1-thiocarbamoyl-3-(2-thienyl)-5-phenyl-2-pyrazoline | 906457-69-0

• 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: 1-thiocarbamoyl-3-(2-thienyl)-5-phenyl-2-pyrazoline
• 英文别名: 5-Phenyl-3-(thiophen-2-yl)-4,5-dihydro-1H-pyrazole-1-carbothioamide；3-phenyl-5-thiophen-2-yl-3,4-dihydropyrazole-2-carbothioamide
• CAS: 906457-69-0
• 化学式: C₁₄H₁₃N₃S₂
• 分子量: 287.409
• InChiKey: BIKIMXKMVLLSSR-UHFFFAOYSA-N

物化性质

• 熔点：
  186-187 °C(Solv: chloroform (67-66-3); ethanol (64-17-5))
• 沸点：
  459.5±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：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-thiocarbamoyl-3-(2-thienyl)-5-phenyl-2-pyrazoline 、 2-氯乙酰乙酸乙酯 以 乙醇 为溶剂， 反应 8.0h， 以76%的产率得到ethyl-4-methyl-2-(5-phenyl-3-(thiophen-2-yl)-4,5-dihydropyrazol-1-yl)thiazole-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 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 11.0h， 生成 1-thiocarbamoyl-3-(2-thienyl)-5-phenyl-2-pyrazoline
  参考文献：
  名称：

  Synthesis and Antimicrobial Activity of Some Thiazolyl-Pyrazoline Derivatives

  摘要：

  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.

  DOI：

  10.1080/10426500601047529

文献信息

• Synthesis and Studies on Antidepressant and Anticonvulsant Activities of Some 3-(2-Thienyl)pyrazoline Derivatives
  作者：Zuhal Ozdemir、H. Burak Kandilci、Bulent Gumusel、Unsal Calis、A. Altan Bilgin

  DOI：10.1002/ardp.200800068

  日期：2008.11

  In this study, the synthesis of twelve 3‐(2‐thienyl)pyrazoline derivatives are described. The structures of all compounds were confirmed by UV, IR, 1H‐NMR, mass spectral data, and microanalyses. In the pharmacological studies, antidepressant and anticonvulsant activities of these compounds have been screened. The antidepressant activities of the compounds were investigated by Porsolt's behavioral despair

  在本研究中，描述了 12 种 3-(2-噻吩基) 吡唑啉衍生物的合成。所有化合物的结构均通过 UV、IR、1H-NMR、质谱数据和微量分析确认。在药理学研究中，已筛选出这些化合物的抗抑郁和抗惊厥活性。通过对白化小鼠的 Porsolt 行为绝望试验（强迫游泳）研究化合物的抗抑郁活性，并与反苯环丙胺进行比较。在所检测的化合物中，化合物 9 和 12 显示出显着的抗抑郁活性。化合物的抗惊厥活性通过最大电休克发作 (MES) 和皮下戊四唑 (metrazol) (scMet.) 试验确定，神经毒性通过对白化病小鼠的旋转毒性试验确定。发现化合物 8 在 30-300 mg/kg 剂量水平范围内在四小时内对 MES 具有保护作用。在 30–300 mg/kg 剂量水平下，合成的化合物均未显示神经毒性。
• Synthesis of New 4-Thiazolidinone-, Pyrazoline-, and Isatin-Based Conjugates with Promising Antitumor Activity
  作者：Dmytro Havrylyuk、Borys Zimenkovsky、Olexandr Vasylenko、Andrzej Gzella、Roman Lesyk

  DOI：10.1021/jm300789g

  日期：2012.10.25

  The synthesis and antitumor activity screening of novel 3-[2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-4-oxo-4,5-dihydro-1,3-thiazol-5-ylidene]-2,3-dihydro-1H-indol-2-ones 1–23 and 3-(3,5-diarylpyrazol-1-yl)-2,3-dihydro-1H-indol-2-ones 24–39 are performed. In vitro anticancer activity of the synthesized compounds was tested by the National Cancer Institute. Most of them displayed anticancer activity on leukemia

  新型3- [2-（3,5-二芳基-4,5-二氢吡唑-1-基）-4-氧代-4,5-二氢-1,3-噻唑-5-亚烷基的合成及抗肿瘤活性的筛选] -2,3-dihydro-1 H-吲哚-2-ones 1 – 23和3-（3,5-diarylpyrazol-1-yl）-2,3-dihydro-1 H -indol-2-ones 24 –执行39次。美国国家癌症研究所测试了合成化合物的体外抗癌活性。他们中的大多数对白血病，黑素瘤，肺癌，结肠癌，中枢神经系统，卵巢癌，肾癌，前列腺癌和乳腺癌细胞系均表现出抗癌活性。讨论了构效关系。发现最有效的抗癌化合物10具有平均GI 50的活性TGI值分别为0.071μM和0.76μM。它显示出对非小细胞肺癌细胞HOP-92（GI 50 <0.01μM），结肠癌细胞系HCT-116（GI 50 = 0.018μM），CNS癌细胞SNB-75（ GI 50 = 0.0159μM），卵巢癌细胞系NCI
• New direction in the reaction of thiocarboxamides with N-substituted maleimides
  作者：R. V. Rudenko、S. A. Komykhov、S. M. Desenko

  DOI：10.1007/s10593-009-0377-5

  日期：2009.8
• 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.
• 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