(2S,2'S)-N,N'-(ethane-1,2-diyl)bis(2,6-diaminohexanamide) | 173262-77-6

• 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: (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(2,6-diaminohexanamide)
• 英文别名: (2S)-2,6-diamino-N-[2-[[(2S)-2,6-diaminohexanoyl]amino]ethyl]hexanamide
• CAS: 173262-77-6
• 化学式: C₁₄H₃₂N₆O₂
• 分子量: 316.447
• InChiKey: VYDUSBLFVXIHSJ-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  22
• 可旋转键数：
  13
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  162
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-马来酰亚胺丁酸 、 (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(2,6-diaminohexanamide) 在 N-甲基吗啉 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.17h， 以35%的产率得到(2S)-N-[2-[[(2S)-2,6-bis[4-(2,5-dioxopyrrol-1-yl)butanoylamino]hexanoyl]amino]ethyl]-2,6-bis[4-(2,5-dioxopyrrol-1-yl)butanoylamino]hexanamide
  参考文献：
  名称：

  A novel and facile synthesis of tetra branched derivatives of nociceptin/orphanin FQ

  摘要：

  Branched peptides have been found to be useful in several research fields however their synthesis and purification is complicated. Here we present a novel and facile synthesis of tetra branched derivatives of nociceptin/orphanin FQ (N/OFQ). Three N/OFQ tetra branched derivatives were prepared using novel cores (PWT1, PWT2 and PWT3) containing a maleimido moiety. [Cys(18)]N/OFQ-NH2 was linked to the cores via thiol-Michael reaction characterized by high yield and purity of the desired final product. In the electrically stimulated mouse vas deferens PWT-N/OFQ derivatives mimicked the inhibitory action of the natural sequence showing similar maximal effects and 3 fold higher potencies. The NOP selective antagonist SB-612111 antagonized the effects of N/OFQ and PWT derivatives with similar pKB values (8.02-8.48). In vivo after supraspinal administration PWT2-N/OFQ stimulated food intake in mice mimicking the action of N/OFQ. Compared to the natural peptide PWT2-N/OFQ was 40 fold more potent and elicited larger effects. These findings suggest that the PWT chemical strategy can be successfully applied to biologically active peptides to generate, with unprecedented high purity and yield, tetra branched derivatives displaying an in vitro pharmacological profile similar to that of the natural sequence associated, in vivo, to increased potency and effectiveness.

  DOI：

  10.1016/j.bmc.2014.05.005
• 作为产物：
  描述：

  (S)-2,6-二叔丁氧羰基氨基己酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 25.08h， 生成 (2S,2'S)-N,N'-(ethane-1,2-diyl)bis(2,6-diaminohexanamide)
  参考文献：
  名称：

  A novel and facile synthesis of tetra branched derivatives of nociceptin/orphanin FQ

  摘要：

  Branched peptides have been found to be useful in several research fields however their synthesis and purification is complicated. Here we present a novel and facile synthesis of tetra branched derivatives of nociceptin/orphanin FQ (N/OFQ). Three N/OFQ tetra branched derivatives were prepared using novel cores (PWT1, PWT2 and PWT3) containing a maleimido moiety. [Cys(18)]N/OFQ-NH2 was linked to the cores via thiol-Michael reaction characterized by high yield and purity of the desired final product. In the electrically stimulated mouse vas deferens PWT-N/OFQ derivatives mimicked the inhibitory action of the natural sequence showing similar maximal effects and 3 fold higher potencies. The NOP selective antagonist SB-612111 antagonized the effects of N/OFQ and PWT derivatives with similar pKB values (8.02-8.48). In vivo after supraspinal administration PWT2-N/OFQ stimulated food intake in mice mimicking the action of N/OFQ. Compared to the natural peptide PWT2-N/OFQ was 40 fold more potent and elicited larger effects. These findings suggest that the PWT chemical strategy can be successfully applied to biologically active peptides to generate, with unprecedented high purity and yield, tetra branched derivatives displaying an in vitro pharmacological profile similar to that of the natural sequence associated, in vivo, to increased potency and effectiveness.

  DOI：

  10.1016/j.bmc.2014.05.005

文献信息

• Intranasal cyclic peptide formulations
  申请人：——

  公开号：US20010038824A1

  公开（公告）日：2001-11-08

  The present invention relates to a nasally administrable composition of a physiologically active cyclic peptide and pharmaceutically acceptable salts thereof that is prepared by homogeneously dispersing a physiologically active cyclic peptide such as antifungal cyclic peptides (aerothricins, echinocandin analogs, pneumocandin analogs, and aureobacidines), antibacterial cyclic peptides (e.g. vancomycin, daptomycin), cyclosporin A, lanreotide, vapreotide, vasopressin antagonist (U.S. Pat. No. 5,095,003) and eptifibatide in unique carrier, i.e. a physiologically acceptable powdery or crystalline carrier containing a water insoluble polyvalent metal carrier, or organic carrier having a mean particle size of 20 to 500 &mgr;m, in the presence or absence of an absorption enhancer and by homogeneously adsorbing onto the carrier, and its use for therapeutic treatment of disease such as systemic fungal infections by intranasal administration. The composition can be nasally administered in powder form.

  本发明涉及一种鼻腔可给药的生理活性环肽及其药学上可接受的盐的组合物，该组合物通过将生理活性环肽（如抗真菌环肽（气菌素、伊曲康定类似物、肺孢子菌素类似物和金黄色细菌素）、抗菌环肽（如万古霉素、达托霉素）、环孢霉素A、兰雷罗肽、瓦普雷罗肽、抗利尿激素拮抗剂（美国专利号5,095,003）和依普利贝肽）均匀分散在独特的载体中制备而成，即含有水不溶性多价金属载体或平均粒径为20至500微米的有机载体的生理上可接受的粉状或结晶载体中，存在或不存在吸收增强剂，通过均匀吸附到载体上，并用于通过鼻内给药治疗疾病，如系统真菌感染。该组合物可以以粉剂形式鼻腔给药。
• Supramolecular aggregates comprising maleimido cores
  申请人：Ufpeptides S.r.l.

  公开号：EP2786766A1

  公开（公告）日：2014-10-08

  The invention relates to a supramolecular aggregate of formula (I) wherein A is an active substance, n is an integer from 4 to 16 and X is a core having at least four binding amino group. In a preferred embodiment the maleimido-funzionalized core X is selected from PWT1, PWT2 and PWT3. The supramolecular aggregates can be used in the field of drugs, vaccines, as ligands for GPCR, i.e. agonists as well as antagonist, as antibiotics and as diagnostics eventually in complex with radionuclides.

  本发明涉及式（I）的超分子聚合体，其中 A 是活性物质，n 是 4 至 16 的整数，X 是至少具有四个结合氨基的核心。在一个优选的实施方案中，马来酰亚胺化核心 X 选自 PWT1、PWT2 和 PWT3。超分子聚合体可用于药物、疫苗、GPCR 配体（即激动剂和拮抗剂）、抗生素以及最终与放射性核素复合的诊断。
• AEROTHRICIN ANALOGS, THEIR PREPARATION AND USE
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1100816A1

  公开（公告）日：2001-05-23
• NASALLY ADMINISTRABLE ANTIFUNGAL CYCLIC PEPTIDE COMPOSITIONS
  申请人：Basilea Pharmaceutica AG

  公开号：EP1251827B1

  公开（公告）日：2004-05-26
• NASALLY ADMINISTRABLE CYCLIC PEPTIDE COMPOSITIONS
  申请人：Basilea Pharmaceutica AG

  公开号：EP1251827A2

  公开（公告）日：2002-10-30