(3-tert-butoxycarbonylamino-propyl)-(3-cyanopropyl)carbamic acid tert-butyl ester | 152844-23-0

• 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-tert-butoxycarbonylamino-propyl)-(3-cyanopropyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-(3-cyanopropyl)-N-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate
• CAS: 152844-23-0
• 化学式: C₁₇H₃₁N₃O₄
• 分子量: 341.451
• InChiKey: YQQWYMOBCXUWRL-UHFFFAOYSA-N

物化性质

• 沸点：
  481.2±38.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  24.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  91.66
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3-tert-butoxycarbonylamino-propyl)-(3-cyanopropyl)carbamic acid tert-butyl ester 在 镍 sodium hydroxide 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 tert-butyl N-[4-[[(E)-3-(4-hydroxyphenyl)prop-2-enoyl]amino]butyl]-N-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate
  参考文献：
  名称：

  Synthese derp-Cumaroylspermidine

  摘要：

  The Synthesis of p‐CumaroylspermidinesThe synthesis of three mono[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines, 10, 20, and 28, three bis[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]spermidines, 6, 16, and 25, and one tris[(E)‐3‐(4‐hydroxyphenyl)prop‐2‐enoyl]‐spermidine is described.

  DOI：

  10.1002/hlca.19960790222
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 sodium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 生成 (3-tert-butoxycarbonylamino-propyl)-(3-cyanopropyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  N-酰化的腐胺，亚精胺和亚精胺衍生物的设计，合成和体外抗动素体评估

  摘要：

  对多胺衍生物的构效关系研究导致了17种化合物的合成和抗运动型活性的测定。其中，亚精胺衍生物（化合物13）在体外对利什曼原虫多虫尼阿米虫（IC 50为5.4μM ；选择性指数> 18.5）具有特异性活性，而亚精胺衍生物（化合物28）对布氏锥虫（Trypanosoma brucei gambiense）具有特异性活性（IC 50对1.9μM;选择性指数> 52）。

  DOI：

  10.1016/j.bmcl.2014.11.073

文献信息

• Design, synthesis and anticancer activity of 2-amidomethoxy-1,4-naphthoquinones and its conjugates with Biotin/polyamine
  作者：Manoj Manickam、Pulla Reddy Boggu、Thanigaimalai Pillaiyar、Yeo Jin Nam、Md. Abdullah、Seung Jin Lee、Jong Seong Kang、Sang-Hun Jung

  DOI：10.1016/j.bmcl.2020.127685

  日期：2021.1

  Among the synthesized compounds, naphthoquinone amines, 5 (0.8; 0.6; 0.8), 14 (0.8; 0.6; 0.5) and the amine precursor, 4 (1.3; 0.3; 1.0) displayed potent anticancer activities. A tumor targeting drug delivery system was achieved by synthesizing the conjugate 6 (1.4; 0.5; 1.1) of naphthoquinone-amine 5 and Biotin which also proved its potency. Finally, to introduce polyamine conjugate, spermidine was attached

  在先前工作的基础上，准备了一系列5-羟基-2-氨基甲氧基-1,4-萘醌，以建立针对三种细胞系的抗癌活性（IC 50以µM为单位）的结构-活性关系研究。colo205（结肠腺癌），T47D（乳腺导管癌）和K562（慢性粒细胞性白血病）。在合成的化合物中，萘醌胺5（0.8; 0.6; 0.8），14（0.8; 0.6; 0.5）和胺前体4（1.3; 0.3; 1.0）具有较强的抗癌活性。通过合成萘醌-胺5的缀合物6（1.4; 0.5; 1.1）实现了肿瘤靶向药物递送系统生物素也证明了其功效。最后，为了引入多胺缀合物，将亚精胺与2-酰胺基甲氧基-1,4-萘醌连接。萘醌-亚精胺缀合物27（1.2； 1.7； 1.7）也保留了活性。因此，探索了有效的萘醌胺，并开发了生物素/聚胺缀合物作为靶向肿瘤的药物递送系统。
• Enzymatic Logic of Anthrax Stealth Siderophore Biosynthesis:  AsbA Catalyzes ATP-Dependent Condensation of Citric Acid and Spermidine
  作者：Daniel Oves-Costales、Nadia Kadi、Mark J. Fogg、Lijiang Song、Keith S. Wilson、Gregory L. Challis

  DOI：10.1021/ja072391o

  日期：2007.7.1

  A unique combination of nonribosomal peptide synthetase (NRPS) and NRPS-independent siderophore (NIS) synthetase enzymes is known to be required for petrobactin biosynthesis in B. anthracis. Here it is shown that AsbA from B. anthracis, the first type A NIS synthetase to be biochemically characterized, catalyzes ATP-dependent regioselective condensation of citric acid with N8 of spermidine, but not

