2-(1H-indol-2-yl)-5-phenyl-1,3,4-oxadiazole | 37574-83-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 2-(1H-indol-2-yl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-(5-Phenyl-1,3,4-oxadiazol-2(3H)-ylidene)-2H-indole
• CAS: 37574-83-7
• 化学式: C₁₆H₁₁N₃O
• 分子量: 261.283
• InChiKey: XBSKXIUAUURIBZ-UHFFFAOYSA-N

物化性质

• 熔点：
  154-157 °C
• 沸点：
  503.3±42.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 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：
  54.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N¹-benzoyl-N²-(3-indolyl)hydrazine 在 三氯氧磷 作用下， 生成 2-(1H-indol-2-yl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Robba; Maume; Lancelot, Bulletin de la Societe Chimique de France, 1977, vol. II, # 3-4, p. 333 - 336

  摘要：

  DOI：

文献信息

• 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。
• Synthesis of Some New Indole-1,3,4-Oxadiazole Hybrids as Tubulin Polymerization Inhibitors
  作者：Sunitha Boda、Satheesh Kumar Nukala、Ravinder Manchal

  DOI：10.1134/s1068162023010077

  日期：2022.12

  Abstract We have synthesized some new molecular hybrids containing indole and 1,3,4-oxadiazole rings from the commercially available ethyl 1H-indole-2-carboxylate (I) in two steps using hydrazine hydrate and different aromatic carboxylic acids consecutively. All the hybrids were screened for the in vitro anticancer activity against SKOV3 (ovarian), A549 (lung) and MCF-7 (breast) cell lines using MTT

  摘要 我们从市售的 1 H -吲哚-2-羧酸乙酯 ( I ) 中连续使用水合肼和不同的芳香族羧酸分两步合成了一些含有吲哚和 1,3,4-恶二唑环的新型分子杂化物。使用 MTT 测定和依托泊苷作为参考，筛选所有杂交体针对 SKOV3（卵巢）、A549（肺）和 MCF-7（乳腺）细胞系的体外抗癌活性。结果表明，化合物 2-(1H-indol-2-yl)-5-(4-methoxyphenyl)-1,3,4-oxadiazole ( Vb ) 对所有细胞系的效力都优于依托泊苷。同样，化合物 2-(3,5-二甲氧基苯基)-5-(1 H -吲哚-2-基)-1,3,4-恶二唑 ( Vc ) 和 4-(5-(1 H )-indol-2-yl)-1,3,4-oxadiazol-2-yl)benzonitrile ( VI ) 被发现比依托泊苷对 MCF-7 细胞系具有更高的效力。三种活性化合物 ( Vb )、(
• 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。
• Highly efficient copper/palladium-catalyzed tandem Ullman reaction/arylation of azoles via C–H activation: synthesis of benzofuranyl and indolyl azoles from 2-(gem-dibromovinyl)phenols(anilines) with azoles
  作者：Wei Chen、Min Wang、Pinhua Li、Lei Wang

  DOI：10.1016/j.tet.2011.06.044

  日期：2011.8

  In this paper, a novel and highly efficient copper/palladium-catalyzed tandem intramolecular Ullman-type C-O(N) coupling reaction of 2-(gem-dibromovinyl)phenols(anilines) followed by an intermolecular arylation of azoles through C-H activation has been developed. In the presence of CuBr with Pd(PPh3)(2)Cl-2 used as co-catalyst, and (LiOBu)-Bu-t as a base, the one-pot reactions of 2-(gem-dibromovinyl)phenols and 2-(gem-dibromovinyl)anilines with a variety of azoles, including oxazoles, imidazoles, thiazoles, and oxadiazoles underwent smoothly in toluene at 100 degrees C to generate the corresponding biheteroaryl products in high yields. A tentative mechanism of copper/palladium-catalyzed tandem reaction was described. (C) 2011 Elsevier Ltd. All rights reserved.
• ROBBA M.; MAUME D.; LANCELOT D. C., BULL. SOC. CHIM. FRANCE, 1977, NO
  作者：ROBBA M.、 MAUME D.、 LANCELOT D. C.

  DOI：——

  日期：——