3,4-O-异亚丙基-3,3',4,5'-四羟基二苯乙烯 | 90275-02-8

• 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: 3,4-O-异亚丙基-3,3',4,5'-四羟基二苯乙烯
• 中文别名: 吡唑并[1,5-a]嘧啶-7-酚,5-甲基-2-苯基-
• 英文名称: 3,4-O-isopropylidene-3,3',4,5'-tetrahydroxystilbene
• 英文别名: 5-[(E)-2-(2,2-dimethyl-1,3-benzodioxol-5-yl)ethenyl]benzene-1,3-diol
• CAS: 90275-02-8
• 化学式: C₁₇H₁₆O₄
• 分子量: 284.312
• InChiKey: WDSMCLLELZZMDO-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  白皮杉醇 、 丙酮 在 phosphorus pentoxide 作用下， 反应 5.0h， 以870 mg的产率得到3,4-O-异亚丙基-3,3',4,5'-四羟基二苯乙烯
  参考文献：
  名称：

  The biological activities of 3,4-O-isopropylidene-3,3',4,5'-tetrahydroxystilbene.

  摘要：

  一种新化合物3,4-O-异丙叉基-3,3',4,5'-四羟基二苯乙烯(I),是由3,3',4,5'-四羟基二苯乙烯(II)化学衍生而来,显示出强大的抗真菌活性、鱼毒性、对离体豚鼠心脏的冠状血管扩张作用以及对大鼠的降血压作用。这些活性都比原始物质(II)强得多。 关于抗真菌活性,化合物I对须癣毛癣菌和番茄黄萎病菌的最小生长抑制浓度(MIC)分别为6和1μg/ml。 关于鱼毒性,在青鳉鱼中48小时的中位耐受限度(TLm)为14.0 ppm。 化合物I在体外对豚鼠心脏也具有强烈的冠状血管扩张作用;ED50值为4.5μg/心脏。 最后,化合物I对大鼠显示出强烈的降血压作用(-43.0±5.2mmHg,静脉注射10mg/kg)。

  DOI：

  10.1248/cpb.33.2904

文献信息

• The antifungal activity of stilbene derivative.
  作者：Yoshihiko Inamori、Mayuri Kubo、Yoshiaki Kato、Masahide Yasuda、Kimiye Baba、Mitsugi Kozawa

  DOI：10.1248/cpb.32.801

  日期：——

  The purpose of the present study is to examine the antimicrobial activity of a new compound, 3, 4-o-isopropylidene-3, 3', 4, 5'-tetrahydroxy-stilbene (1) chemically derived from 3, 3', 4, 5'-tetrahydroxystilbene (2) which was isolated from the heartwood of Cassia garrettiana CRAIB by the authors, and the antifungal activities of which were previously reported. It has become apparent that the antifungal activities of compound (1) are far stronger than those of compound (2), and that the acute toxicity of compound (1) is lower than that of compound (2). It should be emphasized that compound (1) shows its strong antifungal activity especially against Trichophyton rubrum and Trichophyton mentagrophytes.

  本研究旨在考察一种新化合物3,4-O-异亚丙基-3,3',4,5'-四羟基二苯乙烯(1)的抗菌活性。该化合物是由作者从Cassia garrettiana CRAIB心材中分离得到的3,3',4,5'-四羟基二苯乙烯(2)经化学衍生而来，其抗真菌活性此前已有报道。研究表明，化合物(1)的抗真菌活性远强于化合物(2)，且化合物(1)的急性毒性低于化合物(2)。值得强调的是，化合物(1)对红色毛癣菌和须癣菌表现出特别强的抗真菌活性。
• INAMORI, JOSIXIKO;KODZAVA, MITSUGU;TAKEHSITA, YASUESI;TANEHYA, SINITI;SON+
  作者：INAMORI, JOSIXIKO、KODZAVA, MITSUGU、TAKEHSITA, YASUESI、TANEHYA, SINITI、SON+

  DOI：——

  日期：——
• US7173039B2
  申请人：——

  公开号：US7173039B2

  公开（公告）日：2007-02-06
• The biological activities of 3,4-O-isopropylidene-3,3',4,5'-tetrahydroxystilbene.
  作者：YOSHIHIKO INAMORI、MAYURI KUBO、YOSHIAKI KATO、MASAHIDE YASUDA、HIROSHI TSUJIBO、KIMIYE BABA、MITSUGI KOZAWA

  DOI：10.1248/cpb.33.2904

  日期：——

  A new compound, 3, 4-O-isopropylidene-3, 3', 4, 5'-tetrahydroxystilbene (I), chemically derived from 3, 3', 4, 5'-tetrahydroxystilbene (II) showed strong antifungal activity, ichthyotoxicity, coronary vasodilator action on the isolated guinea-pig heart and a hypotensive effect on rats. These activities of I were much stronger than those of the original substance (II). As regards antifungal activity, the minimal growth inhibitory concentrations (MIC) of I for Trichophyton mentagrophytes and Fusarium oxysporum f. sp. lycopersici were 6 and 1μg/ml, respectively. As regards ichthyotoxic activity, the median tolerance limit (TLm) at 48 h was 14.0 ppm in Oryzias latipes TEMMINCK et SCHLEGEL. Compound (I) also had strong coronary vasodilator action on guinea-pig heart in vitro ; the ED50 value was 4.5μg/heart. Finally, I showed a strong hypotensive effect on rats (-43.0±5.2mmHg, 10mg/kg i.v.).

  一种新化合物3,4-O-异丙叉基-3,3',4,5'-四羟基二苯乙烯(I),是由3,3',4,5'-四羟基二苯乙烯(II)化学衍生而来,显示出强大的抗真菌活性、鱼毒性、对离体豚鼠心脏的冠状血管扩张作用以及对大鼠的降血压作用。这些活性都比原始物质(II)强得多。 关于抗真菌活性,化合物I对须癣毛癣菌和番茄黄萎病菌的最小生长抑制浓度(MIC)分别为6和1μg/ml。 关于鱼毒性,在青鳉鱼中48小时的中位耐受限度(TLm)为14.0 ppm。 化合物I在体外对豚鼠心脏也具有强烈的冠状血管扩张作用;ED50值为4.5μg/心脏。 最后,化合物I对大鼠显示出强烈的降血压作用(-43.0±5.2mmHg,静脉注射10mg/kg)。