2-[(chloroacetyl)amino]-5-(4-methoxyphenyl)-1,3,5-oxadiazole | 59940-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-[(chloroacetyl)amino]-5-(4-methoxyphenyl)-1,3,5-oxadiazole
• 英文别名: 2-chloro-N-[5-(4-methoxyphenyl)-[1,3,4]oxadiazol-2-yl]acetamide；2-chloro-N-[5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl]acetamide
• CAS: 59940-09-9
• 化学式: C₁₁H₁₀ClN₃O₃
• 分子量: 267.672
• InChiKey: TUTXAZBZYVPMTO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  77.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(chloroacetyl)amino]-5-(4-methoxyphenyl)-1,3,5-oxadiazole 在 sodium acetate 、 乙酸酐 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 6.0h， 生成 5-Fluoro-3-[2-[(E)-5-(4-methoxy-phenyl)-[1,3,4]oxadiazol-2-ylimino]-4-oxo-thiazolidin-(5Z)-ylidene]-1,3-dihydro-indol-2-one
  参考文献：
  名称：

  Altintas, Handan; Ates, Oeznur; Uydes-Dogan, B. Soenmez, Arzneimittel-Forschung/Drug Research, 2006, vol. 56, # 3, p. 239 - 248

  摘要：

  DOI：
• 作为产物：
  描述：

  4-methoxybenzaldehyde semicarbazone 在 溴 、 sodium acetate 、 potassium carbonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 2-[(chloroacetyl)amino]-5-(4-methoxyphenyl)-1,3,5-oxadiazole
  参考文献：
  名称：

  芳基恶二唑连接的 1,2,4-三嗪衍生物作为抗惊厥药的设计、合成和药理学评价

  摘要：

  一系列新的棒状芳基恶二唑-1,2,4-三嗪衍生物(6a-l)使用适当的化学路线设计和合成。这些结构被设计成具有任何化合物所需的结构元素，以成为潜在的抗惊厥药。使用最大电休克发作 (MES)、皮下戊四唑诱发的癫痫发作 (scPTZ) 进行抗惊厥活性的初步筛选，并通过运动损伤测试和光度计测试评估行为活动。衍生物 6-((5-(4-methoxyphenyl)-1,3,4-oxadiazol-2-yl)amino)-1,2,4-triazine-3(2H)-thione (6f)和 6-( (5-(4-羟基苯基)-1,3,4-恶二唑-2-基)氨基)-1,2,4-三嗪-3(2H)-硫酮(6g)揭示了对 MES 和 scPTZ 的显着活性，表明这些化合物对全身强直-阵挛和失神发作均有效。对先导化合物(6g)进行了进一步的定量评估，并成为最有效的抗惊厥药，中位有效剂量为 28.5 mg/kg (MES

  DOI：

  10.1007/s00044-022-02880-4

文献信息

• Synthesis, telomerase inhibitory and anticancer activity of new 2-phenyl-4H-chromone derivatives containing 1,3,4-oxadiazole moiety
  作者：Xu Han、Yun Long Yu、Duo Ma、Zhao Yan Zhang、Xin Hua Liu

  DOI：10.1080/14756366.2020.1864630

  日期：2021.1.1

  66 2-phenyl-4H-chromone derivatives containing amide and 1,3,4-oxadiazole moieties were prepared as potential telomerase inhibitors. The results showed most of the title compounds exhibited significantly inhibitory activity on telomerase. Among them, some compounds demonstrated the most potent telomerase inhibitory activity (IC50 < 1 µM), which was significantly superior to the staurosporine (IC50

  摘要 根据先前的研究，制备了 66 种含有酰胺和 1,3,4-恶二唑部分的 2-苯基-4H-色酮衍生物作为潜在的端粒酶抑制剂。结果显示大多数标题化合物对端粒酶表现出显着的抑制活性。其中，一些化合物表现出最有效的端粒酶抑制活性（IC 50 < 1 µM），明显优于星形孢菌素（IC 50 = 6.41 µM）。此外，总结了清晰的构效关系，表明甲氧基的取代以及苯环上取代基的位置、类型和数量对端粒酶活性有显着影响。其中，化合物A33对端粒酶有显着的抑制作用。流式细胞仪分析表明，化合物A33可以将MGC-803细胞周期阻滞在G2/M期，并以浓度依赖性方式诱导细胞凋亡。同时，Western blotting 显示该化合物可以降低作为端粒酶片段的dyskerin 的表达。
• Antifibrotic and anticancer action of 5-ene amino/iminothiazolidinones
  作者：Danylo Kaminskyy、Gertjan J.M. den Hartog、Magdalena Wojtyra、Maryan Lelyukh、Andrzej Gzella、Aalt Bast、Roman Lesyk

