4-fluoro-benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone | 493016-38-9

• 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: 4-fluoro-benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone
• 英文别名: N-[(4-fluorophenyl)methylideneamino]-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine
• CAS: 493016-38-9
• 化学式: C₁₇H₁₅FN₄S
• 分子量: 326.397
• InChiKey: FXFZYBDLUZHOOS-UHFFFAOYSA-N

物化性质

• 沸点：
  511.9±50.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-fluoro-benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone 在 lithium iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 生成 5-(4-Fluorophenyl)-10-thia-3,4,6,8-tetrazatetracyclo[7.7.0.02,6.011,16]hexadeca-1(9),2,4,7,11(16)-pentaene
  参考文献：
  名称：

  Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking

  摘要：

  The oxidative cyclisation of a range of benzothieno[2,3-d]pyrimidine hydrazones (7a-j) to the 1,2,4-triazolo[4,3-c]pyrimidines (8a-j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5-c]pyrimidines (10a-j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-triazolo[1,5-c]pyrimidines starting from the amino imine 11 is also reported. The effect of these compounds on Shiga toxin (STx) trafficking in HeLa cells and comparison to the previously reported Exo2 is also detailed (C) 2009 Elsevier Masson SAS. All rights reserved

  DOI：

  10.1016/j.ejmech.2009.10.007
• 作为产物：
  描述：

  对氟苯甲醛 、 4-肼基-5,6,7,8-四氢[1]苯并噻吩并-[2,3-d]嘧啶 以 乙醇 为溶剂， 以99.4%的产率得到4-fluoro-benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone
  参考文献：
  名称：

  Trypanoside, anti-tuberculosis, leishmanicidal, and cytotoxic activities of tetrahydrobenzothienopyrimidines

  摘要：

  The synthesis of 2-(5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl) hydrazone-derivatives (BTPs) and their in vitro evaluation against Trypanosoma cruzi trypomastigotes, Mycobacterium tuberculosis, Leishmania amazonensis axenic amastigotes, and six human cancer cell lines is described. The in vivo activity of the most active and least toxic compounds against T. cruzi and L. amazonensis was also studied. BTPs constitute a new family of drug leads with potential activity against infectious diseases. Due to their drug-like properties, this series of compounds can potentially serve as templates for future drug-optimization and drug-development efforts for use as therapeutic agents in developing countries. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.018

文献信息

• Trypanoside, anti-tuberculosis, leishmanicidal, and cytotoxic activities of tetrahydrobenzothienopyrimidines
  作者：José C. Aponte、Abraham J. Vaisberg、Denis Castillo、German Gonzalez、Yannick Estevez、Jorge Arevalo、Miguel Quiliano、Mirko Zimic、Manuela Verástegui、Edith Málaga、Robert H. Gilman、Juan M. Bustamante、Rick L. Tarleton、Yuehong Wang、Scott G. Franzblau、Guido F. Pauli、Michel Sauvain、Gerald B. Hammond

  DOI：10.1016/j.bmc.2010.03.018

  日期：2010.4

  The synthesis of 2-(5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl) hydrazone-derivatives (BTPs) and their in vitro evaluation against Trypanosoma cruzi trypomastigotes, Mycobacterium tuberculosis, Leishmania amazonensis axenic amastigotes, and six human cancer cell lines is described. The in vivo activity of the most active and least toxic compounds against T. cruzi and L. amazonensis was also studied. BTPs constitute a new family of drug leads with potential activity against infectious diseases. Due to their drug-like properties, this series of compounds can potentially serve as templates for future drug-optimization and drug-development efforts for use as therapeutic agents in developing countries. (C) 2010 Elsevier Ltd. All rights reserved.
• Simple oxidation of pyrimidinylhydrazones to triazolopyrimidines and their inhibition of Shiga toxin trafficking
  作者：Lucie J. Guetzoyan、Robert A. Spooner、J. Michael Lord、Lynne M. Roberts、Guy J. Clarkson

  DOI：10.1016/j.ejmech.2009.10.007

  日期：2010.1

  The oxidative cyclisation of a range of benzothieno[2,3-d]pyrimidine hydrazones (7a-j) to the 1,2,4-triazolo[4,3-c]pyrimidines (8a-j) catalysed by lithium iodide or to the 1,2,4-triazolo[1,5-c]pyrimidines (10a-j) with sodium carbonate is presented. A complementary synthesis of the 1,2,4-triazolo[1,5-c]pyrimidines starting from the amino imine 11 is also reported. The effect of these compounds on Shiga toxin (STx) trafficking in HeLa cells and comparison to the previously reported Exo2 is also detailed (C) 2009 Elsevier Masson SAS. All rights reserved