(3-amino-propyl)-(2-tert-BOCamino-ethyl)-carbamic acid tert-butyl ester | 142039-01-8

• 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-BOCamino-ethyl)-carbamic acid tert-butyl ester
• 英文别名: Di(tert-butyl)-N-(3-aminopropyl)-N,N'-(ethan-1,2-diyl)bis；tert-butyl (3-aminopropyl)(2-((tert-butoxycarbonyl)amino)ethyl)carbamate；tert-butyl N-(3-aminopropyl)-N-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]carbamate
• CAS: 142039-01-8
• 化学式: C₁₅H₃₁N₃O₄
• 分子量: 317.429
• InChiKey: JXUQFYOXWFQCCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  93.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3-amino-propyl)-(2-tert-BOCamino-ethyl)-carbamic acid tert-butyl ester 在 sodium hydroxide 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙腈 为溶剂， 反应 5.5h， 生成
  参考文献：
  名称：

  A ribozyme with michaelase activity

  摘要：

  The ability to generate RNA molecules that can catalyze complex organic transformations not only facilitates the reconstruction and plausibility of possible prebiotic reaction pathways but is also crucial for elucidating the potential of the application of RNA catalysts in organic syntheses. Iterative RNA selection previously identified a ribozyme that catalyzes the Michael addition of a cysteine thiol to an alpha,beta-unsaturated amide. This reaction is chemically similar to the rate limiting step of the thymidylate synthase reaction, which is the corresponding reaction of a cysteine thiol to the double-bond of the uracil nucleobase. Here we provide a detailed description of the synthesis of the ribozyme substrates and the substrate oligonucleotides used for its characterization and the investigation of the background reaction. We also describe the further characterization of the ribozyme with respect to substrate specificity. We show that the thiol group of the cysteine nucleophile is essential for the reaction to proceed. When substituted for a thiomethyl group, no reaction takes place. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00311-5
• 作为产物：
  描述：

  tert-butyl N-[2-(2-cyanoethylamino)ethyl]carbamate 在 锂硼氢 、 三甲基氯硅烷 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 (3-amino-propyl)-(2-tert-BOCamino-ethyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  非共价肽-三吡咯共轭物的序列特异性DNA结合。

  摘要：

  DOI：

  10.1002/anie.200603115

文献信息

• Design, Synthesis, and Biological Evaluation of Indenoisoquinoline Topoisomerase I Inhibitors Featuring Polyamine Side Chains on the Lactam Nitrogen
  作者：Muthukaman Nagarajan、Xiangshu Xiao、Smitha Antony、Glenda Kohlhagen、Yves Pommier、Mark Cushman

  DOI：10.1021/jm030313f

  日期：2003.12.1

  persistent cleavage complexes, and induction of a unique pattern of DNA cleavage sites. Molecular modeling has suggested that substituents on the indenoisoquinoline lactam nitrogen would protrude out of the DNA duplex in the ternary cleavage complex through the major groove. This indicates that relatively large substituents in that location would be tolerated without compromising biological activity. As a

  茚并异喹啉类是一类非喜树碱拓扑异构酶I抑制剂，在人类癌细胞培养中表现出明显的细胞毒性。与喜树碱相比，它们具有许多潜在的优势，包括更高的化学稳定性，更持久的裂解复合物的形成以及DNA裂解位点独特模式的诱导。分子模型表明，茚并异喹啉内酰胺氮上的取代基将从三元裂解复合物中的DNA双链体中穿过主沟突出。这表明在该位置上相对较大的取代基将被耐受而不损害生物活性。作为提高茚并异喹啉的效力和潜在治疗作用的策略，合成了一系列在内酰胺氮上含有多胺侧链的化合物。合成这些化合物的基本原理是，带正电荷的铵阳离子通过与带负电荷的DNA主链的静电结合，可以增加DNA亲和力，并且多胺还可以通过利用多胺转运蛋白来促进细胞摄取。合成中的关键步骤涉及将含有受保护胺侧链的席夫碱与取代的邻苯二甲酸酐缩合，生成顺式-3-芳基-4-羧基-1-异喹啉酮。然后将这些异喹诺酮与亚硫酰氯转化为茚并异喹啉。尽管单胺比先导化合物更有效，通过在侧
• Probing the DNA Reactivity and the Anticancer Properties of a Novel Tubercidin-Pt(II) Complex
  作者：Stefano D’Errico、Andrea Patrizia Falanga、Domenica Capasso、Sonia Di Gaetano、Maria Marzano、Monica Terracciano、Giovanni Nicola Roviello、Gennaro Piccialli、Giorgia Oliviero、Nicola Borbone

  DOI：10.3390/pharmaceutics12070627

  日期：——

  synthesis of a novel Pt(II) neutral complex having as ligand the nucleoside tubercidin, a potent anti-tumor agent extracted from the bacterium Streptomyces Tubercidicus. In detail, the chelation of the metal by a diamine linker installed at C6 purine position of tubercidin assured the introduction of a cisplatin-like unit in the molecular scaffold. The behavior of the synthesized complex with a double-strand

