1-n-butyl-3-(isonicotinamido)-2-thiourea | 74270-74-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-n-butyl-3-(isonicotinamido)-2-thiourea
• 英文别名: abouthiouzine；4-butyl-1-isonicotinoyl-thiosemicarbazide；1-Butyl-3-(pyridine-4-carbonylamino)thiourea
• CAS: 74270-74-9
• 化学式: C₁₁H₁₆N₄OS
• 分子量: 252.34
• InChiKey: OOCYXICFMNIYAZ-UHFFFAOYSA-N

物化性质

• 密度：
  1.192±0.06 g/cm3(Predicted)
• 溶解度：
  32.8 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  98.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-n-butyl-3-(isonicotinamido)-2-thiourea 在 硫酸 作用下， 生成 butyl-(5-pyridin-4-yl-[1,3,4]thiadiazol-2-yl)-amine
  参考文献：
  名称：

  3-芳基（或吡啶基）-5-烷基（或芳基）氨基-1,3,4-噻二唑和4H-1,2,4-三唑的一些磺酰脲衍生物的合成及降血糖活性。

  摘要：

  DOI：

  10.1021/jm00292a035
• 作为产物：
  描述：

  异烟肼 、 丁基异硫氰酸酯 以 四氢呋喃 为溶剂， 以91 %的产率得到1-n-butyl-3-(isonicotinamido)-2-thiourea
  参考文献：
  名称：

  三溴异氰尿酸作为替代氧化剂用于从 1-酰基氨基硫脲合成 2-氨基-1,3,4-恶二唑

  摘要：

  已开发出一种简单、有效且环境友好的方法，通过与三溴异氰尿酸反应将 1-酰基氨基硫脲转化为 2-氨基-1,3,4-恶二唑。由酰肼和异硫氰酸酯制备具有不同取代基（如烷基、苄基和（杂）芳基）的 1-酰基氨基硫脲，收率高达 97%，并以 19–93% 的收率转化为相应的 2-氨基-1,3,4-恶二唑该协议提供了简单的反应条件、易于获取的试剂，无需任何特殊设备。

  DOI：

  10.1016/j.tetlet.2023.154494

文献信息

• Synthesis of isoniazid analogs with promising antituberculosis activity and bioavailability: Biological evaluation and computational studies
  作者：Renu Gavadia、Jyoti Rasgania、Mandira Varma Basil、Varsha Chauhan、Sanjay Kumar、Komal Jakhar

  DOI：10.1016/j.molstruc.2023.135325

  日期：2023.7

  A series of aliphatic isoniazid carbo(x/thio)amides has been synthesized by a facile one-pot green method in aqueous media by harnessing microwave irradiations. In vitro antitubercular screening of the synthesized compounds against Mycobacterium tuberculosis H37Rv (MTB strain) reveals promising antimycobacterial potential with MIC in the range of 1 to 4 µg/ml. A computational approach comprising DFT

  一系列脂肪族异烟肼碳 (x/硫代) 酰胺已通过利用微波辐射在水性介质中通过简便的一锅法绿色方法合成。合成化合物抗结核分枝杆菌的体外抗结核筛选H37Rv（MTB 株）显示出有前途的抗分枝杆菌潜力，MIC 在 1 至 4 µg/ml 范围内。执行了包括 DFT 建模、分子对接和 ADMET 分析的计算方法，以阐明先导化合物的化学性质、结合亲和力和 ADMET 功效。合成类似物与 InhA 的对接显示与受体的结合相互作用较弱，并且不存在直接抑制剂特有的重要相互作用。然而，对接结果表明合成分子与 KatG 受体 1SJ2 具有显着的结合亲和力，化合物3h和3e显示出最佳对接分数（分别为 -7.2 和 -6.8 kcal/mol），表明 KatG 介导的 InhA 抑制机制类似于异烟肼。在计算机中标题化合物的 ADMET 分析表明它们具有出色的药代动力学能力和比异烟肼更低的毒性。生物利用度雷达进一步
• Narrow SAR in odorant sensing Orco receptor agonists
  作者：Ian M. Romaine、Robert W. Taylor、Samsudeen P. Saidu、Kwangho Kim、Gary A. Sulikowski、Laurence J. Zwiebel、Alex G. Waterson

  DOI：10.1016/j.bmcl.2014.04.081

  日期：2014.6

  The systematic exploration of a series of triazole-based agonists of the cation channel insect odorant receptor is reported. The structure-activity relationships of independent sections of the molecules are examined. Very small changes to the compound structure were found to exert a large impact on compound activity. Optimal substitutions were combined using a 'mix-and-match' strategy to produce best-in-class compounds that are capable of potently agonizing odorant receptor activity and may form the basis for the identification of a new mode of insect behavior modification. (C) 2014 Elsevier Ltd. All rights reserved.
• ——
  作者：Rafiq R. A. Abou‐Shaaban、Hamad A. Al‐Khamees、Hisham S. Abou‐Auda、Anthony. P. Simonelli

  DOI：10.1023/a:1016049921842

  日期：——

  Purpose. To design new antithyroid agents with less side effects, the electrotopological-state (E-state) indexes of thiourylene moiety (S-N&S) was utilized as a guideline to develop five acyclic thiourylene-type compounds with reduced antioxidant property.Methods. These agents were synthesized and screened for antithyroid activity in rats using I-125-thiocyanate discharge technique. In addition, chemiluminescence studies on the activated polymorphonuclear leukocytes (PMNLs) were also conducted to reveal antioxidant properties of the tested compounds.Results. A linear relationship between the in vitro literature value of the formation constants of thiourylene-type compounds with iodine (K-c) and the S-N&S was observed and utilized in designing those agents. At least one of the compounds (abouthiouzine) was found to have a potential value as an antithyroid agent. The relative efficacy of abouthiouzine [1-n-butyl-3(isonicotinamido)-2-thiourea], after equimolar dose, was 102% and 51.5% of that of propylthiouracil with respect to the rate of I-125-discharge and I-125-uptake, respectively. In addition, Chemiluminescence studies on PMNLs revealed that abouthiouzine has slight oxidant property. Such properties may provide advantages in avoiding the iatrogenic hypothyroidism and antithyroid-induced immunological reactions.Conclusions. The E-state approach provides guidelines to economize efforts and cost of designing new antithyroid drugs.
• VASILEV, G. N.;VELICHKOV, L. S.;DIMCHEVA, Z. P.;KARAGOZOV, S. K.
  作者：VASILEV, G. N.、VELICHKOV, L. S.、DIMCHEVA, Z. P.、KARAGOZOV, S. K.

  DOI：——

  日期：——
• Pyridine-Based 1,2,4-Triazolo-Tethered Indole Conjugates Potentially Affecting TNKS and PI3K in Colorectal Cancer
  作者：Prasanna A. Yakkala、Samir R. Panda、Vegi G. M. Naidu、Syed Shafi、Ahmed Kamal

  DOI：10.1021/acsmedchemlett.2c00475

  日期：2023.3.9