1-amino-7-tert-butyloxycarbonylaminooctane | 207980-84-5

• 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: 1-amino-7-tert-butyloxycarbonylaminooctane
• 英文别名: tert-butyl N-(8-aminooctan-2-yl)carbamate
• CAS: 207980-84-5
• 化学式: C₁₃H₂₈N₂O₂
• 分子量: 244.378
• InChiKey: LVAWNRBWOWXKGF-UHFFFAOYSA-N

物化性质

• 沸点：
  351.2±25.0 °C(Predicted)
• 密度：
  0.941±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  64.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-amino-7-tert-butyloxycarbonylaminooctane 在 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 7-amino-1-benzyloxycarbonylaminooctane
  参考文献：
  名称：

  Branched-chain and unsaturated 1,7-Diaminoheptane derivatives as deoxyhypusine synthase inhibitors

  摘要：

  Deoxyhypusine synthase catalyzes the first step in the posttranslational biosynthesis of the unusual amino acid hypusine [N-epsilon-(4-amino-2-hydroxybutyl)lysine] in eukaryotic translation initiation factor 5A (eIF-SA). eIF-SA and its single hypusine residue are essential for cell proliferation. Two series of 1,7-diaminoheptane derivatives were prepared and tested as inhibitors of human deoxyhypusine synthase. These include branched-chain saturated derivatives and both branched- and straight-chain unsaturated derivatives providing size and positional variation in branching and different torsional constraints. Of the branched-chain compounds, 7-amino-1-guanidinooctane (39) proved to be the most potent inhibitor in vitro (IC50, 34 nM), while 1,7-diamino-trans-hept-3-ene (20a) displayed the greatest inhibition (IC50, 0.7 mu M) among the unsaturated compounds. Compound 39 also provided effective inhibition of hypusine production in Chinese hamster ovary cells in culture. Considerations of the in vitro inhibition data reported here, along with earlier findings, allowed some speculation concerning the conformation of the substrate spermidine during its productive interaction at the active site of deoxyhypusine synthase. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)10030-x
• 作为产物：
  描述：

  2-(4-戊炔氧基)四氢-2H-吡喃 在 platinum(IV) oxide 六甲基磷酰三胺 、 正丁基锂 、 sodium azide 、 氢气 、 4-甲基苯磺酸吡啶 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 53.0~58.0 ℃ 、275.79 kPa 条件下， 反应 20.0h， 生成 1-amino-7-tert-butyloxycarbonylaminooctane
  参考文献：
  名称：

  Branched-chain and unsaturated 1,7-Diaminoheptane derivatives as deoxyhypusine synthase inhibitors

  摘要：

  Deoxyhypusine synthase catalyzes the first step in the posttranslational biosynthesis of the unusual amino acid hypusine [N-epsilon-(4-amino-2-hydroxybutyl)lysine] in eukaryotic translation initiation factor 5A (eIF-SA). eIF-SA and its single hypusine residue are essential for cell proliferation. Two series of 1,7-diaminoheptane derivatives were prepared and tested as inhibitors of human deoxyhypusine synthase. These include branched-chain saturated derivatives and both branched- and straight-chain unsaturated derivatives providing size and positional variation in branching and different torsional constraints. Of the branched-chain compounds, 7-amino-1-guanidinooctane (39) proved to be the most potent inhibitor in vitro (IC50, 34 nM), while 1,7-diamino-trans-hept-3-ene (20a) displayed the greatest inhibition (IC50, 0.7 mu M) among the unsaturated compounds. Compound 39 also provided effective inhibition of hypusine production in Chinese hamster ovary cells in culture. Considerations of the in vitro inhibition data reported here, along with earlier findings, allowed some speculation concerning the conformation of the substrate spermidine during its productive interaction at the active site of deoxyhypusine synthase. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)10030-x

