3-(5-mercapto-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one | 141334-12-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 3-(5-mercapto-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one
• 英文别名: 3-(5-Sulfanyl-1,3,4-oxadiazol-2-yl)-2h-chromen-2-one；3-(2-sulfanylidene-3H-1,3,4-oxadiazol-5-yl)chromen-2-one
• CAS: 141334-12-5
• 化学式: C₁₁H₆N₂O₃S
• 分子量: 246.246
• InChiKey: NONALZJWTAXJQB-UHFFFAOYSA-N

物化性质

• 熔点：
  162-165 °C(Solv: ethanol (64-17-5))
• 沸点：
  409.7±55.0 °C(Predicted)
• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(5-mercapto-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one 在 potassium hydrogencarbonate 作用下， 以 1,4-二氧六环 、 丙酮 为溶剂， 反应 4.0h， 生成 3-{5-[4-(4-methyl-piperazin-1-yl)-6-(quinolin-8-yloxy)-1,3,5-triazin-2-ylsulfanyl]-[1,3,4]oxadiazol-2-yl}-chromen-2-one
  参考文献：
  名称：

  新型3-（5-硫烷基-1,3,4-恶二唑-2-基）-2H-铬-2--2-缩合的β-三嗪基哌嗪和哌啶类抗微生物剂的合成

  摘要：

  基于各种取代的哌嗪和哌啶并结合了1,3,5的3-（5-硫烷基-1,3,4-恶二唑-2-基）-2H-铬-2-酮的合成及抗菌活性-三嗪部分已在本文中报道。3- {5-[（4,6-二氯-1,3,5-三嗪-2-基）硫烷基] -1,3,4-恶二唑-2-基} -2H-铬-2-酮3为2,4,6-三氯-1,3,5-三嗪1与3-（5-硫烷基-1,3,4-恶二唑-2-基）-2H-铬-2-酮2反应制得通过遵循文献报道的方法获得。然后将中间体3与8-羟基喹啉4缩合形成3-（5-{[4-氯-6-（喹啉-4-基氧基）-1,3,5-三嗪-2-基]硫基} -1， 3,4-恶二唑-2-基）-2H-铬-2--2- 5。将其进一步用各种取代的哌嗪和哌啶处理，得到标题化合物7a - u，然后对其进行体外测定，以确定它们作为两种革兰氏阳性细菌（金黄色葡萄球菌，蜡状芽孢杆菌）对细菌和真菌菌株的体外生物学功效。，六个革兰氏阴性细菌（大

  DOI：

  10.1007/s00044-011-9842-7
• 作为产物：
  描述：

  水杨醛 在 盐酸 、 氯化亚砜 、 水 、 potassium hydroxide 、 sodium hydroxide 、 肼 作用下， 以 甲醇 、 水 为溶剂， 反应 21.5h， 生成 3-(5-mercapto-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one
  参考文献：
  名称：

  Design, synthesis, antibacterial, and antifungal studies of novel 3-substituted coumarinyl-triazine derivatives

  摘要：

  摘要 设计并合成了一系列新颖的3-取代香豆素-三嗪衍生物，通过在水中进行连续的Knoevenagel和Pinner反应从3-羧基香豆素合成而来。所有合成的化合物均通过红外光谱（IR）、1H核磁共振（1H NMR）、13C核磁共振（13C NMR）、质谱（MS）和元素分析进行表征。此外，进行了对四种细菌菌株（金黄色葡萄球菌、枯草杆菌、大肠杆菌和伤寒沙门氏菌）和两种真菌菌株（黑曲霉和鼠李糖曲霉）的体外筛选。

  DOI：

  10.1515/hc-2013-0104

文献信息

• Coumarin-thiazole and -oxadiazole derivatives: Synthesis, bioactivity and docking studies for aldose/aldehyde reductase inhibitors
  作者：Aliya Ibrar、Yildiz Tehseen、Imtiaz Khan、Abdul Hameed、Aamer Saeed、Norbert Furtmann、Jürgen Bajorath、Jamshed Iqbal

