2′-hydroxy-3,4,5-trimethoxybibenzyl | 65817-45-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: 2′-hydroxy-3,4,5-trimethoxybibenzyl
• 英文别名: 2-[2-(3,4,5-trimethoxyphenyl)ethyl]phenol；batatasin V；Batatasin V <2'-Hydroxy-3,4,5-trimethoxybibenzyl>；Batatasin V (2'-Hydroxy-3,4,5-trimethoxybibenzyl)
• CAS: 65817-45-0
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: CCENYSCLQOJNIC-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±40.0 °C(Predicted)
• 密度：
  1.137±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.92
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2′-hydroxy-3,4,5-trimethoxybibenzyl 、 3,4-二甲氧基苄氯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 12.25h， 生成 1-[(3,4-dimethoxybenzyl)oxy]-2-[2-(3,4,5-trimethoxyphenyl)ethyl]benzene
  参考文献：
  名称：

  SAR study on arylmethyloxyphenyl scaffold: Looking for a P-gp nanomolar affinity

  摘要：

  Starting from the previously developed P-gp ligands 1a and 1b (EC50 = 0.25 mu M and 0.65 mu M, respectively), new arylmethyloxyphenyl derivatives have been synthesized as P-gp modulators in order to investigate: (i) the effect of small electron-donor groups (OMe) (5-11), (ii) the effect of the replacement of methoxy groups with an electron-withdrawal substituent (Cl) on C-ring (13) (iii) the effect induced by the replacement of C-ring with heteroaromatic cycles such as thiophene and pyrimidine (13, 15, 16), (iv) the effect induced by molecular constriction on C ring (14,17,18) on P-gp modulating activity. The results demonstrated that P-gp inhibition potency is strongly correlated to the number of methoxy groups in the A-ring whereas the methoxylation of C-ring seems to poorly affect P-gp activity. The best result was found for compound 10 that displays a nanomolar affinity (EC50 = 7.1 nM) towards P-gp pump and, in the meantime lacks of activity against MRP1 pump. (C) 2014 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2014.02.051
• 作为产物：
  描述：

  [(3,4,5-trimethoxyphenyl)methyl]phosphoric acid diethyl ester 在 碘 、 sodium hydride 作用下， 以 四氢呋喃 、 环己烷 为溶剂， 反应 23.0h， 生成 2′-hydroxy-3,4,5-trimethoxybibenzyl
  参考文献：
  名称：

  Naturally occurring Batatasins and their derivatives as α-glucosidase inhibitors

  摘要：

  自然产生的薯蓣素及其衍生物对α-葡萄糖苷酶显示出显著的抑制作用，为抗糖尿病药物开发提供了有希望的化学支架。

  DOI：

  10.1039/c5ra15328j

文献信息

• Synthesis and evaluation of inhibitory activity <i>in vitro</i> of dihydrostilbenes against human neutrophil elastases
  作者：Guo-Li Huang、Bo Liu、Xing-Jun Tian、Ye-Gao Chen

  DOI：10.1080/10286020.2019.1571489

  日期：2020.4.2

  Twelve dihydrostilbenes (including five new analogues) were prepared by the Witting-Hornor reaction from appropriate aromatic aldehydes and phosphonate esters, followed by hydrogenation in five steps. The in vitro inhibition activity against human neutrophil elastase (HNE) of these dihydrostilbenes was evaluated, and three 1,2-dihydroxylated dihydrostilbenes (6b, 6j, and 6l) exhibited stronger inhibitory

  通过Witting-Hornor反应，由适当的芳族醛和膦酸酯制备十二种二氢苯乙烯（包括五个新的类似物），然后分五个步骤进行氢化。评估了这些二氢芪酯对人中性粒细胞弹性蛋白酶（HNE）的体外抑制活性，并且三个1,2-二羟基化二氢芪酯（6b，6j和6l）对HNE的抑制活性比其他类似物强。
• .alpha.-.omega.-diarylalkane compounds serotonin-2 receptor agonists
  申请人：Sankyo Company, Limited

  公开号：US05556864A1

  公开（公告）日：1996-09-17

  Compounds of formula (I): ##STR1## [wherein: R.sup.1 is aryl; R.sup.2 is hydrogen, alkyl, alkoxy, halogen or cyano; R.sup.3 is a group of formula --B--NR.sup.4 R.sup.5, where R.sup.4 and R.sup.5 are independently hydrogen, alkyl or substituted alkyl or R.sup.4 and R.sup.5, together with the nitrogen to which they are attached, form a heterocycle, and B is alkylene or a group of formula --CH.sub.2 CH(OR.sup.6)CH.sub.2 --, where R.sup.6 is hydrogen, alkanoyl, substituted alkanoyl or arylcarbonyl, or a group of formula --D--R.sup.7, where D is a single bond or alkylene and R.sup.7 is a heterocycle; and A is alkylene; and pharmaceutically acceptable salts and esters thereof] are useful for the treatment and prevention of circulatory diseases and psychosis.

