2-(benzo[d]thiazol-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole | 55439-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-(benzo[d]thiazol-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
• 英文别名: 2-(1,3-Benzothiazol-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
• CAS: 55439-46-8
• 化学式: C₁₅H₈ClN₃OS
• 分子量: 313.767
• InChiKey: UGDQARHRQIGXAH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(benzo[d]thiazol-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole 、 diphosphorus pentasulfide 以59%的产率得到
  参考文献：
  名称：

  SAWHNEY S. N; SINGH J.; BANSAL O. P., J. INDIAN CHEM. SOC. , 1974, 51, NO 10, 886-890

  摘要：

  DOI：
• 作为产物：
  描述：

  benzothiazole-2-carboxylic acid N'-(4-chloro-benzoyl)-hydrazide 在 PPA 作用下， 生成 2-(benzo[d]thiazol-2-yl)-5-(4-chlorophenyl)-1,3,4-oxadiazole
  参考文献：
  名称：

  Sawhney,S.N. et al., Journal of the Indian Chemical Society, 1974, vol. 51, p. 886 - 890

  摘要：

  DOI：

文献信息

• Pd(OAc)2 catalyzed C–H activation of 1,3,4-oxadiazoles and their direct oxidative coupling with benzothiazoles and aryl boronic acids using Cu(OAc)2 as an oxidant
  作者：N. Salvanna、Gandolla Chinna Reddy、Biswanath Das

  DOI：10.1016/j.tet.2012.12.080

  日期：2013.3

  The first direct oxidative coupling of 1,3,4-oxadiazoles with benzothiazoles has been accomplished using Pd(OAc)2 as a catalyst and Cu(OAc)2 as an oxidant. The similar combination of the catalyst and the oxidant has also been applied for direct arylation of 1,3,4-oxadiazoles with aryl boronic acids. Several novel oxadiazole derivatives have been prepared in high yields following both the methods.

  使用Pd（OAc）2作为催化剂和Cu（OAc）2作为氧化剂已经实现了1,3,4-恶二唑与苯并噻唑的首次直接氧化偶联。催化剂和氧化剂的类似组合也已用于将1,3,4-恶二唑与芳基硼酸直接芳基化。两种方法都以高收率制备了几种新的恶二唑衍生物。
• OXADIAZOLE AND PHENOL DERIVATIVES AS ANTIBACTERIAL AND/OR HERBICIDAL AGENTS
  申请人：BOARD OF TRUSTEES OF NORTHERN ILLINOIS UNIVERSITY

  公开号：US20180271098A1

  公开（公告）日：2018-09-27

  Antimicrobial resistance is rising at an alarming rate. The methylerythritol phosphate (MEP) pathway is a metabolic pathway that produces the isoprenoids isopentyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP). Notably, the MEP pathway is present in bacteria and not mammals, which made the enzymes of the MEP pathway attractive targets for discovering new anti-infective agents due to reduced chances of off-target interactions leading to side effects. The biophysical properties of 2-C-methyl-D-erythritol 4-phosphate cytidylyltransferase (IspD) and 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase (IspE) were determined to aid discovery of novel inhibitors. Thermal shift screening was used as an initial filter to narrow down a library of compounds with thermal shifts greater than 1° C., which could indicate binding to the IspD and IspE enzymes. Follow-up studies were performed using isothermal titration calorimetry and enzymatic inhibition assays. Results from these studies have revealed compounds with high micromolar inhibition of both IspD from Escherichia coli and IspE from Burkholderia thailandensis . The hit compounds are used for future development of more potent IspD and IspE inhibitors.

  抗微生物药物耐药性正在以令人担忧的速度上升。 甲基赤霉酸磷酸(MEP)途径是一种产生异戊二烯醇磷酸丙酯（IPP）和二甲基磷酸丙酯（DMAPP）的代谢途径。 值得注意的是，MEP途径存在于细菌中而不在哺乳动物中，这使得MEP途径的酶成为发现新抗感染剂的有吸引力的靶点，因为减少了产生副作用的离靶相互作用的机会。 通过测定2-C-甲基-D-赤霉酸4-磷酸胞苷基转移酶（IspD）和4-二磷酸胞苷基-2-C-甲基-D-赤霉酸激酶（IspE）的生物物理特性，有助于发现新的抑制剂。 利用热位移筛选作为初始过滤器，缩小了具有大于1°C热位移的化合物库，这可能表明这些化合物与IspD和IspE酶结合。 随后使用等温滴定热量计和酶抑制测定进行了后续研究。 这些研究结果显示出对大肠杆菌IspD和泰国布氏杆菌IspE均具有高微摩尔抑制作用的化合物。 这些有效化合物将用于未来开发更有效的IspD和IspE抑制剂。
• Oxadiazole and phenol derivatives as antibacterial and/or herbicidal agents
  申请人：NORTHERN ILLINOIS RESEARCH FOUNDATION

  公开号：US11026426B2

  公开（公告）日：2021-06-08

  Compounds of formula I and II are described. In formulae I and II, X is —NH— or —S— and Y is —CH═ or —N═. In formula I, Z is C1-C6 alkylene, C2-C6 alkenylene, C6-C10 arylene, or C3-C6 cycloalkylene, or Z is absent. In formula I, R is hydrogen, halogen, —OH, —NO2, C1-C6 alkyl, C2-C6 alkenyl, C6-C10aryl, —O(C1-C6 alkyl), or —O(C6-C10 aryl), wherein each hydrogen atom in C1-C6 alkyl, C2-C6 alkenyl, C6-C10 aryl, —O(C1-C6 alkyl), and —O(C6-C10 aryl) is independently optionally substituted by halogen, —OH, or —NO2. In formula II, R1, R2, R3, and R4 are each independently hydrogen, halogen, —OH, —NO2, C1-C6 alkyl, C2-C6 alkenyl, or C6-C10 aryl, wherein each hydrogen atom in C1-C6 alkyl, C2-C6 alkenyl, and C6-C10 aryl is independently optionally substituted by halogen, —OH, or —NO2. Methods of inhibiting bacteria are also described.

  式 I 的化合物 和 II 所述。在式 I 和 II 中，X 是-NH-或-S-，Y 是-CH═或-N═。在式 I 中，Z 是 C1-C6 亚烷基、C2-C6 烯基、C6-C10 芳基或 C3-C6 环亚烷基，或不含 Z。在式 I 中，R 是氢、卤素、-OH、-NO2、C1-C6 烷基、C2-C6 烯基、C6-C10 芳基、-O(C1-C6 烷基)或-O(C6-C10 芳基)，其中 C1-C6 烷基、C2-C6 烯基、C6-C10 芳基、-O(C1-C6 烷基)和-O(C6-C10 芳基)中的每个氢原子独立地任选被卤素、-OH 或- 取代。在式 II 中，R1、R2、R3 和 R4 各自独立地为氢、卤素、-OH、- 、C1-C6 烷基、C2-C6 烯基或 C6-C10 芳基，其中 C1-C6 烷基、C2-C6 烯基和 C6-C10 芳基中的每个氢原子独立地任选被卤素、-OH 或 - 取代。还描述了抑制细菌的方法。
• Prakash, Om; Sharma, Vijay; Batra, Hitesh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 8, p. 797 - 800
  作者：Prakash, Om、Sharma, Vijay、Batra, Hitesh、Rani, Neena、Sharma, Pawan K.、Singh, Shiv

  DOI：——

  日期：——