2-溴-1-(2,6-二甲苯基)乙酮 | 123184-19-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 2-溴-1-(2,6-二甲苯基)乙酮
• 英文名称: 2-bromo-1-(2,6-dimethoxyphenyl)ethanone
• 英文别名: 2-bromo-2',6'-dimethoxyacetophenone；2',6'-dimethoxyphenyl α-bromomethyl ketone
• CAS: 123184-19-0
• 化学式: C₁₀H₁₁BrO₃
• 分子量: 259.1
• InChiKey: NCSDTJAJQKENMG-UHFFFAOYSA-N

物化性质

• 沸点：
  323.2±27.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2914700090

反应信息

• 作为反应物：
  描述：

  2-溴-1-(2,6-二甲苯基)乙酮 在 对甲苯磺酸 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 生成 3-[2-(2,6-Dimethoxy-phenyl)-5-isopropyl-pyrrol-1-yl]-propionitrile
  参考文献：
  名称：

  Inhibitors of cholesterol biosynthesis. 1. trans-6-(2-Pyrrol-1-ylethyl)-4-hydroxypyran-2-ones, a novel series of HMG-CoA reductase inhibitors. 1. Effects of structural modifications at the 2- and 5-positions of the pyrrole nucleus

  摘要：

  A novel series of trans-6-(2-pyrrol-1-ylethyl)-4-hydroxypyran-2-ones and their dihydroxy acid derivatives were prepared and evaluated for their ability to inhibit the enzyme HMG-CoA reductase in vitro. A systematic study of substitution at the 2- and 5-positions of the pyrrole ring revealed that optimum potency was realized with the 2-(4-fluorophenyl)-5-isopropyl derivative 8x, which possessed 30% of the in vitro activity of the potent fungal metabolite compactin (I). A molecular modeling analysis led to the description of a pharmacophore model characterized by (A) length limits of 5.9 and 3.3 A for the 2- and 5-substituents, respectively, as well as an overall width limit of 10.6 A across the pyrrole ring from the 2- to the 5-substituent and (B) an orientation of the ethyl(ene) bridge to the 4-hydroxypyran-2-one ring nearly perpendicular to the planes of the parent pyrrole, hexahydronaphthalene, and phenyl rings of the structures examined (Figure 3, theta = 80-110 degrees). Attempts to more closely mimic compactin's polar isobutyric ester side chain with the synthesis of 2-phenylpyrroles containing polar phenyl substituents resulted in analogues with equal or slightly reduced potencies when compared to the 2-[(unsubstituted or 4-fluoro)phenyl]pyrroles, supporting the hypothesis that inhibitory potency is relatively insensitive to side-chain polarity or charge distribution in this area.

  DOI：

  10.1021/jm00163a005
• 作为产物：
  描述：

  2,6-二甲氧基苯乙酮 在 N-溴代丁二酰亚胺(NBS) 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以40%的产率得到2-溴-1-(2,6-二甲苯基)乙酮
  参考文献：
  名称：

  咪唑并[1,2-a]吡啶衍生物的微波辅助合成和发光活性

  摘要：

  在这项工作中，合成了一系列苯甲酰溴衍生物，并用作合成取代的咪唑并[1,2- a ]吡啶的关键中间体。首先，在微波辐射的辅助下，通过苯乙酮的溴化反应获得苯甲酰溴分子，在15分钟的反应中获得产物4a-v，产率在50％至99％之间。随后，这些分子与2-氨基吡啶共轭，产生了咪唑并[1,2- a ]吡啶衍生物（7a-v）在60秒的反应中产率为24％至99％。相对于通过更繁琐的方法（如热辅助和机械辅助路线）获得的产量，确定了更高的产量。根据取代基的性质，在紫外线激发下观察到电磁光谱的紫色和蓝色区域中的强烈发光发射。这种对环境友好的方法有望构成一类重要的有机化合物，用于开发生物标志物，光化学传感器和医学应用。

  DOI：

  10.1002/jhet.3950

文献信息

• Design and synthesis of pyrazolone-based compounds as potent blockers of SARS-CoV-2 viral entry into the host cells
  作者：Vincent A. Obakachi、Narva Deshwar Kushwaha、Babita Kushwaha、Mavela Cleopus Mahlalela、Suraj Raosaheb Shinde、Idowu Kehinde、Rajshekhar Karpoormath

  DOI：10.1016/j.molstruc.2021.130665

  日期：2021.10

  spike glycoprotein (S) mediates virus entry into cells via the human Angiotensin-converting enzyme 2 (hACE2) protein located on many cell types and tissues' outer surface. This study, therefore, aimed to design and synthesize novel pyrazolone-based compounds as potential inhibitors that would interrupt the interaction between the viral spike protein and the host cell receptor to prevent SARS-CoV 2 entrance

  SARS-CoV-2是在细胞质中复制的包膜正链RNA病毒。它依赖于它们的包膜与宿主细胞膜的融合以将其核衣壳递送到宿主细胞中。刺突糖蛋白（S）通过位于许多细胞类型和组织外表面的人类血管紧张素转化酶2（hACE2）蛋白介导病毒进入细胞。因此，本研究旨在设计和合成新型的基于吡唑啉酮的化合物，作为可能的抑制剂，这些化合物会中断病毒突波蛋白与宿主细胞受体之间的相互作用，从而阻止SARS-CoV 2进入细胞。设计并合成了一系列潜在的SARS-CoV-2抑制剂吡唑啉酮化合物。运用计算技术，评估了所设计化合物对刺突蛋白和hACE2的抑制潜力。硅内分析的结合自由能结果表明，三种化合物（7i，7k和8f）和六种化合物（7b，7h，7k，8d，8g和8h）显示出对SARS的更高和更好的结合高亲和力-CoV-2 Sgp和hACE-2分别与标准药物头孢哌酮（CFZ）和MLN-4760相比。此外，在结合抑制剂后对两种
• Synthesis of novel thiazolylpyrazoline derivatives and evaluation of their antimicrobial activities and cytotoxicities
  作者：Aouatef TABBI、Zafer Asım KAPLANCIKLI、Dahmane TEBBANI、Leyla YURTTAŞ、Zerrin CANTÜRK、Özlem ATLI、Merve BAYSAL、Gülhan TURAN-ZITOUNI