  在本文中，我们报道了一种新型的Pt（II）中性复合物的合成，该复合物具有核苷结核菌素作为配体，核苷结核菌素是从细菌链霉菌提取的一种有效的抗肿瘤剂。详细地，通过安装在结核菌素的C6嘌呤位置的二胺连接体对金属的螯合确保了在分子支架中引入顺铂样单元。用CD光谱法监测具有双链DNA模型的合成复合物的行为，并与顺铂和结核菌素进行比较。另外，使用MTT测试评估了针对HeLa，A375和WM266人癌细胞系的细胞生存力。最后，还报道了在HeLa癌细胞系上进行的凋亡分析（FITC Annexin V）的结果。
• DNA-directed alkylating agents. 5. Acridinecarboxamide derivatives of (1,2-diaminoethane)dichloroplatinum(II)
  作者：Ho H. Lee、Brian D. Palmer、Bruce C. Baguley、Michael Chin、W. David McFadyen、Geoffrey Wickham、Deborah Thorsbourne-Palmer、Laurence P. G. Wakelin、William A. Denny

  DOI：10.1021/jm00094a008

  日期：1992.8

  A series of acridine-2- and -4-carboxamide-linked analogues of PtenCl2 has been prepared and evaluated for biological activity against several tumor cell lines in vitro and in vivo. The platinum complexes were generally more cytotoxic than the corresponding ligands against wild-type P388 leukemia cells in vitro, with acridine-4-carboxamide complexes being the more effective. In contrast to cisplatin and PtenCl2, the complexes were equally active in vitro against both wild-type and cisplatin-resistant P388 lines. The 4-carboxamide complexes showed high levels of in vivo activity (ILS >100%) against wild-type P388 using a single-dose protocol, and one compound was also significantly active in vivo in a cisplatin-resistant line, against which cisplatin and PtenCl2 are inactive.
• Structure-activity relationship of a series of C-terminus modified aminoalkyl, diaminoalkyl- and anilino-containing analogues of the benzoic acid mustard distamycin derivative tallimustine: Synthesis, DNA binding and cytotoxicity studies
  作者：Natalie Brooks、John A Hartley、Jacob E Simpson、Stephen R Wright、Shirley Woo、Sara Centioni、Michael D Fontaine、Terry E McIntyre、Moses Lee

  DOI：10.1016/s0968-0896(97)00096-5

  日期：1997.8

  As part of our investigations into the design of more cytotoxic analogues of the experimental anticancer drug tallimustine, 1, C-terminus modified aminoalkyl-, 2a-c, diaminoalkyl-, 3, and anilino-containing, 4, derivatives have been synthesized. Compounds 2a-c differ by 2, 3, or 4 methylene units in the C-terminus, respectively. Results from an ethidium displacement study on poly(dA-dT), poly(dG-dC), calf thymus DNA and T4 coliphage DNA showed that compounds 2-4 interact in the minor groove of the polynucleotides with a preference for poly(dA-dT) over poly(dG-dC). Compound 4 bound more weakly to the DNAs than 2a-c and 3. Using a CD dilution assay compounds 2a-c and 3 were demonstrated to bind irreversibly to calf thymus DNA. The sequence selectivity by which compounds 2-4 alkylate DNA was demonstrated using a Tag polymerase stop assay. All the compounds alkylated preferentially at the 3'-purine residue in a 5'-TTTTGPu-3' sequence (Pu = A or G). This observed sequence specificity is similar to that of tallimustine and a related compound 5. At an equimolar concentration the aminoalkyl compounds 2a-c (2b > 2a > 2c), and diaminoalkyl compound 3 were more efficient at alkylating these sequences than the anilino compound 4. Following a one hour exposure of human chronic myeloid leukemia K562 cells, compounds 2b and 3 have lower IC50 values (1.64 mu M and 3.03 mu M, respectively) than tallimustine (5 mu M) and similar Values to a related compound 5 (2.2 mu M). The order of cytotoxicity for all the compounds is 2b > 5 > 3 > 2a > 1 > 2c = 4. These results indicate that the cytotoxicities of these compounds are related to their relative ability to alkylate the consensus DNA binding sequence. (C) 1997 Elsevier Science Ltd.
• cis-Dichloroplatinum(II) complexes tethered to dibenzo[c,h][1,6]naphthyridin-6-ones: Synthesis and cytotoxicity in human cancer cell lines in vitro
  作者：Nicolas Desbois、David Pertuit、Johnny Moretto、Claire Cachia、Bruno Chauffert、Florence Bouyer

  DOI：10.1016/j.ejmech.2013.09.037

  日期：2013.11

  A novel family of cisplatin-type complexes tethered to dibenzo[c,h][1,6]naphthyridin-6-one topoisomerase inhibitor via a polymethylene chain and their nonplatinated counterparts were prepared. Their potential cytotoxicity was assessed in three human colorectal cancer cell lines HCT 116, SW480 and HT29 and compared to the reference molecules cisplatin and oxaliplatin. Platinated compounds were poorly active whilst nonplatinated dibenzo[c,h][1,6]naphthyridin-6-one moieties exhibited higher cytotoxic properties than cisplatin and oxaliplatin whatever the length of the polymethylene chain; molecules containing the tri- and hexamethylene chain length were the most cytotoxic. (C) 2013 Elsevier Masson SAS. All rights reserved.