds 4a and 4b for 72 h. Furthermore, Compounds 4a and 4b induced apoptosis by 22.82- and 25.81-fold increase in the total apoptosis percentage in breast cancer MCF7 cell line. This apoptotic activity was supported by an increase in the level of apoptotic caspase-9 by 6.17- and 9.07-fold, respectively

  基于多靶点定向药物设计策略，设计合成了一系列新型噻吩并[2,3- d ]嘧啶衍生物。所有新合成的化合物都在美国国家癌症研究所 (NCI) 对一组 60 种肿瘤细胞系的抗增殖活性进行了评估。化合物4a和4b在 10 µM 剂量下显示出显着的抗增殖活性，因此在五个剂量浓度下进行了评估。它们显示出强效和广谱的抗增殖活性，GI 50微摩尔范围内的值分别为 1.44–6.93 µM 和 1.66–5.82 µM。它们还显示 TGI 值分别在 3.49–97.3 µM 和 3.33–77.3 µM 的细胞抑制范围内。这两种化合物有效抑制 VEGFR-2，IC 50  = 0.111 ± 0.006 和 0.049 ± 0.003 µM，BRAF V600E的 IC 50  = 0.089 ± 0.005 和 0.063 ± 0.003 µM 和 BRAF WT IC 50  = 0.071 ± 0.004
• A Facile Microwave-Assisted Synthesis of Some Fused Pyrimidine Derivatives
  作者：S. A. Al Issa

  DOI：10.13005/ojc/300209

  日期：2014.7.1
• Structure–activity relationship analysis of a novel necroptosis inhibitor, Necrostatin-5
  作者：Ke Wang、Jinfeng Li、Alexei Degterev、Emily Hsu、Junying Yuan、Chengye Yuan

  DOI：10.1016/j.bmcl.2006.11.056

  日期：2007.3

  Necrostatin-5 (Nec-5) is a novel potent small-molecule inhibitor of necroptosis structurally distinct from previously described Necrostatin-1 (Nec-1), and therefore, represents a new direction for the inhibition of this cellular caspase-independent necrotic cell death mechanism. Here, we describe a series of structural modifications of Nec-5 and the structure-activity relationship (SAR) of Nec-5 series in inhibiting necroptosis.