1-azido-4-fluoro-2-methylbenzene | 864866-29-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-azido-4-fluoro-2-methylbenzene
• 英文别名: 1-azide-4-fluoro-2-methyl-benzene
• CAS: 864866-29-5
• 化学式: C₇H₆FN₃
• 分子量: 151.143
• InChiKey: AKGBKCHJHBJIRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  14.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-azido-4-fluoro-2-methylbenzene 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 生成 4-(2-(2,2-difluoro-ethyl)-1-oxo-isoindoline-5-yl)-1-(4-fluoro-2-methyl-phenyl)-5-methyl-1H-[1,2,3]triazole
  参考文献：
  名称：

  EP1726585

  摘要：

  公开号：
• 作为产物：
  描述：

  4-氟-2-甲基苯胺 在 盐酸 、 sodium azide 作用下， 以 水 为溶剂， 反应 0.5h， 生成 1-azido-4-fluoro-2-methylbenzene
  参考文献：
  名称：

  合成香豆素-三唑类似物的体外抗血浆功效

  摘要：

  通过将7-羟基-4-甲基-香豆素烷基化，然后在7位进行点击化学反应，合成了22种香豆素-三唑衍生物。评估了这些化合物对恶性疟原虫（3D7）的氯喹敏感菌株的体外抗疟原虫活性。化合物9（7- [1-（2，4-二甲氧基-苯基）-1H- [1-3]三唑-4-基甲氧基] -4-甲基-色烯-2-酮）最具活性，IC 50值为0.763±0.0124μg/ mL。此外，化合物20的结构通过单晶X射线衍射表征。鉴于令人印象深刻的结果，我们认为值得验证体外结果 通过评估这些化合物是否能够抑制DNA促旋酶的催化活性，从而防止其超螺旋功能，从而获得抗血浆活性。

  DOI：

  10.1016/j.ejmech.2018.01.017

文献信息

• Synthesis and biological evaluation of triazole based uracil derivatives as novel DPP-4 inhibitors
  作者：Qing Li、Li Han、Bin Zhang、Jinpei Zhou、Huibin Zhang

  DOI：10.1039/c6ob01818a

  日期：——

  A series of triazole based uracil derivatives were designed and synthesized as novel DPP-4 inhibitors. Compound A01 was identified as a lead compound for SAR studies focused on the structural modification at the S2′ subsite of DPP-4. The novel analogues A02–A25 were obtained by modifying the substituents at the phenyl group, and B01–B09, by introducing the carbonyl group. On screening in DPP-4, compounds

  设计并合成了一系列基于三唑的尿嘧啶衍生物，作为新型DPP-4抑制剂。化合物A01被确定为SAR研究的先导化合物，专注于DPP-4的S 2'亚位点的结构修饰。通过修饰苯基和B01-B09的取代基（通过引入羰基）获得了新的类似物A02-A25。在DPP-4中进行筛选时，与化合物A01相比，化合物B03，B04和B08的DPP-4抑制活性显着提高并显示出与市售DPP-4抑制剂阿格列汀相当的活性。对接研究在S揭示设计的化合物的新的有利的结合模式2'亚位点，并证明了在S结构修饰2'亚位点是增加DPP-4抑制的有效的选择。体外DPP-8和DPP-9测试表明，所有化合物均对DPP-8和DPP-9表现出优异的选择性。进一步的体内评估表明，化合物B04可以显着改善ICR小鼠的口服葡萄糖耐量，并剂量依赖性地降低2型糖尿病C57BL / 6小鼠的葡萄糖水平。这些数据表明化合物B04 可能是将来治疗T2DM的有希望的DPP-4抑制剂。
• Dairyl-substituted five-membered heterocycle derivative
  申请人：Hirata Yukari

  公开号：US20070173507A1

  公开（公告）日：2007-07-26

  The present invention provides the compounds represented by formula (I): (I) or pharmaceutical salts thereof, wherein: X 1 represents oxygen atoms and the like, X 2 represents nitrogen atoms and the like, X 3 represents nitrogen atoms and the like, X 4 represents nitrogen atoms and the like, R 1 represents formula (II-1): wherein X 5 represents sulfur atoms and the like, A 1 represents carbon atoms and the like, A 2 represents nitrogen atoms and the like and A ring represents phenyl group and the like, having mGluR1 inhibiting effect, and being usefull for preventing or treating convulsion, acute pain, inflammatory pain, chronic pain, brain disorder such as cerebral infarction or transient ischemick attack, psychotic disorder such as schizophrenia, anxiety, drug dependence, Parkinson's disease, or gastrointestinal disorder.

