hirsutanonol | 93604-02-5

• 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: hirsutanonol
• 英文别名: bis(demethyl)hexahydrocurcumin；Hirsutal；1,7-bis(3,4-dihydroxyphenyl)-5-hydroxyheptan-3-one
• CAS: 93604-02-5
• 化学式: C₁₉H₂₂O₆
• 分子量: 346.38
• InChiKey: MVIYWFBLVAFZID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  hirsutanonol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以32 mg的产率得到hirsutenone
  参考文献：
  名称：

  Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species

  摘要：

  The natural curcuminoids curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) have been chemically modified to give 46 analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs and these parent curcuminoids and their analogs were assessed against protozoa of the Tryponosoma and Leishmania species. The parent curcuminoids exhibited low antitrypanosomal activity (EC50 for our drug-sensitive Trypanosoma brucei brucei line (WT) of compounds 1, 2 and 3 are 2.5, 4.6 and 7.7 mu M, respectively). Among 43 curcuminoid analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs tested, 8 pure analogs and 5 isomeric mixtures of analogs exhibited high antitrypanosomal activity in sub-micromolar order of magnitude. Among these highly active analogs, 1,7-bis(4-hydroxy-3-methoxy-phenyl)hept-4-en-3-one (40) was the most active compound, with an EC50 value of 0.053 +/- 0.007 mu M; it was about 2-fold more active than the standard veterinary drug diminazene aceturate (EC50 0.12 +/- 0.01 mu M). Using a previously characterized diminazene-resistant T. b, brucei (TbAT1-KO) and a derived multi-drug resistant line (B48), no cross-resistance of curcuminoids was observed to the diamidine and melaminophenyl arsenical drugs that are the current treatments. Indeed, curcuminoids carrying a conjugated keto (enone) motif, including 40, were significantly more active against 7: b. brucei B48. This enone motif was found to contribute to particularly high trypanocidal activity against all Trypanosoma species and strains tested. The parent curcuminoids showed low antileishmanial activity (EC50 values of compounds 1 and 2 for Leishmania mexicana amastigotes are 16 +/- 3 and 37 +/- 6 mu M. respectively) while the control drug, pentamidine, displayed an EC50 of 16 +/- 2 mu M. Among the active curcuminoid analogs, four Compounds exhibited EC50 values of less than 5 mu M against Leishmania major promastigotes and four against L mexicana amastigotes. No significant difference in sensitivity to curcuminoids between L. major promastigotes and L. mexicana amastigotes was observed. The parent curcuminoids and most of their analogs were also tested for their toxicity against human embryonic kidney (HEK) cells. All the curcuminoids exhibited lower toxicity to HEK cells than to T b. brucei bloodstream forms and only one of the tested compounds showed significantly higher activity against HEK cells than curcumin (1). The selectivity index for T b. brucei ranged from 3-fold to 1500-fold. The selectivity index for the most active analog, the enone 40, was 453-fold. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.11.035
• 作为产物：
  描述：

  4-[3,4-bis(phenylmethoxy)phenyl]-1-[2-[2-[3,4-bis(phenylmethoxy)phenyl]ethyl]-1,3-dioxolan-2-yl]butan-2-ol 以67%的产率得到
  参考文献：
  名称：

  KATO, NOBUHARU;HAMADA, YASUMASA;SHIOIRI, TAKAYUKI, CHEM. AND PHARM. BULL., 1984, 32, N 8, 3323-3326

  摘要：

  DOI：

文献信息

• 姜黄素衍生物的用途
  申请人：中国科学院成都生物研究所

  公开号：CN110327315A

  公开（公告）日：2019-10-15

  本发明提供了姜黄素衍生物的用途。具体提供了式Ⅰ所示姜黄衍生物，或其盐在制备抗炎性疾病的药物和/或COX抑制剂的用途。本发明姜黄素衍生物具有良好COX抑制活性和抗炎活性，可用于制备COX抑制剂和抗炎药物。其中，化合物6和化合物7对于COX‑2抑制活性和抗炎活性的效果最优。可用于制备COX‑2抑制剂和抗炎药物。
• Composition for treating atopic dermatitis comprising hirsutanonol or oregonin as an active ingredient
  申请人：Lee Min Won

