3-amino-2-thioxo-1,2,3,5,6,7-hexahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one

• 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-amino-2-thioxo-1,2,3,5,6,7-hexahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one
• 英文别名: 11-Amino-10-sulfanylidene-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-12-one；11-amino-10-sulfanylidene-7-thia-9,11-diazatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-12-one
• 化学式: C₉H₉N₃OS₂
• 分子量: 239.322
• InChiKey: RKRJMMVORHRSKO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-amino-2-thioxo-1,2,3,5,6,7-hexahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one 在 乙醇 、 sodium 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 3-acetyl-1-(4-chlorophenyl)-1,7,8,9-tetrahydro-4H,6H-cyclopenta[4',5']thieno[2',3':4,5]pyrimido[1,2-b][1,2,4,5]tetrazin-6-one
  参考文献：
  名称：

  方便的一锅合成噻吩并[2'，3'：4,5]嘧啶[1,2-b]-[1,2,4,5]四嗪

  摘要：

  通过3-氨基-的反应制备了一系列新的噻吩并[2'，3'：4,5]嘧啶[1,2- b ] [1,2,4,5]四嗪-6-酮衍生物14。 2‐thioxo‐1,2,3,5,6,7‐hexahydro‐4 H ‐cyclopenta [4,5] thieno [2,3 ‐ d ]嘧啶‐4‐one 3或其甲硫基4与酰氯9。已经讨论了所研究反应的机理，并且有关产物指定结构的进一步证据是基于替代合成的。已对化合物14e进行了单晶X射线分析。

  DOI：

  10.1002/jhet.3117
• 作为产物：
  描述：

  2-氨基-5,6-二氢-4H-环戊并[b]噻吩-3-甲酸乙酯 在 hydrazine hydrate 、 potassium hydroxide 作用下， 以 乙醇 、 水 、 二甲基亚砜 为溶剂， 反应 20.25h， 生成 3-amino-2-thioxo-1,2,3,5,6,7-hexahydro-4H-cyclopenta[4,5]thieno[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  方便的一锅合成噻吩并[2'，3'：4,5]嘧啶[1,2-b]-[1,2,4,5]四嗪

  摘要：

  通过3-氨基-的反应制备了一系列新的噻吩并[2'，3'：4,5]嘧啶[1,2- b ] [1,2,4,5]四嗪-6-酮衍生物14。 2‐thioxo‐1,2,3,5,6,7‐hexahydro‐4 H ‐cyclopenta [4,5] thieno [2,3 ‐ d ]嘧啶‐4‐one 3或其甲硫基4与酰氯9。已经讨论了所研究反应的机理，并且有关产物指定结构的进一步证据是基于替代合成的。已对化合物14e进行了单晶X射线分析。

  DOI：

  10.1002/jhet.3117

文献信息

• Click chemistry based synthesis, cytotoxic activity and molecular docking of novel triazole-thienopyrimidine hybrid glycosides targeting EGFR
  作者：Reham R. Khattab、Asma K. Alshamari、Allam A. Hassan、Hussein H. Elganzory、Wael A. El-Sayed、Hanem M. Awad、Eman S. Nossier、Nasser A. Hassan

  DOI：10.1080/14756366.2020.1871335

  日期：2021.1.1

  In the current study, new thienopyrimidine conjugates bearing 1,2,3-triazole core and different sugar moieties have been designed and synthesized by Cu(I)-catalysed click dipolar cycloaddition. The cytotoxic activity of the synthesised conjugates 2, 5, 7, and 13-18 was studied against HCT-116 and MCF-7 cell lines by the MTT assay. The triazole glycosides 16 and 18 provided significant cytotoxic activities against HCT-116 cell lines comparable to that of doxorubicin and other studied compounds. The cytotoxic behaviour against MCF-7 exhibited that all the investigated compounds were more potent than doxorubicin. Moreover, all screened targets were evaluated against mutant EGFR kinase type L858R and the results revealed that the acetylated 1,2,3-triazole glycosides 13-18 exhibited excellent EGFR inhibitory activity in comparison with gefitinib. Furthermore, molecular modelling studies were performed to investigate the binding affinity of the most active compounds to EGFR enzyme.
• High potent and selective arylpiperazine derivatives as ligands for the 5-HT 1A receptor
  作者：Maria Modica、Maria Santagati、Andrea Santagati、Filippo Russo、Alfredo Cagnotto、Mara Goegan、Tiziana Mennini

  DOI：10.1016/s0960-894x(00)00165-7

  日期：2000.5

  This paper reports the synthesis and affinities on the 5HT(1A) versus the alpha(1)A receptors of new arylpiperazinylalkylthiothienopyrimidine and thiadiazole derivatives 16-24. Arylpiperazines 16-23 show affinities values in the nanomolar range for the 5HT(1A) receptor. The compound 16 is highly potent (K-i 0.26 nM, selectivity 28), the derivatives 20 and 21 are less potent, but highly selective (K-i 9.40 and 5.06 nM, selectivity 207 and 73, respectively). (C) 2000 Elsevier Science Ltd. All rights reserved.
• A Convenient One-Pot Synthesis of Thieno[2′,3′:4,5]Pyrimido[1,2-b]-[1,2,4,5]Tetrazines
  作者：Allam A. Hassan、Reham R. Khattab、Ashraf A. F. Wasfy、Khadiga M. Abuzeid、Nasser A. Hassan

  DOI：10.1002/jhet.3117

  日期：2018.4

  A novel series of thieno[2′,3′:4,5]pyrimido[1,2‐b][1,2,4,5]tetrazin‐6‐one derivatives 14 were prepared from the reaction of 3‐amino‐2‐thioxo‐1,2,3,5,6,7‐hexahydro‐4H‐cyclopenta[4,5]thieno[2,3‐d]pyrimidin‐4‐one 3 or its methylthio 4 with hydrazonoyl chlorides 9. The mechanism of the studied reactions has been discussed and further evidence for the assigned structure of the products is based on alternative

  通过3-氨基-的反应制备了一系列新的噻吩并[2'，3'：4,5]嘧啶[1,2- b ] [1,2,4,5]四嗪-6-酮衍生物14。 2‐thioxo‐1,2,3,5,6,7‐hexahydro‐4 H ‐cyclopenta [4,5] thieno [2,3 ‐ d ]嘧啶‐4‐one 3或其甲硫基4与酰氯9。已经讨论了所研究反应的机理，并且有关产物指定结构的进一步证据是基于替代合成的。已对化合物14e进行了单晶X射线分析。