4'-羟基-3'-甲氧基-1,2-二苯基乙烷 | 10366-19-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 4'-羟基-3'-甲氧基-1,2-二苯基乙烷
• 中文别名: 苯酚,2-甲氧基-4-(2-苯基乙基)-
• 英文名称: 4'-hydroxy-3'-methoxy-1,2-diphenylethane
• 英文别名: 4-hydroxy-3-methoxydihydrostilbene；2-methoxy-4-(2-phenylethyl)phenol；4-hydroxy-3-methoxybibenzyl；3-Methoxy-4-hydroxyphenylethylbenzene；3-Methoxy-4-hydroxybibenzyl
• CAS: 10366-19-5
• 化学式: C₁₅H₁₆O₂
• 分子量: 228.291
• InChiKey: MYGRKYSLUYYRKG-UHFFFAOYSA-N

物化性质

• 沸点：
  348.2±27.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4'-羟基-3'-甲氧基-1,2-二苯基乙烷 在 硝酸 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以44%的产率得到2-Methoxy-6-nitro-4-(2-phenylethyl)phenol
  参考文献：
  名称：

  Synthesis of 1-(3,4-Dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and Derivatives as Potent and Long-Acting Peripheral Inhibitors of Catechol-O-methyltransferase

  摘要：

  A homologous series of novel nitro-catechol structures (7a-7e) were synthesized and tested as inhibitors of the enzyme catechol-O-methyltransferase (COMT). Increasing chain length was found to have significant impact on both brain penetration and duration of COMT inhibition in the rat. Of this series, compound 7b (1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone) was found to exhibit the most potent and selective inhibition of peripheral COMT, with an inhibition profile more similar to entacapone 2 than tolcapone 1 (an equipotent peripheral and central inhibitor) but with much improved duration of action (7b, 70% inhibition and 2, 25% inhibition at 9 h after administration). The effects of structural modifications to 7b on COMT inhibitory profile were investigated, and it is concluded that the carbonyl group and preferably unsubstituted aromatic ring are essential features to maintain prolonged peripheral COMT inhibition. The introduction of the alpha-methylene group, the major structural difference between 7b and 1, would appear responsible for the observed enhancement in selectivity of peripheral COMT inhibition of 7b, which has more limited access to the brain than 1.

  DOI：

  10.1021/jm0109964
• 作为产物：
  描述：

  1-(4-benzyloxy-3-methoxyphenyl)-2-phenyl-ethanol 在 10percent Pd/C 盐酸 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以98%的产率得到4'-羟基-3'-甲氧基-1,2-二苯基乙烷
  参考文献：
  名称：

  Synthesis of 1-(3,4-Dihydroxy-5-nitrophenyl)-2-phenyl-ethanone and Derivatives as Potent and Long-Acting Peripheral Inhibitors of Catechol-O-methyltransferase

  摘要：

  A homologous series of novel nitro-catechol structures (7a-7e) were synthesized and tested as inhibitors of the enzyme catechol-O-methyltransferase (COMT). Increasing chain length was found to have significant impact on both brain penetration and duration of COMT inhibition in the rat. Of this series, compound 7b (1-(3,4-dihydroxy-5-nitrophenyl)-2-phenyl-ethanone) was found to exhibit the most potent and selective inhibition of peripheral COMT, with an inhibition profile more similar to entacapone 2 than tolcapone 1 (an equipotent peripheral and central inhibitor) but with much improved duration of action (7b, 70% inhibition and 2, 25% inhibition at 9 h after administration). The effects of structural modifications to 7b on COMT inhibitory profile were investigated, and it is concluded that the carbonyl group and preferably unsubstituted aromatic ring are essential features to maintain prolonged peripheral COMT inhibition. The introduction of the alpha-methylene group, the major structural difference between 7b and 1, would appear responsible for the observed enhancement in selectivity of peripheral COMT inhibition of 7b, which has more limited access to the brain than 1.

  DOI：

  10.1021/jm0109964

文献信息

• Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
  作者：Lindon W. K. Moodie、Rozenn Trepos、Gunnar Cervin、Kari Anne Bråthen、Bente Lindgård、Rigmor Reiersen、Patrick Cahill、Henrik Pavia、Claire Hellio、Johan Svenson

  DOI：10.1021/acs.jnatprod.7b00129

  日期：2017.7.28

  The species of microalgae examined displayed a particular sensitivity toward the evaluated compounds at low ng/mL concentrations. It was shown that several of the natural and synthetic compounds exerted their repelling activities via nontoxic and reversible mechanisms. The activities of the most active compounds such as 3,5-dimethoxybibenzyl (5), 3,4-dimethoxybibenzyl (9), and 3-hydroxy-3′,4,5′-trimethoxybibenzyl

