5-[(9,10-二氧代蒽-2-基)甲氧基]-5-氧代戊酸 | 139571-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 5-[(9,10-二氧代蒽-2-基)甲氧基]-5-氧代戊酸
• 中文别名: 组氨酰-精氨酰-丙氨酰-色氨酰-苯基丙氨酰-赖氨酸酰胺
• 英文名称: 2-hydroxymethyl anthraquinone-hemiglutarate
• 英文别名: Glutaryl-2-(hydroxymethyl)anthraquinone；5-[(9,10-dioxoanthracen-2-yl)methoxy]-5-oxopentanoic acid
• CAS: 139571-00-9
• 化学式: C₂₀H₁₆O₆
• 分子量: 352.343
• InChiKey: GAOGYGSGSZCEKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [D-Lys6]GnRH 、 5-[(9,10-二氧代蒽-2-基)甲氧基]-5-氧代戊酸 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以65%的产率得到[D-Lys6(AntrQ)]GnRH
  参考文献：
  名称：

  Long-acting gonadotropin-releasing hormone analogs and methods of use thereof

  摘要：

  本发明涉及设计、合成和生物评价强效长效性促性腺激素释放激素（GnRH）类似物，包括激动剂和拮抗剂，其包括将GnRH肽与大黄酸或大黄酸衍生物结合的类似物。这些长效类似物与GnRH受体结合亲和力高，没有任何毒性或抗增殖作用。本发明还涉及这些GnRII类似物作为避孕药、控制生育和治疗和/或预防性激素依赖性疾病或症状的治疗用途。

  公开号：

  US20060100154A1

文献信息

• Design, Synthesis, and Evaluation of a Long-Acting, Potent Analogue of Gonadotropin-Releasing Hormone
  作者：Shai Rahimipour、Nurit Ben-Aroya、Mati Fridkin、Yitzhak Koch

  DOI：10.1021/jm010112g

  日期：2001.10.1

  The design, synthesis, and biological evaluation of a gonadotropin-releasing hormone (GnRH) agonist, [D-Lys(6)(1,3,8-trihydroxy-6-carboxyanthraquinone)]GnRH ([D-Lys(6)(Emo)]GnRH), is described. Synthesis of this analogue was carried out in a homogeneous solution as well as on a polymer support. [D-Lys(6)(Emo)]GnRH was found to bind to rat pituitary GnRH receptors (IC50 = 0.25 nM), to induce luteinizing hormone (LH) release (ED50 = 27 pM), and to be devoid of any toxicity. This analogue also proved to be a very potent agonist in vivo and exhibited a prolonged bioactivity. Six hours after its administration to rats, LH levels were substantially higher than those of rats treated with a 10-fold higher dose of the parent peptide. Moreover, chronic treatment of adult male rats with [D-Lys(6)(Emo)]GnRH (0.1 nmol/rat) for one week resulted in a further decrease of the weight of the testes and prostate as compared to those of rats that were treated with a higher dose of [D-Lys] GnRH (1 nmol/rat). The prolonged activity of [D-Lys(6)(Emo)]GnRH may be attributed to its emodic acid moiety, which enhances the binding affinity of the analogue to human serum albumin. Indeed, we found that emodic. acid binds to human serum albumin almost completely at the examined range of concentrations.
• Long-acting gonadotropin-releasing hormone analogs and methods of use thereof
  申请人：Koch Yitzhak

  公开号：US20060100154A1

  公开（公告）日：2006-05-11

  The present invention relates to the design, synthesis and biological evaluation of potent long-acting gonadotropin-releasing hormone (GnRH) analogs including agonists and antagonists comprising a GnRH peptide conjugated to emodic acid or an emodic acid derivative. These long acting analogs bind to GnRH receptors with high affinity and are devoid of any toxicity or antiproliferative effects. The present invention further relates to therapeutic uses of these GnRII analogs as contraceptives, in controlling fertility and in treating and/or preventing sex-hormone dependent diseases or conditions.

  本发明涉及设计、合成和生物评价强效长效性促性腺激素释放激素（GnRH）类似物，包括激动剂和拮抗剂，其包括将GnRH肽与大黄酸或大黄酸衍生物结合的类似物。这些长效类似物与GnRH受体结合亲和力高，没有任何毒性或抗增殖作用。本发明还涉及这些GnRII类似物作为避孕药、控制生育和治疗和/或预防性激素依赖性疾病或症状的治疗用途。