N-{2-[(3-methoxy)benzamido]ethyl}glycyrrhetinamide | 1334318-75-0

• 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-{2-[(3-methoxy)benzamido]ethyl}glycyrrhetinamide
• 英文别名: N-{2-[(3-methoxyphenyl)formamido]ethyl}-glycyrrhetinamide；(2S,4aS,6aR,6aS,6bR,8aR,10S,12aS,14bR)-10-hydroxy-N-[2-[(3-methoxybenzoyl)amino]ethyl]-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxamide
• CAS: 1334318-75-0
• 化学式: C₄₀H₅₈N₂O₅
• 分子量: 646.911
• InChiKey: AHABUALNEMFKEZ-QOODKSGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  47
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  甘草次酸 在 4-二甲氨基吡啶 、 1-羟基苯并三唑 、 N,N-二异丙基乙胺 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 N-{2-[(3-methoxy)benzamido]ethyl}glycyrrhetinamide
  参考文献：
  名称：

  N-(2-{3-[3,5-Bis(trifluoromethyl)phenyl]ureido}ethyl)-glycyrrhetinamide (6b): A Novel Anticancer Glycyrrhetinic Acid Derivative that Targets the Proteasome and Displays Anti-Kinase Activity

  摘要：

  18-beta-Glycyrrhetinic acid (GA; 1) and many of its derivatives are cytotoxic in cancer cells. The current study aims to characterize the anticancer effects of 17 novel 1 derivatives. On the basis of these studies, N-(2-{3-[3,5-bis(trifluoromethyl)phenyl]ureido}ethyl)-glycyrrhetinamide (6b) appeared to be the most potent compound, with IC50 in vitro growth inhibitory concentrations in single-digit micromolarity in a panel of 8 cancer cell lines. Compound 6b is cytostatic and displays similar efficiency in apoptosis-sensitive versus apoptosis-resistant cancer cell lines through, at least partly, the inhibition of the activity of a cluster of a dozen kinases that are implicated in cancer cell proliferation and in the control of the actin cytoskeleton organization. Compound 6b also inhibits the activity of the 3 proteolytic units of the proteasome. Compound 6b thus represents an interesting hit from which future compounds could be derived to improve chemotherapeutic regimens that aim to combat cancers associated with poor prognoses.

  DOI：

  10.1021/jm200285z

文献信息

• [EN] 18-BETA-GLYCYRRHETINIC ACID DERIVATIVES WITH ANTI-TUMOR ACTIVITY<br/>[FR] DÉRIVÉS D'ACIDE 18?-GLYCYRRHÉTINIQUE AYANT UNE ACTIVITÉ ANTITUMORALE
  申请人：UNIV BRUXELLES

  公开号：WO2012022780A1

  公开（公告）日：2012-02-23

  The invention relates to the medical and cosmetic field, more precisely the field of anticancer treatment and treatment of inflammatory diseases and diabetes and the field of anti-aging or anti-wrinkling agents using newly synthesized 18β-glycyrrhetinic acid derivatives and there use in the treatment of said disorders or symptoms.

  这项发明涉及医学和美容领域，更准确地说是抗癌治疗、炎症性疾病和糖尿病治疗以及抗衰老或抗皱剂领域，使用新合成的18β-甘草酸衍生物及其在治疗上述疾病或症状中的应用。
• <i>N</i>-(2-{3-[3,5-Bis(trifluoromethyl)phenyl]ureido}ethyl)-glycyrrhetinamide (<b>6b</b>): A Novel Anticancer Glycyrrhetinic Acid Derivative that Targets the Proteasome and Displays Anti-Kinase Activity
  作者：Benjamin Lallemand、Fabien Chaix、Marina Bury、Céline Bruyère、Jean Ghostin、Jean-Paul Becker、Cédric Delporte、Michel Gelbcke、Véronique Mathieu、Jacques Dubois、Martine Prévost、Ivan Jabin、Robert Kiss

  DOI：10.1021/jm200285z

  日期：2011.10.13

  18-beta-Glycyrrhetinic acid (GA; 1) and many of its derivatives are cytotoxic in cancer cells. The current study aims to characterize the anticancer effects of 17 novel 1 derivatives. On the basis of these studies, N-(2-3-[3,5-bis(trifluoromethyl)phenyl]ureido}ethyl)-glycyrrhetinamide (6b) appeared to be the most potent compound, with IC50 in vitro growth inhibitory concentrations in single-digit micromolarity in a panel of 8 cancer cell lines. Compound 6b is cytostatic and displays similar efficiency in apoptosis-sensitive versus apoptosis-resistant cancer cell lines through, at least partly, the inhibition of the activity of a cluster of a dozen kinases that are implicated in cancer cell proliferation and in the control of the actin cytoskeleton organization. Compound 6b also inhibits the activity of the 3 proteolytic units of the proteasome. Compound 6b thus represents an interesting hit from which future compounds could be derived to improve chemotherapeutic regimens that aim to combat cancers associated with poor prognoses.