2-Methyl-5-(3,4,5-trimethoxy-benzyliden)-oxazolon | 92249-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-Methyl-5-(3,4,5-trimethoxy-benzyliden)-oxazolon
• 英文别名: 2-methyl-4-(3,4,5-trimethoxy-benzylidene)-4H-oxazol-5-one；2-Methyl-4-[(3,4,5-trimethoxyphenyl)methylidene]-1,3-oxazol-5-one
• CAS: 92249-24-6
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: BKYSSHFIJZZSSX-UHFFFAOYSA-N

物化性质

• 熔点：
  161-164 °C
• 沸点：
  403.7±55.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  66.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-Methyl-5-(3,4,5-trimethoxy-benzyliden)-oxazolon 在 四磷十氧化物 、 四丁基溴化铵 、 氧气 、 sodium 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 乙二醇 、 甲苯 为溶剂， 反应 10.5h， 生成 (3-(but-3-en-1-yloxy)quinoxalin-2-yl)(3,4,5-trimethoxyphenyl)methanone
  参考文献：
  名称：

  Activated carbon/Brønsted acid-promoted aerobic benzylic oxidation under “on-water” condition: Green and efficient synthesis of 3-benzoylquinoxalinones as potent tubulin inhibitors

  摘要：

  Green chemistry is becoming the favored approach to preparing drug molecules in pharmaceutical industry. Herein, we developed a clean and efficient method to synthesize 3-benzoylquinoxalines via activated carbon promoted aerobic benzylic oxidation under "on-water" condition. Moreover, biological studies with this class of compounds reveal an antiproliferative profile. Further structure modifications are performed and the investigations exhibited that the most active 12a could inhibit the microtubule polymerization by binding to tubulin and thus induce multipolar mitosis, G2/M phase arrest, and apoptosis of cancer cells, In addition, molecular docking studies allow the rationalization of the pharmacodynamic properties observed. Our systematic studies provide not only guidance for applications of O-2/AC/H2O system, but also a new scaffold targeting tubulin for antitumor agent discovery. (C) 2019 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2019.111894
• 作为产物：
  描述：

  3,4,5-三甲氧基苯甲醛 、 N-乙酰甘氨酸 在 potassium acetate 、 乙酸酐 作用下， 以69.86%的产率得到2-Methyl-5-(3,4,5-trimethoxy-benzyliden)-oxazolon
  参考文献：
  名称：

  新型非核苷HIV-1逆转录酶抑制剂咪唑-5-酮的合成，生物学活性和对接研究

  摘要：

  设计，合成了一系列新的取代的咪唑-5-酮，并使用逆转录酶测定试剂盒（Roche，Colorimetric）评估了其在体外的逆转录酶（RT）抑制活性。从体外筛选观察到，新合成的化合物具有RT抑制活性。进行对接研究以研究合成化合物对RT酶的结合方向和亲和力。

  DOI：

  10.1016/j.bmc.2012.02.037

文献信息

• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
  申请人：Chung Hae Young

  公开号：US20140023603A1

  公开（公告）日：2014-01-23

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白皮肤、抗氧化和PPAR活性的新化合物及其医疗用途，该化合物具有美白皮肤的活性，可抑制酪氨酸酶，因此适用于用于美白皮肤的药物组合物或化妆品；具有抗氧化活性，因此适用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此适用于用于预防和治疗肥胖、代谢性疾病或心血管疾病的药物组合物或保健食品。
• Synthesis, biological activity and docking study of imidazol-5-one as novel non-nucleoside HIV-1 reverse transcriptase inhibitors
  作者：Santosh N. Mokale、Deepak Lokwani、Devanand B. Shinde

  DOI：10.1016/j.bmc.2012.02.037

  日期：2012.5

  A novel series of substituted imidazol-5-ones were designed, synthesized and evaluated for in vitro reverse transcriptase (RT) inhibition activity using reverse transcriptase assay kit (Roche, Colorimetric). It has been observed from in vitro screening that newly synthesized compounds possess RT inhibitory activity. Docking study was performed to study the binding orientation and affinity of synthesized

  设计，合成了一系列新的取代的咪唑-5-酮，并使用逆转录酶测定试剂盒（Roche，Colorimetric）评估了其在体外的逆转录酶（RT）抑制活性。从体外筛选观察到，新合成的化合物具有RT抑制活性。进行对接研究以研究合成化合物对RT酶的结合方向和亲和力。
• 3-(3,4,5-三甲氧基苯甲酰基)喹喔啉类衍生物及其用途
  申请人：沈阳药科大学

  公开号：CN106316968A

  公开（公告）日：2017-01-11

  本发明属于医药技术领域，涉及一种3-(3,4,5-三甲氧基苯甲酰基)喹喔啉类衍生物及其用途，确切地说，涉及该类化合物及其作为肿瘤细胞增殖抑制剂在制备抗肿瘤的药物方面的应用。本发明的化合物结构通式如下：其中，R，R1，R2如权利要求书和说明书所述。
• Synthesis and stereochemistry of 1,4-diazabicyclo[4,3,0]nonane-2,5,9-triones
  作者：Michael R. Harnden

  DOI：10.1039/j39670002341

  日期：——

  1,4-Diazabicyclo[4,3,0]nonane-2,5,9-triones have been prepared by two synthetic routes. The first (Scheme 1) involves cyclisation of α-aminoacyl glutamic acids to 3,6-dioxo-2-piperazinepropionic acids, which undergo a second cyclisation on refluxing with an acid anhydride. In the second (Scheme 2) the bicyclic system is obtained by direct cyclisation of α-acetamidoacyl glutamic acids. N.m.r. studies

  通过两种合成途径制备了1，4-二氮杂双环[4,3,0]壬烷-2,5,9-三酮。第一种（方案1）涉及将α-氨基酰基谷氨酸环化为3，6-二氧代-2-哌嗪丙酸，然后在与酸酐回流下进行第二种环化。在第二种方法（方案2）中，通过直接环化α-乙酰氨基酰谷氨酸来获得双环系统。Nmr研究和旋光性已用于阐明产品的立体化学。
• NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREOF
  申请人：Pusan National University Industry-University Cooperation Foundation

  公开号：US20160102065A1

  公开（公告）日：2016-04-14

  Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.

  提供了一种具有美白、抗氧化和PPAR活性的新化合物及其医疗用途。该化合物具有抑制酪氨酸酶的美白活性，因此可用于美白药物组合物或化妆品产品；具有抗氧化活性，因此可用于预防和治疗皮肤老化；具有PPAR活性，特别是PPARα和PPARγ活性，因此可用于有效预防和治疗肥胖症、代谢疾病或心血管疾病的药物组合物或保健食品。