methyl 3-isopropoxy-4-methoxybenzoate | 1283420-36-9

• 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: methyl 3-isopropoxy-4-methoxybenzoate
• 英文别名: 3-isopropoxy-4-methoxybenzoic acid methyl ester；Methyl 3-isopropoxy-4-methoxybenzoate；methyl 4-methoxy-3-propan-2-yloxybenzoate
• CAS: 1283420-36-9
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: WMYRMSMFWHJKFP-UHFFFAOYSA-N

物化性质

• 沸点：
  309.8±22.0 °C(Predicted)
• 密度：
  1.074±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 3-isopropoxy-4-methoxybenzoate 在 aluminum (III) chloride 、 氯化亚砜 、 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 为溶剂， 反应 13.53h， 生成 (3-isopropoxy-4-methoxyphenyl)(1-(3,4,5-trimethoxyphenyl)-1H-pyrrol-3-yl)methanone
  参考文献：
  名称：

  New Pyrrole Derivatives with Potent Tubulin Polymerization Inhibiting Activity As Anticancer Agents Including Hedgehog-Dependent Cancer

  摘要：

  We synthesized 3-aroyl-1-arylpyrrole (ARAP) derivatives as potential anticancer agents having different substituents at the pendant 1-phenyl ring. Both the 1-phenyl ring and 3-(3,4,5-trimethoxyphenyl)carbonyl moieties were mandatory to achieve potent inhibition of tubulin polymerization, binding of colchicine to tubulin, and cancer cell growth. ARAP 22 showed strong inhibition of the P-glycoprotein-overexpressing NCI-ADR-RES and Messa/Dx5MDR cell lines. Compounds 22 and 27 suppressed in vitro the Hedgehog signaling pathway, strongly reducing luciferase activity in SAG treated NIH3T3 Shh-Light II cells, and inhibited the growth of medulloblastoma D283 cells at nanomolar concentrations. ARAPs 22 and 27 represent a new potent class of tubulin polymerization and cancer cell growth inhibitors with the potential to inhibit the Hedgehog signaling pathway.

  DOI：

  10.1021/jm500561a
• 作为产物：
  描述：

  3-羟基-4-甲氧基苯甲酸甲酯 、 异丙醇 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙酸乙酯 为溶剂， 生成 methyl 3-isopropoxy-4-methoxybenzoate
  参考文献：
  名称：

  Tetrahydroisoquinoline derivatives for treating protein trafficking diseases

  摘要：

  本文披露了四氢异喹啉衍生物、包含它们的药物组合物以及治疗疾病的方法。所披露的化合物在治疗和预防由氯离子通道活性和/或蛋白质运输介导的疾病方面是有用的，包括但不限于与黏液纤毛清除受损有关的疾病，如囊性纤维化、支气管炎、肺气肿等。

  公开号：

  US20050176761A1

文献信息

• New Pyrrole Derivatives with Potent Tubulin Polymerization Inhibiting Activity As Anticancer Agents Including Hedgehog-Dependent Cancer
  作者：Giuseppe La Regina、Ruoli Bai、Antonio Coluccia、Valeria Famiglini、Sveva Pelliccia、Sara Passacantilli、Carmela Mazzoccoli、Vitalba Ruggieri、Lorenza Sisinni、Alessio Bolognesi、Whilelmina Maria Rensen、Andrea Miele、Marianna Nalli、Romina Alfonsi、Lucia Di Marcotullio、Alberto Gulino、Andrea Brancale、Ettore Novellino、Giulio Dondio、Stefania Vultaggio、Mario Varasi、Ciro Mercurio、Ernest Hamel、Patrizia Lavia、Romano Silvestri

  DOI：10.1021/jm500561a

  日期：2014.8.14

  We synthesized 3-aroyl-1-arylpyrrole (ARAP) derivatives as potential anticancer agents having different substituents at the pendant 1-phenyl ring. Both the 1-phenyl ring and 3-(3,4,5-trimethoxyphenyl)carbonyl moieties were mandatory to achieve potent inhibition of tubulin polymerization, binding of colchicine to tubulin, and cancer cell growth. ARAP 22 showed strong inhibition of the P-glycoprotein-overexpressing NCI-ADR-RES and Messa/Dx5MDR cell lines. Compounds 22 and 27 suppressed in vitro the Hedgehog signaling pathway, strongly reducing luciferase activity in SAG treated NIH3T3 Shh-Light II cells, and inhibited the growth of medulloblastoma D283 cells at nanomolar concentrations. ARAPs 22 and 27 represent a new potent class of tubulin polymerization and cancer cell growth inhibitors with the potential to inhibit the Hedgehog signaling pathway.
• Tetrahydroisoquinoline derivatives for treating protein trafficking diseases
  申请人：Pregel J. Marko

  公开号：US20050176761A1

  公开（公告）日：2005-08-11

  Tetrhydroisoquinoline derivatives, pharmaceutical compositions comprising them and methods of treating disease are disclosed herein. The disclosed compounds are useful in the treatment and prevention of diseases mediated by chloride channel activity and/or protein trafficking, including, but not limited to, diseases associated with impaired mucociliary clearance such as cystic fibrosis, bronchitis, emphysema, and the like.

  本文披露了四氢异喹啉衍生物、包含它们的药物组合物以及治疗疾病的方法。所披露的化合物在治疗和预防由氯离子通道活性和/或蛋白质运输介导的疾病方面是有用的，包括但不限于与黏液纤毛清除受损有关的疾病，如囊性纤维化、支气管炎、肺气肿等。