N-(triphenylmethyl)pentane-1,5-diamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: N-(triphenylmethyl)pentane-1,5-diamine
• 英文别名: N1-tritylpentane-1,5-diamine；N-tritylpentane-1,5-diamine；N-trityl-1,5-diaminopentane；N'-tritylpentane-1,5-diamine
• 化学式: C₂₄H₂₈N₂
• 分子量: 344.5
• InChiKey: YIHWNGOLALBJGO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(triphenylmethyl)pentane-1,5-diamine 以 水 、 乙腈 为溶剂， 反应 3.0h， 生成 2-[(5-aminopentyl)amino]-8-isopropyl-5-methyl-3,6-dinitro-4H-1-benzopyran-4-one acetate
  参考文献：
  名称：

  寡核苷酸和稳定剂的缀合物的合成和杂交特性-II。

  摘要：

  合成了具有三或五亚甲基胺接头功能的新的吡喃酮衍生物。这些衍生物通过5'-磷酰胺键共价附于七核苷酸pd（CCAAACA）。测试八核苷酸pd（TGTTTGGC）和上述寡核苷酸缀合物的互补复合物的热力学响应。配合物形成的Tm数据和热力学参数表明色酮（γ-吡喃酮）和香豆素（α-吡喃酮）衍生物具有稳定7-mer / 8-mer互补复合物的能力，最可能是通过吡喃的堆积相互作用邻近核苷酸碱基的芳香系统。色酮（或香豆素）衍生物对寡核苷酸复合物（37摄氏度下的delta delta G）稳定性的影响在-1.0至-1之间。

  DOI：

  10.1016/s0968-0896(97)00127-2
• 作为产物：
  描述：

  在 哌啶 作用下， 以 甲醇 为溶剂， 以256 mg的产率得到N-(triphenylmethyl)pentane-1,5-diamine
  参考文献：
  名称：

  Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity

  摘要：

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.

  DOI：

  10.1021/jm201195m

文献信息

• Solid-phase synthesis of peptide aminoalkylamides using an allyl linker
  作者：Kalle Kaljuste、Anders Undén

  DOI：10.1016/0040-4039(96)00461-3

  日期：1996.4

  The synthesis of an allylic linker is presented to which primary and secondary amino groups can be anchored on solid phase. By acylating MBHA resin with allyl linker HOCH2CHCHCH2OCH2COOH followed by treatment with 4-nitrophenyl chloroformate a mixed carbonate linker is obtained to which amino groups can be attached. The allyl carbamate linkage is stable to both bases and anhydrous acids and

  提出了烯丙基接头的合成，伯氨基和仲氨基可以固定在固相上。通过酰化MBHA树脂与烯丙基接头HOCH 2 CHCHCH 2 OCH 2 COOH接着用4-硝基苯酯获得混合的碳酸酯连接基，其氨基可被附接处理。氨基甲酸烯丙酯键对碱和无水酸均稳定，在温和的反应条件下可被钯催化的烯丙基转移裂解。
• Synthesis of α-PNA containing a functionalized triazine as nucleobase analogue
  作者：Eline Bartolami、Arnaud Gilles、Pascal Dumy、Sébastien Ulrich

  DOI：10.1016/j.tetlet.2015.03.072

  日期：2015.4

  The design of artificial structures such as Peptide Nucleic Acids (PNAs) capable of recognizing nucleic acids has attracted much attention. We report herein the design of L-homoserine derivatives bearing diaminotriazine groups as artificial nucleobase capable of pairing to thymine. We set up an original six-step synthetic route (45% overall yield) that enables the functionalization of the nucleobase analogue. Furthermore, we show that these modified amino acids can be incorporated, by solid-phase peptide synthesis, into alternate and homopolymer alpha-PNAs, thereby giving access to alpha-PNAs in which the nucleobase analogue bears functional groups that may prove useful for the multi-point recognition of nucleic acids. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents. Part 3☆
  作者：Enzo Sottofattori、Maria Anzaldi、Mauro Mazzei、Mariangela Miele、Alessandro Balbi、Dmitri S. Pyshnyi、Olga D. Zakharova、Tatyana V. Abramova