  DOI：10.3906/kim-1512-12

  日期：——

  Several novel thiazolylpyrazoline derivatives were synthesized by reacting substituted 3,5-diaryl-1-thiocarba\-moyl-2-pyrazolines with phenacylbromides. The structures of the synthesized compounds were confirmed by IR, $^1}$H NMR, $^13}$C NMR, and MS spectral data. Their antimicrobial activities against Staphylococcus aureus(ATCC-25923), Enterococcus faecalis} (ATCC-29212), Enterococcus faecalis (ATCC-51922), Listeria monocytogenes (ATCC-1911), Klebsiella pneumoniae (ATCC-700603), Pseudomonas aeruginosa (ATCC-27853), Escherichia coli (ATCC-35218), Escherichia coli (ATCC-25922), Candida albicans (ATCC-90028), Candida glabrata (ATCC-90030), Candida krusei (ATCC-6258), and Candida parapsilosis (ATCC-22019) were investigated. The compounds were also studied for their cytotoxic effects using a MTT assay. Compound 7c showed the highest antimicrobial activity, possessing the same potential as chloramphenicol against K. pneumonia, P. aeruginosa, and E. coli (ATCC-25923).

  通过苯乙酰溴与取代的3,5-二芳基-1-硫脲-2-吡唑啉反应，合成了几种新颖的噻唑啉基吡唑啉衍生物。通过IR、$^1}$H NMR、$^13}$C NMR和MS光谱数据确认了合成化合物的结构。研究了这些化合物对金黄色葡萄球菌(ATCC-25923)、粪肠球菌(ATCC-29212和ATCC-51922)、单核细胞增生李斯特菌(ATCC-1911)、肺炎克雷伯菌(ATCC-700603)、铜绿假单胞菌(ATCC-27853)、大肠埃希菌(ATCC-35218和ATCC-25922)、白色念珠菌(ATCC-90028)、光滑念珠菌(ATCC-90030)、克鲁斯念珠菌(ATCC-6258)和副克鲁斯念珠菌(ATCC-22019)的抗微生物活性。还通过MTT测定法研究了这些化合物的细胞毒性效应。化合物7c显示出最高的抗微生物活性，对肺炎克雷伯菌、铜绿假单胞菌和大肠埃希菌(ATCC-25923)具有与氯霉素相同的潜力。
• Identification of a potent new chemotype for the selective inhibition of PDE4
  作者：Amanda P. Skoumbourdis、Ruili Huang、Noel Southall、William Leister、Vicky Guo、Ming-Hsuang Cho、James Inglese、Marshall Nirenberg、Christopher P. Austin、Menghang Xia、Craig J. Thomas

  DOI：10.1016/j.bmcl.2008.01.028

  日期：2008.2

  A series of substituted 3,6-diphenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines were prepared and analyzed as inhibitors of phosphodiesterase 4 (PDE4). Synthesis, structure-activity relationships, and the selectivity of a highly potent analogue against related phosphodiesterase isoforms are presented.

  制备并分析了一系列取代的 3,6-二苯基-7H-[1,2,4] 三唑并 [3,4-b][1,3,4] 噻二嗪作为磷酸二酯酶 4 (PDE4) 的抑制剂。介绍了合成、构效关系以及针对相关磷酸二酯酶同种型的高效类似物的选择性。
• Thiazole as a carbonyl bioisostere. A novel class of highly potent and selective 5-HT3 receptor antagonists
  作者：Terry Rosen、Arthur A. Nagel、James P. Rizzi、Jeffrey L. Ives、June B. Daffeh、Alan H. Ganong、Karen Guarino、James Heym、Stafford McLean

  DOI：10.1021/jm00172a006

  日期：1990.10

  A novel structural class of highly potent and selective 5-HT3 receptor antagonists is described. The compounds in this new series contain a thiazole moiety linking an aromatic group and a nitrogen-containing basic region; the thiazole group appears to be acting as a carbonyl bioisostere in this system. An optimized member of this series, 4-(2-methoxyphenyl)-2-[[4(5)-methyl-5(4)-imidazolyl]methyl]thiazole

  描述了高效和选择性的5-HT 3受体拮抗剂的新型结构类别。这个新系列的化合物包含连接芳族基团和含氮碱性区域的噻唑部分；噻唑基似乎在该系统中充当羰基生物等排体。该系列的优化成员4-（2-甲氧基苯基）-2-[[[4（5）-甲基-5（4）-咪唑基]甲基]噻唑（5）在Bezold-Jarisch反射范例中表现出口服活性与标准药物恩丹西酮（1）和ICS-205-930（2）相当或更好。根据5-HT3受体结合的计算机药效团模型，合理化了一些构效关系。
• Hepatitis C Virus Inhibitors
  申请人：Sin Ny

  公开号：US20090274652A1

  公开（公告）日：2009-11-05

  Hepatitis C virus inhibitors having the general formula are disclosed. Compositions comprising the compounds and methods for using the compounds to inhibit HCV are also disclosed.

  揭示了具有一般公式的丙型肝炎病毒抑制剂。还揭示了包含这些化合物的组合物和使用这些化合物来抑制HCV的方法。