  化合物的化学式（I）：##STR1## [其中：R.sup.1是芳基；R.sup.2是氢、烷基、烷氧基、卤素或氰基；R.sup.3是化学式--B--NR.sup.4R.sup.5的基团，其中R.sup.4和R.sup.5独立地是氢、烷基或取代烷基或R.sup.4和R.sup.5与它们连接的氮一起形成杂环，B是烷基或化学式--CH.sub.2CH(OR.sup.6)CH.sub.2--的基团，其中R.sup.6是氢、烷酰基、取代烷酰基或芳基甲酰基，或化学式--D--R.sup.7的基团，其中D是单键或烷基且R.sup.7是杂环；A是烷基；以及其药学上可接受的盐和酯] 用于治疗和预防循环系统疾病和精神病。
• Structures and synthesis of the growth inhibitors batatasins IV and V, and their physiological activities
  作者：Tohru Hashimoto、Misao Tajima

  DOI：10.1016/s0031-9422(00)94310-3

  日期：1978.1

  compounds, batatasins IV and V were isolated from dormant bulbils of Chinese yam ( Dioscorea batatas ) and shown to be 2′,3-dihydroxy-5-methoxybibenzyl and 2′-hydroxy-3,4,5-trimethoxybibenzyl, respectively. An analogue, 3,4′-dihydroxy-5-methoxybibenzyl was synthesized. Inhibitory activities of these three compounds as well as batatasin I (6-hydroxy-2,4,7-trimethoxyphenanthrene) and batatasin III (3,3

  摘要 从中国山药 ( Dioscorea batatas ) 休眠球茎中分离得到两种新化合物 batatasin IV 和 V，分别为 2',3-二羟基-5-甲氧基联苯甲基和 2'-羟基-3,4,5-三甲氧基联苯甲基. 合成了类似物 3,4'-二羟基-5-甲氧基联苯。这三种化合物以及batatasin I（6-羟基-2,4,7-三甲氧基菲）和batatasin III（3,3'-二羟基-5-甲氧基-联苄基）在生菜种子萌发、生菜下胚轴伸长和描述了小麦胚芽鞘切片伸长率测试。
• Phenoxyalkylamines, -pyrrolidines and -piperidines for the treatment and prevention of circulatory diseases and psychosis
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0600717A1

  公开（公告）日：1994-06-08

  Compounds of formula (I): [wherein: R¹ is aryl; R² is hydrogen, alkyl, alkoxy, halogen or cyano; R³ is a group of formula -B-NR⁴R⁵, where R⁴ and R⁵ are independently hydrogen, alkyl or substituted alkyl or R⁴ and R⁵, together with the nitrogen to which they are attached, form a heterocycle, and B is alkylene or a group of formula -CH₂CH(OR⁶ )CH₂-, where R⁶ is hydrogen, alkanoyl, substituted alkanoyl or arylcarbonyl, or a group of formula -D-R⁷, where D is a single bond or alkylene and R⁷ is a heterocycle; and A is alkylene; and pharmaceutically acceptable salts and esters thereof] are useful for the treatment and prevention of circulatory diseases and psychosis.

  式(I)的化合物：[其中：R¹为芳基；R²为氢、烷基、烷氧基、卤素或氰基；R³为式-B-NR⁴R⁵的基团，其中R⁴和R⁵独立地为氢、烷基或取代烷基，或者R⁴和R⁵与它们所连接的氮一起形成杂环，B为烷基或式-CH₂CH(OR⁶)CH₂-的基团，其中R⁶为氢、烷酰基、取代烷酰基或芳基羰基，或式-D-R⁷的基团，其中D为单键或烷基烯丙基，R⁷为杂环；且A为烷基；以及其药学上可接受的盐和酯]可用于治疗和预防循环系统疾病和精神病。
• Use of alpha, omega-diarylalkane derivatives in the treatment and prevention of psychosis
  申请人：SANKYO COMPANY LIMITED

  公开号：EP0844000A1

  公开（公告）日：1998-05-27

  Compounds of formula (I): [wherein: R1 is aryl; R2 is hydrogen, alkyl, alkoxy, halogen or cyano; R3 is a group of formula -B-NR4R5, where R4 and R5 are independently hydrogen, alkyl or substituted alkyl or R4 and R5, together with the nitrogen to which they are attached, form a heterocycle, and B is alkylene or a group of formula -CH2CH(OR6)CH2-, where R6 is hydrogen, alkanoyl, substituted alkanoyl or arylcarbonyl, or a group of formula -D-R7, where D is a single bond or alkylene and R7 is a heterocycle; and A is alkylene; and pharmaceutically acceptable salts and esters thereof] are useful for the treatment and prevention of psychosis.

  式(I)化合物： 其中R1 是芳基；R2 是氢、烷基、烷氧基、卤素或氰基；R3 是式-B-NR4R5 的基团，其中 R4 和 R5 独立地是氢、烷基或取代的烷基，或 R4 和 R5 与它们所连接的氮一起构成杂环，B 是亚烷基或式- CH(OR6)CH2-的基团，其中 R6 是氢、烷酰基、取代的烷酰基或芳羰基，或式-D-R7 的基团，其中 D 是单键或亚烷基，R7 是杂环；和 A 是亚烷基；及其药学上可接受的盐和酯]可用于治疗和预防精神病。