tert-butyl N,N-bis[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate | 82409-01-6

• 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: tert-butyl N,N-bis[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate
• CAS: 82409-01-6
• 化学式: C₂₁H₄₁N₃O₆
• 分子量: 431.573
• InChiKey: GADRSXIPMSGEKM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  碘十六烷 、 tert-butyl N,N-bis[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以24%的产率得到
  参考文献：
  名称：

  Structure–activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines

  摘要：

  We have previously shown that simple N-acyl or N-alkyl polyamines bind to and sequester Gram-negative bacterial lipopolysaccharide, affording protection against lethality in animal models of endotoxicosis. Several iterative design-and-test cycles of SAR studies, including high-throughput screens, had converged on compounds with polyamine scaffolds which have been investigated extensively with reference to the number, position, and length of acyl or alkyl appendages. However, the polyamine backbone itself had not been explored sufficiently, and it was not known if incremental variations on the polymethylene spacing would affect LPS-binding and neutralization properties. We have now systematically explored the relationship between variously elongated spermidine [NH2-(CH2)(3)-NH-(CH2)(4)-NH2] and norspermidine [NH2-(CH2)(3)-NH-(CH2)(3)-NH2] backbones, with the N-alkyl group being held constant at C-16 in order to examine if changing the spacing between the inner secondary amines may yield additional SAR information. We find that the norspermine-type compounds consistently showed higher activity compared to corresponding spermine homologues. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.055
• 作为产物：
  描述：

  3,3'-二氨基二丙基胺 、 二碳酸二叔丁酯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 16.0h， 生成 tert-butyl N,N-bis[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]carbamate
  参考文献：
  名称：

  具有抗肿瘤活性的多胺类似物。

  摘要：

  制备了一系列衍生自1,8-二氨基辛烷的四胺并作为抗肿瘤剂进行了测试。1，8-二氨基辛烷与丙烯腈的反应得到N，N′-双（氰基乙基）-1，8-二氨基辛烷，将其还原成四胺20。该化合物的四-Boc衍生物的末端氮原子的烷基化通过甲基或乙基卤化物，然后除去Boc基团，分别得到双（烷基）多胺26a和26b。这三种化合物在小鼠L1210白血病模型中显示出有希望的抗肿瘤活性。多胺氧化酶抑制剂的共同给药增强了抗肿瘤活性。

  DOI：

  10.1021/jm00167a014

文献信息

• Polyamine analogs with antitumor activity
  作者：Michael L. Edwards、N. J. Prakash、D. M. Stemerick、S. P. Sunkara、A. J. Bitonti、G. F. Davis、J. A. Dumont、P. Bey

  DOI：10.1021/jm00167a014

  日期：1990.5

  tetraamines derived from 1,8-diaminooctane was prepared and tested as antitumor agents. The reaction of 1,8-diaminooctane with acrylonitrile gave N,N'-bis(cyanoethyl)-1,8-diaminooctane, which was reduced to tetraamine 20. Alkylation of the terminal nitrogen atoms of the tetra-Boc derivative of this compound by methyl or ethyl halide followed by removal of the Boc groups gave the bis(alkyl)polyamines 26a

  制备了一系列衍生自1,8-二氨基辛烷的四胺并作为抗肿瘤剂进行了测试。1，8-二氨基辛烷与丙烯腈的反应得到N，N′-双（氰基乙基）-1，8-二氨基辛烷，将其还原成四胺20。该化合物的四-Boc衍生物的末端氮原子的烷基化通过甲基或乙基卤化物，然后除去Boc基团，分别得到双（烷基）多胺26a和26b。这三种化合物在小鼠L1210白血病模型中显示出有希望的抗肿瘤活性。多胺氧化酶抑制剂的共同给药增强了抗肿瘤活性。
• Partially Protected Polyamines
  作者：J. B. Hansen、M. C. Nielsen、U. Ehrbar、O. Buchardt

  DOI：10.1055/s-1982-29814

  日期：——
• US5834486A
  申请人：——

  公开号：US5834486A

  公开（公告）日：1998-11-10
• Structure–activity relationships of lipopolysaccharide sequestration in N-alkylpolyamines
  作者：Anurupa Shrestha、Diptesh Sil、Subbalakshmi S. Malladi、Hemamali J. Warshakoon、Sunil A. David

  DOI：10.1016/j.bmcl.2009.03.055

  日期：2009.5

  We have previously shown that simple N-acyl or N-alkyl polyamines bind to and sequester Gram-negative bacterial lipopolysaccharide, affording protection against lethality in animal models of endotoxicosis. Several iterative design-and-test cycles of SAR studies, including high-throughput screens, had converged on compounds with polyamine scaffolds which have been investigated extensively with reference to the number, position, and length of acyl or alkyl appendages. However, the polyamine backbone itself had not been explored sufficiently, and it was not known if incremental variations on the polymethylene spacing would affect LPS-binding and neutralization properties. We have now systematically explored the relationship between variously elongated spermidine [NH2-(CH2)(3)-NH-(CH2)(4)-NH2] and norspermidine [NH2-(CH2)(3)-NH-(CH2)(3)-NH2] backbones, with the N-alkyl group being held constant at C-16 in order to examine if changing the spacing between the inner secondary amines may yield additional SAR information. We find that the norspermine-type compounds consistently showed higher activity compared to corresponding spermine homologues. (c) 2009 Elsevier Ltd. All rights reserved.