5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole-1-carbothioamide | 957761-00-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole-1-carbothioamide
• 英文别名: 5-(4-Methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide；3-(4-methoxyphenyl)-5-thiophen-2-yl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 957761-00-1
• 化学式: C₁₅H₁₅N₃OS₂
• 分子量: 317.436
• InChiKey: SQSNYGYBWPSUKI-UHFFFAOYSA-N

物化性质

• 沸点：
  491.4±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole-1-carbothioamide 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 反应 8.0h， 以78%的产率得到ethyl 2-(5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazol-1-yl)-4-methylthiazole-5-carboxylate
  参考文献：
  名称：

  一些新型吡唑啉基噻唑衍生物的合成及其抗微生物、抗真菌和抗癌活性的评价

  摘要：

  摘要 3-(2-噻吩基)-5-芳基-1-硫代氨基甲酰基-2-吡唑啉与氯丙酮衍生物和腙氯衍生物在乙醇中反应，分别得到相应的噻唑基吡唑啉衍生物和噻吩基吡唑基-5-取代芳基-二烯基噻唑衍生物。新合成化合物的结构通过不同的元素和光谱分析（红外、质谱、 1 H 和 13 C NMR）阐明。针对四种细菌物种和五种真菌菌株评估了新合成化合物的抗菌和抗真菌活性。此外，两个新合成的化合物 1-(2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazol-1-yl)-4-) 的抗肿瘤活性甲基噻唑-5-基)乙-1-酮和2-(5-(4-氯苯基)-3-(噻吩-2-基)-4，5-dihydro-1 H -pyrazol-1-yl)-4-methyl-5-(phenyl-diazenyl)thiazole 对 HEPG-2、HCT-116、MCF-7、BHK 和

  DOI：

  10.1134/s1068162020030061
• 作为产物：
  描述：

  2-乙酰基噻吩 在 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 5-(4-methoxyphenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazole-1-carbothioamide
  参考文献：
  名称：

  Investigating the Anticancer Activity of Isatin/Dihydropyrazole Hybrids

  摘要：

  A series of isatin dihydropyrazole hybrids have been synthesized in order to assess their potential as anticancer agents. In particular, 12 compounds were evaluated for their antiproliferative activity toward A549, IGR39, U87, MDA-MB-231, MCF-7, BT474, BxPC-3, SKOV-3, and H1299 cell lines, and human foreskin fibroblasts. Four compounds exhibited interesting antiproliferative activity and were further examined to determine their ECso values toward a panel of selected tumor cell lines. The best compounds were then investigated for their induced mechanism of cell death. Preliminary structure activity relationship indicates that the presence of a substituent such as a chlorine atom or a methyl moiety in position 5 of the isatin nucleus is beneficial for the antitumor activity. EMAC4001 proved the most promising compound within the studied series with EC50 values ranging from 0.01 to 0.38 mu M.

  DOI：

  10.1021/acsmedchemlett.8b00596

文献信息

• Synthesis and Antimicrobial Activity of Some Thiazolyl-Pyrazoline Derivatives
  作者：Zafer Asım Kaplancıklı、Gülhan Turan-Zitouni、Ahmet Özdemir、Gilbert Revial、Kıymet Güven

  DOI：10.1080/10426500601047529

  日期：2007.2.15

  Some 1-(4-aryl-2-thiazolyl)-3-(2-thienyl)-5-aryl-2-pyrazoline derivatives (TP 1-28) were synthesized by reacting substituted 3-(2-thienyl)-5-aryl-1-thiocarbamoyl-2-pyrazolines (P 1-7) with phenacyl bromides in ethanol. Structures of the synthesized compounds were confirmed by elemental analyses and IR, H-1-NMR and MS-FAB(+) spectral data. Their antimicrobial activities against Escherichia coli (NRRL B-3704), Staphylococcus aureus (NRLL B-767), Salmonella typhimurium (NRRL B-4420), Bacillus cereus (NRRL B-3711), Listeria monocytogenes (Ankara University, Faculty of Veterinary, Ankara, Turkey), Aeromonas hydrophila (Ankara University, Faculty of Veterinary Ankara, Turkey), Candida albicans, and Candida glabrata (isolates obtained from Osmangazi University, Faculty of Medicine, Eskisehir Turkey) were investigated. A significant level of activity was illustrated.
• Investigating the Anticancer Activity of Isatin/Dihydropyrazole Hybrids
  作者：Rita Meleddu、Vilma Petrikaite、Simona Distinto、Antonella Arridu、Rossella Angius、Lorenzo Serusi、Laura Škarnulytė、Ugnė Endriulaitytė、Miglė Paškevičiu̅tė、Filippo Cottiglia、Marco Gaspari、Domenico Taverna、Serenella Deplano、Benedetta Fois、Elias Maccioni

  DOI：10.1021/acsmedchemlett.8b00596

  日期：2019.4.11

  A series of isatin dihydropyrazole hybrids have been synthesized in order to assess their potential as anticancer agents. In particular, 12 compounds were evaluated for their antiproliferative activity toward A549, IGR39, U87, MDA-MB-231, MCF-7, BT474, BxPC-3, SKOV-3, and H1299 cell lines, and human foreskin fibroblasts. Four compounds exhibited interesting antiproliferative activity and were further examined to determine their ECso values toward a panel of selected tumor cell lines. The best compounds were then investigated for their induced mechanism of cell death. Preliminary structure activity relationship indicates that the presence of a substituent such as a chlorine atom or a methyl moiety in position 5 of the isatin nucleus is beneficial for the antitumor activity. EMAC4001 proved the most promising compound within the studied series with EC50 values ranging from 0.01 to 0.38 mu M.
• Synthesis of Some New Pyrazoline-Based Thiazole Derivatives and Evaluation of Their Antimicrobial, Antifungal, and Anticancer Activities
  作者：Safaa I. Elewa、Eman Mansour、Ibrahim F. Nassar、Amal A. I. Mekawey

  DOI：10.1134/s1068162020030061

  日期：2020.5

  chloroacetone derivatives and hydrazonyl chloride derivatives in ethanol to afford the corresponding thiazolylpyrazoline derivatives and thiophenylpyrazolyl-5-substituted aryl-diazenylthiazole derivatives, respectively. The structures of the newly synthesized compounds were elucidated by different elemental and spectral analyses (IR, mass, 1 H and 13 C NMR). The antimicrobial and antifungal activities

  摘要 3-(2-噻吩基)-5-芳基-1-硫代氨基甲酰基-2-吡唑啉与氯丙酮衍生物和腙氯衍生物在乙醇中反应，分别得到相应的噻唑基吡唑啉衍生物和噻吩基吡唑基-5-取代芳基-二烯基噻唑衍生物。新合成化合物的结构通过不同的元素和光谱分析（红外、质谱、 1 H 和 13 C NMR）阐明。针对四种细菌物种和五种真菌菌株评估了新合成化合物的抗菌和抗真菌活性。此外，两个新合成的化合物 1-(2-(5-(4-chlorophenyl)-3-(thiophen-2-yl)-4,5-dihydropyrazol-1-yl)-4-) 的抗肿瘤活性甲基噻唑-5-基)乙-1-酮和2-(5-(4-氯苯基)-3-(噻吩-2-基)-4，5-dihydro-1 H -pyrazol-1-yl)-4-methyl-5-(phenyl-diazenyl)thiazole 对 HEPG-2、HCT-116、MCF-7、BHK 和