ubenimex

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: ubenimex
• 英文别名: bestatin；(2R)-2-[[(2R,3S)-3-amino-2-hydroxy-4-phenylbutanoyl]amino]-4-methylpentanoic acid
• 化学式: C₁₆H₂₄N₂O₄
• 分子量: 308.378
• InChiKey: VGGGPCQERPFHOB-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-氟脲嘧啶 、 ubenimex 在 吡啶 、 三光气 、 甲烷 作用下， 反应 13.0h， 以36.7%的产率得到5FU-bestatin
  参考文献：
  名称：

  含乌苯美司-抗肿瘤药物协同前药衍生物的冻 干粉剂及其制备方法

  摘要：

  本发明涉及药物化学领域，公开了一种含乌苯美司‑抗肿药物协同前药衍生物的冻干粉剂及其制备方法。该冻干粉剂含有药物活性组分和赋形剂，所述药物活性组分与所述赋形剂的质量比为1：0.5‑6，其中，所述药物活性组分为乌苯美司的前药衍生物或其光学异构体、非对映异构体、消旋体混合物及其药学上可接受的盐。本发明所述的含乌苯美司‑抗肿药物协同前药衍生物的冻干粉剂可以延长药物在体内的滞留时间，改善药物的药代动力学性质，提高药物的生物利用度，从而达到更好的抗肿瘤效果。

  公开号：

  CN109528664B
• 作为产物：
  描述：

  (2R,3S)-3-benzyloxycarbonylamino-2-hydroxy-4-phenylbutanoic acid 在 钯 氢气 、 1-羟基苯并三唑 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 ubenimex
  参考文献：
  名称：

  Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase B

  摘要：

  Stereoisomers and analogues of bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, were synthesized and tested for aminopeptidase B and leucine aminopeptidase inhibiting activity. Among the eight stereoisomers, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the L-leucine residue of bestatin was substituted with other amino acids, only the one containing isoleucine showed more activity than bestatin. Norleucine, norvaline, methionine, valine, serine, glutamine, phenylalanine, glutamic acid, proline, and lysine analogues gave, in that order, decreasing activity. Alkyl and phenyl sub stitution for the benzyl group of bestatin decreased the activity markedly. p-Methyl-, p-chloro-, and p-nitrobestatins showed greater activity than bestatin.

  DOI：

  10.1021/jm00214a010

文献信息

• [EN] COUMARIN-MODIFIED ANDROGENS FOR THE TREATMENT OF PROSTATE CANCER<br/>[FR] ANDROGÈNES À COUMARINE MODIFIÉE POUR LE TRAITEMENT DU CANCER DE LA PROSTATE
  申请人：HEALTH RESEARCH INC

  公开号：WO2020223174A1

  公开（公告）日：2020-11-05

  Provided are androstane and dihydrotestosterone compounds functionalized with carbocyclic groups or heterocyclic groups that may be saturated or unsaturated. The compounds may be used in methods of inhibiting cell growth of malignant cells and/or hyperplastic cells and/or treating individuals having diseases associated with malignant cell growth (e.g., cancer, such as, for example, prostate cancer) and/or hyperplastic cell growth and/or molecular imaging of malignant cells and/or hyperplastic cells and/or inducing degradation of a target protein. Also provided are compositions.

  提供的是功能化为碳环族或杂环族的雄烷和二氢睾酮化合物，这些化合物可能是饱和的或不饱和的。这些化合物可以用于抑制恶性细胞和/或增生细胞的细胞生长的方法，治疗患有与恶性细胞生长相关的疾病的个体（例如，癌症，例如前列腺癌）和/或增生细胞生长和/或恶性细胞和/或增生细胞的分子成像和/或诱导目标蛋白的降解。还提供了组合物。
• COUMARIN-MODIFIED ANDROGENS FOR THE TREATMENT OF PROSTATE CANCER
  申请人：Health Research, Inc.

  公开号：US20220218722A1

  公开（公告）日：2022-07-14

  Provided are androstane and dihydrotestosterone compounds functionalized with carbocyclic groups or heterocyclic groups that may be saturated or unsaturated. The compounds may be used in methods of inhibiting cell growth of malignant cells and/or hyperplastic cells and/or treating individuals having diseases associated with malignant cell growth (e.g., cancer, such as, for example, prostate cancer) and/or hyperplastic cell growth and/or molecular imaging of malignant cells and/or hyperplastic cells and/or inducing degradation of a target protein. Also provided are compositions.
• Synthesis and structure-activity relations of bestatin analogs, inhibitors of aminopeptidase B
  作者：Rinzo Nishizawa、Tetsushi Saino、Tomohisa Takita、Hiroyuki Suda、Takaaki Aoyagi、Hamao Umezawa

  DOI：10.1021/jm00214a010

  日期：1977.4

  Stereoisomers and analogues of bestatin, [(2S,3R)-3-amino-2-hydroxy-4-phenylbutanoyl]-L-leucine, were synthesized and tested for aminopeptidase B and leucine aminopeptidase inhibiting activity. Among the eight stereoisomers, the 2S stereoisomers exhibited strong activity. In a series of compounds in which the L-leucine residue of bestatin was substituted with other amino acids, only the one containing isoleucine showed more activity than bestatin. Norleucine, norvaline, methionine, valine, serine, glutamine, phenylalanine, glutamic acid, proline, and lysine analogues gave, in that order, decreasing activity. Alkyl and phenyl sub stitution for the benzyl group of bestatin decreased the activity markedly. p-Methyl-, p-chloro-, and p-nitrobestatins showed greater activity than bestatin.
• 含乌苯美司-抗肿瘤药物协同前药衍生物的冻 干粉剂及其制备方法
  申请人：江西润泽药业有限公司

  公开号：CN109528664B

  公开（公告）日：2021-07-06

  本发明涉及药物化学领域，公开了一种含乌苯美司‑抗肿药物协同前药衍生物的冻干粉剂及其制备方法。该冻干粉剂含有药物活性组分和赋形剂，所述药物活性组分与所述赋形剂的质量比为1：0.5‑6，其中，所述药物活性组分为乌苯美司的前药衍生物或其光学异构体、非对映异构体、消旋体混合物及其药学上可接受的盐。本发明所述的含乌苯美司‑抗肿药物协同前药衍生物的冻干粉剂可以延长药物在体内的滞留时间，改善药物的药代动力学性质，提高药物的生物利用度，从而达到更好的抗肿瘤效果。