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2-azido-1-(2'-fluorophenyl)ethanone

中文名称
——
中文别名
——
英文名称
2-azido-1-(2'-fluorophenyl)ethanone
英文别名
2-azido-1-(2-fluorophenyl)ethan-1-one;2'-Fluoro-alpha-azidoacetophenone;2-azido-1-(2-fluorophenyl)ethanone
2-azido-1-(2'-fluorophenyl)ethanone化学式
CAS
——
化学式
C8H6FN3O
mdl
——
分子量
179.154
InChiKey
PUVXRICGFWGJBH-UHFFFAOYSA-N
BEILSTEIN
——
EINECS
——
  • 物化性质
  • 计算性质
  • ADMET
  • 安全信息
  • SDS
  • 制备方法与用途
  • 上下游信息
  • 反应信息
  • 文献信息
  • 表征谱图
  • 同类化合物
  • 相关功能分类
  • 相关结构分类

计算性质

  • 辛醇/水分配系数(LogP):
    2.8
  • 重原子数:
    13
  • 可旋转键数:
    3
  • 环数:
    1.0
  • sp3杂化的碳原子比例:
    0.12
  • 拓扑面积:
    31.4
  • 氢给体数:
    0
  • 氢受体数:
    4

上下游信息

  • 上游原料
    中文名称 英文名称 CAS号 化学式 分子量

反应信息

  • 作为反应物:
    描述:
    2-azido-1-(2'-fluorophenyl)ethanone2,2,6,6-四甲基哌啶氧化物copper(II) oxide 作用下, 以 甲苯 为溶剂, 以72 %的产率得到2-(2-fluorophenyl)-2-oxoacetamide
    参考文献:
    名称:
    铜/TEMPO 促进的脱氮/氧化反应用于使用 α-叠氮基酮合成初级 α-酮酰胺
    摘要:
    以 α-叠氮基酮为底物,TEMPO 为氧化剂,开发了铜 (II) 促进的脱氮/氧化反应,用于制备初级 α-酮酰胺。α-叠氮基酮原位脱氮形成亚氨基酮中间体,其经过自由基加成过程和自由基迁移形成α-酮酰胺。值得注意的是,亚氨基酮中间体是该反应的关键。
    DOI:
    10.1021/acs.joc.2c01814
  • 作为产物:
    描述:
    2-溴-2'-氟苯乙酮 在 sodium azide 作用下, 以 丙酮 为溶剂, 生成 2-azido-1-(2'-fluorophenyl)ethanone
    参考文献:
    名称:
    鉴定新型苯甲酰肼衍生物作为neddylation途径激活剂以抑制体外肿瘤进展
    摘要:
    Neddylation 修饰在许多类型的人类肿瘤中经常过度表达。因此,靶向neddylation途径已被确定为可行的抗癌治疗策略。 NEDD8 激活酶 (NAE) 在多种细胞功能中发挥着至关重要的作用。在这里,开发、生产了一个新的哌啶类似物文库,并评估了其对 A549、MGC-803、MCF-7KYSE-30 细胞系的抗增殖功效。基于细胞的机制研究表明,带有苯甲酰肼基序的IIb-10可以通过抑制 NEDD8 激活酶来选择性抑制 Cullin1 和 Cullin3 的 Neddylation 修饰,然后通过相互作用导致 UBC12-NEDD8 复合物水平呈剂量依赖性降低。直接与NAE1。细胞机制阐明化合物IIb-10能够使 MGC-803 细胞的细胞周期停止在 G2/M 期并引发细胞凋亡。总而言之,酰肼连接的哌啶衍生物可能是作为开发高效neddylation抑制剂的先导化合物的有前途的候选者。
    DOI:
    10.1007/s00044-024-03193-4
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文献信息

