1-(p-tolylbenzoyl)-4-methylthiosemicarbazide | 154106-03-3

• 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-(p-tolylbenzoyl)-4-methylthiosemicarbazide
• 英文别名: N-Methyl-2-(4-methylbenzoyl)hydrazinecarbothioamide；1-methyl-3-[(4-methylbenzoyl)amino]thiourea
• CAS: 154106-03-3
• 化学式: C₁₀H₁₃N₃OS
• mdl: MFCD00662790
• 分子量: 223.299
• InChiKey: TZTFODKUXPHEBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  85.2
• 氢给体数：
  3
• 氢受体数：
  2

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  1-(p-tolylbenzoyl)-4-methylthiosemicarbazide 在 sodium hydroxide 、 碳酸氢钠 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 4H-1,2,4-Triazole, 4-methyl-3-(4-methylphenyl)-5-(methylthio)-
  参考文献：
  名称：

  Kane; Staeger; Dalton, Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 125 - 132

  摘要：

  DOI：
• 作为产物：
  描述：

  甲胩 、 对甲苯甲酰肼 在 {(η⁵-C₅Me₅)Mo[N(ⁱPr)C(Ph)N(ⁱPr)]}₂(μ-η¹:η¹-N₂) 、 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 以 四氢呋喃 为溶剂， 反应 16.5h， 以96%的产率得到1-(p-tolylbenzoyl)-4-methylthiosemicarbazide
  参考文献：
  名称：

  通过Mo（II）/ Mo（IV）循环催化生产异硫氰酸酯，实现异腈的“软”硫氧化

  摘要：

  In the presence of excess amounts of elemental sulfur, the dimolybdenum dinitrogen complex {Cp*Mo[N(Pr-i)C(Ph)N(Pr-i)]}(2)(mu-N-2) (4; Cp* = eta(5)-C5Me8) serves as a precatalyst for the production of isothiocyanates from isonitriles via highly efficient and atom-economical metal-mediated sulfur atom transfer (SAT) under mild conditions. Mechanistic and structural studies support a catalytic cycle for SAT involving initial formation of a Mo(II) bis(isonitrile) complex that then undergoes sulfination to generate a formal "side-bound" Mo(IV) kappa(2)-(C,S)-isothiocyanate as the key intermediate. This metal-catalyzed SAT process has further been employed for the "on-demand" production of isothiocyanates that are trapped in situ by benzhydrazides to provide thiosemicarbazides, which are useful precursors to biologically active thiadiazoles.

  DOI：

  10.1021/acs.organomet.6b00302

文献信息

• A High-Throughput Glycosyltransferase Inhibition Assay for Identifying Molecules Targeting Fucosylation in Cancer Cell-Surface Modification
  作者：Xiaohua Zhang、Fei Chen、Alessandro Petrella、Franklin Chacón-Huete、Jason Covone、Teng-Wei Tsai、Ching-Ching Yu、Pat Forgione、David H. Kwan

  DOI：10.1021/acschembio.8b01123

  日期：2019.4.19

  molecules, because blocking fucosylation will allow glycosidase-catalyzed hydrolysis of the labeled oligosaccharide to produce a fluorescent signal. Employing this assay, we have screened a focused library of small molecules for inhibitors of a human FUT enzyme involved in the synthesis of sialyl LewisX and demonstrated that our approach can be used to identify potent FUT inhibitors from compound libraries

  在癌症中，由于特定岩藻糖基转移酶（FUT）表达异常上调而导致的细胞表面聚糖上岩藻糖基化（岩藻糖残基的附着）增加，是与恶性肿瘤相关的最重要的聚糖修饰类型之一。在正常的生物过程以及疾病中，细胞表面的岩藻糖基化聚糖参与多种细胞相互作用和信号调节。例如，唾液酸化的LewisX是一种岩藻糖基化的细胞表面聚糖，在某些癌症中异常丰富，这与促进转移有关，它可使循环中的肿瘤细胞与血管内的上皮组织结合并通过利用聚糖介导的相互作用。为了鉴定FUT酶抑制剂作为潜在的癌症治疗剂，我们开发了一种新颖的高通量检测方法，该方法利用了荧光标记的寡糖作为岩藻糖基化的探针。该探针由4-甲基伞形糖基糖苷组成，可被特定的糖苷水解酶识别并水解，释放出荧光的4-甲基伞形酮，但当在用糖苷水解酶处理之前将岩藻糖基化时，不会发生水解，也不会发出荧光信号被生产。我们已经证明该测定法可用于测量小分子对FUT酶的抑制作用，因为阻断岩藻糖基化将使糖
• Kane; Staeger; Dalton, Journal of Medicinal Chemistry, 1994, vol. 37, # 1, p. 125 - 132
  作者：Kane、Staeger、Dalton、Miller、Dudley、Ogden、Kehne、Ketteler、McCloskey、Senyah、Chmielewski、Miller

  DOI：——

  日期：——
• Catalytic Production of Isothiocyanates via a Mo(II)/Mo(IV) Cycle for the “Soft” Sulfur Oxidation of Isonitriles
  作者：Wesley S. Farrell、Peter Y. Zavalij、Lawrence R. Sita

  DOI：10.1021/acs.organomet.6b00302

  日期：2016.7.25

  In the presence of excess amounts of elemental sulfur, the dimolybdenum dinitrogen complex Cp*Mo[N(Pr-i)C(Ph)N(Pr-i)]}(2)(mu-N-2) (4; Cp* = eta(5)-C5Me8) serves as a precatalyst for the production of isothiocyanates from isonitriles via highly efficient and atom-economical metal-mediated sulfur atom transfer (SAT) under mild conditions. Mechanistic and structural studies support a catalytic cycle for SAT involving initial formation of a Mo(II) bis(isonitrile) complex that then undergoes sulfination to generate a formal "side-bound" Mo(IV) kappa(2)-(C,S)-isothiocyanate as the key intermediate. This metal-catalyzed SAT process has further been employed for the "on-demand" production of isothiocyanates that are trapped in situ by benzhydrazides to provide thiosemicarbazides, which are useful precursors to biologically active thiadiazoles.