3-氯-4-丙氧基苯硼酸 | 480438-57-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 3-氯-4-丙氧基苯硼酸
• 中文别名: 3-氯-4-丙氧基苯基硼酸
• 英文名称: 3-chloro-4-propoxyphenylboronic acid
• 英文别名: (3-chloro-4-propoxyphenyl)boronic acid
• CAS: 480438-57-1
• 化学式: C₉H₁₂BClO₃
• mdl: MFCD03701555
• 分子量: 214.456
• InChiKey: IDDBWHWERWCIGU-UHFFFAOYSA-N

物化性质

• 熔点：
  143-148 °C(lit.)
• 沸点：
  364.7±52.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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
• 海关编码：
  2931900090

反应信息

• 作为反应物：
  描述：

  3-氯-4-丙氧基苯硼酸 在 sodium azide 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 甲醇 、 水 为溶剂， 生成 [1-(3-chloro-4-propoxyphenyl)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

• ORGANIC COMPOUNDS
  申请人：Revesz Laszlo

  公开号：US20100069360A1

  公开（公告）日：2010-03-18

  A compound of formula (I) or a pharmaceutically acceptable salt or prodrug ester thereof: wherein the groups R1, R2, R3, R7 and X are as defined in the specification.

  化合物(I)的公式或其药学上可接受的盐或前药酯：其中，基团R1、R2、R3、R7和X如规范所定义。
• Scoparone chemical modification into semi-synthetic analogues featuring 3-substitution for their anti-inflammatory activity
  作者：Chetan Kumar、Pankaj Chibber、Ritu Painuli、Syed Assim Haq、Ram A. Vishwakarma、Gurdarshan Singh、Naresh K. Satti、Ravindra S. Phatake

  DOI：10.1007/s11030-023-10687-7

  日期：——

  investigation, we reported the synthesis of nineteen semi-synthetic 3-substituted scoparone analogues, followed by their characterization using analytical methods such as NMR, HPLC, and HRMS. All compounds screened for in vitro and in vivo study for their ability to reduce inflammation. The SAR study worked effectively for this particular scoparone 3-substitution, as compounds 3, 4, 9, 16, 18, and 20 displayed

  天然产物 （NPs） 继续作为开发新生物活性分子的结构模型，并改进新药的识别过程。香豆素是 NP 中研究最多的化合物之一，目前正在彻底研究其生物学效应。在本研究中，我们报道了 19 种半合成 3-取代东伞酮类似物的合成，然后使用 NMR、HPLC 和 HRMS 等分析方法对其进行表征。所有化合物都经过体外和体内研究筛选，以确定其减轻炎症的能力。SAR 研究对这种特定的 Scoparone 3-取代有效，因为化合物 3、4、9、16、18 和 20 对 TNF-α 的体外结果优于母体分子。同样，化合物 3 和 17 显示出更高的 IL-6 抑制百分比。化合物 3、4 和 12 也被体内研究确定为有前途的候选化合物，其抑制百分比高于母体 Scoparone 分子。从所有体外和体内研究中可以明显看出，化合物 3 显示出最有效的抗炎活性。
• 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.
• Discovery of a Novel Glucagon Receptor Antagonist <i>N</i>-[(4-{(1<i>S</i>)-1-[3-(3, 5-Dichlorophenyl)-5-(6-methoxynaphthalen-2-yl)-1<i>H</i>-pyrazol-1-yl]ethyl}phenyl)carbonyl]-β-alanine (MK-0893) for the Treatment of Type II Diabetes
  作者：Yusheng Xiong、Jian Guo、Mari R. Candelore、Rui Liang、Corey Miller、Qing Dallas-Yang、Guoqiang Jiang、Peggy E. McCann、Sajjad A. Qureshi、Xinchun Tong、Shiyao Sherrie Xu、Jackie Shang、Stella H. Vincent、Laurie M. Tota、Michael J. Wright、Xiaodong Yang、Bei B. Zhang、James R. Tata、Emma R. Parmee

  DOI：10.1021/jm300579z

  日期：2012.7.12

  A potent, selective glucagon receptor antagonist 9m, N-[(4-(1S)-1-[3-(3,5-dichlorophenyl) -5-(6-methoxynaphthalen-2-yl)-1H-pyrazol-1-yl]ethyl}phenyl)-carbonyl]-beta-alanine, was discovered by optimization of a previously identified lead. Compound 9m is a reversible and competitive antagonist with high binding affinity (IC50 of 6.6 nM) and functional cAMP activity (IC50 of 15.7 nM). It is selective for glucagon receptor relative to other family B GPCRs, showing IC50 values of 1020 nM for GIPR, 9200 nM for PAC1, and >10000 nM for GLP-1R, VPAC1, and VPAC2. Compound 9m blunted glucagon-induced glucose elevation in hGCGR mice and rhesus monkeys. It also lowered ambient glucose levels in both acute and chronic mouse models: in hGCGR ob/ob mice it reduced glucose (AUC 0-6 h) by 32% and 39% at 3 and 10 mpk single doses, respectively. In hGCGR mice on a high fat diet, compound 9m at 3, and 10 mpk po in feed lowered blood glucose levels by 89% and 94% at day 10, respectively, relative to the difference between the vehicle control and lean hGCGR mice. On the basis of its favorable biological and DMPK properties, compound 9m (MK-0893) was selected for further preclinical and clinical evaluations.
• Bakuchiol derivatives as novel and potent cytotoxic agents: A report
  作者：Rabiya Majeed、Mallepally V. Reddy、Praveen K. Chinthakindi、Payare L. Sangwan、Abid Hamid、Gousia Chashoo、Ajit K. Saxena、Surrinder Koul

  DOI：10.1016/j.ejmech.2011.12.018

  日期：2012.3

  A library of 28 compounds comprising of acyl, amino, halo, nitro, styryl and cyclized derivatives of bakuchiol have been evaluated against a panel of eight human cancer cell lines. Bioevaluation studies have resulted in the identification of potent cytotoxic molecules exhibiting concentration dependent growth inhibition against leukemia cancer cells with best results observed for compounds 17 and 22 exhibiting IC50 1.8 and 2.0 mu M respectively. As evident from various biological end-points, inhibition of cell proliferation by inducing G2/M cell cycle arrest, mitochondrial membrane disruption followed by DNA fragmentation and apoptosis is demonstrated. (C) 2011 Elsevier Masson SAS. All rights reserved.