2,4-dimethoxy-5-(1,1-dimethylprop-2-enyl)-4'-hydroxy-chalcone

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2,4-dimethoxy-5-(1,1-dimethylprop-2-enyl)-4'-hydroxy-chalcone
• 英文别名: 3-(2,4-Dimethoxy-5-(2-methylbut-3-en-2-yl)phenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one；(E)-3-[2,4-dimethoxy-5-(2-methylbut-3-en-2-yl)phenyl]-1-(4-hydroxyphenyl)prop-2-en-1-one
• 化学式: C₂₂H₂₄O₄
• 分子量: 352.43
• InChiKey: UBSHZUQMFZFAAJ-FMIVXFBMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2,4-dimethoxy-5-(1,1-dimethylprop-2-enyl)-4'-hydroxy-chalcone 在 吡啶 作用下， 以87%的产率得到4-(3-(2,4-Dimethoxy-5-(2-methylbut-3-en-2-yl)phenyl)acryloyl)phenyl acetate
  参考文献：
  名称：

  Inhibitory effect of chalcones and their derivatives from Glycyrrhiza inflata on protein tyrosine phosphatase 1B

  摘要：

  Compounds (1-6) isolated from the CH2Cl2 extract of Glycyrrhiza inflata and semisynthetic licochalcone A derivatives (7-14) were evaluated for their protein tyrosine phosphatase 1B (PTP1B) inhibitory activities. Licochalcones A (4) and E (6), each with an allyl group at position 5 in the B ring exhibited significant inhibitory effects. Licochalcone A derivative 7, the most potent among the series, had an IC50 value of 11.7 +/- 2.0 mu M, ca. twofold better than that of licochalcone A (4). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.054
• 作为产物：
  描述：

  甘草查耳酮A 在 sodium hydroxide 、 4-甲基苯磺酸吡啶 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 2,4-dimethoxy-5-(1,1-dimethylprop-2-enyl)-4'-hydroxy-chalcone
  参考文献：
  名称：

  Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A

  摘要：

  In this paper, a general applicable synthesis of prenylated aromatic compounds exemplified by prenylated benzaldehydes starting from readily available acetophenones is described. The synthesized benzaldehydes are used to prepare a number of novel analogues of Licochalcone A, a known antibacterial compound, and for the exploration of the pharmacophoric elements that are essential for the antibacterial activity. It is shown that the hydroxyl group in the A ring is essential for the activity and that the hydroxyl group in the B ring has no influence on the antibacterial effect of Licochalcone A. Furthermore, it is shown that the prenyl group at the position 5 of the B ring also has a dominating influence on the activity. This aliphatic group can be replaced by other lipophilic long chained substituents in order to maintain the activity.

  DOI：

  10.1016/j.ejmech.2004.07.004

文献信息

• TREATMENT AND PROPHYLAXIS OF DISEASES CAUSED BY PARASITES, OR BACTERIA
  申请人：STATENS SERUMINSTITUT

  公开号：EP0634927A1

  公开（公告）日：1995-01-25
• US5985935A
  申请人：——

  公开号：US5985935A

  公开（公告）日：1999-11-16
• US6603046B1
  申请人：——

  公开号：US6603046B1

  公开（公告）日：2003-08-05
• [EN] TREATMENT AND PROPHYLAXIS OF DISEASES CAUSED BY PARASITES, OR BACTERIA
  申请人：STATENS SERUMINSTITUT