  DOI：10.1016/j.bioorg.2016.08.005

  日期：2016.10

  the development of potent and selective inhibitors of aldose reductase (ALR2), and to control the diabetes mellitus (DM), a chronic metabolic disease, we synthesized novel coumarin-thiazole 6(a-o) and coumarin-oxadiazole 11(a-h) hybrids and screened for their inhibitory activity against aldose reductase (ALR2), for the selectivity against aldehyde reductase (ALR1). Compounds were also screened against

  为了继续致力于开发有效和选择性的醛糖还原酶（ALR2）抑制剂，并控制糖尿病（DM）（一种慢性代谢疾病），我们合成了新型香豆素-噻唑6（ao）和香豆素-恶二唑11（ah）杂种并筛选其对醛糖还原酶（ALR2）的抑制活性，对醛还原酶（ALR1）的选择性。还针对ALR1筛选化合物。在新设计的化合物中，6c，11d和11g是ALR2的选择性抑制剂。而（E）-3-（2-（2-（2-溴苄叉基）肼基）噻唑-4-基）-2H-铬-2--2-酮6c对ALR2的最低IC50值为0.16±0.06μM。此外，化合物（E）-3-（2-（2-亚苄叉肼基）噻唑-4-基）-2H-铬-2--2-酮（6a; ARL1的IC50 = 2.94±1.23μM，0.12±0。ARL2）和（E）-3-（2-（2-（2-（1-（4-溴苯基）亚乙基）肼基）噻唑-4-基）-2H-铬-2-酮（6e; IC50 = 1.71±05μM ARL1的0
• Design ,Synthesis, Insilco Study and Biological Evaluation of New Coumarin-Oxadiazole Derivatives as Potent Histone Deacetylase Inhibitors
  作者：sarah jabbar

  DOI：10.21608/ejchem.2022.134043.5912

  日期：2022.5.30

  Abstract A new series of HDAC inhibitors were designed, synthesized, bearing acyl semicarbazide, hydrazide and hydrazide derivatives as ZBGs, alkyl thio oxadiazole as the linker group and coumarin as the cap group .These derivatives were evaluated for their HDACs inhibitory activities against MDA-MB-231 (a human breast cancer cell line) and HepG2 (a human hepatocellular carcinoma cell line), most of them had substantial HDAC inhibitory action and displayed better inhibitory activities against HepG2 cell line than against MDA-MB-231 cell line .Compound F5 was found to be the most powerful HDAC inhibitor, with an IC50 of 17.92,20.72 µg/ml which were better than that of SAHA's with IC50 = 39.84,36.52 µg/ml against MDA-MB-231 and HepG2 cell lines respectively . Compounds F1 with IC50 of 30.21,30.07 µg/ml, compounds F2 with IC50 of 31.59,26.27 µg/ml and compounds F5 with IC50 of 39.60 ,31.40 µg/ml higher than that of SAHA's with IC50 = 39.84,36.52 µg/ml against MDA-MB-231 and HepG2 cell lines respectively. The probable binding modes of compounds into HDAC enzymes (HDAC1 and 2) is deducted by the docking study which provided a rationale for the greatest inhibitory activity. These findings suggested that these compounds could be a good option for developing novel HDAC inhibitors with anticancer properties.

