1-[(5-chloro-2-oxoindol-3-yl)amino]-3-(4-chlorophenyl)thiourea

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-[(5-chloro-2-oxoindol-3-yl)amino]-3-(4-chlorophenyl)thiourea
• 化学式: C₁₅H₁₀Cl₂N₄OS
• 分子量: 365.243
• InChiKey: ZFHRCLAUHURCPO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.64
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  65.52
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-[(5-chloro-2-oxoindol-3-yl)amino]-3-(4-chlorophenyl)thiourea 在 NaOH adsorbed on neutral alumina 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  AQUA MEDIATED ONE POT FACILE SYNTHESIS OF NOVEL THIOXO-1,2,4-TRIAZIN-5(2H)-ONE AND [1,2,4] TRIAZINO[5,6-A]INDOLE DERIVATIVES AND THEIR BIOLOGICAL ACTIVITIES

  摘要：

  Rapid and highly efficient one pot green chemical synthesis of substituted 6-(2-aminophenyl)-4-(4-substitutedphenyl)-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one and 8-substituted-3,5-dihydro-2H-[1,2,4]triazino[5,6-b]indole is carried out in aqueous medium under microwave irradiation. Improved synthesis of potent bioactive Schiff and N-Mannich bases of hexahydro-1H-indole-2,3-dione is also reported. The title compounds are easily accessible by various approaches; even waste free approaches have been developed. The operational simplicity, environmentally benign conditions and high yield achieved in a very short reaction time are major benefits that meet the requirements of green production, including saving energy and high efficiency. The results obtained under microwaves are compared with that of conventional heating. Structural assignments are based on spectroscopic data. Compounds have also been screened for antibacterial and antifungal activities.

  DOI：

  10.4067/s0717-97072012000400004
• 作为产物：
  描述：

  对氯苯胺 在 硫酸 、 溶剂黄146 、 sodium sulfate 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 1-[(5-chloro-2-oxoindol-3-yl)amino]-3-(4-chlorophenyl)thiourea
  参考文献：
  名称：

  Synthesis and cytostatic evaluation of some 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide

  摘要：

  Various substituted 2-(5-substituted-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 4a-g and 2-(5-substituted-1-(4-substituted benzyl)-2-oxoindolin-3-ylidene)-N-substituted hydrazine carbothioamide 5a-k were synthesized. The compounds were evaluated for their cytostatic activity against human Molt4/C8 and CEM T-lymphocytes as well as murine L1210 leukemia cells. Several of these compounds were endowed with low micromolar 50%-inhibitory concentration (IC50) values, and some were virtually equally potent as melphalan. The most potent inhibitors against the murine leukemia cells were also most inhibitory against human T-lymphocyte tumor cells. 2-(5-fluoro-1-(4-fluorobenzyl)-2-oxoindolin-3-ylidene)-N-p-tolylhydrazine carbothioamide (5b) emerged as the most potent cytostatic compound among the tested compounds. The encouraging cytostatic data provide an adequate rationale for further modification of these molecular scaffolds.

  DOI：

  10.1007/s00044-010-9458-3

文献信息

• 一种PTP1B抑制剂及其合成方法和用途
  申请人：复旦大学

  公开号：CN114634500A

  公开（公告）日：2022-06-17

  本发明属于医药技术领域，具体为一种含5‑取代‑3‑(3‑芳基取代噻唑烷‑4‑酮‑2‑叉基亚肼基)吲哚‑2‑酮类衍生物及其合成方法和应用。本发明利用拼合原理、药效团模型以及PTP1B抑制剂的结构特征，结合PTP1B酶活性位点的特性，设计合成具有生物碱吲哚‑3‑取代1,3‑噻唑烷‑4‑酮基本结构的化合物。体外对PTP1B酶抑制活性测试表明：本发明化合物在浓度为5μg/mL下都显示出了良好的PTP1B抑制活性，抑制率为50％以上，其半数抑制浓度(IC50值)在0.45～14.53μM之间；抑制率最高达92.70％，活性最好的IC50值达0.45μM，可成为PTP1B抑制剂的先导化合物。对接结果表明所设计的化合物与酶的多个作用位点都有很好的相互作用，包括氢键，疏水相互作用，范德华力等。
• 含吲哚生物碱杂环取代-1,3-噻唑烷酮类衍生物及其制备方法和用途
  申请人：复旦大学

  公开号：CN114634503A

  公开（公告）日：2022-06-17

  本发明属于医药技术领域，具体为一种含生物碱1H‑吲哚‑3‑取代‑1,3‑噻唑烷‑4‑酮类衍生物及其合成方法和应用。本发明利用拼合原理、药效团模型以及PTP1B抑制剂的结构特征，结合PTP1B酶活性位点的特点，设计合成具有生物碱1H‑吲哚‑3‑取代‑1,3‑噻唑烷‑4‑酮基本结构的化合物；本发明还包含其药用盐，水合物及溶剂化物，其多晶或共晶，其同样生物功能的前体和衍生物。测试表明：该化合物体外对PTP1B酶具有良好的抑制活性；实施例合成的14个化合物在浓度为5μg/mL下都显示出优秀的PTP1B抑制活性，其半数抑制浓度(IC50值)在4.56～14.53μM之间，抑制率最高达80.61％，活性最好的IC50值为4.56μM，可成为PTP1B抑制剂的潜在先导化合物。
• Varma, Rajendra S.; Garg, Pradeep K., Journal of the Indian Chemical Society, 1981, vol. 58, p. 980 - 981
  作者：Varma, Rajendra S.、Garg, Pradeep K.

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