4-(5-(4-氯苯基)-1,3,4-恶二唑-2-基)苯胺 | 101094-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(5-(4-氯苯基)-1,3,4-恶二唑-2-基)苯胺
• 英文名称: 4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl) aniline
• 英文别名: 4-[5-(4-Chlorophenyl)-1,3,4-oxadiazol-2-yl]aniline
• CAS: 101094-89-7
• 化学式: C₁₄H₁₀ClN₃O
• 分子量: 271.706
• InChiKey: BWBNYZHOMGTTMK-UHFFFAOYSA-N

物化性质

• 熔点：
  201-203 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  465.0±55.0 °C(Predicted)
• 密度：
  1.335±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-bromoethoxy)-2H-chromen-2-one 、 4-(5-(4-氯苯基)-1,3,4-恶二唑-2-基)苯胺 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以67%的产率得到4-(2-(4-(5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl)phenylamino)ethoxy)-2H-chromen-2-one
  参考文献：
  名称：

  Chavan; Nirmal; Bhosale, Asian Journal of Chemistry, 2011, vol. 23, # 9, p. 3919 - 3922

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氨基-5-(4-氯苯基)-1,3,4-噁二唑 在 四(三苯基膦)钯 、 sodium carbonate 、 copper(ll) bromide 、 亚硝酸异戊酯 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成 4-(5-(4-氯苯基)-1,3,4-恶二唑-2-基)苯胺
  参考文献：
  名称：

  From Sphingosine Kinase to Dihydroceramide Desaturase: A Structure–Activity Relationship (SAR) Study of the Enzyme Inhibitory and Anticancer Activity of 4-((4-(4-Chlorophenyl)thiazol-2-yl)amino)phenol (SKI-II)

  摘要：

  The sphingosine kinase (SK) inhibitor, SKI-II, has been employed extensively in biological investigations of the role of SK1 and SK2 in disease and has demonstrated impressive anticancer activity in vitro and in vivo. However, interpretations of results using this pharmacological agent are complicated by several factors: poor SK1/2 selectivity, additional activity as an inducer of SK1-degradation, and off-target effects, including its recently identified capacity to inhibit dihydroceramide desaturase-1 (Des1). In this study, we have delineated the structure-activity relationship (SAR) for these different targets and correlated them to that required for anticancer activity and determined that Des1 inhibition is primarily responsible for the antiproliferative effects of SKI-II and its analogues. In the course of these efforts, a series of novel SK1, SK2, and Des1 inhibitors have been generated, including compounds with significantly greater anticancer activity.

  DOI：

  10.1021/acs.jmedchem.5b01439

文献信息

• Design, synthesis, modelling studies and biological evaluation of 1,3,4-oxadiazole derivatives as potent anticancer agents targeting thymidine phosphorylase enzyme
  作者：Shalini Bajaj、Maushmi S. Kumar、Hussain Tinwala、Mayur YC

  DOI：10.1016/j.bioorg.2021.104873

  日期：2021.6

  identified no signs of clinical toxicity was observed. The SARs study of synthesized derivatives revealed that the substitution of phenyl ring with electron withdrawing group at ortho position showed significant TP inhibitory activity compared to para substitution. The experimental data suggests that 1,3,4-oxadiazole with substituted phenyl can be taken as a lead for the design of efficient TP inhibitors

  设计并合成了一系列具有取代苯环的新型 1,3,4-恶二唑衍生物，目的是发现靶向胸苷磷酸化酶 (TP) 的新型抗癌药物。1,3,4-恶二唑衍生物在实验室中通过简单方便的方法合成。所有合成化合物的化学结构均通过 IR、1 H NMR 和质谱方法表征，并通过 MTT 方法评估对两种乳腺癌细胞系（MCF-7 和 MDA-MB-231）的细胞毒性。此外，TP 测定的结果确定 1,3,4-恶二唑分子部分通过抑制胸苷磷酸化显示出抗癌活性。TP 测定鉴定了SB8和SB9作为对两种细胞系都具有抗癌活性的潜在抑制剂。分子对接研究确认了分子在 TP 活性位点氨基酸残基处的取向和结合相互作用（PDB：1UOU）。化合物SB8在 5000 mg/kg 剂量下的急性毒性研究已确定未观察到临床毒性迹象。合成衍生物的非典研究表明，与在电子吸引性基团的苯基环的取代邻相比位置表明显著TP抑制活性对代换。实验数据表明，具有取代苯基的1
• Synthesis, Anti–HIV, and Antifungal Activity of New Benzensulfonamides Bearing the 2,5-Disubstituted-1,3,4-Oxadiazole Moiety
  作者：Muhammad Zareef、Rashid Iqbal、Najim A. Al-Masoudi、Javid H. Zaidi、Muhammad Arfan、Sohail A. Shahzad

  DOI：10.1080/10426500600919074

  日期：2007.1.1

  and KOH. Another series of new secondary benzenesulfonamides 10a–j and bis-benzenesulfonamides 11a–j have been synthesized by a new approach using Et3N and dimethylaminopyridine. All synthesized compounds were characterized by physical, microanalytical, and spectral data. Some of the synthesized compounds were screened in vitro for their anti–HIV and antifungal activities.

  通过 4-(4-甲基, 氯代) 反应制备了一系列新型手性和非手性 N-[1-(1,3,4-恶二唑-2基硫基)烷基]-4-甲基/氯/甲氧基苯磺酰胺 5a-l , 甲氧基苯基磺酰氨基) 烷基羧酸酰肼 4a-l 与 CS2 和 KOH。使用 Et3N 和二甲氨基吡啶的新方法合成了另一系列新的二级苯磺酰胺 10a-j 和双苯磺酰胺 11a-j。所有合成的化合物均通过物理、微量分析和光谱数据进行表征。一些合成的化合物在体外筛选了它们的抗 HIV 和抗真菌活性。
• A new synthetic route to 1,3,4-oxadiazoles. Pharmacological study of some new derivatives
  作者：Pierre Reynaud、Youssef El Hamad、Catherine Davrinche、Emmanuel Nguyen-Tri-Xuong、Gilles Tran、Pierre Rinjard

  DOI：10.1002/jhet.5570290454

  日期：1992.7

  2-Substituted 1,3,4-oxadiazoles have been examined as possible prodrugs of antidepressant hydrazides. A new method of synthesis of this heterocycle from thionoester and five new oxadiazoles substituted at the 2-position by a 4-pyridyl or 4-aminophenyl group and at the 5-position by a phenyl group are described.

  已经研究了2-取代的1,3,4-恶二唑作为抗抑郁剂酰肼的可能前药。描述了一种由硫代磺酸酯和五种新的恶二唑合成该杂环的新方法，所述五种新的二唑在2-位被4-吡啶基或4-氨基苯基取代，在5-位被苯基取代。
• Process for optically brightening fibrous materials
  申请人：CIBA LTD

  公开号：US02856311A1

  公开（公告）日：1958-10-14
• Oxadiazole compounds
  申请人：CIBA LTD

  公开号：US02845419A1

  公开（公告）日：1958-07-29