(3-amino-propyl)-(5-tert-butoxycarbonylamino-pentyl)-carbamic acid tert-butyl ester | 1055230-46-0

• 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-amino-propyl)-(5-tert-butoxycarbonylamino-pentyl)-carbamic acid tert-butyl ester
• 英文别名: 1,5-di(tert-butyloxycarbonylamino)-N-(3-aminopropyl)pentane；N4,N9-di-tert-butoxycarbonyl-4-azanonane-1,9-diamine
• CAS: 1055230-46-0
• 化学式: C₁₈H₃₇N₃O₄
• 分子量: 359.509
• InChiKey: RIZPLWSEYPHBPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.27
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  93.89
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3-amino-propyl)-(5-tert-butoxycarbonylamino-pentyl)-carbamic acid tert-butyl ester 、 丙烯腈 以 甲醇 为溶剂， 以98%的产率得到1,5-di(tert-butyloxycarbonylamino)-N-(3-(2-cyanoethyl)aminopropyl)pentane
  参考文献：
  名称：

  The total large-scale synthesis of argiopine

  摘要：

  The total large-scale synthesis of a natural toxin argiopine, a polymethylenepolyamine derivative, was developed. It consisted of 26 stages and included three key block schemes. Most of the stages proceeded quantitatively, which excluded the necessity of using the chromatographic separation of intermediates.

  DOI：

  10.1134/s1068162009060120
• 作为产物：
  描述：

  (5-tert-butoxycarbonylamino-pentyl)-(2-cyano-ethyl)-carbamic acid tert-butyl ester 在 氨 、 氢气 作用下， 以 乙醇 为溶剂， 25.0 ℃ 、600.01 kPa 条件下， 反应 72.0h， 生成 (3-amino-propyl)-(5-tert-butoxycarbonylamino-pentyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Targeting the Polyamine Transport System with Benzazepine- and Azepine-Polyamine Conjugates

  摘要：

  The polyamine transport system (PTS) whose activity is up-regulated in cancer cells is an attractive target for drug design. Two heterocyclic (azepine and benzazepine) systems were conjugated to various polyamine moieties through an amidine bound to afford 18 compounds which were evaluated for their affinity for the PTS and their ability to use the PTS for cell delivery. Structure-activity relationship studies and lead optimization afforded two attractive PTS targeting compounds. The azepine-spermidine conjugate 14 is a very selective substrate of the PTS that may serve as a vector for radioelements used for diagnoses or therapeutics in nuclear medicine. The nitrobenzazepine-spermine conjugate 28 is a very powerful PTS inhibitor with very low intrinsic cytotoxicity, able to prevent the growth of polyamine depleted cells in presence of exogenous polyamines.

  DOI：

  10.1021/jm1007648

文献信息

• Parallel Synthesis and Cytotoxicity Evaluation of a Polyamine−Quinone Conjugates Library
  作者：Maria Laura Bolognesi、Natalia Calonghi、Chiara Mangano、Lanfranco Masotti、Carlo Melchiorre

  DOI：10.1021/jm800637b

  日期：2008.9.11

  A library of 24 derivatives designed by combining two natural products-derived fragments was prepared and tested to determine their anticancer potential in HT29 colon cancer cells. All library members inhibit cell proliferation as measured by MTT mitochondrial functional assay, with IC50 values in the 1-100 mu M range. Entry 1b caused apoptotic EGFR-mediated intracellular signaling. Thus, polyamino-quinones emerged as readily accessible and easily diversified scaffolds for anticancer lead discovery.