1-[3-(1H-四唑-1-基)苯基]-乙酮 | 125620-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-[3-(1H-四唑-1-基)苯基]-乙酮
• 英文名称: 1-[3-(1H-tetrazol-1-yl)phenyl]ethan-1-one
• 英文别名: 1-[3-(1H-tetrazol-1-yl)phenyl]ethanone；1-[3-(tetrazol-1-yl)phenyl]ethanone
• CAS: 125620-15-7
• 化学式: C₉H₈N₄O
• mdl: MFCD02911420
• 分子量: 188.189
• InChiKey: AWLGWHRYGSCBPO-UHFFFAOYSA-N

物化性质

• 沸点：
  383.1±44.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  60.7
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-[3-(1H-四唑-1-基)苯基]-乙酮 在 一水合肼 、 potassium hydroxide 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 26.33h， 生成 1-{3-[5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl]phenyl}-1H-tetrazole
  参考文献：
  名称：

  Novel tetrazole-based selective COX-2 inhibitors: Design, synthesis, anti-inflammatory activity, evaluation of PGE2, TNF-α, IL-6 and histopathological study

  摘要：

  To search for effective and selective COX-2 inhibitors, four novel series of tetrazole derivatives were designed based on bioisosteric replacement of SO₂NH₂ in celecoxib with tetrazole ring incorporating different central moieties as chalcone (2a-f), isoxazole (3a-c) or pyrazole (4a-c & 5a-c). Target tetrazoles were synthesized and their structures were confirmed by spectroscopic techniques and elemental analyses. All target compounds were more selective for COX-2 isozyme than COX-1 when compared to standard drugs indomethacin and celecoxib. Compounds 3b, 3c, 4b, 4c, 5b and 5c exhibited potent in vitro COX-2 inhibitory activity (IC₅₀ = 0.039-0.065 μM). Trimethoxy derivatives 3c, 4c and 5c acquired superior COX-2 selectivity index values (SI = 297.67-317.95) and were 1.1 fold higher than celecoxib (SI = 282.22). The most active six compounds were evaluated for their in vivo anti-inflammatory activity and serum levels of PGE₂, TNF-α and IL-6 in addition to their ulcerogenic liability and histopathological profile. At a dose of 50 mg/Kg, compounds 3c and 5c showed better anti-inflammatory activity (% edema inhibition = 29.209-42.643) than celecoxib (% edema inhibition = 28.694-40.114) at different time intervals and were less ulcerogenic (UI = 0.123 and 0.11 in sequent) than celecoxib (UI = 0.167). Also, they displayed potent inhibitory effect on the production of PGE₂ (% inhibition = 81.042 and 82.724 in sequent) greater than celecoxib (% inhibition = 79.666). Compound 5c decreased rat serum concentrations of both TNF-α (% inhibition = 55.349) and IL-6 (% inhibition = 61.561) in a comparable or better activity to celecoxib as reference drug. Finally, docking poses of the most active compounds showed strong binding interactions and effective overall docking energy scores explaining their remarkable COX-2 inhibitory activity.

  DOI：

  10.1016/j.bioorg.2020.104308

文献信息

• [DE] 5-IODTETRAZOLE<br/>[EN] 5-IODOTETRAZOLES<br/>[FR] 5-IODE TETRAZOLE
  申请人：LANXESS DEUTSCHLAND GMBH

  公开号：WO2006012996A1

  公开（公告）日：2006-02-09

  Die Verbindungen der Formel (I), in welcher R1 für Wasserstoff oder jeweils gegebenenfalls substituiertes Alkyl, Alkenyl, Alkinyl oder Phenyl steht, eignen sich hervorragend als Mikrobizide zum Schutz von Pflanzen und Materialien.

  公式（I）中R1代表氢或者可能被取代的烷基，烯基，炔基或苯基，这些连接物非常适用作为杀菌剂，用于保护植物和材料。
• Phenyl pyrrolidine ether tachykinin receptor antagonists
  申请人：DeVita J. Robert

  公开号：US20070043015A1

  公开（公告）日：2007-02-22

  The present invention is directed to certain phenyl pyrrolidine ether compounds which are useful as neurokinin-1 (NK-1) receptor antagonists, and inhibitors of tachykinin and in particular substance P. The invention is also concerned with pharmaceutical formulations comprising these compounds as active ingredients and the use of the compounds and their formulations in the treatment of certain disorders, including emesis, depression, and anxiety.

  本发明涉及某些苯基吡咯烷醚化合物，其作为神经激肽-1（NK-1）受体拮抗剂和快速激肽，特别是物质P的抑制剂具有用途。本发明还涉及包含这些化合物作为活性成分的制药配方以及这些化合物及其配方在治疗某些疾病，包括呕吐、抑郁和焦虑方面的应用。
• 10a-Azalide Compound
  申请人：Sugimoto Tomohiro

  公开号：US20090281292A1

  公开（公告）日：2009-11-12

  [Object]: To provide a compound having a novel structure effective against Hemophilus influenzae and erythromycin resistant bacteria (for example, resistant pneumococci and streptococci) as well as against conventional erythromycin sensitive bacteria. [Solution]: A novel 10a-azalide compound represented by the formula (I), a pharmaceutically acceptable salt thereof or a solvate thereof, or an intermediate for the preparation of the same. The compound of the present invention has superior antibacterial activity against Hemophilus influenzae , erythromycin resistant pneumococci and the like, and therefore, the compound can be used as a therapeutic agent of infectious diseases.

  【目标】提供一种具有新结构的化合物，对流感嗜血杆菌和红霉素耐药菌（例如耐药肺炎球菌和链球菌）以及传统的红霉素敏感菌具有有效作用。 【解决方案】本发明提供了一种新型10a-氮杂环十六元化合物，其化学式为（I），其药学上可接受的盐或其溶剂化物，或其制备的中间体。该化合物对流感嗜血杆菌、红霉素耐药性肺炎球菌等具有卓越的抗菌活性，因此可以作为治疗传染病的药物。
• 10a-AZALIDE COMPOUND
  申请人：TAISHO PHARMACEUTICAL CO., LTD

  公开号：EP1985620A1

  公开（公告）日：2008-10-29

  [Object]: To provide a compound having a novel structure effective against Hemophilus influenzae and erythromycin resistant bacteria (for example, resistant pneumococci and streptococci) as well as against conventional erythromycin sensitive bacteria. [Solution]: A novel 10a-azalide compound represented by the formula (I), a pharmaceutically acceptable salt thereof or a solvate thereof, or an intermediate for the preparation of the same. The compound of the present invention has superior antibacterial activity against Hemophilus influenzae, erythromycin resistant pneumococci and the like, and therefore, the compound can be used as a therapeutic agent of infectious diseases.

  [目的]：提供一种具有新型结构的化合物，该化合物对流感嗜血杆菌和红霉素耐药菌（例如耐药肺炎球菌和链球菌）以及传统的红霉素敏感菌有效。 [解决方案］一种由式（I）代表的新型 10a-azalide 化合物、其药学上可接受的盐或其溶液，或制备其的中间体。本发明的化合物对流感嗜血杆菌、耐红霉素肺炎球菌等具有优异的抗菌活性，因此可用作传染性疾病的治疗剂。
• 5-IODTETRAZOLE
  申请人：LANXESS Deutschland GmbH

  公开号：EP1773125A1

  公开（公告）日：2007-04-18