N-(1-((4-((3-aminopropyl)amino)butyl)amino)-1-oxo-4-phenylbutan-2-yl)-7-guanidinoheptanamide

• 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: N-(1-((4-((3-aminopropyl)amino)butyl)amino)-1-oxo-4-phenylbutan-2-yl)-7-guanidinoheptanamide
• 英文别名: 10-[N-(7-guanidinoheptanoyl)-glycyl]-1,5,10-triazadecane；Heptanamide,7-[(aminoiminomethyl)amino]-N-[2-[[4-[(3-aminopropyl)amino]butyl]amino]-2-oxoethyl]-；N-[2-[4-(3-aminopropylamino)butylamino]-2-oxoethyl]-7-(diaminomethylideneamino)heptanamide
• 化学式: C₁₇H₃₇N₇O₂
• 分子量: 371.526
• InChiKey: PPIJBKDZMOYFAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  26
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  161
• 氢给体数：
  6
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  庚酸 在 ammonium cerium (IV) nitrate 、 磷酸 、 三乙酰氧基硼氢化钠 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.33h， 生成 N-(1-((4-((3-aminopropyl)amino)butyl)amino)-1-oxo-4-phenylbutan-2-yl)-7-guanidinoheptanamide
  参考文献：
  名称：

  Improved synthesis of 15-deoxyspergualin analogs using the Ugi multi-component reaction

  摘要：

  Spergualin is a natural product that exhibits immunosuppressive, anti-tumor and anti-bacterial activities. Its derivatives, such as 15-deoxyspergualin (15-DSG), have been clinically approved for acute allograft rejection. However, the reported syntheses are cumbersome (>10 steps) and they suffer from low overall yields (similar to 0.3% to 18%). Moreover, spergualin and its derivatives are chemically unstable and rapidly hydrolyzed in aqueous buffer. Here, we have re-explored these issues and report a modified synthetic route with significantly improved overall yield (similar to 31% to 47%). The key transformation is a microwave-accelerated Ugi multi-component reaction that is used to generate the peptoid core in a single step. Using the products of this route, we found that modifications of the hemiaminal significantly increased chemical stability. Thus, we anticipate that this synthetic route will improve access to biologically active 15-DSG derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.079

文献信息

• Spergualin-related compounds, processes for the preparation thereof and their use as medicaments
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：EP0105193A2

  公开（公告）日：1984-04-11

  This invention relates to novel spergualin-related compounds of the formula (I) wherein R1 represents a hydrogen atom, a hydroxyl group, or an aliphatic acyloxy group with 1 to 10 carbon atoms; R2 represents a residue of an a- or ω-amino acid remaining after removing one of the hydrogen atoms from the a- or ω-amino group and the hydroxyl group from the a-carboxyl group with the proviso that R2 does not include a residue of a-hydroxyglycine, said R2 being attached to the adjacent carbonyl group and amino group by amide bonds; and m denotes an integer of 4 to 6, and their physiologically acceptable salts, and to a process for preparing the same. The compounds according to the present invention exhibit high stability and antitumor activity.

  本发明涉及式 (I) 的新型 spergualin 相关化合物 其中 R1 代表氢原子、羟基或具有 1 至 10 个碳原子的脂肪族酰氧基；R2 代表从 a-或 ω-氨基中去除一个氢原子和从 a-羧基中去除羟基后剩余的 a-或 ω-氨基酸残基，但 R2 不包括 a-羟基甘氨酸残基，所述 R2 通过酰胺键连接到相邻的羰基和氨基上；和 m 表示 4 至 6 的整数，以及它们的生理上可接受的盐和制备它们的工艺。本发明的化合物具有高稳定性和抗肿瘤活性。
• Use of spergualin derivatives for the preparation of medicaments having immunosuppressive activity
  申请人：MICROBIAL CHEMISTRY RESEARCH FOUNDATION

  公开号：EP0181592A2

  公开（公告）日：1986-05-21

  The present invention relates to the use of compounds of the formula or pharmacologically acceptable salts thereof, for the preparation of medicaments having immunosuppressive activity.

  本发明涉及使用式中化合物或其药理上可接受的盐类制备具有免疫抑制活性的药物。
• UMEZAWA, HAMAO;TAKEUCHI, TOMIO;NISHIZAWA, RINZO;TAKAHASHI, KATSUTOSHI;NAK+
  作者：UMEZAWA, HAMAO、TAKEUCHI, TOMIO、NISHIZAWA, RINZO、TAKAHASHI, KATSUTOSHI、NAK+

  DOI：——

  日期：——
• MORIGUTI, MAKOTO;UMEHDA, JOSIXISA;IGAI, KATSUSIGEH;NAKAMURA, TEHRUYA;TOI,+
  作者：MORIGUTI, MAKOTO、UMEHDA, JOSIXISA、IGAI, KATSUSIGEH、NAKAMURA, TEHRUYA、TOI,+

  DOI：——

  日期：——
• JPS5942356A
  申请人：——

  公开号：JPS5942356A

  公开（公告）日：1984-03-08