  Petrobactin 是一种铁螯合铁载体，最初从 Marinobactercarbonoclastus 中分离出来，已被证明在缺铁条件下的生长和致命的生物恐怖主义剂炭疽芽孢杆菌的毒力中发挥重要作用。最近显示它不与铁钙蛋白结合，使其被指定为可以避开哺乳动物免疫系统的“隐形铁载体”。已知非核糖体肽合成酶 (NRPS) 和不依赖 NRPS 的铁载体 (NIS) 合成酶的独特组合是炭疽芽孢杆菌中石油杆菌素生物合成所必需的。此处显示来自炭疽芽孢杆菌的 AsbA，第一种被生化表征的 A 型 NIS 合成酶，催化柠檬酸与亚精胺的 N8 的 ATP 依赖性区域选择性缩合，但不与 N1-(3,4-二羟基苯甲酰基)-亚精胺.
• Synthesis of New Alkylaminooxysterols with Potent Cell Differentiating Activities: Identification of Leads for the Treatment of Cancer and Neurodegenerative Diseases
  作者：Philippe de Medina、Michael R. Paillasse、Bruno Payré、Sandrine Silvente-Poirot、Marc Poirot

  DOI：10.1021/jm901063e

  日期：2009.12.10

  We describe here the syntheses and the biological properties of new alkylaminooxysterols. Compounds were synthesized through the trans-diaxial aminolysis of 5,6-alpha-epoxysterols with various natural amines including histamine, putrescine, spermidine, or spermine. The regioselective synthesis of these 16 new 5 alpha-hydroxyl-6 beta-aminoalkylsterols is presented. Compounds were first screened for dendrite outgrowth and cytotoxicity in vitro, and two leads were selected and further characterized. 5 alpha-Hydroxy-6 beta-[2-(1-H-imidazol-4-yl)ethylamino]cholestan -3 beta-ol, called dendrogenin A, induced growth control, differentiation, and the death of tumor cell lines representative of various cancers including metastatic melanoma and breast cancer. 5 alpha-hydroxyl-6 beta-[3-(4-aminobutylamino)propylamino]cholest-7-en-3 beta-ol, called dendrogenin B, induced neurite outgrowth on various cell lines, neuronal differentiation in pluripotent cells, and survival of normal neurones at nanomolar concentrations. In summary, we report that two new alkylaminooxysterols, dendrogenin A and dendrogenin B, are the first members of a class of compounds that induce cell differentiation at nanomolar concentrations and represent promising new leads for the treatment of cancer or neurodegenerative diseases.
• New Ianthelliformisamine Derivatives as Antibiotic Enhancers against Resistant Gram-Negative Bacteria
  作者：Cyril Pieri、Diane Borselli、Carole Di Giorgio、Michel De Méo、Jean-Michel Bolla、Nicolas Vidal、Sébastien Combes、Jean Michel Brunel

  DOI：10.1021/jm500194e

  日期：2014.5.22

  A series consisting of ianthelliformisamimes A, B, and C as well as its synthetic analogues was prepared in high chemical yield, from 27 to 91%, using peptide coupling as the key step, and the compounds were evaluated for their in vitro antibiotic enhancer properties against resistant Gram-negative bacteria and clinical isolates. The mechanism of action of one of these derivatives against Pseudomonas aeruginosa when combined with doxycycline was precisely evaluated utilizing bioluminescence to measure ATP efflux and fluorescence to evaluate membrane depolarization.
• Design, synthesis and antimalarial/anticancer evaluation of spermidine linked artemisinin conjugates designed to exploit polyamine transporters in Plasmodium falciparum and HL-60 cancer cell lines
  作者：James Chadwick、Michael Jones、Amy E. Mercer、Paul A. Stocks、Stephen A. Ward、B. Kevin Park、Paul M. O’Neill

  DOI：10.1016/j.bmc.2010.02.035

  日期：2010.4

  A series of artemisinin-spermidine conjugates designed to utilise the upregulated polyamine transporter found in cancer cells have been prepared. These conjugates were evaluated against human promyelocytic leukaemia HL-60 cells and chloroquine-sensitive 3D7 Plasmodium falciparum and several show promising anticancer and antimalarial activity. Although some limitations in this vector-based approach are apparent, a number of high potency Boc-protected analogues were identified with activity against malaria parasites as low as 0.21 nM. (C) 2010 Elsevier Ltd. All rights reserved.