5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-amine | 1016494-31-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-amine
• 英文别名: 5-naphthalen-1-yl-1,3,4-oxadiazol-2-amine
• CAS: 1016494-31-7
• 化学式: C₁₂H₉N₃O
• mdl: MFCD09812391
• 分子量: 211.223
• InChiKey: VYISJPAVHRPXIH-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C
• 沸点：
  437.8±28.0 °C(Predicted)
• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 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：
  64.9
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-amine 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 24.0h， 生成 2-(5,7-dimethoxy-4-oxo-2-(3,4,5-trimethoxyphenyl)-4H-chromen-3-yloxy)-N-(5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-yl)acetamide
  参考文献：
  名称：

  含有1,3,4-恶二唑部分的新型2-苯基-4H-色酮衍生物的合成、端粒酶抑制和抗癌活性

  摘要：

  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。

  DOI：

  10.1080/14756366.2020.1864630
• 作为产物：
  描述：

  1-naphthaldehyde semicarbazone 在 N-溴代丁二酰亚胺(NBS) 、 sodium acetate 、 溶剂黄146 作用下， 反应 0.25h， 以82%的产率得到5-(naphthalen-1-yl)-1,3,4-oxadiazol-2-amine
  参考文献：
  名称：

  通过NBS介导的缩氨基脲氧化环化超声辅助合成2-氨基-1,3,4-恶二唑

  摘要：

  摘要 建立了在乙酸钠存在下使用 N-溴代琥珀酰亚胺进行缩氨基脲的超声辅助氧化环化，提供了对各种 2-氨基-1,3,4-恶二唑的高效快速访问。此外，新的合成方案提供了一个简单的程序，利用更安全的氧化系统，以高区域选择性、令人满意的收率和更高的纯度提供目标产品。图形概要

  DOI：

  10.1080/00397911.2017.1324626

文献信息

• [EN] INHIBITORS OF HUMAN 15-LIPOXYGENASE-1<br/>[FR] INHIBITEURS DE LA 15-LIPOXYGÉNASE-1 HUMAINE
  申请人：US HEALTH

  公开号：WO2011028651A1

  公开（公告）日：2011-03-10

  Disclosed are inhibitors of human 15 lipoxygenase 1, for example, of formula (I), wherein R1, R2, R3, R4, X, Y, and Z are as defined herein, that are useful in treating a 15-lipoxygenase mediated disease or disorder, e.g., prostate cancer. Also disclosed is a composition comprising a pharmaceutically suitable carrier and at least one compound of the invention, and a method of treating prostate cancer in a mammal.

  本文披露了人类15-脂氧合酶1的抑制剂，例如式（I）中的抑制剂，其中R1、R2、R3、R4、X、Y和Z如本文所定义，这些抑制剂对治疗15-脂氧合酶介导的疾病或紊乱，例如前列腺癌，具有有用性。还披露了一种包含药用载体和本发明中至少一种化合物的组合物，以及一种治疗哺乳动物前列腺癌的方法。
• PRODUCTION METHOD OF QUINOLINECARBOXAMIDE DERIVATIVE OR PRODUCTION INTERMEDIATE THEREOF
  申请人：KABUSHIKI KAISHA YAKULT HONSHA

  公开号：US20220169640A1

  公开（公告）日：2022-06-02

  Provided is a method for industrially advantageously synthesizing a production intermediate of a quinolinecarboxamide derivative or a salt thereof. The present invention provides a method for producing a quinolinecarboxylic acid derivative of formula (4) or a salt thereof, including reacting an aniline of the following formula (1), in the presence of boron trifluoride-tetrahydrofuran complex or boron trifluoride-diethyl ether complex, with an aldehyde of formula (2) and subsequently reacting the resulting compound with an α-keto acid of formula (3), wherein R 1 , R 2 , R 3 and R 4 are the same or different and each represent a hydrogen atom, a halogen atom, a lower alkyl group, or the like, R 5 represents a hydrogen atom, a lower alkyl group, or the like, and R 6 represents a hydrogen atom, a lower alkyl group, or the like.

  提供了一种工业上优势合成喹啉羧酰胺衍生物或其盐的生产中间体的方法。本发明提供了一种制备喹啉羧酸衍生物的方法，其化学式为（4）或其盐，包括在三氟化硼-四氢呋喃复合物或三氟化硼-二乙醚复合物的存在下，用化学式（1）的苯胺与化学式（2）的醛反应，然后用化学式（3）的α-酮酸反应所得化合物，其中R1、R2、R3和R4相同或不同，每个代表氢原子、卤素原子、低级烷基或类似物，R5代表氢原子、低级烷基或类似物，R6代表氢原子、低级烷基或类似物。
• Discovery of Potent and Selective Inhibitors of Human Reticulocyte 15-Lipoxygenase-1
  作者：Ganesha Rai、Victor Kenyon、Ajit Jadhav、Lena Schultz、Michelle Armstrong、J. Brian Jameson、Eric Hoobler、William Leister、Anton Simeonov、Theodore R. Holman、David J. Maloney

  DOI：10.1021/jm1008852

  日期：2010.10.28

  There are a variety of lipoxygenases in the human body (hLO), each having a distinct role in cellular biology. Human reticulocyte 15-lipoxygenase-1 (15-hLO-1), which catalyzes the dioxygenation of 1,4-cis,cis-pentadiene-containing polyunsaturated fatty acids, is implicated in a number of diseases including cancer, atherosclerosis, and neurodegenerative conditions. Despite the potential therapeutic relevance of this target, few inhibitors have been reported that are both potent and selective. To this end, we have employed a quantitative high-throughput (qHTS) screen against similar to 74000 small molecules in search of reticulocyte 15-hLO-1 selective inhibitors. This screen led to the discovery of a novel chemotype for 15-hLO-1 inhibition, which displays nM potency and is > 7500-fold selective against the related isozymes, 5-hLO, platelet 12-hLO, epithelial 15-hLO-2, ovine cyclooxygenase-1, and human cyclooxygenase-2. In addition, kinetic experiments were performed which indicate that this class of inhibitor is tight binding, reversible, and appears not to reduce the active-site ferric ion.
• Synthesis of 2-Amino-1,3,4-oxadiazoles and 2-Amino-1,3,4-thiadiazoles via Sequential Condensation and I₂-Mediated Oxidative C–O/C–S Bond Formation
  作者：Pengfei Niu、Jinfeng Kang、Xianhai Tian、Lina Song、Hongxu Liu、Jie Wu、Wenquan Yu、Junbiao Chang

  DOI：10.1021/jo502518c

  日期：2015.1.16

  2-Amino-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were synthesized via condensation of semicarbazide/thiosemicarbazide and the corresponding aldehydes followed by I-2-mediated oxidative C-O/C-S bond formation. This transition-metal-free sequential synthesis process is compatible with aromatic, aliphatic, and cinnamic aldehydes, providing facile access to a variety of diazole derivatives bearing a 2-amino substituent in an efficient and scalable fashion.
• Sharma, Laxmi Kant; Singh, Sushma; Singh, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2011, vol. 50, # 1, p. 110 - 114
  作者：Sharma, Laxmi Kant、Singh, Sushma、Singh

  DOI：——

  日期：——