1-溴-3-(2,6-二氟苯基)丙烷-2-酮 | 1045820-62-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-溴-3-(2,6-二氟苯基)丙烷-2-酮
• 英文名称: 1-bromo-3-(2,6-difluorophenyl)propan-2-one
• 英文别名: 3-Bromo-1-(2,6-difluorophenyl)propan-2-one
• CAS: 1045820-62-9
• 化学式: C₉H₇BrF₂O
• 分子量: 249.055
• InChiKey: FETLGKRVAVIGQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-溴-3-(2,6-二氟苯基)丙烷-2-酮 在 sodium azide 作用下， 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Optimization of Azoles as Anti-Human Immunodeficiency Virus Agents Guided by Free-Energy Calculations

  摘要：

  Efficient optimization of an inactive 2-anilinyl-5-benzyloxadiazole core has been guided by free energy perturbation (FEP) calculations to provide potent non-nucleoside inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (NNRTIs). An FEP "chlorine scan" was performed to identify the most promising sites for substitution of aryl hydrogens. This yielded NNRTIs 8 and 10 with activities (EC(50)) of 820 and 310 nM for protection of human T-cells from infection by wild-type HIV-1. FEP calculations for additional substituent modifications and change of the core heterocycle readily led to oxazoles 28 and 29, which were confirmed as highly potent anti-HIV agents with activities in the 10-20 nM range. The designed compounds were also monitored for possession of desirable pharmacological properties by use of additional computational tools. Overall, the trends predicted by the FEP calculations were well borne out by the assay results. FEP-guided lead optimization is confirmed as a valuable tool for molecular design including drug discovery; chlorine scans are particularly attractive since they are both straightforward to perform and highly informative.

  DOI：

  10.1021/ja8019214
• 作为产物：
  描述：

  2,6-二氟苯乙酸 在 氯化亚砜 、 水 、 氢溴酸 、 溶剂黄146 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 1-溴-3-(2,6-二氟苯基)丙烷-2-酮
  参考文献：
  名称：

  动态手性决定了Symplectin-Dehydrocoelenterazine系统中生物发光的关键作用。

  摘要：

  Symplectin是一种含有脱氢腔肠素（DCL）发色团的光蛋白，该发色团通过共价键与半胱氨酸残基连接在一起，发出蓝光。这项研究的重点是新兴的立体遗传学中心的立体化学过程。由于其不同的生物发光活性，使用了两种异构的氟化DCL类似物（2,4-diF-和2,6-diF-DCL），与天然DCL相比分别为200％和20％。发现这些diF-DCL中的每一个都可以在pH 6.0的辛普列汀中与天然DCL交换。新兴的立体异构碳在结合位点是外消旋的。将这种储存形式的pH值更改为蛋白质的最佳溶解度pH（pH 7.8），会导致2,4-diF-DCL结合的symplectin发光，然后对用过的溶液进行分析，并在肽酶消化后检测腔肠酰胺-390-CGLK-肽和腔肠胺。另一方面，对2,6-diF-DCL结合的symplectin的相同分析仅提供了腔肠素，而没有腔肠酰胺。当外消旋体diF‐DCL移至pH 7.8的活性位点

  DOI：

  10.1002/asia.201100089

文献信息

• Optimization of Azoles as Anti-Human Immunodeficiency Virus Agents Guided by Free-Energy Calculations
  作者：Jacob G. Zeevaart、Ligong Wang、Vinay V. Thakur、Cheryl S. Leung、Julian Tirado-Rives、Christopher M. Bailey、Robert A. Domaoal、Karen S. Anderson、William L. Jorgensen

  DOI：10.1021/ja8019214

  日期：2008.7.1

  Efficient optimization of an inactive 2-anilinyl-5-benzyloxadiazole core has been guided by free energy perturbation (FEP) calculations to provide potent non-nucleoside inhibitors of human immunodeficiency virus (HIV) reverse transcriptase (NNRTIs). An FEP "chlorine scan" was performed to identify the most promising sites for substitution of aryl hydrogens. This yielded NNRTIs 8 and 10 with activities (EC(50)) of 820 and 310 nM for protection of human T-cells from infection by wild-type HIV-1. FEP calculations for additional substituent modifications and change of the core heterocycle readily led to oxazoles 28 and 29, which were confirmed as highly potent anti-HIV agents with activities in the 10-20 nM range. The designed compounds were also monitored for possession of desirable pharmacological properties by use of additional computational tools. Overall, the trends predicted by the FEP calculations were well borne out by the assay results. FEP-guided lead optimization is confirmed as a valuable tool for molecular design including drug discovery; chlorine scans are particularly attractive since they are both straightforward to perform and highly informative.
• Dynamic Chirality Determines Critical Roles for Bioluminescence in Symplectin-Dehydrocoelenterazine System
  作者：Vorawan Kongjinda、Yosuke Nakashima、Naoki Tani、Masaki Kuse、Toshio Nishikawa、Chin-Hui Yu、Nobuyuki Harada、Minoru Isobe

  DOI：10.1002/asia.201100089

  日期：2011.8.1

  diF‐DCLs moved to the active site at pH 7.8, a change in the chirality with the 390‐Cys residue resulted. Model experiments using L‐cysteine‐containing CGLK‐peptide supported two diastereoisomers from each diF‐DCL. The significant difference in the luminescence from these two chromophores is attributed to a plausible mechanism including the dynamically variable stereogenic center emerging at the storage and

  Symplectin是一种含有脱氢腔肠素（DCL）发色团的光蛋白，该发色团通过共价键与半胱氨酸残基连接在一起，发出蓝光。这项研究的重点是新兴的立体遗传学中心的立体化学过程。由于其不同的生物发光活性，使用了两种异构的氟化DCL类似物（2,4-diF-和2,6-diF-DCL），与天然DCL相比分别为200％和20％。发现这些diF-DCL中的每一个都可以在pH 6.0的辛普列汀中与天然DCL交换。新兴的立体异构碳在结合位点是外消旋的。将这种储存形式的pH值更改为蛋白质的最佳溶解度pH（pH 7.8），会导致2,4-diF-DCL结合的symplectin发光，然后对用过的溶液进行分析，并在肽酶消化后检测腔肠酰胺-390-CGLK-肽和腔肠胺。另一方面，对2,6-diF-DCL结合的symplectin的相同分析仅提供了腔肠素，而没有腔肠酰胺。当外消旋体diF‐DCL移至pH 7.8的活性位点