Propyl-spermidine

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: Propyl-spermidine
• 英文别名: N'-[3-(propylamino)propyl]butane-1,4-diamine
• 化学式: C₁₀H₂₅N₃
• 分子量: 187.329
• InChiKey: RHIPJLRZVLOPIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  50.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  6,10-Bis(mesitylenesulfonyl)-1-triphenylmethyl-1,6,10-triazatridecane 在 氢溴酸 、 苯酚 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 24.0h， 生成 Propyl-spermidine
  参考文献：
  名称：

  A Comparison of Structure−Activity Relationships between Spermidine and Spermine Analogue Antineoplastics

  摘要：

  A systematic investigation of the impact of spermidine analogues both in vitro and in vivo is described. The study characterizes the effects of these analogues on L1210 cell growth, polyamine pools, ornithine decarboxylase, S-adenosyl-L-methionine decarboxylase, spermidine/spermine N-1-acetyltransferase, the maintenance of cellular charge, i.e., cationic equivalence associated with the polyamines and their analogues, and compares their ability to compete with spermidine for transport. The findings clearly demonstrate that the activity of-the linear polyamine analogues is highly dependent on the length of the triamines and the size of the N-alpha,N-omega-substituents. It appears that there is an optimum chain length for various activities and that the larger the N-alpha,N-omega-alkyls, the less active the compound. Metabolic transformation including N-dealkylation of these compounds is also evaluated. While there is no monotonic relationship between chain length and the ability of the analogue to be metabolized, the dipropyl triamines are clearly more actively catabolized than the corresponding methyl and ethyl systems. A comparison of the triamines with the corresponding tetraamines is made throughout the text regarding both in vitro activity against L1210 cells and in vivo toxicity measurements, suggesting that several triamine analogues may offer therapeutic advantages over the corresponding tetraamines.

  DOI：

  10.1021/jm960849j

文献信息

• [EN] PHARMACEUTICAL OR COSMETIC COMPOSITION FOR TREATING ALOPECIA<br/>[FR] COMPOSITION PHARMACEUTIQUE OU COSMÉTIQUE DESTINÉE AU TRAITEMENT DE L'ALOPÉCIE
  申请人：GIULIANI SPA

  公开号：WO2014016407A1

  公开（公告）日：2014-01-30

  The present invention relates to a cosmetic or pharmaceutical composition for treating alopecia, and in general for counteracting excessive hair loss, comprising as an active ingredient a compound of formula (I) R-N1-spermidine, or 1,4-butanediamine,N-(3-aminopropyl)-N1-R. The compounds of general formula (I) are active in accordance with the objects of the present invention, and also sufficiently stable to allow effective application for topical use on the scalp without potentially being transformed into a different substance, which is no longer active, as a result of oxidation.

  本发明涉及一种用于治疗脱发，通常用于对抗过度脱发的化妆品或药用组合物，其活性成分为化合物R-N1-精胺，或1,4-丁二胺，N-(3-氨丙基)-N1-R的化合物。根据本发明的目的，通用式(I)的化合物是活性的，同时也足够稳定，可以有效地应用于头皮表面，而不会因为氧化而转化为不再活性的不同物质。
• PHARMACEUTICAL OR COSMETIC COMPOSITION FOR TREATING ALOPECIA
  申请人：GIULIANI S.P.A.

  公开号：US20150202132A1

  公开（公告）日：2015-07-23

  The present invention relates to a cosmetic or pharmaceutical composition for treating alopecia, and in general for counteracting excessive hair loss, comprising as an active ingredient a compound of formula (I) R—N 1 -spermidine, or 1,4-butane-diamine,N-(3-aminopropyl)-N 1 —R. The compounds of general formula (I) are active in accordance with the objects of the present invention, and also sufficiently stable to allow effective application for topical use on the scalp without potentially being transformed into a different substance, which is no longer active, as a result of oxidation.

