1-(3,4-dimethoxyphenyl)-4-phenylbutane-1,4-dione | 67756-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3,4-dimethoxyphenyl)-4-phenylbutane-1,4-dione
• 英文别名: 1-(3,4-Dimethoxyphenyl)-4-phenyl-1,4-butandion；1-(3,4-Dimethoxyphenyl)-4-phenylbutane-1,4-dione
• CAS: 67756-25-6
• 化学式: C₁₈H₁₈O₄
• 分子量: 298.339
• InChiKey: ROHBOLHZFHKZJK-UHFFFAOYSA-N

物化性质

• 沸点：
  475.7±35.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(3,4-dimethoxyphenyl)-4-phenylbutane-1,4-dione 在 三氟甲磺酸 作用下， 以 乙腈 为溶剂， 反应 0.33h， 以75%的产率得到2-(3,4-dimethoxyphenyl)-5-phenylfuran
  参考文献：
  名称：

  新型木聚糖基二芳基-四氢呋喃和-呋喃类似物的合成和二维DSAR研究，对克鲁斯锥虫具有显着活性，并评估了锥虫硫醚还原酶的活性

  摘要：

  合成了两个系列的二芳基-四氢呋喃和-呋喃，并针对锥虫病（锥虫）的锥虫病和锥虫病形式，对锥虫的抗锥虫活性进行了筛选。基于有证据表明，对天然产物进行修饰可能比天然产物本身更有效，并且使用已知的新木脂素抑制剂veraguensin 1和grandisin 2作为模板来合成更简单的类似物，发现对于3具有显着的抗锥虫活性和选择性EC 50 0.01μM和EC 50的1,5-二甲氧基化二芳基呋喃5c和2,4-二甲氧基化二芳基-四氢呋喃4e类似物分别为0.75μM，前者的效力比维拉菌素1高260倍，比苯甲硝唑（目前可用于查加斯病治疗的药物）强150倍。测试了最有效的抗锥虫类化合物穿透感染了克氏锥虫变形虫的LLC-MK2细胞的能力，揭示了4e和5e类似物是最有效的，不会对哺乳动物细胞造成损害。特别地，大多数衍生物对小鼠脾细胞无毒。2D-QSAR研究表明，刚性中心核和二甲氧基-芳基取代基的位置极大地影响了抗

  DOI：

  10.1016/j.ejmech.2017.08.064
• 作为产物：
  描述：

  1-(3,4-dimethoxyphenyl)-4-phenylbutane-1,4-diol 在 2-碘酰基苯甲酸 作用下， 以 乙酸乙酯 为溶剂， 生成 1-(3,4-dimethoxyphenyl)-4-phenylbutane-1,4-dione
  参考文献：
  名称：

  新型木聚糖基二芳基-四氢呋喃和-呋喃类似物的合成和二维DSAR研究，对克鲁斯锥虫具有显着活性，并评估了锥虫硫醚还原酶的活性

  摘要：

  合成了两个系列的二芳基-四氢呋喃和-呋喃，并针对锥虫病（锥虫）的锥虫病和锥虫病形式，对锥虫的抗锥虫活性进行了筛选。基于有证据表明，对天然产物进行修饰可能比天然产物本身更有效，并且使用已知的新木脂素抑制剂veraguensin 1和grandisin 2作为模板来合成更简单的类似物，发现对于3具有显着的抗锥虫活性和选择性EC 50 0.01μM和EC 50的1,5-二甲氧基化二芳基呋喃5c和2,4-二甲氧基化二芳基-四氢呋喃4e类似物分别为0.75μM，前者的效力比维拉菌素1高260倍，比苯甲硝唑（目前可用于查加斯病治疗的药物）强150倍。测试了最有效的抗锥虫类化合物穿透感染了克氏锥虫变形虫的LLC-MK2细胞的能力，揭示了4e和5e类似物是最有效的，不会对哺乳动物细胞造成损害。特别地，大多数衍生物对小鼠脾细胞无毒。2D-QSAR研究表明，刚性中心核和二甲氧基-芳基取代基的位置极大地影响了抗

