2-溴-6-氟-3-甲氧基苯硼酸 | 957062-89-4

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2-溴-6-氟-3-甲氧基苯硼酸
• 中文别名: 2-溴-3-甲氧基6-氟苯硼酸
• 英文名称: 2-bromo-6-fluoro-3-methoxy phenylboronic acid
• 英文别名: 2-Bromo-6-fluoro-3-methoxyphenylboronic acid；(2-bromo-6-fluoro-3-methoxyphenyl)boronic acid
• CAS: 957062-89-4
• 化学式: C₇H₇BBrFO₃
• 分子量: 248.844
• InChiKey: WCXHRSAUPYPWHO-UHFFFAOYSA-N

物化性质

• 熔点：
  130-135°C

计算性质

• 辛醇/水分配系数(LogP)：
  0.28
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2931900090
• 危险性防范说明：
  P233,P260,P261,P264,P270,P271,P280,P301+P312,P302+P352,P304,P304+P340,P305+P351+P338,P312,P321,P330,P332+P313,P337+P313,P340,P362,P403,P403+P233,P405,P501
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-溴-6-氟-3-甲氧基苯硼酸 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 水 为溶剂， 生成 [1-(2-bromo-6-fluoro-3-methoxyphenyl)triazol-4-yl]methyl (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
  参考文献：
  名称：

  A novel triazole derivative of betulinic acid induces extrinsic and intrinsic apoptosis in human leukemia HL-60 cells

  摘要：

  In an attempt to arrive at more potent cytotoxic agent than the bioactive natural product betulinic acid, influence of small structural modifications of its 1, 2, 3 triazole derivatives tethered at C-28 and both C3, C-28 using click chemistry approach has been studied. The chemically characterized triazoles have been screened for in vitro cytotoxicity against four human cancer cell lines HL-60, MiaPaCa-2, PC-3 and A549 which has allowed to identify triazole derivative 28{1N (4-fluoro phenyl)-1H-1, 2, 3-triazol-4-yl} methyloxy betulinic ester having better potency profile than the parent compound with IC50 values in the range of 5-7 mu M. It caused disruption of mitochondrial membrane potential, rendered Bcl-2 cleavage, Bax translocation and decrease Bcl-2/Bax ratio. These events are accompanied by activation of caspases -9, similar to 3, which cleave the PARP-1. It also induces caspase-8, which is involved in extrinsic apoptotic pathway. Therefore, it induces apoptosis through both intrinsic and extrinsic pathways in human leukemia HL-60 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.11.018

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.
• A novel triazole derivative of betulinic acid induces extrinsic and intrinsic apoptosis in human leukemia HL-60 cells
  作者：Imran Khan、Santosh K. Guru、Santosh K. Rath、Praveen K. Chinthakindi、Buddh Singh、Surrinder Koul、Shashi Bhushan、Payare L. Sangwan

  DOI：10.1016/j.ejmech.2015.11.018

  日期：2016.1

  In an attempt to arrive at more potent cytotoxic agent than the bioactive natural product betulinic acid, influence of small structural modifications of its 1, 2, 3 triazole derivatives tethered at C-28 and both C3, C-28 using click chemistry approach has been studied. The chemically characterized triazoles have been screened for in vitro cytotoxicity against four human cancer cell lines HL-60, MiaPaCa-2, PC-3 and A549 which has allowed to identify triazole derivative 281N (4-fluoro phenyl)-1H-1, 2, 3-triazol-4-yl} methyloxy betulinic ester having better potency profile than the parent compound with IC50 values in the range of 5-7 mu M. It caused disruption of mitochondrial membrane potential, rendered Bcl-2 cleavage, Bax translocation and decrease Bcl-2/Bax ratio. These events are accompanied by activation of caspases -9, similar to 3, which cleave the PARP-1. It also induces caspase-8, which is involved in extrinsic apoptotic pathway. Therefore, it induces apoptosis through both intrinsic and extrinsic pathways in human leukemia HL-60 cells. (C) 2015 Elsevier Masson SAS. All rights reserved.