(2S)-2-[[(1E)-1-[(9bR)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-1,3-dioxodibenzofuran-2-ylidene]ethyl]amino]-5-(diaminomethylideneamino)pentanoic acid | 1428361-08-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S)-2-[[(1E)-1-[(9bR)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-1,3-dioxodibenzofuran-2-ylidene]ethyl]amino]-5-(diaminomethylideneamino)pentanoic acid
• CAS: 1428361-08-3
• 化学式: C₂₄H₂₈N₄O₈
• 分子量: 500.508
• InChiKey: STMJUJGJYVGGLC-PIHYHCHMSA-N

物化性质

• 沸点：
  808.9±75.0 °C(predicted)
• 密度：
  1.53±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  215
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  L-精氨酸 、 (+)-usnic acid 以 乙醇 为溶剂， 反应 5.0h， 以89%的产率得到(2S)-2-[[(1E)-1-[(9bR)-6-acetyl-7,9-dihydroxy-8,9b-dimethyl-1,3-dioxodibenzofuran-2-ylidene]ethyl]amino]-5-(diaminomethylideneamino)pentanoic acid
  参考文献：
  名称：

  (+)-Usnic acid enamines with remarkable cicatrizing properties

  摘要：

  Wound healing is a significant concern in many pathologies (post-surgeries, burns, scars) and the search for new chemical entities is advisable. The lichen compound (+)-usnic acid (1) has found application in dermatological and cosmetic preparations, due to its bacteriostatic and antioxidant activities. The compound has also been shown to stimulate the wound closure of keratinocyte monolayers at subtoxic doses. Here we describe the design and synthesis of usnic acid enamines (compounds 2-11), obtained through nucleophilic attack of amino acids or decarboxyamino acids at the acyl carbonyl of the enolized 1,3 diketone. The wound repair properties of these derivatives were evaluated using in vitro and in vivo assays: Compounds 8 and 9 combine low cytotoxicity with high wound healing performance, suggesting their possible use in wound healing-promoting or antiage skin preparations. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.01.045

文献信息

• (+)-Usnic acid enamines with remarkable cicatrizing properties
  作者：Michela Bruno、Beatrice Trucchi、Bruno Burlando、Elia Ranzato、Simona Martinotti、Esra Küpeli Akkol、Ipek Süntar、Hikmet Keleş、Luisella Verotta

  DOI：10.1016/j.bmc.2013.01.045

  日期：2013.4

  Wound healing is a significant concern in many pathologies (post-surgeries, burns, scars) and the search for new chemical entities is advisable. The lichen compound (+)-usnic acid (1) has found application in dermatological and cosmetic preparations, due to its bacteriostatic and antioxidant activities. The compound has also been shown to stimulate the wound closure of keratinocyte monolayers at subtoxic doses. Here we describe the design and synthesis of usnic acid enamines (compounds 2-11), obtained through nucleophilic attack of amino acids or decarboxyamino acids at the acyl carbonyl of the enolized 1,3 diketone. The wound repair properties of these derivatives were evaluated using in vitro and in vivo assays: Compounds 8 and 9 combine low cytotoxicity with high wound healing performance, suggesting their possible use in wound healing-promoting or antiage skin preparations. (C) 2013 Elsevier Ltd. All rights reserved.