  本发明涉及一种用于治疗脱发的化妆品或药用组合物，一般用于对抗过度脱发，包括作为活性成分的化合物，其化学式为(I) R—N1-精胺，或1,4-丁二胺，N-(3-氨基丙基)-N1-R。根据本发明的目的，一般式(I)的化合物是活性的，同时也足够稳定，可以在头皮上有效应用于局部使用，而不会由于氧化而可能转化为不再活性的不同物质。
• Biologically active spermidine analogues, pharmaceutical compositions and methods of treatment
  申请人：——

  公开号：US20020045780A1

  公开（公告）日：2002-04-18

  Polyamines having the formula: 1 or a salt thereof with a pharmaceutically acceptable acid wherein: R 1 -R 5 may be the same or different and are alkyl, aryl, aryl alkyl, cycloalkyl or hydrogen; at least one of R 1 and R 2 and at least one of R 4 and R 5 are not hydrogen, and any of the alkyl chains may optionally be interrupted by at least one etheric oxygen atom, excluding N 1 ,N 3 -diethylspermidine and N 1 ,N 3 -dipropylspermidine; and A and B are bridging groups which effectively maintain the distance between the nitrogen atoms such that the polyamine: (i) is capable of uptake by a target cell upon administration of the polyamine to a human or non-human animal; and (ii) upon uptake by the target cell, competitively binds via an electrostatic interaction between the positively charged nitrogen atoms to substantially the same biological counter-anions as the intracellular natural polyamines in the target cell.

  具有以下公式1或其药学上可接受的酸盐的多胺，其中：R1-R5可以相同或不同，且为烷基，芳基，芳基烷基，环烷基或氢；R1和R2中至少有一个，以及R4和R5中至少有一个不是氢，任何烷基链都可以选择性地被至少一个醚氧原子中断，但不包括N1，N3-二乙基亚精胺和N1，N3-二丙基亚精胺；A和B是桥接基团，有效地保持氮原子之间的距离，使得多胺：（i）在将多胺用于人类或非人类动物的治疗时，能够被目标细胞吸收；（ii）在被目标细胞吸收后，通过正电荷氮原子之间的静电相互作用与目标细胞中的细胞内天然多胺基本相同地竞争性结合生物计数离子。
• Polyamine-metal chelator conjugates
  申请人：Bergeron J. Raymond

  公开号：US20060211773A1

  公开（公告）日：2006-09-21

  Many metal collators have polar or charged functional groups, which render them difficult to transport across a cell membrane. Polyimide-metal collator conjugates of the invention are compounds comprising a first moiety which is a metal collator and a second moiety which is a polyimide, where the polyimide moiety includes three or more nitrogen atoms which are capable of being positively charged at physiological pH. A sperms-L1 conjugate has been shown to accumulate in L1210 cells several hundred fold more than the unconjugated L1 chelator.

  许多金属配体具有极性或带电的功能基团，这使它们难以穿过细胞膜。本发明的聚酰亚胺-金属配体共轭物是由第一部分为金属配体，第二部分为聚酰亚胺的化合物组成，其中聚酰亚胺部分包含三个或更多的氮原子，在生理pH下能够呈正电荷。已经证明，精子-L1共轭物在L1210细胞中的积累量比未共轭的L1螯合剂高出数百倍。
• Polyamine-Metal Chelator Conjugates
  申请人：Bergeron Raymond

  公开号：US20080096974A2

  公开（公告）日：2008-04-24

  Many metal chelators have polar or charged functional groups, which render them difficult to transport across a cell membrane. Polyamine-metal chelator conjugates of the invention are compounds comprising a first moiety which is a metal chelator and a second moiety which is a polyamine, where the polyamine moiety includes three or more nitrogen atoms which are capable of being positively charged at physiological pH. A spermine-L1 conjugate has been shown to accumulate in L1210 cells several hundred fold more than the unconjugated L1 chelator.

  许多金属螯合剂具有极性或带电的功能基团，这使得它们难以跨越细胞膜。本发明的多胺-金属螯合剂共轭物是化合物，包括第一部分是金属螯合剂，第二部分是多胺，其中多胺部分包括三个或更多的氮原子，在生理pH下能够呈正电荷。已经证明精胺-L1共轭物在L1210细胞中的积累比未共轭的L1螯合剂高出数百倍。