(4-{[3-(4-benzothiazol-2-yl-benzylamino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester | 1247874-27-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: (4-{[3-(4-benzothiazol-2-yl-benzylamino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[3-[[4-(1,3-benzothiazol-2-yl)phenyl]methylamino]propyl]-N-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]carbamate
• CAS: 1247874-27-6
• 化学式: C₃₉H₅₉N₅O₆S
• 分子量: 725.993
• InChiKey: JTMLJAZFMSDNOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  51
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  151
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  丁二酸酐 、 (4-{[3-(4-benzothiazol-2-yl-benzylamino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 N-(4-benzothiazol-2-yl-benzyl)-N-[3-(tert-butoxycarbonyl-{4-[tert-butoxycarbonyl-(3-tert-butoxycarbonylamino-propyl)-amino]-butyl}-amino)-propyl]-succinamic acid
  参考文献：
  名称：

  Polyamine Conjugation of Curcumin Analogues toward the Discovery of Mitochondria-Directed Neuroprotective Agents

  摘要：

  Mitochondria-directed antioxidants 2-5 were designed by conjugating curcumin congeners with different polyamine motifs as vehicle tools. The conjugates emerged as efficient antioxidants in mitochondria and fibroblasts and also exerted a protecting role through heme oxygenase-1 activation. Notably, the insertion of a polyamine function into the curcumin-like moiety allowed an efficient intracellular uptake and mitochondria targeting. It also resulted in a significant decrease in the cytotoxicity effects. 2-5 are therefore promising molecules for neuroprotectant lead discovery.

  DOI：

  10.1021/jm100637k
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 生成 (4-{[3-(4-benzothiazol-2-yl-benzylamino)-propyl]-tert-butoxycarbonyl-amino}-butyl)-(3-tert-butoxycarbonylamino-propyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Polyamine Conjugation of Curcumin Analogues toward the Discovery of Mitochondria-Directed Neuroprotective Agents

  摘要：

  Mitochondria-directed antioxidants 2-5 were designed by conjugating curcumin congeners with different polyamine motifs as vehicle tools. The conjugates emerged as efficient antioxidants in mitochondria and fibroblasts and also exerted a protecting role through heme oxygenase-1 activation. Notably, the insertion of a polyamine function into the curcumin-like moiety allowed an efficient intracellular uptake and mitochondria targeting. It also resulted in a significant decrease in the cytotoxicity effects. 2-5 are therefore promising molecules for neuroprotectant lead discovery.

  DOI：

  10.1021/jm100637k

文献信息

• Polyamine Conjugation of Curcumin Analogues toward the Discovery of Mitochondria-Directed Neuroprotective Agents
  作者：Elena Simoni、Christian Bergamini、Romana Fato、Andrea Tarozzi、Sandip Bains、Roberto Motterlini、Andrea Cavalli、Maria Laura Bolognesi、Anna Minarini、Patrizia Hrelia、Giorgio Lenaz、Michela Rosini、Carlo Melchiorre

  DOI：10.1021/jm100637k

  日期：2010.10.14

  Mitochondria-directed antioxidants 2-5 were designed by conjugating curcumin congeners with different polyamine motifs as vehicle tools. The conjugates emerged as efficient antioxidants in mitochondria and fibroblasts and also exerted a protecting role through heme oxygenase-1 activation. Notably, the insertion of a polyamine function into the curcumin-like moiety allowed an efficient intracellular uptake and mitochondria targeting. It also resulted in a significant decrease in the cytotoxicity effects. 2-5 are therefore promising molecules for neuroprotectant lead discovery.