4-Acetyl-2-acetylamino-5-fur-2-yl-4,5-dihydro-1,3,4-thiadiazol | 107261-67-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 4-Acetyl-2-acetylamino-5-fur-2-yl-4,5-dihydro-1,3,4-thiadiazol
• 英文别名: N-[4-acetyl-5-(furan-2-yl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide；N-(3-acetyl-2-(2-furyl)-1,3,4-thiadiazolin-5-yl)acetamide；N-[3-acetyl-2-(furan-2-yl)-2H-1,3,4-thiadiazol-5-yl]acetamide
• CAS: 107261-67-6
• 化学式: C₁₀H₁₁N₃O₃S
• 分子量: 253.282
• InChiKey: MFNIKJVCTDXGKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  100
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  糠醛 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 144.0h， 生成 4-Acetyl-2-acetylamino-5-fur-2-yl-4,5-dihydro-1,3,4-thiadiazol
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.10.023

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 and properties of 5-furyl(aryl)-?2-1,2,4-triazolines and -?2-1,3,4-thiadiazolines. Molecular and crystal structure of 2-acetylamino-5-phenyl-?2-1,3,4-thiadiazoline
  作者：E. B. Usova、G. D. Krapivin、V. E. Zavodnik、V. G. Kul'nevich

  DOI：10.1007/bf01184877

  日期：1994.10
• Andreae, Siegfried; Schmitz, Ernst; Seeboth, Helmuth, Journal fur praktische Chemie (Leipzig 1954), 1986, vol. 328, # 2, p. 205 - 214
  作者：Andreae, Siegfried、Schmitz, Ernst、Seeboth, Helmuth

  DOI：——

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• Usowa E. B., Khimija i tekhnol. furanow. soed, (1993) , S 68-72, 119
  作者：Usowa E. B.

  DOI：——

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• ANDREAE S.; SCHMITZ E.; SEEBOTH H., J. PRAKT. CHEM., 328,(1986) N 2, 205-214
  作者：ANDREAE S.、 SCHMITZ E.、 SEEBOTH H.

  DOI：——

  日期：——