四氢脱甲氧基二阿魏酰甲烷 | 149579-07-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 四氢脱甲氧基二阿魏酰甲烷
• 英文名称: 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
• 英文别名: 1-(3-methoxy-4-hydroxyphenyl)-7-(4'-hydroxyphenyl)heptane-3,5-dione；tetrahydrodemethoxydiferuloylmethane；tetrahydrodemethoxycurcumin；1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)heptane-3,5-dione
• CAS: 149579-07-7
• 化学式: C₂₀H₂₂O₅
• 分子量: 342.392
• InChiKey: HJFYFYWETUVIHT-UHFFFAOYSA-N

物化性质

• LogP：
  2.420 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  四氢脱甲氧基二阿魏酰甲烷 在 sodium tetrahydroborate 、 对甲苯磺酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 苯 、 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 4.0h， 生成 1-(4-hydroxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)heptan-3-one 、 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-3-heptanone
  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：

  脱甲氧姜黄 在 platinum(IV) oxide 氢气 作用下， 以42.5%的产率得到四氢脱甲氧基二阿魏酰甲烷
  参考文献：
  名称：

  Antioxidative Activity of Tetrahydrocurcuminoids

  摘要：

  为了开发一种在同一分子中同时具有酚和β-二酮分子的新型抗氧化化合物，我们将姜黄的天然抗氧化剂姜黄素（二月桂酰甲烷，U1）、（4-羟基-3-甲氧基肉桂酰）甲烷（U2）和双（4-羟基肉桂酰）甲烷（U3）转化为四氢姜黄素（THU1、THU2和THU3）。(姜黄）中的天然抗氧化剂--姜黄素（THU1）、姜黄素（THU2）和姜黄素（THU3），通过氢化将其转化为四氢姜黄素（THU1、THU2 和 THU3），并在乙醇/水体系中以亚油酸为底物评估其抗氧化活性。此外，我们还以兔红细胞膜幽灵和大鼠肝微粒体为体外系统，测定了这些姜黄素的抗氧化活性。当我们通过这些检测方法评估它们的抗氧化活性时，发现在所有姜黄类化合物中，THU1 在每个检测系统中都具有最强的抗氧化活性。据报道，THU1 是 U1 在体内的主要代谢产物之一 [Holder 等人，Xenohiotica，8，761-768（1978 年）]。这些结果表明，THU1 通过将 U1 转化为 THU1，在体内 U1 的抗氧化机制中发挥了重要作用。

  DOI：

  10.1271/bbb.59.1609

文献信息

• Curcuminoid analogs inhibit nitric oxide production from LPS-activated microglial cells
  作者：Jiraporn Tocharus、Sataporn Jamsuwan、Chainarong Tocharus、Chatchawan Changtam、Apichart Suksamrarn

  DOI：10.1007/s11418-011-0599-6

  日期：2012.4

  The chemically modified analogs, the demethylated analogs 4–6, the tetrahydro analogs 7–9 and the hexahydro analogs 10–12, of curcumin (1), demethoxycurcumin (2) and bisdemethoxycurcumin (3) were evaluated for their inhibitory activity on lipopolysaccharide activated nitric oxide (NO) production in HAPI microglial cells. Di-O-demethylcurcumin (5) and O-demethyldemethoxycurcumin (6) are the two most

  对姜黄素 ( 1 )、脱甲氧基姜黄素( 2 ) 和双脱甲氧基姜黄素 ( 3 )的化学修饰类似物、去甲基化类似物4 – 6、四氢类似物7 – 9和六氢类似物10 – 12对脂多糖活化的抑制活性进行了评估HAPI 小胶质细胞中一氧化氮 (NO) 的产生。Di- O-去甲基姜黄素 ( 5 ) 和O-去甲基去甲氧基姜黄素 ( 6 ) 是抑制 NO 生成的两种最有效的化合物。类似物5和6分别比母体姜黄素1和2 的活性高两倍或几乎两倍。此外，这两种化合物抑制了诱导型 NO 合酶的 mRNA 表达水平。类似物5和6的强大神经保护活性提供了潜在的替代化合物，可作为与活化小胶质细胞相关的神经系统疾病的治疗剂进行开发。
• Novel racemic tetrahydrocurcuminoid dihydropyrimidinone analogues as potent acetylcholinesterase inhibitors
  作者：Sarawalee Arunkhamkaew、Anan Athipornchai、Nuttapon Apiratikul、Apichart Suksamrarn、Vachiraporn Ajavakom

  DOI：10.1016/j.bmcl.2013.03.069

  日期：2013.5

  The synthesis of racemic tetrahydrocurcumin- (THC-), tetrahydrodemethoxycurcumin- (THDC-) and tetrahydrobisdemethoxycurcumin- (THBDC-) dihydropyrimidinone (DHPM) analogues was achieved by utilizing the multi-component Biginelli reaction in the presence of copper sulphate as a catalyst. The evaluation of acetylcholinesterase inhibitors for Alzheimer’s disease of these compounds showed that they exhibited

