acerogenin A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: acerogenin A
• 英文别名: 2-Oxatricyclo[13.2.2.13,7]icosa-1(17),3,5,7(20),15,18-hexaene-4,12-diol
• 化学式: C₁₉H₂₂O₃
• 分子量: 298.382
• InChiKey: JHRMYLCWJWLUQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基3-(3-羟基-4-甲氧基苯基)丙酸酯 在 palladium on activated charcoal 吡啶 、 盐酸 、 sodium tetrahydroborate 、 lithium aluminium tetrahydride 、 三氯化铝 、 亚硝酸特丁酯 、 氢气 、 三氯化硼 、 sodium hydride 、 potassium carbonate 、 cesium fluoride 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 121.32h， 生成 acerogenin A
  参考文献：
  名称：

  Acerogenin型大环化合物合成的统一策略：Acerogenins A，B，C和L与Aceroside IV的总合成。

  摘要：

  已经开发了用于合成含有环内联芳基醚键的铜绿蛋白原型二芳基庚烷类化合物的一般策略，并且已经完成了铜绿蛋白原A，B，C和L以及皂苷IV的会聚总合成。线性二芳基庚烷1-（4-氟-3-硝基苯基）-7-（3-羟基-4-甲氧基苯基）庚烷-3-酮（18）在温和条件下（CsF，DMF，0.01 M，rt，5的环醚化） h）得到大环化合物4-甲氧基-17-硝基-2-氧杂三环[13.2.2（3,7）]二十碳-1（18），3,5,7（20），15（19），16-己烯-12一（19），产率95％。除去硝基，然后进行O-去甲基化，得到了金黄色素A（2），还原后得到了金黄色素A（1）。用2,3,4,6-α-D-四苯甲酰基吡喃葡萄糖基溴化物对2进行糖苷化，然后进行皂化，从而得到极好的总收率的皂苷IV（3）。以类似于线性化合物29的关键分子内S（N）Ar反应的方式合成了Acerogenins B（4）和L（5）。提出了环

  DOI：

  10.1021/jo981844s

文献信息

• Synthesis of Acerogenin C and (+)-Acerogenin A, Two Macrocyclic Diarylheptanoid Constituents ofAcer nikoense
  作者：György Miklós Keserü、Mihály Nógrádi、Áron Szöllösy

  DOI：10.1002/(sici)1099-0690(199803)1998:3<521::aid-ejoc521>3.0.co;2-i

  日期：1998.3

  The macrocyclic ketone acerogenin C (3) and the corresponding alcohol (+)-accerogenin A (1), diarylheptanoid constituents of the maple Acer nikoense were synthesized. The key steps were the selective reduction of the double bond of an α,β-unsaturated ketone (10) and macrocyclization of an iodophenol (13) by a modified Ullmann diarylether synthesis.

  合成了大环酮 acerogenin C (3) 和相应的醇 (+)-accerogenin A (1)，合成了枫树 Acer nikoense 的 diarylheptanoid 成分。关键步骤是通过改进的 Ullmann 二芳醚合成选择性还原 α,β-不饱和酮 (10) 的双键和碘苯酚 (13) 的大环化。
• PHARMACEUTICAL COMPOSITION FOR PREVENTION AND/OR TREATMENT OF BONE DISEASE, FUNCTIONAL FOOD OR HEALTH FOOD COMPRISING THE COMPOSITION, AND PHARMACEUTICAL PREPARATION COMPRISING THE COMPOSITION AS ACTIVE INGREDIENT
  申请人：Akihisa, Toshihiro

  公开号：EP2050442A1

  公开（公告）日：2009-04-22

  The present invention provides a highly safe pharmaceutical composition for preventing and/or treating bone disease, a pharmaceutical preparation comprising thereof, a health food comprising thereof, a functional food comprising thereof. Since the present invention comprises the arylheptanoid compound shown in the following formula (I) and the derivatives thereof, it enables to prevent and/or treat the bone disease. (In the formula (I), R1 and R5 are a functional group selected from the group consisting of a hydrogen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R2, R3, and R4 are a functional group selected from the group consisting of a hydrogen atom, an oxygen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R5 may be bound on meta-position against heptylene group of another aryl group to form a ring.)

  本发明提供了一种用于预防和/或治疗骨病的高安全性药物组合物、由其组成的药物制剂、由其组成的保健食品、由其组成的功能性食品。由于本发明包含下式（I）所示的芳基庚烷类化合物及其衍生物，因此能够预防和/或治疗骨病。 (在式(I)中，R1和R5是选自氢原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R2、R3和R4是选自氢原子、氧原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R5可与另一芳基的庚基在元位置上结合形成环)。
• Pharmaceutical composition for prevention and/or treatment of bone disease, functional food or health food comprising the composition, and pharmaceutical preparation comprising the composition as active ingredient
  申请人：Akihisa, Toshihiro

  公开号：EP2407160A1

  公开（公告）日：2012-01-18

  The present invention provides a highly safe pharmaceutical composition for preventing and/or treating bone disease, a pharmaceutical preparation comprising thereof, a health food comprising thereof, a functional food comprising thereof. Since the present invention comprises the arylheptanoid compound shown in the following formula (I) and the derivatives thereof, it enables to prevent and/or treat the bone disease. (In the formula (I), R1 and R5 are a functional group selected from the group consisting of a hydrogen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R2, R3, and R4 are a functional group selected from the group consisting of a hydrogen atom, an oxygen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R5 may be bound on meta-position against heptylene group of another aryl group to form a ring.)

  本发明提供了一种用于预防和/或治疗骨病的高安全性药物组合物、由其组成的药物制剂、由其组成的保健食品、由其组成的功能性食品。由于本发明包含下式（I）所示的芳基庚烷类化合物及其衍生物，因此能够预防和/或治疗骨病。 (在式(I)中，R1和R5是选自氢原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R2、R3和R4是选自氢原子、氧原子、碳原子数为1至3的烷基、单糖和二糖的官能团；R5可与另一芳基的庚基在元位置上结合形成环)。
• Total synthesis of ovalifoliolatin B, acerogenins A and C
  作者：G.D. Kishore Kumar、Amarnath Natarajan

  DOI：10.1016/j.tetlet.2008.01.135

  日期：2008.3

  A short and concise route for the synthesis of ovalifoliolatin B, a highly strained macrocyclic diaryl ether heptanoid natural product that also provides quick access to acerogenins A and C natural products has been reported. (C) 2008 Elsevier Ltd. All rights reserved.
• PHARMACEUTICAL COMPOSITION FOR PREVENTING AND/OR TREATING BONE DISEASE, FUNCTIONAL FOOD OR HEALTH FOOD AND PHARMACEUTICAL PREPARATION COMPRISING THEREOF AS ACTIVE INGREDIENT
  申请人：Woo Je-Tae

  公开号：US20090227527A1

  公开（公告）日：2009-09-10

  The present invention provides a highly safe pharmaceutical composition for preventing and/or treating bone disease, a pharmaceutical preparation comprising thereof, a health food comprising thereof, a functional food comprising thereof. Since the present invention comprises the arylheptanoid compound shown in the following formula (I) and the derivatives thereof, it enables to prevent and/or treat the bone disease. (In the formula (I), R 1 and R 5 are a functional group selected from the group consisting of a hydrogen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R 2 , R 3 , and R 4 are a functional group selected from the group consisting of a hydrogen atom, an oxygen atom, alkyl group having carbon numbers 1 to 3, monosaccharide and disaccharide; R 5 may be bound on meta-position against heptylene group of another aryl group to form a ring.)