  公开号：US20100190729A1

  公开（公告）日：2010-07-29

  The present invention relates to a composition for treating atopic dermatitis comprising hirsutanonol as an active ingredient. Hirsutanonol or oregonin as the active ingredient of the present composition decreases the number of eosinophil increased in atopic dermatitis and regulates expression amounts of immune regulatory cytokines, IL-4, IL-5, IL-10 and IL-13 associated with atopic dermatitis. In addition, hirsutanonol and oregonin increase MBD (mouse beta-defensin)-1, MBD-2 and MBD-3 expression and decrease COX-2 and iNOS expression in mouse animal model of atopic dermatitis. Hirsutanonol and oregonin as the active ingredient of the present composition could be effectively used in drugs, cosmetics and foods for treating atopic dermatitis.
• Curcuminoid analogs with potent activity against Trypanosoma and Leishmania species
  作者：Chatchawan Changtam、Harry P. de Koning、Hasan Ibrahim、M. Sohail Sajid、Matthew K. Gould、Apichart Suksamrarn

  DOI：10.1016/j.ejmech.2009.11.035

  日期：2010.3

  The natural curcuminoids curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) have been chemically modified to give 46 analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs and these parent curcuminoids and their analogs were assessed against protozoa of the Tryponosoma and Leishmania species. The parent curcuminoids exhibited low antitrypanosomal activity (EC50 for our drug-sensitive Trypanosoma brucei brucei line (WT) of compounds 1, 2 and 3 are 2.5, 4.6 and 7.7 mu M, respectively). Among 43 curcuminoid analogs and 8 pairs of 1: 1 mixture of curcuminoid analogs tested, 8 pure analogs and 5 isomeric mixtures of analogs exhibited high antitrypanosomal activity in sub-micromolar order of magnitude. Among these highly active analogs, 1,7-bis(4-hydroxy-3-methoxy-phenyl)hept-4-en-3-one (40) was the most active compound, with an EC50 value of 0.053 +/- 0.007 mu M; it was about 2-fold more active than the standard veterinary drug diminazene aceturate (EC50 0.12 +/- 0.01 mu M). Using a previously characterized diminazene-resistant T. b, brucei (TbAT1-KO) and a derived multi-drug resistant line (B48), no cross-resistance of curcuminoids was observed to the diamidine and melaminophenyl arsenical drugs that are the current treatments. Indeed, curcuminoids carrying a conjugated keto (enone) motif, including 40, were significantly more active against 7: b. brucei B48. This enone motif was found to contribute to particularly high trypanocidal activity against all Trypanosoma species and strains tested. The parent curcuminoids showed low antileishmanial activity (EC50 values of compounds 1 and 2 for Leishmania mexicana amastigotes are 16 +/- 3 and 37 +/- 6 mu M. respectively) while the control drug, pentamidine, displayed an EC50 of 16 +/- 2 mu M. Among the active curcuminoid analogs, four Compounds exhibited EC50 values of less than 5 mu M against Leishmania major promastigotes and four against L mexicana amastigotes. No significant difference in sensitivity to curcuminoids between L. major promastigotes and L. mexicana amastigotes was observed. The parent curcuminoids and most of their analogs were also tested for their toxicity against human embryonic kidney (HEK) cells. All the curcuminoids exhibited lower toxicity to HEK cells than to T b. brucei bloodstream forms and only one of the tested compounds showed significantly higher activity against HEK cells than curcumin (1). The selectivity index for T b. brucei ranged from 3-fold to 1500-fold. The selectivity index for the most active analog, the enone 40, was 453-fold. (C) 2009 Elsevier Masson SAS. All rights reserved.
• KATO, NOBUHARU;HAMADA, YASUMASA;SHIOIRI, TAKAYUKI, CHEM. AND PHARM. BULL., 1984, 32, N 8, 3323-3326
  作者：KATO, NOBUHARU、HAMADA, YASUMASA、SHIOIRI, TAKAYUKI

  DOI：——

  日期：——