  本发明提供了由公式（I）所表示的化合物：（I）或其药物盐，其中：X1代表氧原子等，X2代表氮原子等，X3代表氮原子等，X4代表氮原子等，R1代表公式（II-1）：其中X5代表硫原子等，A1代表碳原子等，A2代表氮原子等，A环代表苯基等，具有mGluR1抑制作用，适用于预防或治疗惊厥、急性疼痛、炎症性疼痛、慢性疼痛、脑部疾病如脑梗死或短暂性脑缺血发作、精神疾病如精神分裂症、焦虑、药物依赖、帕金森病或胃肠道疾病。
• DIARYL-SUBSTITUTED FIVE-MEMBERED HETEROCYCLE DERIVATIVE
  申请人：Hirata Yukari

  公开号：US20110160208A1

  公开（公告）日：2011-06-30

  The present invention provides the compounds represented by formula (I): or pharmaceutical salts thereof, wherein: X 1 represents oxygen atoms and the like, X 2 represents nitrogen atoms and the like, X 3 represents nitrogen atoms and the like, X 4 represents nitrogen atoms and the like, R 1 represents formula (II-1): wherein X 5 represents sulfur atoms and the like, A 1 represents carbon atoms and the like, A 2 represents nitrogen atoms and the like and A ring represents phenyl group and the like, having mGluR1 inhibiting effect, and being useful for preventing or treating convulsion, acute pain, inflammatory pain, chronic pain, brain disorder such as cerebral infarction or transient ischemick attack, psychotic disorder such as schizophrenia, anxiety, drug dependence, Parkinson's disease, or gastrointestinal disorder.

  本发明提供了以下式子(I)所代表的化合物或其药物盐，其中：X1代表氧原子等，X2代表氮原子等，X3代表氮原子等，X4代表氮原子等，R1代表式子(II-1)：其中X5代表硫原子等，A1代表碳原子等，A2代表氮原子等，环A代表苯基等，具有mGluR1抑制作用，并且对于预防或治疗惊厥、急性疼痛、炎症性疼痛、慢性疼痛、脑部疾病如脑梗死或短暂性缺血性发作、精神障碍如精神分裂症、焦虑、药物依赖、帕金森病或胃肠疾病有用。
• In Situ “Click” Assembly of Small Molecule Matrix Metalloprotease Inhibitors Containing Zinc-Chelating Groups
  作者：Mingyu Hu、Junqi Li、Shao Q. Yao

  DOI：10.1021/ol802286g

  日期：2008.12.18

  A panel of small molecule-based MMP inhibitors containing rhodanine warheads was assembled using "one-pot" click chemistry. Upon biological screening, moderate inhibitors were identified which specifically targets MMP-7 and MMP-13 over other MMPs.
• Design, synthesis and antimicrobial activity of novel benzothiazole analogs
  作者：Manavendra K. Singh、Ragini Tilak、Gopal Nath、Satish K. Awasthi、Alka Agarwal

  DOI：10.1016/j.ejmech.2013.02.027

  日期：2013.5

  In an attempt to design and synthesize a new class of antimicrobials, dialkyne substituted 2-aminobenzothiazole was reacted with various substituted aryl azides to generate a small library of 20 compounds (3a-t) by click chemistry. Structures of the newly synthesized compounds were established on the basis of spectral data. These compounds were screened for their antibacterial activity against Gram+ bacteria (Staphylococcus aureus and Enterococcus faecalis), Gram- bacteria (Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Pseudomonas aeruginosa, Shigella boydii) and antifungal activity against Candida tropicalis, Candida albicans, Candida krusei, Cryptococcus neoformans) as well as molds (Aspergillus niger, Aspergillus fumigatus). The compound 3e showed maximum potency against all Gram+/gram- bacterial strains with MIC value 3.12 mu g/ml, which is two fold more active as compared to standard drug ciprofloxacin (MIC 6.25 mu g/ml). However, all compounds were found ineffective against S. boydii (clinical isolate). Further, only one compound 3n was found to be the most active against all fungal strains with MIC value in the range of 1.56 mu g/ml-12.5 mu g/ml while the remaining compounds showed moderate to weak antifungal activity. (c) 2013 Elsevier Masson SAS. All rights reserved.