  DOI：10.1016/j.ejmech.2016.02.011

  日期：2016.4

  Here we describe the synthesis and the antifibrotic and anticancer activity determination of amino(imino)thiazolidinone derivatives. An efficient one-pot three-component reaction which involved [2 + 3]-cyclocondensation and Knoevenagel condensation was used for the synthesis of 5-ene-2-amino(imino)-4-thiazolidinones. Following amino-imino tautomerism, the compound structures were confirmed by X-ray

  在这里，我们描述了氨基（亚氨基）噻唑烷酮衍生物的合成以及抗纤维化和抗癌活性的测定。一种高效的一锅三组分反应，涉及[2 + 3]-环缩合和Knoevenagel缩合反应，用于合成5-烯-2-氨基（亚氨基）-4-噻唑烷酮。氨基亚氨基互变异构之后，通过X射线分析证实了化合物的结构。对成纤维细胞和癌细胞进行SRB分析的比较表明，显着降低成纤维细胞活力的化合物不具有抗癌作用。已经鉴定出一系列噻唑烷酮衍生物作为进一步测试的有趣候选物。在测试的化合物中，2- 3-呋喃-2-基甲基-2-[（（2-甲基-3-苯基亚烷基）肼基]-噻唑烷丁-4-一-5-基} -N-（3-三氟甲基苯基）-乙酰胺（5），N-（2-甲氧基苯基）-2- [5-（4-氧噻唑烷-2--2-亚氨基氨基）-[1,3,4]噻二唑-2-基硫烷基]-乙酰胺（12），3- [3-烯丙基-4-氧-2-（噻唑-2-亚胺基）噻唑烷-5-基] -1,3-二氢吲哚-2-一（33）和5（Z）-
• Bradykinin antagonists and thiazolidinone derivatives as new potential anti-cancer compounds
  作者：Stanislav Avdieiev、Lajos Gera、Dmytro Havrylyuk、Robert S. Hodges、Roman Lesyk、Vincent Ribrag、Yegor Vassetzky、Vadym Kavsan

  DOI：10.1016/j.bmc.2014.06.046

  日期：2014.8

  Glioblastoma (GB), the most aggressive brain tumour, and mantle cell lymphoma (MCL), a rare but very aggressive type of lymphoma, are highly resistant to chemotherapy. GB and MCL chemotherapy gives very modest results, the vast majority of patients experience recurrent disease. To find out the new treatment modality for drug-resistant GB and MCL cells, combining of bradykinin (BK) antagonists with conventional temozolomide (TMZ) treatment, and screening of thiazolidinones derivatives were the main objectives of this work. As it was revealed here, BKM-570 was the lead compound among BK antagonists under investigation (IC50 was 3.3 mu M) in human GB cells. It strongly suppressed extracellular signal-regulated kinases 1/2 (ERK1/2) and protein kinase B (AKT) phosphorylation. BK antagonists did not decrease the viability of MCL cells, thus showing the cell-specific mode, while thiazolidinone derivatives, a novel group of promising anti-tumour compounds inhibited proliferation of MCL cells: IC50 of ID 4526 and ID 4527 compounds were 0.27 mu M and 0.16 mu M, correspondingly. However, single agents are often not effective in clinic due to activation of collateral pathways in tumour cells. We demonstrated a strong synergistic effect after combinatorial treatment by BKM-570 together with TMZ that drastically increased cytotoxic action of this drug in rat and human glioma cells. Small proportion of cells was still viable after such treatment that could be explained by presence of TMZ-resistant cells in the population.It is possible to expect that the combined therapy aimed simultaneously at different elements of tumourigenesis will be more effective with lower drug concentrations than the first-line drug temozolomide used alone in clinics. (C) 2014 Elsevier Ltd. All rights reserved.
• Singh,H.; Yadav,L.D.S., Journal of the Indian Chemical Society, 1976, vol. 53, p. 323 - 326
  作者：Singh,H.、Yadav,L.D.S.

  DOI：——

  日期：——
• SINGH H.; YADAV L. D. S., J. INDIAN CHEM. SOC <JICS-AH>, 1976, 53, NO 3, 323-326
  作者：SINGH H.、 YADAV L. D. S.

  DOI：——

  日期：——