4-(1-phenyl-ethyl)-thiosemicarbazide | 4312-19-0

• 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: 4-(1-phenyl-ethyl)-thiosemicarbazide
• 英文别名: 4-(α-Phenaethyl)-thiosemicarbazid；4-(1-Phenyl-aethyl)-thiosemicarbazid；4-(α-Methylbenzyl)-3-thiosemicarbazid；4-(α-Methylbenzyl)-thiosemicarbazid；N-(1-Phenylethyl)hydrazinecarbothioamide；1-amino-3-(1-phenylethyl)thiourea
• CAS: 4312-19-0
• 化学式: C₉H₁₃N₃S
• 分子量: 195.288
• InChiKey: VPKCPEZYVHRLEP-UHFFFAOYSA-N

物化性质

• 熔点：
  84 °C
• 沸点：
  319.8±35.0 °C(Predicted)
• 密度：
  1.177±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  potassium tetrachloropalladate(II) 、 4-(1-phenyl-ethyl)-thiosemicarbazide 在 sodium acetate 作用下， 以 乙醇 、 水 为溶剂， 以30%的产率得到C18H24N6PdS2, gray green
  参考文献：
  名称：

  Kazakova, E. I.; Dunina, V. V.; Potapov, V. M., Journal of general chemistry of the USSR, 1985, vol. 55, p. 1334 - 1343

  摘要：

  DOI：
• 作为产物：
  描述：

  (±)-1-苯乙基硫代异氰酸酯 在 肼 作用下， 以 乙醚 为溶剂， 生成 4-(1-phenyl-ethyl)-thiosemicarbazide
  参考文献：
  名称：

  Jensen,K.A. et al., Acta Chemica Scandinavica (1947), 1968, vol. 22, p. 1 - 50

  摘要：

  DOI：

文献信息

• New 1,3,4-thiadiazole compounds including pyrazine moiety: Synthesis, structural properties and antimicrobial features
  作者：Mahmut Gür、Nesrin Şener、Halit Muğlu、M. Serdar Çavuş、Osman Emre Özkan、Fatma Kandemirli、İzzet Şener

  DOI：10.1016/j.molstruc.2017.03.019

  日期：2017.7

  study, some new 1,3,4-thiadiazole compounds were synthesized and we have reported identification of the structures by using UV-Vis, FT-IR, 1H NMR, 13C NMR and Mass spectroscopic methods. Antimicrobial activities of the compounds against three microorganisms, namely, Candida albicans ATCC 26555, Staphylococcus aureus ATCC 9144, and Escherichia coli ATCC 25922 were investigated by using disk diffusion

  摘要 本研究合成了一些新的1,3,4-噻二唑化合物，并利用紫外-可见光、红外、1H NMR、13C NMR和质谱等方法对其结构进行了鉴定。采用圆盘扩散法研究了化合物对三种微生物的抗菌活性，即白色念珠菌 ATCC 26555、金黄色葡萄球菌 ATCC 9144 和大肠杆菌 ATCC 25922。这些噻二唑对金黄色葡萄球菌和白色念珠菌具有抗菌活性。实验数据得到了量子化学计算的支持。使用 B3LYP、M06 和 PBE1PBE 方法进行密度泛函理论 (DFT) 计算以获得分子的基态优化几何形状，3–21 g、4–31 g、6–311++g(2d,2p) , cc-pvtz 和 cc-pvqz 基组的不同组合。利用上述方法和基组计算了前沿分子轨道（FMOs）能量、带隙能量和一些化学反应性参数，并将结果与​​实验UV-Vis数据进行了比较。
• 3-amino-5-methyl-1H-pyrazole-4-carboxylic acids and esters thereof as anticonvulsants, muscle relaxants and anxiolytics
  申请人：A.H. ROBINS COMPANY, INCORPORATED

  公开号：EP0315433A2

  公开（公告）日：1989-05-10

  Pharmaceutical compositions which comprise a compound represented by the formula where R¹ represents a hydrogen atom, a lower alkyl group or a pharmaceutically acceptable cation; R² and R³ independently represent a hydrogen atom, a lower alkyl group, an aryl group, a cycloalkyl group, a lower alkenyl group, a 1-adamantyl group, a hetero­cyclicaminoalkyl group, a diloweralkylaminoloweralkyl group, or R² together with R³ and the adjacent nitrogen atom may form a heterocyclic ring structure; and/or a pharmaceutically acceptable acid salt thereof; the use of such compounds in medicine; and the use of such compounds in the preparation of anticonvul­sant agents, muscle relaxants and anxiolytic agents, are disclosed.

  药物组合物，其中包含由式表示的化合物 其中 R¹ 代表氢原子、低级烷基或药学上可接受的阳离子； R²和R³各自代表氢原子、低级烷基、芳基、环烷基、低级烯基、1-金刚烷基、杂环氨基烷基、稀释烷基氨基低级烷基，或R²与R³及相邻氮原子可形成杂环环结构； 和/或其药学上可接受的酸盐；公开了此类化合物在医药中的用途；以及此类化合物在制备抗惊厥剂、肌肉松弛剂和抗焦虑剂中的用途。
• Novel selective thiadiazine DYRK1A inhibitor lead scaffold with human pancreatic β-cell proliferation activity
  作者：Kunal Kumar、Peter Man-Un Ung、Peng Wang、Hui Wang、Hailing Li、Mary K. Andrews、Andrew F. Stewart、Avner Schlessinger、Robert J. DeVita

  DOI：10.1016/j.ejmech.2018.08.007

  日期：2018.9

  The Dual-Specificity Tyrosine Phosphorylation-Regulated Kinase 1A (DYRK1A) is an enzyme that has been implicated as an important drug target in various therapeutic areas, including neurological disorders (Down syndrome, Alzheimer's disease), oncology, and diabetes (pancreatic beta-cell expansion). Current small molecule DYRK1A inhibitors are ATP-competitive inhibitors that bind to the kinase in an active conformation. As a result, these inhibitors are promiscuous, resulting in pharmacological side effects that limit their therapeutic applications. None are in clinical trials at this time. In order to identify a new DYRK1A inhibitor scaffold, we constructed a homology model of DYRK1A in an inactive, DFG-out conformation. Virtual screening of 2.2 million lead-like compounds from the ZINC database, followed by in vitro testing of selected 68 compounds revealed 8 hits representing 5 different chemical classes. We chose to focus on one of the hits from the computational screen, thiadiazine I which was found to inhibit DYRK1A with IC50 of 9.41 mu m (K-d = 7.3 mu M). Optimization of the hit compound 1, using structure-activity relationship (SAR) analysis and in vitro testing led to the identification of potent thiadiazine analogs with significantly improved binding as compared to the initial hit (K-d = 71-185 nM). Compound 3-5 induced human beta-cell proliferation at 5 mu M while showing selectivity for DYRK1A over DYRK1B and DYRK2 at 10 mu M. This newly developed DYRK1A inhibitor scaffold with unique kinase selectivity profiles has potential to be further optimized as novel therapeutics for diabetes. (C) 2018 Published by Elsevier Masson SAS.
• Baird; Burns; Wilson, Journal of the Chemical Society, 1927, p. 2532
  作者：Baird、Burns、Wilson

  DOI：——

  日期：——
• DUNINA V. V.; POTAPOV V. M.; RUXADZE E. G.; KAZAKOVA E. I., ZH. OBSHCH. XIMII, 1977, 47, HO 10, 2309-2317
  作者：DUNINA V. V.、 POTAPOV V. M.、 RUXADZE E. G.、 KAZAKOVA E. I.

  DOI：——

  日期：——