5-bromo-2-hydroxy-4-methoxy-3-nitrobenzaldehyde | 873980-72-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-bromo-2-hydroxy-4-methoxy-3-nitrobenzaldehyde
• CAS: 873980-72-4
• 化学式: C₈H₆BrNO₅
• 分子量: 276.043
• InChiKey: IZUOXIAVRSWZSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 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：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-bromo-2-hydroxy-4-methoxy-3-nitrobenzaldehyde 生成 5-bromo-2-hydroxy-4-methoxy-3-nitro-benzaldehyde phenylhydrazone
  参考文献：
  名称：

  Long-Term Therapy using GHB (Sodium Gamma Hydroxybutyrate) for Treatment-Resistant Chronic Alcoholics

  摘要：

  Thirty-five alcohol-dependent patients according to DSM-IV criteria who also met criteria for treatment resistance were treated with doses of gamma hydroxybutyrate (GHB) ranging between 25 and 100 mg/kg/die in an open one-year study. The results show that no patients discontinued the program during the first month of treatment. Sixty percent of these patients successfully completed the protocol; 11.4% showed complete abstinence (full responder patients); 14.3% strongly reduced their alcohol intake (partial responder patients) and 34.3% of the patients were still under treatment after one year. Forty percent of the patients were nonresponders. The retention rate under treatment of the studied sample was statistically higher than that found during the last treatment of the same subjects. No significant differences were found between full responder and partial responder patients regarding changes in clinical features, alcohol intake or social adjustment. Patients still in treatment after one year significantly differed from nonresponder patients on all the variables investigated. A six-times/daily fractionated administration of the GHB dose was the only significant predictor of the retention rate.

  DOI：

  10.1080/02791072.2001.10400478
• 作为产物：
  描述：

  2-hydroxy-4-methoxy-3-nitrobenzaldehyde 在 溴 、 溶剂黄146 作用下， 生成 5-bromo-2-hydroxy-4-methoxy-3-nitrobenzaldehyde
  参考文献：
  名称：

  Long-Term Therapy using GHB (Sodium Gamma Hydroxybutyrate) for Treatment-Resistant Chronic Alcoholics

  摘要：

  Thirty-five alcohol-dependent patients according to DSM-IV criteria who also met criteria for treatment resistance were treated with doses of gamma hydroxybutyrate (GHB) ranging between 25 and 100 mg/kg/die in an open one-year study. The results show that no patients discontinued the program during the first month of treatment. Sixty percent of these patients successfully completed the protocol; 11.4% showed complete abstinence (full responder patients); 14.3% strongly reduced their alcohol intake (partial responder patients) and 34.3% of the patients were still under treatment after one year. Forty percent of the patients were nonresponders. The retention rate under treatment of the studied sample was statistically higher than that found during the last treatment of the same subjects. No significant differences were found between full responder and partial responder patients regarding changes in clinical features, alcohol intake or social adjustment. Patients still in treatment after one year significantly differed from nonresponder patients on all the variables investigated. A six-times/daily fractionated administration of the GHB dose was the only significant predictor of the retention rate.

  DOI：

  10.1080/02791072.2001.10400478

文献信息

• 3-取代香豆素类衍生物及应用和GPR35受体 的激动剂
  申请人：中国科学院大连化学物理研究所

  公开号：CN108069929B

  公开（公告）日：2021-06-15

  本发明公开了一种3‑取代香豆素衍生物及药学上可接受的盐、溶剂化物、水合物或晶型。本发明化合物对人源G蛋白偶联受体35(GPR35)普遍表现出高激动活性，是人源性GPR35受体的特异性激动剂。本发明提供的化合物是新型GPR35受体的活性配体，该类化合物及其药学上可接受的盐、溶剂化物、水合物或晶型对人源GPR35普遍表现出较高的活性以及很好的选择性。本发明是GPR35受体的的特异性激动剂，可在制备治疗、预防和抑制由GPR35受体介导的疾病的药物中应用。
• Discovery of 2<i>H</i>-Chromen-2-one Derivatives as G Protein-Coupled Receptor-35 Agonists
  作者：Lai Wei、Jixia Wang、Xiuli Zhang、Ping Wang、Yaopeng Zhao、Jiaqi Li、Tao Hou、Lala Qu、Liying Shi、Xinmiao Liang、Ye Fang

  DOI：10.1021/acs.jmedchem.6b01431

  日期：2017.1.12

  A family of 2H-chromen-2-one derivatives were identified as G protein-coupled receptor-35 (GPR35) agonists using dynamic mass redistribution assays in HT-29 cells. The compounds with 1H-tetrazol-5-y1 in 3-substituted position displayed higher potency than the corresponding carboxyl analogs, and the hydroxyl group in the 7-position also played an important role in GPR35 agonistic activity. 6-Bromo-7-hydroxy-8-nitro-3-(1H-tetrazol-5-71)-2H-chromen-2-one (50) was found to be the most potent GPR35 agonist with an EC50 of 5.8 nM. Calculating the physicochemical properties of compounds with moderate to high potency suggested that compounds 30, 50, and 51 showed good druggability. This study provides a novel series of GPR35 agonists, and compound 50 may be a powerful tool to study GPR35.