N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-O-acetylursolamide | 1018969-33-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-O-acetylursolamide
• 英文别名: N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide；N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-acetylursolamide；[(3S,4aR,6aR,6bS,8aS,11R,12S,12aS,14aR,14bR)-8a-[3-[4-(3-aminopropyl)piperazin-1-yl]propylcarbamoyl]-4,4,6a,6b,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picen-3-yl] acetate
• CAS: 1018969-33-9
• 化学式: C₄₂H₇₂N₄O₃
• 分子量: 681.059
• InChiKey: IUJKWMKQXCXZKK-BLNYKQIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  87.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-O-acetylursolamide 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以50%的产率得到N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}ursolamide
  参考文献：
  名称：

  评价从巴拉圭冬青及其衍生物中分离得到的熊果酸对芳香化酶的抑制作用。

  摘要：

  评估了从南美番石榴（Ilex paraguariensis）提取的熊果酸的抑菌能力，该植物在南美人中被称为茶伴侣，用于茶制品；其衍生物具有抑制芳香化酶活性的作用，并与植物雌激素芹菜素和甾体芳香化酶抑制剂4-hyyryandrostenedione（ 4-OHA）。在所有测试的化合物中，只有乌索酸1像芹菜素（IC50 = 10 microM）一样显示出有效且剂量依赖性的芳香酶抑制作用，IC50值为32 microM，而4-OHA的IC50值为0.8 microM。我们的结果表明，将金属茂部分并入熊果酸衍生物中会降低对芳香化酶的抑制作用。而且，

  DOI：

  10.1016/j.ejmech.2007.11.021
• 作为产物：
  描述：

  熊果酸 在 吡啶 、 草酰氯 、 水 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 54.0h， 生成 N-{3-[4-(3-aminopropyl)piperazin-1-yl]propyl}-3-O-acetylursolamide
  参考文献：
  名称：

  Synthesis of Isosteric Triterpenoid Derivatives and Antifungal Activity

  摘要：

  Dermatomycoses are among the most widespread and common superficial and cutaneous fungal infections in humans. There is an urgent need to develop efficient and non‐toxic antimycotic agents with a specific spectrum of activity. Triterpenes have been demonstrated to exhibit a wide range of biological activities, including antifungal activities. In this study, through hemisynthesis, we aimed to obtain triterpene‐isosteric molecules from betulinic and ursolic acids to improve the antifungal activity and spectrum of action of these compounds. Six compounds were resynthesized and tested against eleven mucocutaneous and cutaneous mycotic agents. The results of the susceptibility assays were expressed as the minimal inhibitory concentration (MIC). The MIC values of the piperazinyl derivatives of ursolic and betulinic acids that were active against pathogenic yeasts were in the range of 16–32 μg/mL and 4–16 μg/mL, respectively, whereas fungicidal effects were observed at concentrations ranging from 16 to 128 μg/mL and 8 to 128 μg/mL, respectively. The piperazinyl derivative of betulinic acid exhibited an antifungal profile similar to that of terbinafine and was the most effective derivative against dermatophytes. This strategy led to a promising candidate for the development of a new antifungal agent.

  DOI：

  10.1111/cbdd.12251

文献信息

• Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents
  作者：Simone C.B. Gnoatto、Sophie Susplugas、Luciana Dalla Vechia、Thais B. Ferreira、Alexandra Dassonville-Klimpt、Karine R. Zimmer、Catherine Demailly、Sophie Da Nascimento、Jean Guillon、Philippe Grellier、Hugo Verli、Grace Gosmann、Pascal Sonnet

  DOI：10.1016/j.bmc.2007.10.031

  日期：2008.1

  A series of new piperazine derivatives of ursolic acid was synthesized and tested against Plasmodium falciparum strains. They were also tested on their cytotoxicity effects upon MRC-5 cells. Seven new piperazinyl analogues showed significant activity in the nanomolar range (IC(50)=78-167nM) against Plasmodium falciparum CQ-resistant strain FcB1. A possible mechanism of interaction implicating binding

  合成了一系列新的乌索酸哌嗪衍生物，并针对恶性疟原虫菌株进行了测试。还测试了它们对MRC-5细胞的细胞毒性作用。七个新的哌嗪基类似物显示出在纳摩尔范围（IC（50）= 78-167nM）对抗恶性疟原虫CQ耐药菌株FcB1的显着活性。体外测试支持了可能的相互作用机制，暗示了这些化合物与β-血红素的结合。此外，还通过分子动力学模拟探索了连接在三萜环上的双-（3-氨基丙基）哌嗪末端氮原子上亲水框架的重要性。
• Synthesis of Isosteric Triterpenoid Derivatives and Antifungal Activity
  作者：Adrine Innocente、Bruna B. Casanova、Fernanda Klein、Aline D. Lana、Dariane Pereira、Mauro N. Muniz、Pascal Sonnet、Grace Gosmann、Alexandre M. Fuentefria、Simone C. B. Gnoatto

  DOI：10.1111/cbdd.12251

  日期：2014.3

  Dermatomycoses are among the most widespread and common superficial and cutaneous fungal infections in humans. There is an urgent need to develop efficient and non‐toxic antimycotic agents with a specific spectrum of activity. Triterpenes have been demonstrated to exhibit a wide range of biological activities, including antifungal activities. In this study, through hemisynthesis, we aimed to obtain triterpene‐isosteric molecules from betulinic and ursolic acids to improve the antifungal activity and spectrum of action of these compounds. Six compounds were resynthesized and tested against eleven mucocutaneous and cutaneous mycotic agents. The results of the susceptibility assays were expressed as the minimal inhibitory concentration (MIC). The MIC values of the piperazinyl derivatives of ursolic and betulinic acids that were active against pathogenic yeasts were in the range of 16–32 μg/mL and 4–16 μg/mL, respectively, whereas fungicidal effects were observed at concentrations ranging from 16 to 128 μg/mL and 8 to 128 μg/mL, respectively. The piperazinyl derivative of betulinic acid exhibited an antifungal profile similar to that of terbinafine and was the most effective derivative against dermatophytes. This strategy led to a promising candidate for the development of a new antifungal agent.
• Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition
  作者：Simone C.B. Gnoatto、Alexandra Dassonville-Klimpt、Sophie Da Nascimento、Philippe Galéra、Karim Boumediene、Grace Gosmann、Pascal Sonnet、Safa Moslemi

  DOI：10.1016/j.ejmech.2007.11.021

  日期：2008.9

  The inhibitory potency of ursolic acid extracted from Ilex paraguariensis, a plant used in South American population for a tea preparation known as mate, and its derivatives to inhibit aromatase activity was assessed and compared to a phytoestrogen apigenin and a steroidal aromatase inhibitor 4-hyroxyandrostenedione (4-OHA). Among all compounds tested only ursolic acid 1 showed an efficient and dose-dependent

  评估了从南美番石榴（Ilex paraguariensis）提取的熊果酸的抑菌能力，该植物在南美人中被称为茶伴侣，用于茶制品；其衍生物具有抑制芳香化酶活性的作用，并与植物雌激素芹菜素和甾体芳香化酶抑制剂4-hyyryandrostenedione（ 4-OHA）。在所有测试的化合物中，只有乌索酸1像芹菜素（IC50 = 10 microM）一样显示出有效且剂量依赖性的芳香酶抑制作用，IC50值为32 microM，而4-OHA的IC50值为0.8 microM。我们的结果表明，将金属茂部分并入熊果酸衍生物中会降低对芳香化酶的抑制作用。而且，