  摘要 设计、合成了一系列新的 HDAC 抑制剂，以酰基半肼、肼和肼衍生物为 ZBGs，以烷基硫代噁二唑为连接基团，以香豆素为帽基团。评估了这些衍生物对 MDA-MB-231（一种人乳腺癌细胞系）和 HepG2（一种人肝癌细胞系）的 HDACs 抑制活性，其中大多数衍生物都具有很强的 HDAC 抑制作用，而且对 HepG2 细胞系的抑制活性优于对 MDA-MB-231 细胞系的抑制活性。化合物 F5 是最强的 HDAC 抑制剂，对 MDA-MB-231 和 HepG2 细胞株的 IC50 分别为 17.92 和 20.72 µg/ml，优于 IC50 分别为 39.84 和 36.52 µg/ml 的 SAHA。化合物 F1 的 IC50 为 30.21、30.07 µg/ml，化合物 F2 的 IC50 为 31.59、26.27 µg/ml，化合物 F5 的 IC50 为 39.60、31.40 µg/ml，分别高于 SAHA 对 MDA-MB-231 和 HepG2 细胞株的 IC50 = 39.84、36.52 µg/ml。对接研究推断了化合物与 HDAC 酶（HDAC1 和 HDAC2）的可能结合模式，这为最大的抑制活性提供了依据。这些发现表明，这些化合物可能是开发具有抗癌特性的新型 HDAC 抑制剂的良好选择。
• Modh, Rahul P; Shah, Dhruvin; Chikhalia, Kishor H, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2013, vol. 52, # 10, p. 1318 - 1324
  作者：Modh, Rahul P、Shah, Dhruvin、Chikhalia, Kishor H

  DOI：——

  日期：——
• Synthesis and Antibacterial Studies of Some Novel 2-(Coumarin-3-yl)-5-mercapto-1,3,4-oxadiazoles Containing 2,4,6-Trisubstituted s-Triazine Derivatives
  作者：Amit C. Patel、Dharmesh H. Mahajan、Kishor H. Chikhalia

  DOI：10.1080/10426500902797285

  日期：2010.1.29

  A new series of 2-(coumarin-3-yl)-5-mercapto-1,3,4-oxadiazoles based on various aryl thiourea/ureas incorporating a 1,3,5-s-triazine moiety is reported. The components of this series have been obtained by the reaction of cyanuric chloride (1) with 2-(coumarin-3-yl)-5-mercapto-1,3,4-oxadiazole (2). The prepared 2-(coumarin-3-yl-1,3,4-oxadiazolyl)-5-thio}-4,6-dichloro-s-triazine (3) was subsequently treated with morpholine (4) to form 2-(coumarin-3-yl-1,3,4-oxadiazolyl)-5-thio}-4-(morpholino)-6-chloro-s-triazine (5). This was further treated with various substituted aryl urea/thioureas (6a-k/7a-k) to afford the title compounds 8a-k and 9a-k, which were and tested for their antibacterial activity (MIC) against different microorganisms. The structures of the novel synthesized compound have been established on the basis of 1H NMR and FT-IR data together with elemental analysis. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.
• Synthesis of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides as antimicrobial and antituberculosis agents
  作者：Rahul V. Patel、Premlata Kumari、Dhanji P. Rajani、Kishor H. Chikhalia

  DOI：10.1007/s00044-012-0026-x

  日期：2013.1

  In an attempt to find new agents to fight against microbial infections, a series of coumarin-based 1,3,4-oxadiazol-2ylthio-N-phenyl/benzothiazolyl acetamides was synthesized starting from coumarin-3-carboxylic acid ethyl ester obtained through Knoevenagel and Pinner reaction. In vitro antimicrobial activity against several bacteria (S. aureus, B. cereus, E. coli, P. aeruginosa, K. pneumoniae, S. typhi, P. vulgaris, S. flexneri), fungi (A. niger, A. fumigatus, A. clavatus, C. albicans) and antimycobacterial activity against Mycobacterium tuberculosis H37Rv strain was assessed. This study shows to what extent the presence of various electron withdrawing/donating substituents on the phenyl or benzothiazole ring affects the activity profiles of the newer molecules. The relationship between activity profiles (MICs, 3.12-25 mu g/mL) and the lipophilic character (LogP) of the prepared products is also discussed and the MIC values of the active conjugates seem to correlate to some extent with the lipophilicity profiles. Two (5e and 6c) of the final analogues displayed promising antimycobacterial activity at 12.5 mu g/mL of MIC, half fold potent to the standard drug pyrazinamide (6.25 mu g/mL). Compounds were characterized by IR, H-1 NMR, C-13 NMR spectroscopy and elemental analysis.