tetrahydroobovatol | 83864-79-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: tetrahydroobovatol
• 英文别名: 5-propyl-3-(4-propylphenoxy)benzene-1,2-diol；JJK694；3-(4-propylphenoxy)-5-propylbenzene-1,2-diol；Tetrahydroobvatol
• CAS: 83864-79-3
• 化学式: C₁₈H₂₂O₃
• 分子量: 286.371
• InChiKey: OGJJXRXSJDUVGA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  tetrahydroobovatol 、 碘甲烷 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 5.0h， 以90%的产率得到3-(4-propylphenoxy)-2-methoxy-5-propylphenol
  参考文献：
  名称：

  COMPOSITION FOR THE TREATMENT OF DIABETES AND METABOLIC SYNDROME CONTAINING OBOVATOL AND ITS SYNTHESIZED DERIVATIVES

  摘要：

  本发明揭示了一种含有以式1表示的obovatol及其衍生物的制药组合物。obovatol及其衍生物能够有效提高AMPK（AMP激活蛋白激酶）的活性，在糖尿病和代谢综合征中发挥重要作用，因此可以用于治疗糖尿病和代谢综合征。（在式1中，R1、R2和R3与上述定义相同）。

  公开号：

  US20100125103A1
• 作为产物：
  描述：

  和厚朴新酚 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 tetrahydroobovatol
  参考文献：
  名称：

  厚朴叶的厚朴叶和长卵形，新颖的联苯醚木脂素。

  摘要：

  从厚朴（Magnolia obovata THUNB.(通过化学和光谱研究，确定了它们的化学结构为 4'，5-二烯丙基-2，3-二羟基联苯醚和 3，4-二羟基-5-（烯丙基苯氧基）肉桂醛。前一种物质对致癌细菌变异链球菌具有抗菌活性，但活性低于 magnolol（5）和 honokiol（6）。

  DOI：

  10.1248/cpb.30.3347

文献信息

• Synthesis and anti-platelet activity of obovatol derivatives
  作者：Jae-Hwan Kwak、Seul Lee、Eun-Seok Park、Jin-Kyung In、Jiho Song、Young Jin Kim、Nam Song Choi、Heesoon Lee、Yeo-Pyo Yun、Jin Tae Hong、Young-Shin Kwak、Kyung Hoon Min、Jae-Kyung Jung

  DOI：10.1007/s12272-011-0708-9

  日期：2011.7

  Obovatol derivatives were synthesized and evaluated for anti-platelet activity. Three derivatives (1, 2, 4i) displayed equipotent activity to obovatol in arachidonic acid-induced platelet aggregation. An initial SAR study revealed that the introduction of alkoxy group in B ring could enhance inhibitory activity.

  合成了Obovatol衍生物并评估其抗血小板活性。三个衍生物（1、2、4i）在花生四烯酸诱导的血小板聚集中显示出与Obovatol相等的活性。初步的SAR研究表明，在B环中引入烷氧基团可以增强抑制活性。
• Obovatol and obovatal, novel biphenyl ether lignans from the leaves of Magnolia obovata Thunb.
  作者：KAZUO ITO、TOSHIYUKI IIDA、KAZUHIKO ICHINO、MASA TSUNEZUKA、MASAO HATTORI、TSUNEO NAMBA

  DOI：10.1248/cpb.30.3347

  日期：——

  Two new biphenyl ether lignans, named obovatol (1) and obovatal (2) were isolated from the leaves of Magnolia obovata THUNB. (Magnoliaceae) and their chemical structures were determined to be 4', 5-diallyl-2, 3-dihydroxybiphenyl ether and 3, 4-dihydroxy-5-(pallylphenoxy) cinnamic aldehyde by means of chemical and spectral studies. The former substance showed antibacterial activity against a cariogenic bacterium, Streptococcus mutans, but was less active than magnolol (5) and honokiol (6).

  从厚朴（Magnolia obovata THUNB.(通过化学和光谱研究，确定了它们的化学结构为 4'，5-二烯丙基-2，3-二羟基联苯醚和 3，4-二羟基-5-（烯丙基苯氧基）肉桂醛。前一种物质对致癌细菌变异链球菌具有抗菌活性，但活性低于 magnolol（5）和 honokiol（6）。
• Novel obovatol derivatives or pharmaceutically acceptable salts thereof, preparation method thereof and pharmaceutical composition for the prevention and treatment of cancer containing the same as an active ingredient
  申请人：Kwon Byoung-Mog

  公开号：US20090239955A1

  公开（公告）日：2009-09-24

  Disclosed herein are novel obovatol derivatives represented by Chemical Formula 1, and pharmaceutically acceptable salts thereof. Having the ability to inhibit the growth of cancer cells and induce apoptosis in cancer cells, the derivatives or pharmaceutically acceptable salts thereof are useful in the prevention and treatment of cancer and in the suppression of cancer metastasis. Also, a method for preparing the derivatives, and pharmaceutical compositions comprising the derivatives as active ingredients are disclosed. wherein R 1 ,R 2 and R 3 are as defined in the specification.

  本文披露了一种新颖的以化学式1表示的obovatol衍生物及其药学上可接受的盐。这些衍生物或其药学上可接受的盐具有抑制癌细胞生长和诱导癌细胞凋亡的能力，可用于预防和治疗癌症以及抑制癌症转移。此外，还披露了一种制备这些衍生物的方法，以及包含这些衍生物作为活性成分的药物组合物。其中，R1、R2和R3如规范中所定义。
• US8183405B2
  申请人：——

  公开号：US8183405B2

  公开（公告）日：2012-05-22
• JJK694, a Synthesized Obovatol Derivative, Inhibits Platelet Activation by Suppressing Cyclooxygenase and Lipoxygenase Activities
  作者：Ji-Yeon YU、Jung-Jin LEE、Jae-Kyung JUNG、Yong-Ki MIN、Tack-Joong KIM、Jin Yeul MA、Mi-Yea LEE、Yeo-Pyo YUN

  DOI：10.1271/bbb.120369

  日期：2012.11.23

  Obovatol has various biological activities, including anti-proliferative, neurotrophic, anti-fibrillogenic, antiplatelet, anti-fungal and anti-inflammatory activities. In this study, we investigated the effects of JJK694, a synthesized obovatol derivative, on rabbit platelet activation and its molecular mechanisms. JJK694 significantly inhibited washed rabbit platelet aggregation and serotonin secretion induced by collagen and arachidonic acid, but had little effect on thrombin- or U46619-induced aggregation. These results suggest that JJK694 selectively inhibits collagen- and arachidonic acid-mediated signaling. JJK694 also showed a concentration-dependent decrease in cytosolic Ca2+ mobilization, but it had no effect on arachidonic acid liberation. On the other hand, it significantly inhibited the formation of arachidonic acid metabolites, including thromboxane A(2) (TXA(2)), prostaglandin D-2, and 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE), by suppression of cyclooxygenase (COX)-1 and lipoxygenase (LOX) activities. These results indicate that JJK694 hasanti-platelet activities through inhibition of arachidonic acid metabolite production by suppression of COX-1 and LOX activities.