(3-Amino-propyl)-{2-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-ethyl}-carbamic acid tert-butyl ester | 284035-10-5

• 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: (3-Amino-propyl)-{2-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl (3-aminopropyl)(2-((tert-butoxycarbonyl)(3-((tert-butoxycarbonyl)amino)propyl)amino)ethyl)carbamate
• CAS: 284035-10-5
• 化学式: C₂₃H₄₆N₄O₆
• 分子量: 474.641
• InChiKey: KFEGRSQCFNPTPX-UHFFFAOYSA-N

物化性质

• 沸点：
  570.4±50.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  33.0
• 可旋转键数：
  10.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  123.43
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (3-Amino-propyl)-{2-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-ethyl}-carbamic acid tert-butyl ester 在 TEA 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 {3-[2-(3-Amino-propylamino)-ethylamino]-propyl}-carbamic acid (3S,8S,9S,10R,13R,14S,17R)-17-((R)-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester
  参考文献：
  名称：

  Synthesis of cholesterol-polyamine carbamates: pKa studies and condensation of calf thymus DNA

  摘要：

  我们制备了新型胆固醇-多胺氨基甲酸酯，并通过电位计测定了它们与最多五个氨基官能团取代的共轭物的 pKas，还测定了它们与小牛胸腺 DNA 的结合亲和力；这些多胺氨基甲酸酯是基因递送（脂质体感染）方面脂质体形成的模型，而脂质体感染是基因治疗的关键第一步。

  DOI：

  10.1039/a803284j
• 作为产物：
  描述：

  {2-[tert-Butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-ethyl}-[3-(2,2,2-trifluoro-acetylamino)-propyl]-carbamic acid tert-butyl ester 在 氨 、 水 作用下， 以 甲醇 为溶剂， 生成 (3-Amino-propyl)-{2-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of cholesterol-polyamine carbamates: pKa studies and condensation of calf thymus DNA

  摘要：

  我们制备了新型胆固醇-多胺氨基甲酸酯，并通过电位计测定了它们与最多五个氨基官能团取代的共轭物的 pKas，还测定了它们与小牛胸腺 DNA 的结合亲和力；这些多胺氨基甲酸酯是基因递送（脂质体感染）方面脂质体形成的模型，而脂质体感染是基因治疗的关键第一步。

  DOI：

  10.1039/a803284j

文献信息

• Arylazopyrazoles as Light-Responsive Molecular Switches in Cyclodextrin-Based Supramolecular Systems
  作者：Lucas Stricker、Eva-Corinna Fritz、Martin Peterlechner、Nikos L. Doltsinis、Bart Jan Ravoo

  DOI：10.1021/jacs.6b00484

  日期：2016.4.6

  most efficient AAP shows binding affinities comparable to azobenzenes, but more effective switching and higher thermal stability of the Z-isomer. As a proof-of-principle, we investigated two CD-based supramolecular systems, containing either cyclodextrin vesicles (CDVs) or cyclodextrin-functionalized gold nanoparticles (CDAuNPs), which revealed excellent reversible, light-responsive aggregation and

  报道了具有优异光物理特性的水溶性芳基并吡唑 (AAP) 的简单和高产率合成。羧酸的引入允许 AAP 的多样化功能化。基于开关单元的结构修改，可以调整 AAP 的光物理特性以获得具有有利光静止状态的分子开关。此外，AAP 与 β-环糊精 (β-CD) 形成稳定且光响应的主客体复合物。我们最高效的 AAP 显示出与偶氮苯相当的结合亲和力，但 Z 异构体的转换效率更高，热稳定性更高。作为原理证明，我们研究了两种基于 CD 的超分子系统，包含环糊精囊泡 (CDV) 或环糊精功能化金纳米粒子 (CDAuNP)，这显示出优异的可逆、光响应聚集和分散行为。总而言之，AAP 具有在高要求和多价光响应系统中作为分子开关的巨大潜力。
• New TRAP1 and Hsp90 chaperone inhibitors with cationic components: Preliminary studies on mitochondrial targeting
  作者：R. Rondanin、G. Lettini、P. Oliva、R. Baruchello、C. Costantini、C. Trapella、D. Simoni、T. Bernardi、L. Sisinni、M. Pietrafesa、G. Ponterini、M.P. Costi、T. Vignudelli、R. Luciani、D.S. Matassa、F. Esposito、M. Landriscina

  DOI：10.1016/j.bmcl.2018.05.031

  日期：2018.7

  TRAP1 (Hsp75) is the mitochondrial paralog of the Hsp90 molecular chaperone family. Due to structural similarity among Hsp90 chaperones, a potential strategy to induce apoptosis through mitochondrial TRAP1 ATPase inhibition has been envisaged and a series of compounds has been developed by binding the simple pharmacophoric core of known Hsp90 inhibitors with various appendages bearing a permanent cationic