  DOI：10.1016/j.bmc.2004.12.030

  日期：2005.3.1

  New compounds having tri- or pentamethylenamine linker functions were synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The T-m data and thermodynamic parameters for complex formation confirmed the ability of chromone (gamma-pyrone) derivatives to stabilize strongly the 7-mer/8-mer complementary complex. Moreover, benzochromone (naphthopyrane) and, surprisingly, tetrallydropyrimidinethanone derivatives showed the capacity of stabilizing this 7-mer/8-mer complementary complex. The effect of all these compounds on the stability of the oligonucleotide complexes (DeltaG at 37degreesC ranged from - 1.2 to -2.0 kcal/mol) was shown to be comparable to the effect of one nucleotide base pair and similar to the effect (DeltaDeltaG at 37degreesC ranged from -1.5 to -2.0 kcal/mol) found for acridine-oligonucleotide conjugates, which served as a reference in this study. (C) 2004 Elsevier Ltd. All rights reserved.
• Triphenylbutanamines: Kinesin Spindle Protein Inhibitors with in Vivo Antitumor Activity
  作者：Fang Wang、James A. D. Good、Oliver Rath、Hung Yi Kristal Kaan、Oliver B. Sutcliffe、Simon P. Mackay、Frank Kozielski

  DOI：10.1021/jm201195m

  日期：2012.2.23

  The human mitotic kinesin Eg5 represents a novel mitotic spindle target for cancer chemotherapy. We previously identified S-trityl-L-cysteine (STLC) and related analogues as selective potent inhibitors of Eg5. We herein report on the development of a series of 4,4,4-triphenylbutan-1-amine inhibitors derived from the STLC scaffold. This new generation systematically improves on potency: the most potent C-trityl analogues exhibit K-i(aPP) <= 10 nM and GI(50) approximate to 50 nM, comparable to results from the phase II clinical benchmark ispinesib. Crystallographic studies reveal that they adopt the same overall binding configuration as S-trityl analogues at an allosteric site formed by loop L5 of Eg5. Evaluation of their druglike properties reveals favorable profiles for future development and, in the clinical candidate ispinesib, moderate hERG and CYP inhibition. One triphenylbutanamine analogue and ispinesib possess very good bioavailability (51% and 45%, respectively), with the former showing in vivo antitumor growth activity in nude mice xenograft studies.
• Synthesis and hybridization properties of the conjugates of oligonucleotides and stabilization agents—II
  作者：A. Balbi、E. Sottofattori、T. Grandi、M. Mazzei、Dmitri S. Pyshnyi、Sergej G. Lokhov、Alexander V. Lebedev

  DOI：10.1016/s0968-0896(97)00127-2

  日期：1997.10

  synthesized. These derivatives were covalently attached through the 5'-phosphoramide linkage to heptanucleotide pd(CCAAACA). Complementary complexes of the octanucleotide pd(TGTTTGGC) and above oligonucleotide conjugates were tested for their thermodynamic response. The Tm data and thermodynamic parameters for complex formation have demonstrated the ability of chromone (gamma-pyrone) and coumarin (alpha-pyrone)

  合成了具有三或五亚甲基胺接头功能的新的吡喃酮衍生物。这些衍生物通过5'-磷酰胺键共价附于七核苷酸pd（CCAAACA）。测试八核苷酸pd（TGTTTGGC）和上述寡核苷酸缀合物的互补复合物的热力学响应。配合物形成的Tm数据和热力学参数表明色酮（γ-吡喃酮）和香豆素（α-吡喃酮）衍生物具有稳定7-mer / 8-mer互补复合物的能力，最可能是通过吡喃的堆积相互作用邻近核苷酸碱基的芳香系统。色酮（或香豆素）衍生物对寡核苷酸复合物（37摄氏度下的delta delta G）稳定性的影响在-1.0至-1之间。