4-benzyl-1-formyl-3-thiosemicarbazide | 93114-14-8

• 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: 4-benzyl-1-formyl-3-thiosemicarbazide
• 英文别名: N-benzyl-2-formylhydrazinecarbothioamide；1-Formyl-4-benzyl-3-thiosemicarbazid；N-(benzylcarbamothioylamino)formamide
• CAS: 93114-14-8
• 化学式: C₉H₁₁N₃OS
• mdl: MFCD03900706
• 分子量: 209.272
• InChiKey: AIWCNMYBFUMMJR-UHFFFAOYSA-N

物化性质

• 熔点：
  166 °C
• 沸点：
  340.6±35.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-benzyl-1-formyl-3-thiosemicarbazide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以80%的产率得到4-benzyl-4H-1,2,4-triazole-3-thiol
  参考文献：
  名称：

  Synthesis of 5-substituted 3-mercapto-1,2,4-triazoles via Suzuki–Miyaura reaction

  摘要：

  3-Bromo- and 3-iodo-N,S-dibenzyl-5-mercapto-1,2,4-triazoles were prepared and demonstrated as versatile building blocks for Suzuki-Miyaura cross-coupling with aryl, heteroaryl, and vinyl boronic acid derivatives. Deprotection of the resulting coupling products provided 5-substituted-3-mercapto-1,2,4-triazoles in good overall yields. This represents a novel and convenient approach for the introduction of a 3-mercapto-1,2,4-triazole substructure into target compounds. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.06.067
• 作为产物：
  描述：

  苄胺 在 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-benzyl-1-formyl-3-thiosemicarbazide
  参考文献：
  名称：

  二芳基甲烷骨架的系统构效关系 (SAR) 探索和高效新型尿酸转运蛋白 1 (URAT1) 抑制剂的发现

  摘要：

  为了系统地探索和更好地理解二芳基甲烷骨架在设计强效尿酸转运蛋白 1 (URAT1) 抑制剂时的构效关系 (SAR)，设计并合成了 33 种化合物（1a-1x 和 1ha-1hi），并测定了它们的体外 URAT1 抑制活性 (IC50)。三轮系统的 SAR 探索导致发现了一种高效的新型 URAT1 抑制剂，1h，其效力分别比母体 lesinurad 和苯溴马隆强 200 倍和 8 倍（IC50 = 0.035 μM 对人 URAT1 1 小时 vs lesinurad 和苯溴马隆分别为 7.18 μM 和 0.28 μM）。化合物 1h 是迄今为止我们实验室发现的最有效的 URAT1 抑制剂，也可与目前正在临床试验中开发的最有效的抑制剂相媲美。

  DOI：

  10.3390/molecules23020252

文献信息

• Some benzyl-substituted imidazoles, triazoles, tetrazoles, pyridinethiones, and structural relatives as multisubstrate inhibitors of dopamine .beta.-hydroxylase. 4. Structure-activity relationships at the copper binding site
  作者：Lawrence I. Kruse、Carl Kaiser、Walter E. DeWolf、Joseph A. Finkelstein、James S. Frazee、Eileen L. Hilbert、Stephen T. Ross、Kathryn E. Flaim、John L. Sawyer

  DOI：10.1021/jm00164a051

  日期：1990.2

  Structure-activity relationships (SAR) were determined for novel multisubstrate inhibitors of dopamine beta-hydroxylase (DBH; EC 1.14.17.1) by examining the effects upon in vitro inhibitory potencies resulting from structural changes at the copper-binding region of inhibitor. Attempts were made to determine replacement groups for the thione sulfur atom of the prototypical inhibitor 1-(4-hydroxybenzyl)imidazole-2-thione described previously. The synthesis and evaluation of oxygen and nitrogen analogues of the soft thione group demonstrated the sulfur atom to be necessary for optimal activity. An additional series of imidazole-2-thione relatives was prepared in an effort to probe the relationship between the pKa of the ligand group and inhibitory potency. In vitro inhibitory potency was shown not to correlate with ligand pKa over a range of approximately 10 pKa units, and a rationale for this is advanced. Additional ligand modifications were prepared in order to explore bulk tolerance at the enzyme oxygen binding site and to determine the effects of substituting a six-membered ligand group for the five-membered imidazole-2-thione ligand.
• Synthesis of 5-substituted 3-mercapto-1,2,4-triazoles via Suzuki–Miyaura reaction
  作者：Sarmite Katkevica、Pavlo Salun、Aigars Jirgensons

  DOI：10.1016/j.tetlet.2013.06.067

  日期：2013.8

  3-Bromo- and 3-iodo-N,S-dibenzyl-5-mercapto-1,2,4-triazoles were prepared and demonstrated as versatile building blocks for Suzuki-Miyaura cross-coupling with aryl, heteroaryl, and vinyl boronic acid derivatives. Deprotection of the resulting coupling products provided 5-substituted-3-mercapto-1,2,4-triazoles in good overall yields. This represents a novel and convenient approach for the introduction of a 3-mercapto-1,2,4-triazole substructure into target compounds. (c) 2013 Elsevier Ltd. All rights reserved.
• Systematic Structure-Activity Relationship (SAR) Exploration of Diarylmethane Backbone and Discovery of A Highly Potent Novel Uric Acid Transporter 1 (URAT1) Inhibitor
  作者：Wenqing Cai、Jingwei Wu、Wei Liu、Yafei Xie、Yuqiang Liu、Shuo Zhang、Weiren Xu、Lida Tang、Jianwu Wang、Guilong Zhao

  DOI：10.3390/molecules23020252

  日期：——

  In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a–1x and 1ha–1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly

  为了系统地探索和更好地理解二芳基甲烷骨架在设计强效尿酸转运蛋白 1 (URAT1) 抑制剂时的构效关系 (SAR)，设计并合成了 33 种化合物（1a-1x 和 1ha-1hi），并测定了它们的体外 URAT1 抑制活性 (IC50)。三轮系统的 SAR 探索导致发现了一种高效的新型 URAT1 抑制剂，1h，其效力分别比母体 lesinurad 和苯溴马隆强 200 倍和 8 倍（IC50 = 0.035 μM 对人 URAT1 1 小时 vs lesinurad 和苯溴马隆分别为 7.18 μM 和 0.28 μM）。化合物 1h 是迄今为止我们实验室发现的最有效的 URAT1 抑制剂，也可与目前正在临床试验中开发的最有效的抑制剂相媲美。