3-[2"-chlorophenylaminomethyl]-5-(2'-hydroxyphenyl)-1,3,4-oxadiazoline-2-thione

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-[2"-chlorophenylaminomethyl]-5-(2'-hydroxyphenyl)-1,3,4-oxadiazoline-2-thione
• 英文别名: 3-[(2-Chloro-phenylamino)-methyl]-5-(2-hydroxy-phenyl)-3H-[1,4]oxadi azole-2-thione；3-[(2-chloroanilino)methyl]-5-(2-hydroxyphenyl)-1,3,4-oxadiazole-2-thione
• 化学式: C₁₅H₁₂ClN₃O₂S
• 分子量: 333.798
• InChiKey: IYXZOBVMRICUEY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  89.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  水杨酰肼 在 aluminum oxide 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.07h， 生成 3-[2"-chlorophenylaminomethyl]-5-(2'-hydroxyphenyl)-1,3,4-oxadiazoline-2-thione
  参考文献：
  名称：

  新型恶二唑衍生物的合成和生物学评估：新型胸苷磷酸化酶抑制剂作为潜在的抗肿瘤剂

  摘要：

  基于胸腺嘧啶磷酸化酶抑制剂被认为是潜在的抗肿瘤剂这一事实，通过简单而又容易的合成途径设计并合成了一系列新型的恶二唑衍生物3a - 3u。生物学分析表明，大多数化合物在低微摩尔浓度（IC 50 173.23±3.04至14.40±2.45μM）下显示出对胸苷磷酸化酶的适度抑制活性。在本研究中，活性最高的化合物为3h和3q，IC 50值分别为14.40±2.45和17.60±1.07μM。对活性最强的化合物（3h，3k，3o – 3q）以显示其绑定模式。

  DOI：

  10.1016/j.bmc.2013.12.043

文献信息

• Novel 5-(2-hydroxyphenyl)-3-substituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives: Promising anticancer agents
  作者：Ahmed S. Aboraia、Hamdy M. Abdel-Rahman、Nadia M. Mahfouz、Mahmoud A. EL-Gendy

  DOI：10.1016/j.bmc.2005.09.053

  日期：2006.2

  A series of 5-(2-hydroxyphenyl)-3-susstituted-2,3-dihydro-1,3,4-oxadiazole-2-thione derivatives was synthesized and 13 of them were selected by the National Cancer Institute (NCl) and evaluated for their in vitro anticancer activity. Seven of the investigated compounds, 3i, 3j, 3k, 3o, 3p, 3q, and 3r, displayed high anticancer activity in the primary assay. These compounds have been selected for a full anticancer screening against a 60-cell panel assay where they showed non-selective broad spectrum and promising activity against all cancer cell lines. Compounds 3j and 3k proved to be the active members in this Study compared to 5-fluorouracil and cyclophosphamide as reference drugs, respectively. Compounds 3j and 3k were identified as promising lead compounds. (c) 2005 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of novel oxadiazole derivatives: A new class of thymidine phosphorylase inhibitors as potential anti-tumor agents
  作者：Sohail Anjum Shahzad、Muhammad Yar、Marek Bajda、Bushra Jadoon、Zulfiqar Ali Khan、Syed Ali Raza Naqvi、Ahson Jabbar Shaikh、Khizar Hayat、Adeem Mahmmod、Nasir Mahmood、Sławomir Filipek

  DOI：10.1016/j.bmc.2013.12.043

  日期：2014.2

  derivatives 3a–3u was designed and synthesized by a simple and facile synthetic route. The biological assay revealed that majority of compounds displayed modest inhibitory activity against thymidine phosphorylase at low micromolar concentrations (IC50 173.23 ± 3.04 to 14.40 ± 2.45 μM). In the current study the most active compounds were 3h and 3q with IC50 values 14.40 ± 2.45 and 17.60 ± 1.07 μM, respectively

  基于胸腺嘧啶磷酸化酶抑制剂被认为是潜在的抗肿瘤剂这一事实，通过简单而又容易的合成途径设计并合成了一系列新型的恶二唑衍生物3a - 3u。生物学分析表明，大多数化合物在低微摩尔浓度（IC 50 173.23±3.04至14.40±2.45μM）下显示出对胸苷磷酸化酶的适度抑制活性。在本研究中，活性最高的化合物为3h和3q，IC 50值分别为14.40±2.45和17.60±1.07μM。对活性最强的化合物（3h，3k，3o – 3q）以显示其绑定模式。