  DOI：

  10.1016/j.ejmech.2017.08.064

文献信息

• Development of a Palladium-Catalyzed Carbonylative Coupling Strategy to 1,4-Diketones
  作者：Hongfei Yin、Dennis U. Nielsen、Mette K. Johansen、Anders T. Lindhardt、Troels Skrydstrup

  DOI：10.1021/acscatal.6b00733

  日期：2016.5.6

  We report on a three-component palladium-catalyzed coupling strategy for accessing a wide range of 1,4-diketones, which represent important precursors to heterocycles. Our method relies on a carbonylative Heck reaction employing substituted allylic alcohols, aryl iodides, and carbon monoxide. The reaction conditions are mild and do not require high CO pressure, and a wide functional group tolerance

  我们报告了一种三组分钯催化的偶联策略，可用于广泛的1,4-二酮，这些化合物代表杂环的重要前体。我们的方法依赖于采用取代的烯丙醇，芳基碘化物和一氧化碳的羰基Heck反应。反应条件温和并且不需要高的CO压力，并且揭示了宽的官能团耐受性，以中等至良好的产率提供了所需的1，4-二酮。此外，该方法适用于在羰基位置之一或两个位置选择性地安装13 C-碳同位素。
• γ-diketones as Wnt/β-catenin signaling pathway activators
  申请人：Samumed, LLC

  公开号：US10457672B2

  公开（公告）日：2019-10-29

  The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.

  本公开提供了γ-二酮或其类似物，它们能激活Wnt/β-catenin信号转导，从而治疗或预防与信号转导有关的疾病，如骨质疏松症和骨关节病；成骨不全症、骨缺损、骨折、牙周病、耳硬化症、伤口愈合、颅面缺损、溶瘤性骨病、脑外伤或脊柱损伤、脑萎缩/与中枢神经系统分化和发育有关的神经系统疾病，包括帕金森病、中风、缺血性脑病、癫痫、阿尔茨海默病、抑郁症、躁狂症、精神分裂症；耳部疾病，如耳蜗毛细胞缺失；眼部疾病，如老年性黄斑变性、糖尿病性黄斑水肿或视网膜色素变性；以及与干细胞分化和生长有关的疾病，如脱发、造血相关疾病和组织再生相关疾病。
• Synthesis and trypanocidal activity of 1,4-bis-(3,4,5-trimethoxy-phenyl)-1,4-butanediol and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol
  作者：Lilian Sibelle Campos Bernardes、Massuo Jorge Kato、Sérgio Albuquerque、Ivone Carvalho

  DOI：10.1016/j.bmc.2006.07.006

  日期：2006.11

  Chagas' disease is endemic in Central and South American countries. Specific chemotherapy with nifurtimox or benznidazole has been recommended for treatment of recent infection but they have limited efficacy. The natural products veraguensin (1) and grandisin (2) have shown potent in vitro activity against trypomastigote parasite (Y strain) with IC50 2.3 mu M (1) and 3.7 mu M (2). We report herein the synthesis and in vitro trypanocidal evaluation of symmetrical and unsymmetrical 1,4-diaryl-1,4-diol derivatives as potential trypanocidal analogs of natural compounds 1 and 2. Among the synthesized products, compounds 1,4-bis-(3,4,5-trimethoxyphenyl)-1,4-butanediol (6a) and 1,4-bis-(3,4-dimethoxyphenyl)-1,4-butanediol (6b) showed better activity against Trypanosoma cruzi trypomastigotes with IC50 100 and 105 mu M (Y strain), respectively, and 110 mu M (Bolivia strain) for both compounds. However, the most active compound of this series was 1,4-bis-(3,4-dimethoxyphenyl)butane-1,4-dione (7b) with IC50 10 and 200 mu M against Y and Bolivia strains, respectively. (c) 2006 Elsevier Ltd. All rights reserved.
• Stetter,H.; Nienhaus,J., Chemische Berichte, 1978, vol. 111, p. 2825 - 2832
  作者：Stetter,H.、Nienhaus,J.

  DOI：——

  日期：——
• GAMMA-DIKETONES AS WNT/BETA -CATENIN SIGNALING PATHWAY ACTIVATORS
  申请人：Samumed, LLC

  公开号：US20190055227A1

  公开（公告）日：2019-02-21

  The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.