  TRAP1（Hsp75）是Hsp90分子伴侣家族的线粒体旁系同源物。由于Hsp90分子伴侣之间的结构相似性，已设想了一种潜在的通过线粒体TRAP1 ATPase抑制作用诱导凋亡的策略，并且通过将已知Hsp90抑制剂的简单药效学核心与带有永久阳离子头的各种附件结合，开发了一系列化合物在生理pH下高度可离子化的碱性基团。选择阳离子附件作为将药物递送至线粒体的媒介。实际上，已证明大量新衍生物积聚在结肠癌细胞的线粒体级分中，以及一系列带有胍类附属物的化合物，
• Novel Polyamine–Naphthalene Diimide Conjugates Targeting Histone Deacetylases and DNA for Cancer Phenotype Reprogramming
  作者：Alice Pasini、Chiara Marchetti、Claudia Sissi、Marilisa Cortesi、Emanuele Giordano、Anna Minarini、Andrea Milelli

  DOI：10.1021/acsmedchemlett.7b00289

  日期：2017.12.14

  A series of hybrid compounds was designed to target histone deacetylases and ds-/G-quadruplex DNAs by merging structural features deriving from Scriptaid and compound 1. Compound 6 binds different DNA arrangements, inhibits HDACs both in vitro and in cells, and is able to induce a reduction of cell proliferation. Moreover, compound 6 displays cell phenotype-reprogramming properties since it prevents the epithelial to mesenchymal transition in cancer cells, inducing a less aggressive and migratory phenotype, which is one of the goals of present innovative strategies in cancer therapies.
• Naphthalene diimide-polyamine hybrids as antiproliferative agents: Focus on the architecture of the polyamine chains
  作者：Andrea Milelli、Chiara Marchetti、Maria Laura Greco、Federica Moraca、Giosuè Costa、Eleonora Turrini、Elena Catanzaro、Nibal Betari、Cinzia Calcabrini、Claudia Sissi、Stefano Alcaro、Carmela Fimognari、Vincenzo Tumiatti、Anna Minarini

  DOI：10.1016/j.ejmech.2017.01.025

  日期：2017.3

  Naphthalene diimides (NDIs) have been widely used as scaffold to design DNA-directed agents able to target peculiar DNA secondary arrangements endowed with relevant biochemical roles. Recently, we have reported disubstituted linear- and macrocyclic-NDIs that bind telomeric and non-telomeric G-quadruplex with high degree of affinity and selectivity. Herein, the synthesis, biological evaluation and molecular modelling studies of a series of asymmetrically substituted NDIs are reported. Among these, compound 9 emerges as the most interesting of the series being able to bind telomeric G-quadruplex (Delta Tm = 29 degrees C at 2.5 mu M), to inhibit the activity of DNA processing enzymes, such as topoisomerase II and TAQ-polymerase, and to exert antiproliferative effects in the NCI panel of cancer cell lines with GI(50) values in the micro-to nanomolar concentration range (i.e. SR cell line, GI50 = 76 nM). Molecular mechanisms of cell death have been investigated and molecular modelling studies have been performed in order to shed light on the antiproliferative and DNA-recognition processes. (C) 2017 Elsevier Masson SAS. All rights reserved.
• Synthesis and cellular studies of polyamine conjugates of a mercaptomethyl–carboranylporphyrin
  作者：N.V.S. Dinesh K. Bhupathiraju、M. Graça H. Vicente

  DOI：10.1016/j.bmc.2012.11.007

  日期：2013.1

  Seven polyamine conjugates of a tri(p-carboranylmethylthio)tetrafluorophenylporphyrin were prepared in high yields by sequential substitution of the p-phenyl fluoride of tetrakis(pentafluorophenyl) porphyrin (TPPF), and investigated as boron delivery agents for boron neutron capture therapy (BNCT). The polyamines used were derivatives of the natural-occurring spermine with different lengths of the carbon chains, terminal primary amine groups and, in two of the conjugates, additional aminoethyl moieties. A tri(polyethylene glycol) conjugate was also synthesized for comparison purposes. The polyamine conjugates showed low dark cytotoxicity (IC50 >400 mu M) and low phototoxicity (IC50 >40 mu M at 1.5 J/cm(2)). All polyamine conjugates, with one exception, showed higher uptake into human glioma T98G cells (up to 12-fold) than the PEG conjugate, and localized preferentially in the cell ER, Golgi and the lysosomes. Our results show that spermine derivatives can serve as effective carriers of boronated porphyrins for the BNCT of tumors. (C) 2012 Elsevier Ltd. All rights reserved.