异丁酰阿卡宁 | 87562-78-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 异丁酰阿卡宁
• 英文名称: isobutyrylalkannin
• 英文别名: (S)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl isobutyrate；Isobutyryl Alkannin；[(1S)-1-(5,8-dihydroxy-1,4-dioxonaphthalen-2-yl)-4-methylpent-3-enyl] 2-methylpropanoate
• CAS: 87562-78-5
• 化学式: C₂₀H₂₂O₆
• 分子量: 358.391
• InChiKey: BVRYLTBIGIAADD-INIZCTEOSA-N

物化性质

• 沸点：
  561.9±50.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  紫草素 、 异丁酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 异丁酰阿卡宁
  参考文献：
  名称：

  Antimicrobial Activities of Naphthazarins from Arnebia euchroma

  摘要：

  Bioassay-directed fractionation of extract of Arnebia euchroma led to the isolation of alkannin (1), shikonin (2), and their derivatives (3-8) as the active principles against methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant enterococci (VRE). The stereochemistry of alpha-methylbutyryl alkannin (8) is revealed for the first time, and the antimicrobial activity of 8 was compared with its corresponding diastereomer (9). The derivatives 3-9 showed stronger anti-MRSA activity [minimum inhibitory concentrations (MICs) ranged from 1.56 to 3.13 mug/mL] than alkannin or shikonin (MIC = 6.25 mug/mL). Anti-MRSA activity of derivatives was bactericidal with minimum bactericidal concentration (MBC)/ MIC less than or equal to 2. In a time-kill assay, the bactericidal activity against MRSA was achieved as rapidly as 2 h. The derivatives 3-9 were also active against vancomycin-resistant Enterococcus faecium (F935) and vancomycin-resistant Enterococcus faecalis (CKU-17) with MICs similar to those with MRSA. Aromatic ester derivatives were also synthesized for antimicrobial activity comparison. None of these compounds were active against Gram-negative bacteria tested. Their cytotoxicity was also evaluated on selected cancer cell lines, and they expressed their activity in the range 0.6-5.4 mug/mL (CD50). Our results indicate that the ester derivatives of alkannin are potential candidates of anti-MRSA and anti-VRE agents with antitumor activity.

  DOI：

  10.1021/np010599w

文献信息

• NAPHTHALENEDIONE COMPOUNDS
  申请人：Sunten Phytotech Co., Ltd.

  公开号：EP2004174A2

  公开（公告）日：2008-12-24
• Naphthalenedione Compounds
  申请人：Chien Du-Shieng

  公开号：US20070238782A1

  公开（公告）日：2007-10-11

  This invention relates to compositions containing a compound of formula (I) shown below: Each variable is defined in the specification. Also disclosed are methods of using these compositions to treat acne, psoriasis, and infective skin ulcer.
• US7622506B2
  申请人：——

  公开号：US7622506B2

  公开（公告）日：2009-11-24
• [EN] NAPHTHALENEDIONE COMPOUNDS<br/>[FR] COMPOSÉS DE NAPHTALÈNEDIONE
  申请人：SUNTEN PHYTOTECH CO LTD

  公开号：WO2007118227A2

  公开（公告）日：2007-10-18

  [EN] This invention relates to compositions containing a compound of formula (I). Each variable is defined in the specification. Also disclosed are methods of using these compositions to treat acne, psoriasis, and infective skin ulcer.
  [FR] L'invention concerne des compositions contenant un composé représenté par la formule (I). Chaque variable est définie dans le descriptif. L'invention concerne aussi des procédés d'utilisation de ces compositions pour traiter l'acné, le psoriasis et un ulcère cutané infectieux.
• [EN] PATCH<br/>[FR] PATCH<br/>[JA] 貼付剤
  申请人：MEDICAL FRONT CO LTD

  公开号：WO2020162629A1

  公开（公告）日：2020-08-13

  【課題】粘着剤層から皮膚へシコニン類が適度に放出され、皮膚から剥脱しにくく、剥がすときに糊残りを生じさせにくい貼付剤を提供する。 【課題を解決するための手段】支持体と粘着剤層を備え、粘着剤層は樹脂組成物と液状組成物を含んで成り樹脂組成物の含有量が２５質量％以上１００質量％未満であり、液状組成物はシコニン類とノニオン界面活性剤を含有し、アクリル系共重合体は、（メタ）アクリル酸アルキルエステル、分子内にヒドロキシ基を有しない（メタ）アクリル酸アルコキシアルキルエステル、及び飽和脂肪酸ビニルエステルから選ばれたモノマーに由来する第１構成単位と、（メタ）アクリル酸ヒドロキシアルキルエステル、及びヒドロキシアルキル（メタ）アクリルアミドから選ばれたモノマーに由来する第２構成単位と、で構成されたアクリル系共重合体が、イソシアネート系架橋剤で架橋された網目構造を有する貼付剤である。