5,5-Pentamethylen-4-propionyl-2-propionylamino-4,5-dihydro-1,3,4-thiadiazol | 107261-60-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物
• 英文名称: 5,5-Pentamethylen-4-propionyl-2-propionylamino-4,5-dihydro-1,3,4-thiadiazol
• 英文别名: N-[1-(1-oxopropyl)-4-thia-1,2-diazaspiro[4.5]dec-2-en-3-yl]propanamide；N-(4-propanoyl-1-thia-3,4-diazaspiro[4.5]dec-2-en-2-yl)propanamide
• CAS: 107261-60-9
• 化学式: C₁₃H₂₁N₃O₂S
• 分子量: 283.395
• InChiKey: OAEHVEMGBOXGMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.43
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  61.77
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  环己酮 在 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 144.0h， 生成 5,5-Pentamethylen-4-propionyl-2-propionylamino-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

• 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：——

  日期：——
• Andreae, Siegfried; Schmitz, Ernst, Zeitschrift fur Chemie, 1983, vol. 23, # 12, p. 450 - 451
  作者：Andreae, Siegfried、Schmitz, Ernst

  DOI：——

  日期：——
• 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：——