5-bromo-4-hydroxy-2-methoxy-benzaldehyde | 552845-88-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5-bromo-4-hydroxy-2-methoxy-benzaldehyde
• 英文别名: 5-bromo-2-methoxy-4-hydroxybenzaldehyde；5-bromo-4-hydroxy-2-methoxybenzaldehyde
• CAS: 552845-88-2
• 化学式: C₈H₇BrO₃
• 分子量: 231.046
• InChiKey: CFGUKQNALIAYFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  199-201 °C(Solv: ethanol (64-17-5))
• 沸点：
  324.8±37.0 °C(Predicted)
• 密度：
  1.653±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-bromo-4-hydroxy-2-methoxy-benzaldehyde 在 二(三叔丁基膦)钯 potassium fluoride 、 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 4-(3-hydroxy-2-hydroxymethyl-propoxy)-2-methoxy-5-thiophen-2-yl-benzaldehyde
  参考文献：
  名称：

  Carboxylated, Heteroaryl-Substituted Chalcones as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases

  摘要：

  Starting from a simple chalcone template, structure-activity relationship (SAR) studies led to a series of carboxylated, heteroaryl-substituted chalcone derivatives as novel, potent inhibitors of vascular cell adhesion molecule-1 (VCAM-1) expression. Correlations between lipophilicity determined by calculated logP values and inhibitory efficacy were observed among structurally similar compounds of the series. Various substituents were found to be tolerated at several positions of the chalcone backbone as long as the compounds fell into the right range of lipophilicity. The chalcone alpha,beta-unsaturated ketone moiety seemed to be the pharmacophore required for inhibition of VCAM-1 expression. Compound 19 showed significant antiinflammatory effects in a mouse model of allergic inflammation, indicating that this series of compounds might have therapeutic value for human asthma and other inflammatory disorders.

  DOI：

  10.1021/jm0614230
• 作为产物：
  描述：

  4-羟基-2-甲氧基苯甲醛 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到5-bromo-4-hydroxy-2-methoxy-benzaldehyde
  参考文献：
  名称：

  Carboxylated, Heteroaryl-Substituted Chalcones as Inhibitors of Vascular Cell Adhesion Molecule-1 Expression for Use in Chronic Inflammatory Diseases

  摘要：

  Starting from a simple chalcone template, structure-activity relationship (SAR) studies led to a series of carboxylated, heteroaryl-substituted chalcone derivatives as novel, potent inhibitors of vascular cell adhesion molecule-1 (VCAM-1) expression. Correlations between lipophilicity determined by calculated logP values and inhibitory efficacy were observed among structurally similar compounds of the series. Various substituents were found to be tolerated at several positions of the chalcone backbone as long as the compounds fell into the right range of lipophilicity. The chalcone alpha,beta-unsaturated ketone moiety seemed to be the pharmacophore required for inhibition of VCAM-1 expression. Compound 19 showed significant antiinflammatory effects in a mouse model of allergic inflammation, indicating that this series of compounds might have therapeutic value for human asthma and other inflammatory disorders.

  DOI：

  10.1021/jm0614230

文献信息

• 一种化合物的合成路线及在抗糖尿病药物制备领域的应用
  申请人：深圳市灵兰生物医药科技有限公司

  公开号：CN110937987B

  公开（公告）日：2022-09-06

  本发明属于药品合成技术领域，尤其涉及一种化合物的合成路线及在抗糖尿病药物制备领域的应用。本发明提供了SN158的一种合成路线，还提供了一种上述合成路线在抗糖尿病药物制备领域的应用。本发明中，原料2,4‑二羟基苯甲醛溴化后，以甲氧基甲基保护对位羟基，采用硫酸二甲酯或碘甲烷行邻位羟基甲基化，以HATU或EDCI与HOBt为酰胺化反应的偶合剂，采用盐酸乙醇或三氟化硼乙醚溶液进行克莱森‑施密特缩合反应，制备SN158的产率可达60％以上；同时，制备过程中无需柱层析纯化，重结晶就可得到纯度99％以上的终产物，适合于大规模/工业化生产；解决了现有技术中，SN158存在着合成产率低以及纯化复杂的技术缺陷。
• 一种化合物合成方法及在改善胰岛素抵抗药物领域的应用
  申请人：深圳市灵兰生物医药科技有限公司

