N-[4-acetyl-5-(pyridin-4-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide | 62236-04-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-[4-acetyl-5-(pyridin-4-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide
• 英文别名: 2-acetylamino-4-acetyl-5-(4-pyridyl)-1,3,4-thiadiazoline；3-acetyl-5-acetylamino-2-pyridin-4-yl-2,3-dihydro-[1,3,4]thiadiazole；N-(4-acetyl-5-[4]pyridyl-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-acetamide；N-(4-Acetyl-5-[4]pyridyl-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-acetamid；N-(4-Acetyl-5-(pyridin-4-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide；N-(3-acetyl-2-pyridin-4-yl-2H-1,3,4-thiadiazol-5-yl)acetamide
• CAS: 62236-04-8
• 化学式: C₁₁H₁₂N₄O₂S
• 分子量: 264.308
• InChiKey: ZCXPVLSZPSTSRE-UHFFFAOYSA-N

物化性质

• 熔点：
  220-222 °C
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[4-acetyl-5-(pyridin-4-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide 在 盐酸 、 双氧水 、 溶剂黄146 作用下， 生成 2-氨基-5-(4-吡啶基)-1,3,4-噻重氮
  参考文献：
  名称：

  吡啶基-1,3,4-噻二唑; 噻二唑合成的新变体

  摘要：

  芳族醛的硫代氨基甲唑酮与乙酸酐反应，得到定义明确的N 4，S-二乙酰基衍生物，该衍生物易于氧化环化成2-芳基-4-乙酰氨基-1,3,4-噻二唑。从这些中间体，可以通过酸性脱乙酰基化，SANDMEYER取代和催化脱卤来获得芳基-噻二唑，尤其是2-（2'-吡啶基）-1,3,4-噻二唑，这是常规方法难以达到的。

  DOI：

  10.1002/hlca.19580410714
• 作为产物：
  描述：

  (吡啶-4-基亚甲基氨基)硫脲 在 乙酸酐 作用下， 生成 N-[4-acetyl-5-(pyridin-4-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide
  参考文献：
  名称：

  吡啶基-1,3,4-噻二唑; 噻二唑合成的新变体

  摘要：

  芳族醛的硫代氨基甲唑酮与乙酸酐反应，得到定义明确的N 4，S-二乙酰基衍生物，该衍生物易于氧化环化成2-芳基-4-乙酰氨基-1,3,4-噻二唑。从这些中间体，可以通过酸性脱乙酰基化，SANDMEYER取代和催化脱卤来获得芳基-噻二唑，尤其是2-（2'-吡啶基）-1,3,4-噻二唑，这是常规方法难以达到的。

  DOI：

  10.1002/hlca.19580410714

文献信息

• 1H,13C,15N and19F NMR study of acetylation products of heterocyclic thiosemicarbazones
  作者：Lyudmila I. Larina、Valentina N. Elokhina、Tatyana I. Yaroshenko、Anatolii S. Nakhmanovich、Gennadii V. Dolgushin

  DOI：10.1002/mrc.2006

  日期：2007.8

  eryl)‐1,3,4‐thiadiazoles, and some of their salts were prepared and studied by multinuclear 1H, 13C, 15N, 19F and 2D NMR spectroscopy. The acetylation of thiosemicarbazones is accompanied by ring closure to form the corresponding 1,3,4‐thiadiazolines and 1,3,4‐thiadiazoles. 15N NMR spectroscopy is a unique method for the identification of thiadiazole pyridinium salts. Copyright © 2007 John Wiley &

  制备了新型 2-乙酰氨基-4-乙酰基-5-芳基(杂基)-1,3,4-噻二唑啉、2-乙酰氨基-5-芳基(杂基)-1,3,4-噻二唑及其部分盐并通过多核 1H、13C、15N、19F 和 2D 核磁共振波谱研究。缩氨基硫脲的乙酰化伴随着闭环形成相应的 1,3,4-噻二唑啉和 1,3,4-噻二唑。15N NMR 光谱是鉴定噻二唑吡啶鎓盐的独特方法。版权所有 © 2007 John Wiley & Sons, Ltd.
• Synthesis of 4-acyl-2-(acylamino)-.DELTA.2-1,3,4-thiadiazolines and 4-acyl-2-amino-.DELTA.2-1,3,4-thiadiazolines by acylation of thiosemicarbazones
  作者：Seiju Kubota、Yasufumi Ueda、Kazuichi Fujikane、Kouhei Toyooka、Masayuki Shibuya

  DOI：10.1021/jo01296a025

  日期：1980.4
• Kubota,S. et al., Heterocycles, 1976, vol. 4, p. 1909 - 1912
  作者：Kubota,S. et al.

  DOI：——

  日期：——
• Synthesis and pharmacological screening of a large library of 1,3,4-thiadiazolines as innovative therapeutic tools for the treatment of prostate cancer and melanoma
  作者：Celeste De Monte、Simone Carradori、Daniela Secci、Melissa D'Ascenzio、Paolo Guglielmi、Adriano Mollica、Stefania Morrone、Susanna Scarpa、Anna Maria Aglianò、Sabrina Giantulli、Ida Silvestri

  DOI：10.1016/j.ejmech.2015.10.023

  日期：2015.11

  Antimitotic agents are widely used in cancer chemotherapy but the numerous side effects and the onset of resistance limit their clinical efficacy. Therefore, with the purpose of discovering more selective and efficient anticancer agents to be administered alone or in combination with traditional drugs, we synthesized a large library of 1,3,4-thiadiazoline analogues, maintaining the pharmacophoric structure of an antiproliferative compound known as K858: this is a new inhibitor of kinesin Eg5, able to induce the mitotic arrest in colorectal cancer cells and in xenograft ovarian cancer cells. We screened 103 compounds to assess their antiproliferative activity on PC3 prostate cancer cell line. Two derivatives, compounds 32 (corresponding to K858) and 33, have shown to be the most effective against prostate tumor cells and also towards two melanoma cell lines (SK-MEL-5 and SK-MEL-28) at low micromolar concentrations, confirming the pharmacological activity of this scaffold and revealing the potential role of 1,3,4-thiadiazolines in the management of cancer. (C) 2015 Elsevier Masson SAS. All rights reserved.
• KUBOTA S.; UEDA Y.; FUJIKANE K.; TOYOOKA K.; SHIBUYA M., J. ORG. CHEM., 1980, 45, NO 8, 1473-1477
  作者：KUBOTA S.、 UEDA Y.、 FUJIKANE K.、 TOYOOKA K.、 SHIBUYA M.

  DOI：——

  日期：——