2-(4-fluorophenyl)-5-(ethylthio)-1,3,4-oxadiazole | 459860-95-8

• 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-(4-fluorophenyl)-5-(ethylthio)-1,3,4-oxadiazole
• 英文别名: 2-Ethylsulfanyl-5-(4-fluorophenyl)-1,3,4-oxadiazole
• CAS: 459860-95-8
• 化学式: C₁₀H₉FN₂OS
• 分子量: 224.259
• InChiKey: ARDIKNCDCDNYTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  3
• 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：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-fluorophenyl)-5-(ethylthio)-1,3,4-oxadiazole 在 potassium permanganate 、 溶剂黄146 作用下， 反应 0.17h， 以80.3%的产率得到2-(ethylsulfonyl)-5-(4-fluorophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety

  摘要：

  A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by H-1 and C-13 nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 mu g/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c:, 5'h, 5'i, and 5, could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC50) at 39.8, 60.3, 47.9, and 32.1 mu g/mL, respectively. Among them, compound 5) was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 55 against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.

  DOI：

  10.1021/jf203772d
• 作为产物：
  描述：

  4-氟苯甲酰肼 在 sodium carbonate 、 potassium hydroxide 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 28.0h， 生成 2-(4-fluorophenyl)-5-(ethylthio)-1,3,4-oxadiazole
  参考文献：
  名称：

  [EN] 1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, AND 1,3,4-THIADIAZOLE DERIVATIVES AND THEIR ANTIMYCOBACTERIAL ACTIVITY
  [FR] DÉRIVÉS DE 1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, 1,3,4-THIADIAZOLE ET LEUR ACTIVITÉ ANTIMYCOBACTÉRIENNE

  摘要：

  本文披露了一种新型的五元杂环化合物，其化学式为（I），其中，X为S或SO2；n为0或1；m为1或2；Y为N、O或S；R2独立表示H或烷基或卤素，选自-Cl、-F、-CF3、-OH、-NH2或-NO2；R1独立表示H或C1至C5的直链或支链烷基、烯基、炔基或一个基团-(CH2)5Br或吡咯烷或-NHR'，其中R'为H或异丙基或(II)或(III)，这些化合物对休眠的致病性结核杆菌具有选择性作用，并表现出抗增殖活性，用于治疗与GroEL1/GroEL2活性相关的疾病或紊乱。该发明涉及一种制备化学式I的新型五元杂环化合物的方法及其药物组合物。

  公开号：

  WO2016108249A1

文献信息

• [EN] 1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, AND 1,3,4-THIADIAZOLE DERIVATIVES AND THEIR ANTIMYCOBACTERIAL ACTIVITY<br/>[FR] DÉRIVÉS DE 1,2,4-TRIAZOLE, 1,3,4-OXADIAZOLE, 1,3,4-THIADIAZOLE ET LEUR ACTIVITÉ ANTIMYCOBACTÉRIENNE
  申请人：COUNCIL SCIENT IND RES

  公开号：WO2016108249A1

  公开（公告）日：2016-07-07

  Disclosed herein are novel five membered heterocyclic compounds of Formula (I) wherein, X is S or SO2; n is 0, 1; m is1 or 2; Y is N, O or S; R2 independently represents H or alkyl or halo selected from -CI, -F; or -CF3, or -OH or-NH2 or - NO2; and R1 independently represents H or C1 to C5 straight or branched chain alkyl, alkenyl, alkynyl or a group -(CH2)5Br or pyrrolidine or - NHR' wherein R' is H or isopropyl or (II) or (III) which selectively act against dormant pathogenic tuberculi bacilli and exhibit antiproliferative activities and for treatment of a disease or disorder associated with GroEL1/GroEL2 activity. The invention relates to a process for preparation of novel five membered heterocyclic compounds of Formula I and to pharmaceutical compositions thereof.

  本文披露了一种新型的五元杂环化合物，其化学式为（I），其中，X为S或SO2；n为0或1；m为1或2；Y为N、O或S；R2独立表示H或烷基或卤素，选自-Cl、-F、-CF3、-OH、-NH2或-NO2；R1独立表示H或C1至C5的直链或支链烷基、烯基、炔基或一个基团-(CH2)5Br或吡咯烷或-NHR'，其中R'为H或异丙基或(II)或(III)，这些化合物对休眠的致病性结核杆菌具有选择性作用，并表现出抗增殖活性，用于治疗与GroEL1/GroEL2活性相关的疾病或紊乱。该发明涉及一种制备化学式I的新型五元杂环化合物的方法及其药物组合物。
• Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety
  作者：Wei-Ming Xu、Fei-Fei Han、Ming He、De-Yu Hu、Jiang He、Song Yang、Bao-An Song

  DOI：10.1021/jf203772d

  日期：2012.2.1

  A series of new sulfone compounds containing the 1,3,4-oxadiazole moiety were designed and synthesized. Their structures were identified by H-1 and C-13 nuclear magnetic resonance and elemental analyses. Antibacterial bioassays indicated that most compounds exhibited promising in vitro antibacterial bioactivities against tobacco bacterial wilt at 200 mu g/mL. The relationship between structure and antibacterial activity was also discussed. Among the title compounds, 5'c:, 5'h, 5'i, and 5, could inhibit mycelia growth of Ralstonia solanacearum in vitro by approximately 50% (EC50) at 39.8, 60.3, 47.9, and 32.1 mu g/mL, respectively. Among them, compound 5) was identified as the most promising candidate due to its stronger effect than that of Kocide 3000 [Cu(OH)(2)] within the same concentration range. Field trials demonstrated that the control effect of compound 55 against tobacco bacterial wilt was better than that of the commercial bactericide Saisentong. For the first time, the present work demonstrated that sulfone derivatives containing 1,3,4-oxadiazole can be used to develop potential bactericides for plants.