2-[5-(4-甲氧基苯基)-1,3,4-恶二唑-2-基]苯胺 | 88185-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-[5-(4-甲氧基苯基)-1,3,4-恶二唑-2-基]苯胺
• 英文名称: 2-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)aniline
• 英文别名: 2-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]aniline
• CAS: 88185-03-9
• 化学式: C₁₅H₁₃N₃O₂
• 分子量: 267.287
• InChiKey: FZJZNABYDBBGHY-UHFFFAOYSA-N

物化性质

• 熔点：
  146 °C(Solv: ligroine (8032-32-4))
• 沸点：
  468.5±55.0 °C(Predicted)
• 密度：
  1.240±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[5-(4-甲氧基苯基)-1,3,4-恶二唑-2-基]苯胺 、 对甲氧基苯甲酰氯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到4-methoxy-N-(2-(5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)phenyl)benzamide
  参考文献：
  名称：

  Structure activity relationships, multidrug resistance reversal and selectivity of heteroarylphenyl ABCG2 inhibitors

  摘要：

  An overexpression of the transmembrane ATP-binding cassette transporter G2 (ABCG2, BCRP) in cancer tissues is supposed to play a role in the multidrug resistance (MDR) of tumors resulting in an inefficient chemotherapy. Therefore, co-administration of selective and non-toxic ABCG2 inhibitors is a promising strategy for improving the efficacy of chemotherapy by blocking ABCG2-mediated export of the cytostatic drugs. In the present study, we designed a small library of 38 novel compounds containing a heteroaryl-phenyl scaffold possessing several (bioisosteric) moieties, and twelve new precursors. We investigated the library for ABCG2 inhibition, for the selectivity against MDR-involved efflux pump ABCBI (P-gp) and for toxicity. Structure activity relationship (SAR) studies revealed that, at least a phenylheteroaryl-phenylamide scaffold is necessary for observing an ABCG2 inhibition. 4-Methoxy-N-(2(2-(6-methoxypyridin-3-yl)-2H-tetrazol-5-yl)phenyl)benzamide (43) exhibited a high potency (IC50 = 61 nM)), selectivity, low intrinsic toxicity and reversed the ABCG2-mediated drug resistance in presence of only 0.1 mu M. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.01.012
• 作为产物：
  描述：

  对甲氧基苯甲酰肼 在 对甲苯磺酸 、 三氯氧磷 作用下， 以 溶剂黄146 为溶剂， 反应 12.0h， 生成 2-[5-(4-甲氧基苯基)-1,3,4-恶二唑-2-基]苯胺
  参考文献：
  名称：

  A Facile Synthesis of 2-Aryl-3,4-dihydro-5H-1,3,4-benzotriazepin-5-ones

  摘要：

  DOI：

  10.1055/s-1983-30538

文献信息

• Electrosynthesis of 2-(1,3,4-Oxadiazol-2-yl)aniline Derivatives with Isatins as Amino-Attached C1 Sources
  作者：Peng Qian、Zhenghong Zhou、Li Wang、Zhicheng Wang、Zhongwei Wang、Zhenlei Zhang、Liangquan Sheng

  DOI：10.1021/acs.joc.0c01700

  日期：2020.10.16

  intramolecular decarboxylative coupling reaction for the construction of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives was developed from readily available isatins and hydrazides by virtue of electrochemistry. In this reaction, isatins were employed as amino-attached C1 sources, providing a variety of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives with moderate to good yields.

  通过电化学从易得的靛红和酰肼中开发出用于构建2-（1,3,4-恶二唑-2-基）苯胺衍生物的分子内脱羧偶联反应。在该反应中，靛红被用作氨基连接的C1来源，以中等至良好的产率提供了各种2-（1,3,4-恶二唑-2-基）苯胺衍生物。
• Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation–cyclization of hydrazides and diketones
  作者：Pinhui Diao、Yanqin Ge、Wenpei zhang、Chen Xu、Nannan Zhang、Cheng Guo

  DOI：10.1016/j.tetlet.2018.01.037

  日期：2018.2

  A visible-light-induced synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from simple diketones and hydrazides with the assistant of the photocatalyst eosin Y catalyzed decarboxylation and cyclization under mild conditions has been discovered. The reaction tolerates a wide range of functional groups and gives a variety of valuable 1,3,4-oxadiazoles in moderate to good yields. Finally, a plausible reaction

  发现了在光催化条件下，由简单的二酮和酰肼在光催化曙红Y的催化下可见光诱导的2,5-二取代的1,3,4-恶二唑的合成。该反应可耐受各种官能团，并以中等至良好的收率得到各种有价值的1,3,4-恶二唑。最后，提出了合理的反应机理。
• Synthesis of 3-Aminoquinazolinones via a SnCl₂-Mediated ANRORC-like Reductive Rearrangement of 1,3,4-Oxadiazoles
  作者：Mohamed Elagawany、Lingaiah Maram、Bahaa Elgendy

  DOI：10.1021/acs.joc.3c01973

  日期：2023.12.15

  Herein, we developed a new SnCl2-mediated ANRORC (addition of nucleophile, ring-opening, and ring-closure)-like rearrangement for the synthesis of 3-amino-2-substituted-quinazolin-4(3H)-one from 2-(2-nitrophenyl)-5-substituted-1,3,4-oxadiazole. The new method is solvent-dependent and features the use of a green solvent system (i.e., ethanol/water), high yields, and simple workup. The reduced product

  在此，我们开发了一种新的SnCl 2介导的ANRORC（亲核试剂加成、开环和闭环）类重排，用于合成3-氨基-2-取代-喹唑啉-4(3 H )-one 2-(2-硝基苯基)-5-取代-1,3,4-恶二唑。新方法依赖于溶剂，具有使用绿色溶剂系统（即乙醇/水）、高产率和简单后处理的特点。将溶剂改为乙腈即可独家合成还原产物。
• Reddy, P. S. N.; Reddy, P. Pratap, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 763 - 765
  作者：Reddy, P. S. N.、Reddy, P. Pratap

  DOI：——

  日期：——
• REDDY, CH. K.;REDDY, P. S. N.;RATNAM, C. V., SYNTHESIS, BRD, 1983, N 10, 842-844
  作者：REDDY, CH. K.、REDDY, P. S. N.、RATNAM, C. V.

  DOI：——

  日期：——