  本研究报告了对海洋环境中化感作用的陆地天然产物作为防污剂的首次综合评估。为了研究天然二氢二苯乙烯支架的防污潜力，制备了22种具有不同取代模式的合成二氢二苯乙烯类化合物的文库，并评估了它们的防污能力，其中许多取代型自然存在于陆生植物中。在针对16种污染海洋生物的广泛筛选中评估了这些化合物。研究表明，二氢二苯乙烯骨架对海洋微污垢和大型污垢均具有强大的一般防污效果，并在低浓度下具有抑制活性。在低ng / mL浓度下，所检查的微藻物种对所评估的化合物表现出特殊的敏感性。结果表明，几种天然和合成化合物均通过无毒和可逆的机制发挥其排斥作用。活性最高的化合物，例如3,5-二甲氧基联苄（5），3，4-二甲氧基联苄基（9）和3-羟基-3′，4，5′-三甲氧基联苄基（20）与用作防污助剂的商业防污剂Sea-n相当。陆地化感化天然产物对付海洋污染的研究代表了一种设计“绿色”防污技术的新颖策略，这些化合物为传统的杀生物防污剂提供了潜在的替代品。
• Structure-fungicidal properties of some 3- and 4-hydroxylated stilbenes and bibenzyl analogues
  作者：T.P. Schultz、W.D. Boldin、T.H. Fisher、D.D. Nicholas、K.D. Mcmurtrey、K. Pobanz

  DOI：10.1016/s0031-9422(00)97531-9

  日期：1992.1

  hypothesis that white-rot extracellular enzymes oxidatively degrade stilbenes which makes white-rot fungi immune to stilbenes may need to be reexamined. No structure-activity relationship was apparent for stilbenes tested against the two brown-rot fungi Gloeophyllum trabeum and Poria placenta . Of the two natural hydroxylated stilbenes studied, pinosylvin was slightly more active against G. trabeum and

  摘要 使用琼脂平板技术测定了一些取代羟基二苯乙烯和联苄对三种破坏木材的真菌的杀真菌活性。四种 3-羟基二苯乙烯衍生物和 3-羟基-联苄对白腐真菌 Coriolus versicolor 具有活性。提出了二苯乙烯 C. versicolor 活性的初步构效关系。先前提出的假设，即白腐菌胞外酶氧化降解芪类，从而使白腐类真菌对芪类免疫，可能需要重新研究。对于两种褐腐真菌 Gloeophyllum trabeum 和 Poria placenta 测试的芪，没有明显的构效关系。在研究的两种天然羟基化芪中，松香素对 G. trabeum 和 C. 杂色比松香素单甲醚。令人惊讶的是，这两种天然二苯乙烯都没有显示出对耐铜真菌胎盘假单胞菌的大量活性。
• GUANIDINOBENZOIC ACID COMPOUND
  申请人：Fujiyasu Jiro

  公开号：US20140378459A1

  公开（公告）日：2014-12-25

  [Problem] Provided is a compound which is useful as an agent for preventing and/or treating renal diseases. [Means for Solution] The present inventors have conducted extensive studies on compounds having a trypsin inhibitory action, and as a result, they have found that a guanidinobenzoic acid compound has a trypsin inhibitory action, thereby completing the present invention. The guanidinobenzoic acid compound of the present invention can be used as an agent for preventing and/or treating renal disease as an agent which will substitute low-protein diet therapy, and an agent for preventing and/or treating trypsin-related diseases, for example, pancreatitis, gastroesophageal reflux disease, hepatic encephalopathy, influenza, and the like.

  [问题] 提供了一种化合物，可用作预防和/或治疗肾脏疾病的药剂。[解决方案] 现有发明人对具有胰蛋白酶抑制作用的化合物进行了广泛的研究，结果发现一种鸟氨酸苯甲酸化合物具有胰蛋白酶抑制作用，从而完成了本发明。本发明的鸟氨酸苯甲酸化合物可用作代替低蛋白饮食疗法的药剂，以及预防和/或治疗胰蛋白酶相关疾病（例如，胰腺炎，胃食管反流病，肝性脑病，流感等）的药剂。
• [EN] 9,10-DIHYDROPHENANTHRENE COMPOUNDS AND USE THEREOF IN TREATMENT OF LIVER INJURY<br/>[FR] COMPOSÉS DE 9,10-DIHYDROPHÉNANTHRÈNE ET LEUR UTILISATION DANS LE TRAITEMENT D'UNE LÉSION HÉPATIQUE<br/>[ZH] 9,10-二氢菲类化合物及其用于肝损伤治疗的用途
  申请人：SHANGHAI INST MATERIA MEDICA CAS

  公开号：WO2021160139A1

  公开（公告）日：2021-08-19

  一类9,10-二氢菲类化合物及其用于肝损伤治疗的用途，具体地，提供了一类式I化合物或式II化合物，其在肝组织中表现出抗炎以及抗氧化活性，因而可以用于肝损伤类疾病，尤其是炎症和脂质过氧化为病理学基础的肝损伤类疾病的治疗或预防。
• Tori, Motoo; Sono, Masakazu; Takikawa, Keiko, Journal of Chemical Research, Miniprint, 1999, # 8, p. 2001 - 2019
  作者：Tori, Motoo、Sono, Masakazu、Takikawa, Keiko、Matsuda, Reiko、Toyota, Masao、Cheminat, Annie、Asakawa, Yoshinori

  DOI：——

  日期：——