  外消旋四氢姜黄素-（THC-），四氢去甲氧基姜黄素-（THDC-）和四氢双去甲氧基姜黄素-（THBDC-）二氢嘧啶酮（DHPM）类似物的合成是通过在硫酸铜作为催化剂的情况下利用多组分Biginelli反应来实现的。对这些化合物的阿尔茨海默氏病的乙酰胆碱酯酶抑制剂的评估表明，它们显示出比其母体类似物更高的抑制活性。THBDC-DHPM表现出最强的抑制活性，IC 50值为1.34± 0.03μM ，比经批准的加兰他敏药（IC 50  = 1.45±0.04μM）更具活性。
• ORALLY ACTIVE CURCUMINOID COMPOUNDS
  申请人：Chaniyilparampu Ramchand Nanappan

  公开号：US20110112190A1

  公开（公告）日：2011-05-12

  The invention discloses a compound of formula (I) wherein, at least one of R 1 , R 2 , R 3 and R 4 is —C(═O)R n and R 1 , R 2 R 3 and R 4 are H or CH 3 and R n is alkyl or alkenyl group. The alkenyl group have one or more number of double bonds either in cis form or trans form or both. In R n , where n is 12 to 30 carbons; and pharmaceutically acceptable salt thereof. The said alkenyl groups are preferably selected from the group consisting of eicosapentaenoic acid (EPA) or DHA (docosahexaenoic acid). This invention further discloses processes for their preparation of compounds of formula I and pharmaceutical compositions that contain these compounds.

  本发明公开了一种化合物，其化学式为(I)，其中，R1，R2，R3和R4中至少一个为—C(═O)Rn，且R1，R2，R3和R4为H或CH3，Rn为烷基或烯基基团。烯基基团具有一个或多个双键，可以是顺式或反式，或两者都有。在Rn中，n为12到30个碳；以及其药学上可接受的盐。所述烯基基团优选选自二十碳五烯酸（EPA）或二十二碳六烯酸（DHA）的群。本发明还公开了制备化合物I的方法和含有这些化合物的药物组合物。
• Cosmetic/dermatological compositions comprising a tetrahydrocurcuminoid and an amide oil
  申请人：SOCIETE L'OREAL S.A.

  公开号：US20040009200A1

  公开（公告）日：2004-01-15

  The invention relates to a cosmetic or dermatological composition containing a carrier comprising at least one fatty phase characterized in that it contains at least one derivative or a mixture of derivatives of 1,7-diphenyl-3,5-heptanedione having a particular structure and at least one oil having, in its structure, at least one amide unit. The invention also relates to its uses in cosmetics and dermatology, in particular for preventing or combating the harmful effects of UV radiation and pollution on human keratinous materials, and more particularly for preventing and/or treating photoaging of the skin. The invention also relates to a method for solubilizing a derivative or a mixture of derivatives of 1,7-diphenyl-3,5-heptanedione having a particular structure with at least one oil having, in its structure, at least one amide unit.

  本发明涉及一种化妆品或皮肤科组合物，其中包含至少一个脂肪相载体，其特征在于它含有至少一种具有特定结构的1,7-二苯基-3,5-庚二酮衍生物或混合物，以及至少一种在其结构中具有至少一个酰胺单元的油。本发明还涉及其在化妆品和皮肤科中的用途，特别是用于预防或对抗紫外线辐射和污染对人类角质材料的有害影响，更特别地用于预防和/或治疗皮肤光老化。本发明还涉及一种用至少一种在其结构中具有至少一个酰胺单元的油溶解具有特定结构的1,7-二苯基-3,5-庚二酮衍生物或混合物的方法。
• Composition cosmétique ou dermatologique contenant l'association d'un tetrahydrocurcuminoide et d'une huile amidée
  申请人：L'OREAL

  公开号：EP1348418A1

  公开（公告）日：2003-10-01

  L'invention concerne une composition cosmétique ou dermatologique contenant un support comprenant au moins une phase grasse caractérisée par le fait qu'elle contient au moins un dérivé ou un mélange de dérivés de la 1,7-bisphényl heptane-3,5-dione de structure particulière et au moins une huile présentant dans sa structure au moins un motif amide L'invention concerne également ses utilisations en cosmétique et dermatologie notamment pour prévenir et/ou lutter contre les effets néfastes des UV et de la pollution sur les matières kératiniques humaines et notamment pour prévenir et/ou traiter le photovieillissement de la peau. L'invention se rapporte également à un procédé de solubilisation d'un dérivé ou d'un mélange de dérivés de la 1,7-bisphényl heptane-3,5-dione de structure particulière par au moins une huile présentant dans sa structure au moins un motif amide.

  本发明涉及一种化妆品或皮肤科组合物，该组合物含有至少一种脂肪相组成的支撑物，其特征在于它含有至少一种特定结构的 1,7-二苯基庚烷-3,5-二酮的衍生物或衍生物混合物，以及至少一种在其结构中含有至少一个酰胺单元的油。 本发明还涉及其在化妆品和皮肤病学中的用途，特别是用于预防和/或对抗紫外线和污染对人体角质材料的有害影响，尤其是用于预防和/或治疗皮肤的光老化。 本发明还涉及一种将特定结构的 1,7-二苯基庚烷-3,5-二酮的衍生物或衍生物混合物与至少一种在其结构中含有至少一个酰胺单元的油类溶解的工艺。