(E)-2-(3,4-dimethoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan | 41744-29-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (E)-2-(3,4-dimethoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan
• 英文别名: Eupomatenoid 4；eupomatenoid-4；2-(3,4-Dimethoxyphenyl)-3-methyl-5-(prop-1-en-1-yl)benzofuran；2-(3,4-dimethoxyphenyl)-3-methyl-5-[(E)-prop-1-enyl]-1-benzofuran
• CAS: 41744-29-0
• 化学式: C₂₀H₂₀O₃
• 分子量: 308.377
• InChiKey: HKMQKWZDPMJSBO-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,3,5-tribromo-2,3-dihydrobenzofuran 在 1,2-双(二苯基膦)乙烷氯化镍 氢氧化钾 、 溴 、 叔丁基锂 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 正戊烷 为溶剂， 反应 38.67h， 生成 (E)-2-(3,4-dimethoxyphenyl)-3-methyl-5-(prop-1-enyl)benzo[b]furan
  参考文献：
  名称：

  Bach, Thorsten; Bartels, Marc, Synthesis, 2003, # 6, p. 925 - 939

  摘要：

  DOI：

文献信息

• Activity of Neolignans Isolated from Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi
  作者：Patrícia Shima Luize、Tânia Ueda-Nakamura、Benedito Prado Dias Filho、Diógenes Aparício Garcia Cortez、Celso Vataru Nakamura

  DOI：10.1248/bpb.29.2126

  日期：——

  The in vitro antiproliferative effects of 4 neolignans purified from the ethyl-acetate extract from leaves of Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK against Trypanosoma cruzi were investigated. These isolated compounds were identified through spectral analyses of UV, EI-MS, 1H-, 13C-NMR, H–H COSY, gNOE, HETCOR, and HMBC. The compounds eupomatenoid-5, eupomatenoid-6, and conocarpan showed considerable activity against epimastigote forms of T. cruzi, with 50% inhibition concentrations (IC50) of 7.0, 7.5, and 8.0 μg/ml respectively. After methylation, these compounds showed a lessened inhibitory activity to the growth of the protozoan, suggesting that loss of the hydroxyl group from their molecules reduces the activity. The compound eupomatenoid-3 showed lower activity than the hexane fraction. Eupomatenoid-5 was significantly more active than benznidazole, the antiparasitic drug of choice for treatment of Chagas' disease. The crude extract, hexane fraction, and eupomatenoid-5 caused no lysis in sheep blood at concentrations which inhibit the growth of epimastigote forms. The compound eupomatenoid-5 showed low cytotoxic effects against Vero cells. These results provide new perspectives on the development of novel drugs obtained from natural products with trypanocidal activity. However, the extracts and active compound isolated from P. regnellii var. pallescens should be further studied in animal models for in vivo efficacy.

  研究了从 Piper regnellii (MIQ.) C. DC. var. pallescens (C. DC.) YUNCK 叶子的乙酸乙酯提取物中纯化的 4 种新木质素对克鲁斯锥虫的体外抗增殖作用。通过紫外光谱、EI-MS、1H-、13C-NMR、H-H COSY、gNOE、HETCOR 和 HMBC 等光谱分析鉴定了这些分离化合物。化合物 eupomatenoid-5、eupomatenoid-6 和 conocarpan 对 T. cruzi 的表皮原虫具有相当高的活性，其 50% 抑制浓度（IC50）分别为 7.0、7.5 和 8.0 μg/ml。甲基化后，这些化合物对原生动物生长的抑制活性减弱，表明其分子中羟基的缺失降低了活性。化合物 eupomatenoid-3 的活性低于正己烷馏分。Eupomatenoid-5 的活性明显高于苯并咪唑，后者是治疗南美锥虫病的首选抗寄生虫药物。粗萃取物、正己烷馏分和 eupomatenoid-5 在绵羊血液中不会造成裂解，其浓度可抑制上皮细胞的生长。化合物 eupomatenoid-5 对 Vero 细胞的细胞毒性较低。这些结果为从具有杀锥虫活性的天然产物中开发新型药物提供了新的视角。然而，从 P. regnellii var. pallescens 中分离出的提取物和活性化合物还需要在动物模型中进一步研究其体内疗效。
• Synthesis of eupomatenoids by three consecutive transition metal-catalyzed cross-coupling reactions
  作者：Thorsten Bach、Marc Bartels

  DOI：10.1016/s0040-4039(02)02287-6

  日期：2002.12

  Six different eupomatenoids (1a-c, 1f-h) were prepared from 2,3,5-tribroinobenzofuran (2) in a concise and high-yielding synthetic sequence. The overall yields vary between 29 and 60% over four to six steps. Key to the success of the syntheses is the high regioselectivity achieved in three Pd(0)- and Ni(0)-catalyzed cross-coupling reactions which were conducted consecutively. The order of substitution at the benzofuran nucleus is C-2, C-5 and C-3. (C) 2002 Elsevier Science Ltd. All rights reserved.
• McKittrick, Brian A.; Stevenson, Robert, Journal of the Chemical Society. Perkin transactions I, 1983, # 2, p. 475 - 482
  作者：McKittrick, Brian A.、Stevenson, Robert

  DOI：——

  日期：——
• Bach, Thorsten; Bartels, Marc, Synthesis, 2003, # 6, p. 925 - 939
  作者：Bach, Thorsten、Bartels, Marc

  DOI：——

  日期：——