  公开号：WO1993017671A1

  公开（公告）日：1993-09-16

  (EN) Aromatic compounds, or prodrugs thereof, which contain an alkylating site and which are capable of alkylating the thiol group in N-acetyl-L-cysteine, in particular bis-aromatic $g(a),$g(b)-unsaturated ketones, are used for the preparation of pharmaceutical compositions or medicated feed, food or drinking water for the treatment or prophylaxis of diseases caused by microorganisms or parasites, in particular protozoa such as $i(Leishmania, Trypanosoma, Toxoplasma, Plasmodium, Pneumocystis, Babesia) and $i(Theileria), intestinal protozoa such as $i(Trichomonas) and $i(Ciardia; Coccidia) such as $i(Eimeria, Isospora, Cryptosporidium; Cappilaria, Microsporidium, Sarcocystis, Trichodina, Trichodinella, Dacthylogurus, Pseudodacthylogurus, Acantocephalus, Ichthylophtherius, Botrecephalus); and intracellular bacteria, in particular $i(Mycobacterium, Legionella) species, $i(Listeria) and $i(Salmonella). Preferred compounds have the formula (II): Xm-Ph-C(O)-CH=CH-Ph-Yn, wherein each phenyl group (Ph) may be mono- or polysubstituted; X and Y designate ARH or AZ, wherein A is O, S, NH or N(C1-6alkyl), RH designates aliphatic hydrocarbyl, and Z is H or a masking group which is decomposed to liberate AH; m is 0, 1 or 2, and n is 0, 1, 2 or 3, whereby, when m is 2, then the two X are the same or different, and when n is 2 or 3, then the two or three Y are the same or different, with the proviso that n and m are not both 0. As examples of such compounds, chalcones, e.g. licochalcone A (obtainable i.a. from batches of Chinese licorice root of Glycyrrhiza species, e.g. $i(G. uralensis) or $i(G. inflata)) as well as hydroxy, alk(en)yl, and/or alk(en)yloxy analogues thereof are active $i(in vitro) and/or $i(in vivo) against i.a. $i(L. major) and $i(P. falciparum).(FR) Composés aromatiques, ou pro-médicaments issus de ces composés, comportant un site d'alkylation et aptes à réaliser l'alkylation du groupe thiol dans la N-acétyl-L-cystéine, en particulier $g(a),$g(b)-cétones insaturées bisaromatiques, utilisés pour la production de préparations pharmaceutiques ou d'aliments médicamenteux, d'aliments ou d'eaux de boisson pour le traitement ou la prophylaxie de maladies causées par des microorganismes ou des parasites, en particulier par des protozoaires tels que $i(Leishmania, Trypanosoma, Toxoplasma, Plasmodium, Pneumocystis, Babesia) et $i(Theileria), par des protozoaires intestinaux tels que les $i(Trichomonas) et $i(Ciardia; Coccidia) tels que $i(Emeria, Isospora, Cryptosporidium, Cappilaria, Microsporidium, Sarcocystis, Trichodina, Trichodinella, Dacthylogurus, Pseudodacthylogurus, Acantocephalus, Ichthylophtherius, Botrecephalus); et des bactéries intracellulaires, notamment les espèces $i(Mycobacterium, Legionella, Listeria) et $i(Salmonella). Les composés préférés présentent la formule (II): Xm-Ph-C(O)-CH=CH-Ph-Yn, dans laquelle chacun des groupes phényle (pH) peut être mono ou polysubstitué; X et Y désignent ARH ou AZ, dans lequel A est O, S, NH ou N(C1-6alkyle), RH désigne un radical hydrocarbyle aliphatique, et Z est H ou un groupe écran qui est décomposé pour libérer AH; m est 0, 1 ou 2 et n est 0, 1, 2 ou 3, de telle sorte que, quand m est égal à 2, les deux X sont identiques ou différents, et lorsque n est égal à 2 ou 3, les deux ou trois Y sont identiques ou différents, pourvu que n et m ne soient pas tous les deux égaux à 0. Comme exemples de ces composés, on citera les chalcones, par exemple licochalcone A (pouvant être obtenu notamment à partir de racines de réglisse de l'espèce Glycyrrhiza, par exemple $i(G. uralensis) ou $i(G. inflata)) ainsi que leurs analogues hydroxy, alk(én)yle et/ou alk(én)yloxy, actifs $i(in vitro) et/ou $i(in vivo) contre notamment $i(L. major) et $i(P. falciparum).
• Synthesis of prenylated benzaldehydes and their use in the synthesis of analogues of licochalcone A
  作者：Hasse Kromann、Mogens Larsen、Thomas Boesen、Kristian Schønning、Simon Feldbæk Nielsen

  DOI：10.1016/j.ejmech.2004.07.004

  日期：2004.11

  In this paper, a general applicable synthesis of prenylated aromatic compounds exemplified by prenylated benzaldehydes starting from readily available acetophenones is described. The synthesized benzaldehydes are used to prepare a number of novel analogues of Licochalcone A, a known antibacterial compound, and for the exploration of the pharmacophoric elements that are essential for the antibacterial activity. It is shown that the hydroxyl group in the A ring is essential for the activity and that the hydroxyl group in the B ring has no influence on the antibacterial effect of Licochalcone A. Furthermore, it is shown that the prenyl group at the position 5 of the B ring also has a dominating influence on the activity. This aliphatic group can be replaced by other lipophilic long chained substituents in order to maintain the activity.