2-(methylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole | 78874-84-7

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(methylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole
• 英文别名: 2-(methylthio)-5-(p-tolyl)-1,3,4-oxadiazole；2-methylsulfanyl-5-p-tolyl-[1,3,4]oxadiazole；2-Methylmercapto-5-p-tolyl-1,3,4-oxadiazol；2-(4-Methylphenyl)-5-(methylsulfanyl)-1,3,4-oxadiazole；2-(4-methylphenyl)-5-methylsulfanyl-1,3,4-oxadiazole
• CAS: 78874-84-7
• 化学式: C₁₀H₁₀N₂OS
• mdl: MFCD01832399
• 分子量: 206.268
• InChiKey: QSCOVGMVQFLCGD-UHFFFAOYSA-N

物化性质

• 熔点：
  50 °C(Solv: benzene (71-43-2))
• 沸点：
  342.2±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  64.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(methylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole 在 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 作用下， 以 四氯化碳 、 N,N-二甲基甲酰胺 为溶剂， 反应 50.0h， 生成 2-(methylthio)-5-(4-((2-propynyloxy)methyl)phenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Sulfone-Based Probes Unraveled Dihydrolipoamide S-Succinyltransferase as an Unprecedented Target in Phytopathogens

  摘要：

  Target validation of current drugs remains the major challenge for target-based drug discovery, especially for agrochemical discovery. The bactericide 0 represents a novel lead structure and has shown potent efficacy against those diseases that are extremely difficult to control, such as rice bacterial leaf blight. However, no detailed target analysis of this bactericide has been reported. Here, we developed a panel of 0-derived probes 1-6, in which a conservative modification (alkyne tag) was introduced to keep the antibacterial activity of 0 and provide functionality for target identification via click chemistry. With these cell-permeable probes, we were able to discover dihydrolipoamide S-succinyltransferase (DLST) as an unprecedented target in living cells. The probes showed good preference for DLST, especially probe 1, which demonstrated distinct selectivity and reactivity. Also, we reported 0 as the first covalent DLST inhibitor, which has been used to confirm the involvement of DLST in the regulation of energy production.

  DOI：

  10.1021/acs.jafc.9b02059
• 作为产物：
  描述：

  对甲苯甲酰肼 在 氢氧化钾 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 生成 2-(methylthio)-5-(4-methylphenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Najer; Giudicelli; Morel, Bulletin de la Societe Chimique de France, 1966, vol. 1, p. 153 - 159

  摘要：

  DOI：

文献信息

• One-pot Synthesis of 2-Alkylthio-1,3,4-oxadiazole and Bis-(1,3,4-oxadiazole-2-yl)thio alkyl Derivatives from Acid Hydrazides and CS2
  作者：Mohammad Soleiman-Beigi、Mohammad Alikarami、Tahereh Hosseinzadeh

  DOI：10.14233/ajchem.2013.14148

  日期：——

  An efficient and one-pot method for synthesis of 2-alkylthio-1,3,4-oxadiazole derivatives in mild conditions is described. Some novel derivatives such as bis-1,3,4-oxadiazole analogs are also synthesized.

  介绍了一种在温和条件下合成 2-烷硫基-1,3,4-恶二唑衍生物的高效单锅方法。此外，还合成了一些新型衍生物，如双-1,3,4-恶二唑类似物。
• [EN] LIPID CONJUGATES FOR THE DELIVERY OF THERAPEUTIC AGENTS<br/>[FR] CONJUGUÉS LIPIDIQUES POUR L'ADMINISTRATION D'AGENTS THÉRAPEUTIQUES
  申请人：ARROWHEAD PHARMACEUTICALS INC

  公开号：WO2022056273A1

  公开（公告）日：2022-03-17

  Disclosed herein are compounds according to Formula (I) comprising PK/PD modulators for delivery of oligonucleotide-based agents, e.g., double stranded RNAi agents, to certain cell types, such for example skeletal muscle cells, in vivo. The PK/PD modulators disclosed herein, when conjugated to an oligonucleotide-based therapeutic or diagnostic agent, such as an RNAi agent, can enhance the delivery of the composition to the specified cells being targeted to facilitate the inhibition of gene expression in those cells.

  本文公开了公式（I）中的化合物，包括PK/PD调节剂，用于将基于寡核苷酸的制剂（例如双链RNAi制剂）递送到体内某些细胞类型，例如骨骼肌细胞。本文所披露的PK/PD调节剂与基于寡核苷酸的治疗或诊断制剂（如RNAi制剂）结合后，可以增强将该组合物递送到特定的目标细胞，以促进在这些细胞中抑制基因表达。
• A novel one-pot synthesis of 2-alkylthio-1,3,4-oxadiazoles in water
  作者：F. Aryanasab、H. Maleki、M. R. Saidi

  DOI：10.1007/bf03249086

  日期：2011.6

  A facile and one-pot protocol for the synthesis of 2-alkylthio-1,3,4-oxadiazoles is reported. This green method relies on the reaction of acid hydrazides with CS2 and an alkyl halide. The reaction is carried out under mild and environmentally friendly procedure in water with high to excellent yields. Thirteen different valuable alkylthio-1,3,4-oxadiazoles are synthesized from cheap and easily available CS2 with this method. This is the first report for the synthesis of 1,3,4-oxadiazoles in water.
• EL-BARBARY A. A.; ANWAR M.; GHATTAS A. A.; HASHEM A. F., REV. ROUM. CHIM., 1981, 26, NO 3, 449-456
  作者：EL-BARBARY A. A.、 ANWAR M.、 GHATTAS A. A.、 HASHEM A. F.

  DOI：——

  日期：——
• PRODRUGS COMPRISING AN GLP-1/GLUCAGON DUAL AGONIST LINKER HYALURONIC ACID CONJUGATE
  申请人：SANOFI

  公开号：EP3302567B1

  公开（公告）日：2019-09-11