  公开号：CN110937986B

  公开（公告）日：2022-09-06

  本发明属于药品合成技术领域，尤其涉及一种化合物合成方法及在改善胰岛素抵抗药物领域的应用。本发明提供了SN159的一种合成方法，原料2，4‑二羟基苯甲醛溴化后，以甲氧基甲基保护对位羟基，采用硫酸二甲酯或碘甲烷甲基化，采用碱性或酸性条件下的克莱森‑施密特缩合反应，可将终产物的产率由现有技术的18.9％提升至68％以上；同时，制备过程中无需柱层析纯化，重结晶就可得到纯度99％以上的终产物，适合于大规模/工业化生产。本发明提供的一种化合物的合成方法及在改善胰岛素抵抗药物药物制备领域的应用，解决了现有技术中，SN159存在着合成产率低以及纯化复杂的技术缺陷。
• Design, synthesis and docking study of 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives as inhibitors of protein tyrosine phosphatase 1B
  作者：Zengtao Wang、Zhiguo Liu、Woojung Lee、Su-Nam Kim、Goo Yoon、Seung Hoon Cheon

  DOI：10.1016/j.bmcl.2014.05.099

  日期：2014.8

  A series of novel 5-(substituted benzylidene)thiazolidine-2,4-dione derivatives was designed, and synthesized based on our previous studies. Also their activities were evaluated as competitive inhibitors of protein tyrosine phosphatase 1B (PTP1B). Compounds 6d–6g, 7b, 7c, 7e, 7j, 7k, 7m, 14b and 14e–14f showed potent inhibitory effects against PTP1B, and compound 7e, the most potent among the series

  根据我们以前的研究，设计并合成了一系列新颖的5-（取代亚苄基）噻唑烷-2,4-二酮衍生物。还评估了它们的活性，将其作为蛋白酪氨酸磷酸酶1B（PTP1B）的竞争性抑制剂。化合物6d - 6g，7b，7c，7e，7j，7k，7m，14b和14e - 14f显示出对PTP1B的有效抑制作用，而化合物7e是该系列中最有效的，其IC 50为4.6μM。也是7e的Surflex-Dock对接模型被研究了。化合物7e在活性位点的负结合能为-7.35 kcal / mol，对PTP1B残基（Gly220，Ala217，Arg221，Asp181，Ser216，Cys215，Phe182，Gln262和Ile219）具有高亲和力，表明它可以稳定开放形式，并与PTP1B的催化位点产生更紧密的结合。
• Synthesis and biological evaluation of benzocyclobutane-C-glycosides as potent and orally active SGLT1/SGLT2 dual inhibitors
  作者：Gee-Hong Kuo、Micheal D. Gaul、Yin Liang、June Z. Xu、Fuyong Du、Pamela Hornby、Guozhang Xu、Jenson Qi、Nathaniel Wallace、Seunghun Lee、Eugene Grant、William V. Murray、Keith Demarest

  DOI：10.1016/j.bmcl.2018.02.057

  日期：2018.4

  Synthesis and biological evaluation of benzocyclobutane-C-glycosides as potent and orally active SGLT1/SGLT2 dual inhibitors are described. Compound 19 showed high inhibitory potency at SGLT1 (IC50 = 45 nM), and excellent potency at SGLT2 (IC50 = 1 nM). It also displayed excellent PK profiles in mice, rats, dogs and monkeys (F = 78–107%). In SD rats, compound 19 treatments significantly reduced blood

  描述了作为有效和口服活性的SGLT1 / SGLT2双重抑制剂的苯并环丁烷-C-糖苷的合成和生物学评估。化合物19在SGLT1（IC 50  = 45 nM）上显示出高抑制效能，在SGLT2（IC 50  = 1 nM）上显示出优异的效能。它还在小鼠，大鼠，狗和猴子中表现出出色的PK分布（F  = 78–107％）。在SD大鼠中，化合物19的治疗以剂量依赖性方式显着降低了血糖水平。在ZDF大鼠中，化合物19最多显示24小时的降血糖作用。因此，化合物19可以用作有价值的药理学工具，并且可以潜在地用作代谢综合征的治疗方法。
• Chalcone derivatives and their use to treat diseases
  申请人：Ni Liming

  公开号：US20060189549A1

  公开（公告）日：2006-08-24

  The invention relates to compounds, pharmaceutical compositions and methods of using compounds of the general formula or its pharmaceutically acceptable salt or ester, wherein the substituents are defined in the application.

  本发明涉及一般式化合物、药物组合物及使用该一般式化合物或其药学上可接受的盐或酯的方法，其中取代基在申请中定义。