6-methoxynaphtho[1,2-d]oxazole | 1276118-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-methoxynaphtho[1,2-d]oxazole
• 英文别名: 6-Methoxybenzo[e][1,3]benzoxazole
• CAS: 1276118-99-0
• 化学式: C₁₂H₉NO₂
• 分子量: 199.209
• InChiKey: JVYJLTYUFYAEIN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-甲氧基肉桂醛 在 碘 、 potassium carbonate 作用下， 以 甲醇 、 苯 为溶剂， 反应 20.0h， 生成 6-methoxynaphtho[1,2-d]oxazole
  参考文献：
  名称：

  Photochemical Approach to Naphthoxazoles and Fused Heterobenzoxazoles from 5-(Phenyl/heteroarylethenyl)oxazoles

  摘要：

  A new synthetic approach is presented for the synthesis of naphthoxazoles and fused heterobenzoxazoles. The starting 5-(aryl/furyl/thienyl/pyridyl ethenyl)oxazoles are prepared from the corresponding alpha,beta-unsaturated aldehydes using Van Leusen reagent in very good yields and are transformed into naphthoxazoles and fused heterobenzoxazoles on irradiation under aerobic conditions and in the presence of iodine.

  DOI：

  10.1021/jo1025942

文献信息

• Antiinflammatory and Antiproliferative Activity of Naphthoxazole, Fused Hetero-benzoxazole and Bridged Benzobicyclic Photoproducts
  作者：Ivana Šagud、Ana Ratković、Matea Cedilak、Martina Bosnar、Vanja Kelava、Irena Škorić

  DOI：10.5562/cca3530

  日期：——

  Biological activity of naphthoxazoles, fused hetero-benzoxazoles and benzobicyclo[3.2.1]-derivatives was investigated in proliferation and inflammation based assays. The tested compounds were prepared by photocylization or photocycloaddition reactions. Effect of compounds on proliferation of several cancer cell lines was determined by measuring cell metabolic activity through time. Lipopolysaccharide (LPS) stimulation of peripheral blood mononuclear cells (PBMC) was used to investigate antiinflammatory properties of the compounds. Several naphthoxazoles and fused hetero-benzoxazoles inhibited TNFα protein expression in LPS stimulated PBMC, indicating possible antiinflammatory role which would be interesting to further investigate. Physico-chemical properties of tested compounds have been also studied using chromatographic lipophilicity measure, chrom logD and logP was calculated as the importance of physico-chemical properties of compounds at early stage of discovery of new drugs is well established. The similarities in structure and activity of some representative compounds affirm the need to further address their antiinflammatory properties.

  研究了萘氧唑类化合物、融合的杂环苯并噁唑类化合物和苯并双环[3.2.1]-衍生物在增殖和炎症性实验中的生物活性。经过光环化或光环加成反应制备了被测试的化合物。通过测量细胞代谢活性来确定化合物对几种癌细胞系增殖的影响。使用脂多糖（LPS）刺激外周血单核细胞（PBMC）来研究化合物的抗炎性质。几种萘氧唑类化合物和融合的杂环苯并噁唑类化合物抑制了LPS刺激的PBMC中TNFα蛋白的表达，表明可能具有抗炎作用，值得进一步研究。还研究了被测试化合物的理化性质，使用色谱疏水性测量，计算了色谱logD和logP，因为在新药物发现的早期阶段，化合物的理化性质的重要性已经被确立。一些代表性化合物在结构和活性上的相似性证实了有必要进一步探讨它们的抗炎性质。
• Naphthoxazoles and heterobenzoxazoles: cholinesterase inhibition andantioxidant activity
  作者：Ivana ŠAGUD、Irena ŠKORIĆ、Franko BURČUL

  DOI：10.3906/kim-1807-133

  日期：——

  of seven oxazole derivatives. These compounds have been efficiently and sustainably prepared by photochemical electrocyclization reaction. Various naphthoxazoles have been previously investigated as potential antibacterial, antituberculosis, and anticancer agents. They have also been tested for antioxidant activity, but never for cholinesterase inhibitory activity. Among the tested oxazole derivatives

  寻找能够穿越血脑屏障，具有良好的药代动力学参数，降低肝毒性以及其他副作用的新型胆碱酯酶抑制剂，一直是阿尔茨海默氏病研究的主要重点。在这项研究中，我们评估了7种恶唑衍生物对胆碱酯酶的抑制和抗氧化活性。这些化合物已经通过光化学电环化反应有效且可持续地制备。先前已经研究了各种萘甲唑类作为潜在的抗菌剂，抗结核药和抗癌药。还对它们的抗氧化剂活性进行了测试，但从未对胆碱酯酶的抑制活性进行过测试。在测试的恶唑衍生物中，具有吡啶和噻吩部分的稠合杂苯并恶唑化合物，恶唑并[5,4-h $]异喹啉，显示噻吩[2'，3'：5,6]苯并[1,2- $ d $]恶唑和噻吩[3'，2'：5,6]苯并[1,2- $ d $]恶唑胆碱酯酶抑制和抗氧化活性的最大潜力。其中，噻吩并[2'，3'：5,6]苯并[1,2- $ d $]恶唑是最好的。
• Photochemical Approach to Naphthoxazoles and Fused Heterobenzoxazoles from 5-(Phenyl/heteroarylethenyl)oxazoles
  作者：Ivana Šagud、Fabio Faraguna、Željko Marinić、Marija Šindler-Kulyk

  DOI：10.1021/jo1025942

  日期：2011.4.15

  A new synthetic approach is presented for the synthesis of naphthoxazoles and fused heterobenzoxazoles. The starting 5-(aryl/furyl/thienyl/pyridyl ethenyl)oxazoles are prepared from the corresponding alpha,beta-unsaturated aldehydes using Van Leusen reagent in very good yields and are transformed into naphthoxazoles and fused heterobenzoxazoles on irradiation under aerobic conditions and in the presence of iodine.