  • Synthesis and In vitro Evaluation of Dibenzoazepine Triazole Derivatives: A Novel Class of Antileishmanial Agents
    作者:Maria Aqeel Khan、Aliyan Saleem、Nida Ghouri、Abdul Hameed、M. Choudhary、Fatima Basha
    DOI:10.2174/1570180812999150225111959
    日期:2015.6.6
    In the present study, a series of dibenzoazepine triazole derivatives (24-39) were synthesized and evaluated for their in vitro bioactivities including antiglycation, antibacterial, DPPH radical scavenging, urease inhibition, antileishmanial and immunomodulatory activities. The compounds were found to be moderately active only against leishmania. Within this series, compound 26 was found to be the most active antileishaminals with IC50 value 37.4 ± 0.4 µM. Structure-activity relationships for this novel class are discussed.
    在本研究中,合成了一系列二苯并氮杂卓三唑衍生物(24-39),并评估了它们的体外生物活性,包括抗糖基化、抗菌、DPPH自由基清除、尿素酶抑制、抗利什曼和免疫调节活性。这些化合物仅对利什曼原虫表现出适度的活性。在这一系列中,化合物26被发现是活性最强的抗利什曼药物,IC50值为37.4 ± 0.4 µM。对这一新型化合物的构效关系进行了讨论。
  • In vitro α-Glucosidase Inhibition by Non-sugar based Triazoles of Dibenzoazepine, their Structure-Activity Relationship, and Molecular Docking
    作者:Maria A. Khan、Kulsoom Javaid、Abdul Wadood、Alam Jamal、Farhana Batool、Saba Fazal-ur-Rehman、Fatima Z. Basha、Muhammad I. Choudhary
    DOI:10.2174/1573406413666170726142949
    日期:2017.10.17
    Background: α-Glucosidase inhibitors (AGIs) have been reported for their clinical potential against postprandial hyperglycemia, which is responsible for the risks associated with diabetes mellitus 2 and cardiovascular diseases (CVDs). Besides, a number of compounds have been reported as potent AGIs, several side effects are associated with them. Methods: The aim of present work is to explore new and potent molecules as AGIs. Therefore, a library of dibenzoazepine linked triazoles (1-15) was studied for their in vitro α-glucosidase inhibitory activity. The binding modes of potent compounds in the active site of α-glucosidase enzyme were also explored through molecular docking studies. Results and Conclusion: Among the reported triazoles, compounds 3-9, 11, and 13 (IC50 = 6.0 ± 0.03 to 19.8 ± 0.28 µM) were found to be several fold more active than the standard drug acarbose (IC50 = 840 ± 1.73 µM). Compound 5 (IC50 = 6.0 ± 0.03 µM) was the most potent AGIs in the series, about 77- fold more active than acarbose. Therefore, dibenzoazepine linked-triazoles described here can serve as leads for further studies as new non-sugar AGIs.
    背景:α-葡萄糖苷酶抑制剂(AGIs)在对抗餐后高血糖方面显示出临床潜力,而餐后高血糖与2型糖尿病和心血管疾病(CVDs)的风险相关。此外,已经报告有多种化合物作为有效的AGIs,但它们也伴随一些副作用。 方法:本研究的目的是探索新的有效分子作为AGIs。因此,研究了一个含有二苯并氮杂环的三唑化合物库(1-15)对α-葡萄糖苷酶的体外抑制活性。还通过分子对接研究探索了这些有效化合物在α-葡萄糖苷酶酶活性位点的结合方式。 结果与结论:在报告的三唑化合物中,化合物3-9、11和13(IC50 = 6.0 ± 0.03至19.8 ± 0.28 µM)比标准药物阿卡波糖(IC50 = 840 ± 1.73 µM)活性高出数倍。化合物5(IC50 = 6.0 ± 0.03 µM)是系列中最有效的AGIs,大约比阿卡波糖活性高出77倍。因此,这里描述的二苯并氮杂环连接的三唑化合物可以作为新型非糖AGIs进一步研究的先导。
  • A Novel and Efficient Method for the Synthesis of α-Azidoketones and α-Ketothiocyanates
    作者:J. S. Yadav、B. V. Subba Reddy、M. Srinivas
    DOI:10.1246/cl.2004.882
    日期:2004.7
    α-Diazoketones underwent insertion smoothly with sodium azide and potassium thiocyanate in the presence of CeCl3·7H2O under mild reaction conditions to afford the corresponding α-azidoketones and α-ketothiocyanates in excellent yields.
    CeCl3-7H2O 存在下,α-重氮酮在温和的反应条件下与叠氮硫氰酸钾顺利发生插入反应,以优异的产率得到相应的 α-叠氮酮和α-酮硫氰酸盐。
  • Cascade Cope/Winstein Rearrangements: Synthesis of Azido-Cycloheptadienes from Dialkenylcyclopropanes Possessing a Vinyl Azide
    作者:Thomas Abegg、Janine Cossy、Christophe Meyer
    DOI:10.1021/acs.orglett.2c01888
    日期:2022.7.15
    2-Dialkenylcyclopropanes incorporating a vinyl azide, generated by Knoevenagel condensations between the corresponding cyclopropanecarbaldehydes and α-azido ketones, undergo cascade Cope and Winstein [3,3]-sigmatropic rearrangements, under mild conditions. The sequence allows access to diversely substituted 1,4-cycloheptadienes armed with a secondary allylic azide with up to three stereocenters.
    顺式-1,2-二烯基环丙烷包含乙烯基叠氮化物,由相应的环丙烷甲醛和 α-叠氮基酮之间的 Knoevenagel 缩合产生,在温和条件下发生级联 Cope 和 Winstein [3,3]-σ 重排。该序列允许使用具有多达三个立体中心的二级烯丙基叠氮化物的多种取代的 1,4-环庚二烯
  • Utilization of the 1,2,3,5-thiatriazolidin-3-one 1,1-dioxide scaffold in the design of potential inhibitors of human neutrophil proteinase 3
    作者:Dengfeng Dou、Guijia He、Yi Li、Zhong Lai、Liuqing Wei、Kevin R. Alliston、Gerald H. Lushington、David M. Eichhorn、William C. Groutas
    DOI:10.1016/j.bmc.2009.12.057
    日期:2010.2
    The S' subsites of human neutrophil proteinase 3 (Pr 3) were probed by constructing diverse libraries of compounds based on the 1,2,3,5-thiatriazolidin-3-one 1,1-dioxide using combinational and click chemistry methods. The multiple points of diversity embodied in the heterocyclic scaffold render it well-suited to the exploration of the S' subsites of Pr 3. Molecular modeling studies suggest that further exploration of the S' subsites of Pr 3 using the aforementioned heterocyclic scaffold may lead to the identification of highly selective, reversible competitive inhibitors of Pr 3. (C) 2009 Elsevier Ltd. All rights reserved.
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