benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone | 81154-29-2

• 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: benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone
• 英文别名: 4-benzalhydrazino-5,6-tetramethylenothieno<2,3-d>pyrimidine；4-benzalhydrazino-5,6-tetramethylenothieno[2,3-d]pyrimidine；N-(benzylideneamino)-5,6,7,8-tetrahydro-[1]benzothiolo[2,3-d]pyrimidin-4-amine
• CAS: 81154-29-2
• 化学式: C₁₇H₁₆N₄S
• 分子量: 308.407
• InChiKey: HDYWBJKAYZQZAG-UHFFFAOYSA-N

物化性质

• 熔点：
  232-234 °C(Solvent: Ethanol)
• 沸点：
  517.0±50.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(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：
  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：
  5

反应信息

• 作为反应物：
  描述：

  benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone 在 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以76%的产率得到3-phenyl-1,2,4-triazolo<3,4-c>pyrimido<4,5-b>tetrahydrobenzothiophene
  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：

  5,6,7,8-四氢-[1]-苯并噻吩[2,3-d]嘧啶-4(1h)-酮 在 肼 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 6.0h， 生成 benzaldehyde (5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4-yl)hydrazone
  参考文献：
  名称：

  [EN] COMPOUNDS, THEIR SYNTHESES, AND THEIR USES
  [FR] COMPOSÉS, LEUR SYNTHÈSE ET LEURS UTILISATIONS

  摘要：

  本发明实施例提供化合物（如式（I）化合物、式（II）化合物及其各种实施例）。还提供包含这些化合物的组合物。包括它们的制备方法。此外，还包括化合物的用途，如给药和治疗疾病（例如癌症和感染）。

  公开号：

  WO2010019861A1

文献信息

• Ram; Pandey; Vlietinck, Journal of Heterocyclic Chemistry, 1981, vol. 18, # 7, p. 1277 - 1280
  作者：Ram、Pandey、Vlietinck

  DOI：——

  日期：——
• 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.
• [EN] COMPOUNDS, THEIR SYNTHESES, AND THEIR USES<br/>[FR] COMPOSÉS, LEUR SYNTHÈSE ET LEURS UTILISATIONS
  申请人：UNIV LOUISVILLE RES FOUND

  公开号：WO2010019861A1

  公开（公告）日：2010-02-18

  Embodiments of the present invention provide compounds (such as Formula (I) compounds, Formula (II) compounds, and various embodiments thereof). Compositions comprising those compounds are also provided. Methods for their preparation are included. Also, uses of the compounds are included, such as administering and treating diseases (e.g., cancer and infections).

  本发明实施例提供化合物（如式（I）化合物、式（II）化合物及其各种实施例）。还提供包含这些化合物的组合物。包括它们的制备方法。此外，还包括化合物的用途，如给药和治疗疾病（例如癌症和感染）。
• 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