3-溴-5-甲基-2-甲氧基苯基硼酸 | 870717-99-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-溴-5-甲基-2-甲氧基苯基硼酸
• 中文别名: 3-溴-5-甲基-2-甲氧基苯硼酸；3-溴-2-甲氧基-5-甲基苯硼酸
• 英文名称: 3-bromo-2-methoxy-5-methyl phenylboronic acid
• 英文别名: 3-Bromo-5-methyl-2-methoxyphenylboronic acid；(3-bromo-2-methoxy-5-methylphenyl)boronic acid
• CAS: 870717-99-0
• 化学式: C₈H₁₀BBrO₃
• 分子量: 244.881
• InChiKey: WHQCYDMSPACJBE-UHFFFAOYSA-N

物化性质

• 熔点：
  102-106 °C(lit.)
• 沸点：
  392.5±52.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.45
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2931900090
• 安全说明：
  S36/37
• 危险标志：
  GHS07
• 危险性描述：
  H315,H319,H335
• 危险性防范说明：
  P261,P305 + P351 + P338

反应信息

• 作为反应物：
  描述：

  3-溴-5-甲基-2-甲氧基苯基硼酸 在 sodium chlorite 、 sodium dihydrogenphosphate 、 四(三苯基膦)钯 、 potassium carbonate 、 叔丁醇 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 2-(3-bromo-5-methyl-2-methoxyphenyl)benzoic acid
  参考文献：
  名称：

  The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain

  摘要：

  Alternariol and monomethylalternariol are natural phytotoxins produced by some fungal strains, such as Nimbya and Alternaria. These substances confer virulence to phytopathogens, yet no information is available concerning their mode of action. Here we show that in the micromolar range alternariol 9-methyl ether is able to inhibit the electron transport chain (IC50 = 29.1 +/- 6.5 mu M) in isolated spinach chloroplasts. Since its effectiveness is limited by poor solubility in water, several alternariol analogues were synthesized using different aromatic aldehydes. The synthesized 6H-benzo[c]cromen-6-ones, 5H-chromene[4,3-b]pyridin-5-one, and 5H-chromene[4,3-c]pyridin-5-one also showed inhibitory properties, and three 6H-benzo[c]cromen-6-ones were more effective (IC50 =12.8-22.8 mu M) than the lead compound. Their addition to the culture medium of a cyanobacterial model strain was found to inhibit algal growth, with a relative effectiveness that was consistent with their activity in vitro. In contrast, the growth of a nonphotosynthetic plant cell culture was poorly affected. These compounds may represent a novel lead for the development of new active principles targeting photosynthesis.

  DOI：

  10.1021/np4005882

文献信息

• Diminutive effect on T and B-cell proliferation of non-cytotoxic α-santonin derived 1,2,3-triazoles: A report
  作者：Praveen K. Chinthakindi、Payare L. Sangwan、Saleem Farooq、Rajeshwar R. Aleti、Anupurna Kaul、Ajit K. Saxena、Y.L.N. Murthy、Ram A. Vishwakarma、Surrinder Koul

  DOI：10.1016/j.ejmech.2012.12.018

  日期：2013.2

  alpha-Santonin derived new series of 1,2,3-triazoles synthesized through Azide Alkyne Huisgen 1,3-dipolar cycloaddition reaction between substituted aryl azide and a propargylated alpha-desmotrosantonin were bio-evaluated for their diminutive effect on ConA induced T-cell and LPS induced B-cell proliferation. Interestingly, most of the synthesized compounds showed better immunosuppressant activity than alpha-santonin. Triazole derivatives 9, 10, 17, 18, 29, and 30 displayed significant diminutive effect on cell proliferation. Compounds 12 and 13 were found selective against ConA T-cell proliferation exhibiting >90% inhibition at 1 x 10(-6) M concentration. The present study resulted in identification of several triazole derivatives as effective immunosuppressive agents. (C) 2012 Elsevier Masson SAS. All rights reserved.
• Development of constrained tamoxifen mimics and their antiproliferative properties against breast cancer cells
  作者：Sivakumar Archana、Ramasatyaveni Geesala、Narasimha B. Rao、Suresh Satpati、Giridhar Puroshottam、Akhila Panasa、Anshuman Dixit、Amitava Das、Ajay Kumar Srivastava

  DOI：10.1016/j.bmcl.2014.11.077

  日期：2015.2

  An efficient synthesis of a new series of tamoxifen mimics is described by employing iodine catalyzed ipsocyclization strategy followed by Suzuki coupling. A molecular docking studies of the synthesized compounds 11a-n and 12 in estrogen receptor (ER-alpha) showed that the scaffolds are fitting well in the groove, thereby suggesting them as promising antiproliferative agents for estrogen dependent breast cancer lines. All compounds were tested in vitro against breast cancer cell lines-ER positive, MCF-7; ER negative, MDA-MB-231; and control mammary epithelial cells, MEpiC. The biological results showed that most of the compounds are active against MCF-7 with IC50 values less than 6.5 mu M which corroborate the results of molecular docking studies. (C) 2014 Elsevier Ltd. All rights reserved.
• Microwave-assisted synthesis of ethynylarylboronates for the construction of boronic acid-based fluorescent sensors for carbohydrates
  作者：Shi-Long Zheng、Suazette Reid、Na Lin、Binghe Wang

  DOI：10.1016/j.tetlet.2006.02.012

  日期：2006.4

  A reliable and operationally simple procedure for the synthesis of 2.2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 was developed. The key step is microwave-facilitated selective formation of 2,2-dimethylpropane-1,3-diyl trimethylsilylethynylaryl boronates by Sonogashira reaction front the corresponding bromides. The use of microwave was found to significantly improve the reaction yield and shorten the reaction time. The 2,2-dimethylpropane-1,3-diyl ethynylaryl boronates 4 prepared can be used in the construction of diboronic acid libraries through [2+3] Huisgen cycloaddition for carbohydrate fluorescent sensor development. (c) 2006 Elsevier Ltd. All rights reserved.
• The Fungal Phytotoxin Alternariol 9-Methyl Ether and Some of Its Synthetic Analogues Inhibit the Photosynthetic Electron Transport Chain
  作者：Antonio Jacinto Demuner、Luiz Cláudio Almeida Barbosa、Ana Cristina Mendes Miranda、Guilherme Carvalho Geraldo、Cleiton Moreira da Silva、Samuele Giberti、Michele Bertazzini、Giuseppe Forlani

  DOI：10.1021/np4005882

  日期：2013.12.27

  Alternariol and monomethylalternariol are natural phytotoxins produced by some fungal strains, such as Nimbya and Alternaria. These substances confer virulence to phytopathogens, yet no information is available concerning their mode of action. Here we show that in the micromolar range alternariol 9-methyl ether is able to inhibit the electron transport chain (IC50 = 29.1 +/- 6.5 mu M) in isolated spinach chloroplasts. Since its effectiveness is limited by poor solubility in water, several alternariol analogues were synthesized using different aromatic aldehydes. The synthesized 6H-benzo[c]cromen-6-ones, 5H-chromene[4,3-b]pyridin-5-one, and 5H-chromene[4,3-c]pyridin-5-one also showed inhibitory properties, and three 6H-benzo[c]cromen-6-ones were more effective (IC50 =12.8-22.8 mu M) than the lead compound. Their addition to the culture medium of a cyanobacterial model strain was found to inhibit algal growth, with a relative effectiveness that was consistent with their activity in vitro. In contrast, the growth of a nonphotosynthetic plant cell culture was poorly affected. These compounds may represent a novel lead for the development of new active principles targeting photosynthesis.