3-phenyl-4-thiosemicarbazonomethyl-sydnone | 14484-87-8

• 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: 3-phenyl-4-thiosemicarbazonomethyl-sydnone
• 英文别名: N-Phenyl-sydnon-4-carbaldehyd-thiosemicarbazon
• CAS: 14484-87-8
• 化学式: C₁₀H₉N₅O₂S
• 分子量: 263.28
• InChiKey: RGFILBNUEPJOGB-UHFFFAOYSA-O

物化性质

• 熔点：
  188-190 °C(Solvent: Dichloromethane; Ethanol)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103.38
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-phenyl-4-thiosemicarbazonomethyl-sydnone 在 iron(III) chloride 、 sodium citrate 、 柠檬酸 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 4-{6'-(coumarin-3''-yl)-imidazo-[2,1-b][1,3,4]thiadiazol-2'-yl}-3-phenylsydnone
  参考文献：
  名称：

  Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents

  摘要：

  A novel series of 3-aryl-4{6'-(6''-substituted-coumarin-3''-yl) imidazo[2,1-b][1,3,4]thiadiazol-2'-yl}-sydnones 5h-5s were synthesized and screened for their anticancer and DNA cleavage activities and analyzed for pharmacological parameters such as toxicity, drug-likeliness, and drug score for oral bioavailability. In vitro toxicity assay was carried out by assessing the survival E. coli AB1157 (wild type) cultures. Some of the compounds have shown significant anticancer activities also.

  DOI：

  10.1007/s00044-012-0441-z
• 作为产物：
  描述：

  3-苯雪梨酮 在 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 0.17h， 生成 3-phenyl-4-thiosemicarbazonomethyl-sydnone
  参考文献：
  名称：

  Synthesis of novel imidazo[2,1-b][1,3,4]thiadiazoles appended to sydnone as anticancer agents

  摘要：

  A novel series of 3-aryl-4{6'-(6''-substituted-coumarin-3''-yl) imidazo[2,1-b][1,3,4]thiadiazol-2'-yl}-sydnones 5h-5s were synthesized and screened for their anticancer and DNA cleavage activities and analyzed for pharmacological parameters such as toxicity, drug-likeliness, and drug score for oral bioavailability. In vitro toxicity assay was carried out by assessing the survival E. coli AB1157 (wild type) cultures. Some of the compounds have shown significant anticancer activities also.

  DOI：

  10.1007/s00044-012-0441-z

文献信息

• Syntheses and evaluation of antioxidant activity of sydnonyl substituted thiazolidinone and thiazoline derivatives
  作者：Mei-Hsiu Shih、Fang-Ying Ke

  DOI：10.1016/j.bmc.2004.06.033

  日期：2004.9

  and thiazoline groups. The antioxidant activity of synthesized compounds 5a-7h was evaluated. Among these compounds, 4-methyl-2-[(3-arylsydnon-4-yl-methylene)hydrazono]-2,3-dihydro-thiazole-5-carbox ylic acid ethyl ester (6e-h) and 4-phenyl-2-[(3-arylsydnon-4-yl-methylene)hydrazono]-2,3-dihydro-thiazoles (7e-h) exhibit the potent DPPH (1,1-diphenyl-2-picrylhydrazyl) radical scavenging activity, comparable

  3-芳基-4-甲酰基sydnone 4'-苯基硫代半碳唑酮（3a-d）和3-芳基-4-甲酰基亚砜基硫代半碳唑酮（3e-h）是3-芳基-4-杂环丁酮的前体，是通过缩合制备的。 3-芳基-4-甲酰基sydnones（1a-d）分别与4'-苯基硫代氨基脲（2a）和硫代氨基脲（2b）。硫代半氨基甲酮3与诸如氯乙酸乙酯（4a），2-氯乙酰乙酸乙酯（4b）和2-溴乙酰苯酮（4c）之类的环状试剂反应，生成具有4-氧代-噻唑烷和噻唑啉基的杂环取代的丁二酮衍生物5-7。评价了合成化合物5a-7h的抗氧化活性。在这些化合物中，4-甲基-2-[（（3-芳基sydnon-4-基-亚甲基）肼基] -2,3-二氢噻唑-5-羧甲基丙烯酸乙酯（6e-h）和4-苯基- 2-[（3-芳基sydnon-4-基-亚甲基）hydr] -2，
• Efficient syntheses of thiadiazoline and thiadiazole derivatives by the cyclization of 3-aryl-4-formylsydnone thiosemicarbazones with acetic anhydride and ferric chloride
  作者：Mei-Hsiu Shih、Cheng-Ling Wu

  DOI：10.1016/j.tet.2005.08.107

  日期：2005.11

  3-Aryl-4-formylsydnone 4'-phenylthiosemicarbazones 3a-d and 3-aryl-4-formylsydnone thiosemicarbazones 3e-h are effective precursors of sydnonyl-substituted heterocycles. The thiosemicarbazones 3a-d reacted with acetic anhydride (4a) to give 4-acetyl-2-phenylamino-5-(3-arylsydnon-4-yl)-4,5-dihydro-[1,3,4]thiadiazoles 5a-d and 4-acetyl-2-(N-phenylacetamido)-5-(3-aryisydnon-4-yl)-4,5-dihydro-[1,3,4]thiadiazoles 6a-d. However, under similar method, thiosemicarbazones 3e-h produced only 4-acetyl-2-acetamido5-(3-arylsydnon-4-yl)-4,5-dihydro-[1,3,4]thiadiazoles 6e-h in high yield. The sydnonyl-substituted thiadiazole derivatives 7a-h were also obtained successfully by the cyclization of 3-aryl-4-formylsydnone thiosemicarbazones 3a-h with ferric chloride (4b). In the cyclization, the thiosemicarbazones 3a-d are more reactive than the thiosemicarbazones 3e-h. (c) 2005 Elsevier Ltd. All rights reserved.