4-acetyl-2-acetylamino-5-phenyl-Δ²-1,3,4-thiadiazoline | 62236-01-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-acetyl-2-acetylamino-5-phenyl-Δ²-1,3,4-thiadiazoline
• 英文别名: 4-Acetyl-2-acetylamino-5-phenyl-4,5-dihydro-1,3,4-thiadiazol；2-(Acetamido)-4-acetyl-5-phenyl-Δ²-1,3,4-thiadiazoline；N-(4-acetyl-4,5-dihydro-5-phenyl-1,3,4-thiadiazol-2-yl)acetamide；N-(4-acetyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide；N-(4-Acetyl-5-phenyl-4,5-dihydro-[1,3,4]thiadiazol-2-yl)-acetamid；3-acetyl-5-acetylamino-2-phenyl-2,3-dihydro-[1,3,4]thiadiazole；2-acetamido-4-acetyl-5-phenyl-4,5-dihydro-1,3,4-thiadiazole；N-(3-acetyl-2-phenyl-2H-1,3,4-thiadiazol-5-yl)acetamide
• CAS: 62236-01-5
• 化学式: C₁₂H₁₃N₃O₂S
• 分子量: 263.32
• InChiKey: TYZWEONFZGQVSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-acetyl-2-acetylamino-5-phenyl-Δ²-1,3,4-thiadiazoline 在 一水合肼 作用下， 生成 1-(5-氨基-2-苯基-[1,3,4]噻二唑-3-基)-乙酮
  参考文献：
  名称：

  Kubota,S. et al., Heterocycles, 1976, vol. 4, p. 1909 - 1912

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 以 乙醇 、 水 为溶剂， 反应 0.5h， 生成 4-acetyl-2-acetylamino-5-phenyl-Δ²-1,3,4-thiadiazoline
  参考文献：
  名称：

  Cytotoxicity of New 5-Phenyl-4,5-dihydro-1,3,4-thiadiazole Analogues

  摘要：

  一系列5-苯基-4,5-二氢-1,3,4-噻二唑被合成并对四种人癌细胞系（例如肺癌(A549)、卵巢癌(SK-OV-3)、皮肤癌(SK-MEL-2)和结肠癌(HCT15)）进行了细胞毒性测试。标题化合物通过硫脲与取代苯甲醛的缩合反应合成，随后用乙酸酐环化得到良好产率。大多数化合物对所有癌细胞系的生长表现出显著抑制活性。5-苯基-4,5-二氢-1,3,4-噻二唑的4-羟基类似物(2h)在抑制SK-MEL-2细胞生长方面活性最高，IC50值为4.27 μg/ml；其次是化合物2a（IC50 5.16 μg/ml）。化合物2j、2h和2b分别在C-5苯环上具有3-甲氧基-4-羟基、4-羟基和4-甲基取代基，它们对SK-OV-3（IC50 7.35 μg/ml）、HCT15（IC50 8.25 μg/ml）和A549（IC50 9.40 μg/ml）细胞系表现出最高活性。结构-活性关系研究揭示，1,3,4-噻二唑C-5苯环上的最佳电子密度对本研究中使用的人癌细胞系的细胞毒性活性至关重要。

  DOI：

  10.1248/cpb.59.1413

文献信息

• Pyridyl-1,3,4-thiadiazole; eine neue Variante der Thiadiazol-Synthese
  作者：P. Hemmerich、B. Prijs、H. Erlenmeyer

  DOI：10.1002/hlca.19580410714

  日期：——

  Thiosemicarbazones of aromatic aldehydes react with acetic anhydride to give well-defined N4,S-diacetyl derivatives, which readily undergo oxidative cyclisation to 2-aryl-4-acetamido-1,3,4-thiadiazoles. From these intermediates, aryl-thiadiazoles – especially 2-(2′-pyridyl)-1,3,4-thiadiazole, inaccessible by the common methods – can be obtained by acidic deacetylation, SANDMEYER substitution and catalytic

  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。
• Stereoselective S-oxidation of 5-substituted 4-acetyl-Δ²-1,3,4-thia-diazolines: X-ray crystal structure of 4-acetyl-2-acetylamino-5-methy-5-phenyl-Δ²-1,3,4-thiadiazoline 1-oxide
  作者：Seiju Kubota、Kouhei Toyooka、Naoya Yamamoto、Masayuki Shibuya、Masaru Kido

  DOI：10.1039/c39820000901

  日期：——

  N.m.r. spectroscopy and X-ray crystallography show that oxidation of 5-substituted 4-acetyl-2-acetylamino-Δ2-1,3,4-thiadiazolines with m-chloroperbenzoic acid gives the corresponding Δ2-1,3,4-thiadiazoline 1-oxides; the novel reactions of the product (2a) are also described.

  N.m.r. 光谱和 X 射线晶体学显示，用间氯过苯甲酸氧化 5-取代的 4-乙酰基-2-乙酰氨基δ2-1,3,4-噻二唑啉，可得到相应的δ2-1,3,4-噻二唑啉 1-氧化物；还描述了产物 (2a) 的新型反应。
• 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
• 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.
• 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