5-<(2,5-dimethoxybenzyl)oxy>-2-hydroxybenzoic acid methyl ester

• 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-<(2,5-dimethoxybenzyl)oxy>-2-hydroxybenzoic acid methyl ester
• 英文别名: 5-(2,5-dimethoxybenzyloxy)-2-hydroxybenzoic acid methyl ester；Methyl 2-hydroxy-5-(2,5-dimethoxybenzyloxy)benzoate；methyl 5-[(2,5-dimethoxyphenyl)methoxy]-2-hydroxybenzoate
• 化学式: C₁₇H₁₈O₆
• 分子量: 318.326
• InChiKey: AONNOPWDVAGRDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-<(2,5-dimethoxybenzyl)oxy>-2-hydroxybenzoic acid methyl ester 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以80%的产率得到5-<(2,5-dimethoxybenzyl)oxy>-2-hydroxybenzoic acid
  参考文献：
  名称：

  Novel Antiproliferative Agents Derived from Lavendustin A

  摘要：

  The active partial structure of the potent tyrosine kinase inhibitor lavendustin A was derivatized in the search for novel agents against cellular proliferation. The antiproliferative potential of the new derivatives was determined using the human keratinocyte cell line HaCaT as the primary test system. Whereas the lavendustin A partial structure is ineffective in inhibiting cell proliferation, esterification of its carboxylic acid function leads to measurable antiproliferative activity. Additional O-methylation of the 2,5-dihydroxyphenyl moiety yields activity in the micromolar range. Further substantial increases in activity are achieved by replacing the nitrogen with oxygen and carbon within the 2,5-dimethoxyphenyl series (but not within the 2,5-dihydroxyphenyl analogs) leading to 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid methyl ester (13) as the most potent analog identified to date. These increases in antiproliferative activity are paralleled, however, by the disappearance of activity against the epidermal growth factor receptor-associated tyrosine kinase, suggesting another mechanism of action.

  DOI：

  10.1021/jm00050a005
• 作为产物：
  描述：

  2,5-二甲氧基苄溴 、 2,5-二羟基苯甲酸甲酯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 30.0h， 以64%的产率得到5-<(2,5-dimethoxybenzyl)oxy>-2-hydroxybenzoic acid methyl ester
  参考文献：
  名称：

  Novel Antiproliferative Agents Derived from Lavendustin A

  摘要：

  The active partial structure of the potent tyrosine kinase inhibitor lavendustin A was derivatized in the search for novel agents against cellular proliferation. The antiproliferative potential of the new derivatives was determined using the human keratinocyte cell line HaCaT as the primary test system. Whereas the lavendustin A partial structure is ineffective in inhibiting cell proliferation, esterification of its carboxylic acid function leads to measurable antiproliferative activity. Additional O-methylation of the 2,5-dihydroxyphenyl moiety yields activity in the micromolar range. Further substantial increases in activity are achieved by replacing the nitrogen with oxygen and carbon within the 2,5-dimethoxyphenyl series (but not within the 2,5-dihydroxyphenyl analogs) leading to 5-[2-(2,5-dimethoxyphenyl)ethyl]-2-hydroxybenzoic acid methyl ester (13) as the most potent analog identified to date. These increases in antiproliferative activity are paralleled, however, by the disappearance of activity against the epidermal growth factor receptor-associated tyrosine kinase, suggesting another mechanism of action.

  DOI：

  10.1021/jm00050a005

文献信息

• [EN] NEW COMPOUNDS, METHODS FOR THEIR PREPARATION AND USE THEREOF<br/>[FR] NOUVEAUX COMPOSES, PROCEDES DESTINES A LEUR PREPARATION ET UTILISATION CORRESPONDANTE
  申请人：ACTIVE BIOTECH AB

  公开号：WO2005075410A1

  公开（公告）日：2005-08-18

  Compounds of formula (I), for clinical treatment of autoimmune diseases, inflammatory diseases, organ transplant rejection and malignant neoplasia. A pharmaceutical composition comprising a compound of formula (I) in an amount giving a daily dosage of from 0.005 mg/kg to 10 mg/kg body weight, in particular from 0.025 mg/kg to 2 mg/kg body weight.

  化合物的化学式（I），用于临床治疗自身免疫性疾病、炎症性疾病、器官移植排斥反应和恶性肿瘤。一种药物组合物包括化学式（I）的化合物，剂量为每天0.005毫克/千克至10毫克/千克体重，特别是每天0.025毫克/千克至2毫克/千克体重。
• New compounds, methods for their preparation and use thereof
  申请人：Jonsson Stig

  公开号：US20050187297A1

  公开（公告）日：2005-08-25

  Compounds of formula (I) for clinical treatment of autoimmune diseases, inflammatory diseases, organ transplant rejection and malignant neoplasia. A pharmaceutical composition comprising a compound of formula (I) in an amount giving a daily dosage of from 0.005 mg/kg to 10 mg/kg body weight, in particular from 0.025 mg/kg to 2 mg/kg body weight.

  公式（I）的化合物，用于临床治疗自身免疫疾病、炎症性疾病、器官移植排斥和恶性肿瘤。一种药物组合物，包括公式（I）的化合物，其剂量每日为0.005毫克/千克至10毫克/千克体重，特别是从0.025毫克/千克至2毫克/千克体重。
• ANTHRANILIC ACID DERIVATIVES
  申请人：Andersson Helén Tuvesson

  公开号：US20100029767A1

  公开（公告）日：2010-02-04

  Compounds of formula (I) are provided, wherein X is CH═CH, CH 2 O wherein the oxygen atom is bound to ring B, or OCH 2 wherein the oxygen atom is bound to ring A; Y is hydrogen, straight or branched C1-C6 alkyl or a pharmaceutically acceptable inorganic cation; R1 is ethyl or cyclopropyl; and R2 and R3 are the same or different and are selected from F, Cl, Br, CF 3 and OCF 3 . The compounds are useful for the treatment of autoimmune diseases, inflammatory diseases, organ transplant rejection, and malignant neoplasia. Pharmaceutical compositions comprising the compounds, methods of using the compounds, and methods for preparing the compounds are also provided.

  提供了化学式（I）的化合物，其中X是CH═CH，CH2O（其中氧原子与环B结合），或OCH2（其中氧原子与环A结合）; Y是氢，直链或支链C1-C6烷基或药学上可接受的无机阳离子; R1是乙基或环丙基; R2和R3相同或不同，选择自F、Cl、Br、CF3和OCF3。该化合物可用于治疗自身免疫性疾病、炎症性疾病、器官移植排斥和恶性肿瘤。还提供了包含该化合物的制药组合物、使用该化合物的方法以及制备该化合物的方法。
• Benzyloxyphenyl derivatives
  申请人：SANDOZ LTD.

  公开号：EP0497740B1

  公开（公告）日：1994-12-14
• NEW COMPOUNDS, METHODS FOR THEIR PREPARATION AND USE THEREOF
  申请人：Active Biotech AB

  公开号：EP1720825A1

  公开（公告）日：2006-11-15