文献信息

• Substituierte Aethylendiaminderivate
  申请人：CIBA-GEIGY AG

  公开号：EP0144290A2

  公开（公告）日：1985-06-12

  Aethylendiaminderivate der Formel worin R, Wasserstoff oder Acyl, X, einen gegebenenfalls N-alkylierten natürlichen Aminosäurerest, der N-terminal mit R, und C-terminal mit X2 verbunden ist, X2 einen gegebenenfalls N-alkylierten natürlichen Aminosäurerest, der N-terminal mit X, und C-terminal mit der Gruppe -NR2- verbunden ist. R2 Wasserstoff oder Niederalkyl, R3 und R5 unabhängig voneinander Wasserstoff, unsubstituiertes oder substituiertes Niederalkyl, unsubstituiertes oder substituiertes Arylniederalkyl oder Aryl, R4 Wasserstoff, Niederalkyl oder Acyl und R6 substituiertes Amino oder substituiertes Hydroxy darstellen, und Salze von solchen Verbindungen hemmen die blutdrucksteigernde Wirkung des Enzyms Renin und können als Antihypertensiva verwendet werden.

  一种乙二胺衍生物，其式如下 其中 R 是氢或酰基，X 是任选 N-烷基化的天然氨基酸残基，其 N-端与 R 连接，C-端与 X2 连接，X2 是任选 N-烷基化的天然氨基酸残基，其 N-端与 X 连接，C-端与基团 -NR2- 连接。R2代表氢或低级烷基，R3和R5独立地代表氢、未取代或取代的低级烷基、未取代或取代的芳基低级烷基或芳基，R4代表氢、低级烷基或酰基，R6代表取代的氨基或取代的羟基，这类化合物的盐能抑制肾素酶的降压作用，可用作降压药。
• 5-Amino-4-Hydroxyvalerylderivate, als Zwischenprodukte in der Herstellung von Renin-Hemmern benutzbar
  申请人：CIBA-GEIGY AG

  公开号：EP0400290A1

  公开（公告）日：1990-12-05

  Verbindungen der Formel worin R3 Wasserstoff, Alkyl, Cycloalkyl, Arylniederalkyl oder Aryl, R4 Hydroxy oder veräthertes oder verestertes Hydroxy, R5 Alkyl, Cycloalkyl, Arylniederalkyl oder Aryl und R6 substituiertes Amino oder substituiertes Hydroxy darstellen, und Salze von solchen Verbindungen sind Zwischenprodukte zur Herstellung von Renininhibitoren.

  式中的化合物 其中 R3 为氢、烷基、环烷基、芳基-低级烷基或芳基，R4 为羟基或醚化或酯化羟基，R5 为烷基、环烷基、芳基-低级烷基或芳基，R6 为取代氨基或取代羟基，此类化合物及其盐类是制备肾素抑制剂的中间体。
• Branched-chain and unsaturated 1,7-Diaminoheptane derivatives as deoxyhypusine synthase inhibitors
  作者：Young Bok Lee、J.E. Folk

  DOI：10.1016/s0968-0896(97)10030-x

  日期：1998.3

  Deoxyhypusine synthase catalyzes the first step in the posttranslational biosynthesis of the unusual amino acid hypusine [N-epsilon-(4-amino-2-hydroxybutyl)lysine] in eukaryotic translation initiation factor 5A (eIF-SA). eIF-SA and its single hypusine residue are essential for cell proliferation. Two series of 1,7-diaminoheptane derivatives were prepared and tested as inhibitors of human deoxyhypusine synthase. These include branched-chain saturated derivatives and both branched- and straight-chain unsaturated derivatives providing size and positional variation in branching and different torsional constraints. Of the branched-chain compounds, 7-amino-1-guanidinooctane (39) proved to be the most potent inhibitor in vitro (IC50, 34 nM), while 1,7-diamino-trans-hept-3-ene (20a) displayed the greatest inhibition (IC50, 0.7 mu M) among the unsaturated compounds. Compound 39 also provided effective inhibition of hypusine production in Chinese hamster ovary cells in culture. Considerations of the in vitro inhibition data reported here, along with earlier findings, allowed some speculation concerning the conformation of the substrate spermidine during its productive interaction at the active site of deoxyhypusine synthase. Published by Elsevier Science Ltd.