[(S)-5-tert-Butoxycarbonylamino-5-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester | 761456-85-3

• 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: [(S)-5-tert-Butoxycarbonylamino-5-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester
• CAS: 761456-85-3
• 化学式: C₁₈H₃₅N₃O₆
• 分子量: 389.492
• InChiKey: ZVMFOUCEYTZSKD-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.59
• 重原子数：
  27.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  106.2
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  [(S)-5-tert-Butoxycarbonylamino-5-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester 在 四氢呋喃 、 lithium aluminium tetrahydride 、 四氯化钛 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 12-[(S)-2,6-Diamino-hex-(E)-ylidene]-2,3-dimethoxy-6-methyl-6H,12H-8,10-dioxa-6-aza-benzo[a]cyclopenta[h]fluoren-5-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of cytotoxic 11-aminoalkenylindenoisoquinoline and 11-diaminoalkenylindenoisoquinoline topoisomerase I inhibitors

  摘要：

  The cytotoxic indenoisoquinolines are a novel class of noncamptothecin topoisomerase I inhibitors having certain features that compare favorably with the camptothecins. A new strategy was adopted to attach aminoalkenyl substituents at C-11 of the indenoisoquinoline ring system, which, according to molecular modeling, would orient the side chains toward the DNA minor groove. All of the newly synthesized compounds were more cytotoxic than the parent indenoisoquinoline NSC 314622. Despite an imperfect correlation between cytotoxicities and topoisomerase I inhibition results, the hypothetical structural model of the cleavage complex presented here provides a conceptual framework to explain the structure-activity relationships. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.027
• 作为产物：
  描述：

  (S)-2,6-二叔丁氧羰基氨基己酸 、 二甲羟胺盐酸盐 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到[(S)-5-tert-Butoxycarbonylamino-5-(methoxy-methyl-carbamoyl)-pentyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of cytotoxic 11-aminoalkenylindenoisoquinoline and 11-diaminoalkenylindenoisoquinoline topoisomerase I inhibitors

  摘要：

  The cytotoxic indenoisoquinolines are a novel class of noncamptothecin topoisomerase I inhibitors having certain features that compare favorably with the camptothecins. A new strategy was adopted to attach aminoalkenyl substituents at C-11 of the indenoisoquinoline ring system, which, according to molecular modeling, would orient the side chains toward the DNA minor groove. All of the newly synthesized compounds were more cytotoxic than the parent indenoisoquinoline NSC 314622. Despite an imperfect correlation between cytotoxicities and topoisomerase I inhibition results, the hypothetical structural model of the cleavage complex presented here provides a conceptual framework to explain the structure-activity relationships. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.027

文献信息

• Universal Peptidomimetics
  作者：Eunhwa Ko、Jing Liu、Lisa M. Perez、Genliang Lu、Amber Schaefer、Kevin Burgess

  DOI：10.1021/ja1071916

  日期：2011.1.26

  This paper concerns peptidomimetic scaffolds that can present side chains in conformations resembling those of amino acids in secondary structures without incurring excessive entropic or enthalpic penalties. Compounds of this type are referred to here as minimalist mimics. The core hypothesis of this paper is that small sets of such scaffolds can be designed to analogue local pairs of amino acids (including noncontiguous ones) in any secondary structure; i.e., they are universal peptidomimetics. To illustrate this concept, we designed a set of four peptidomimetic scaffolds. Libraries based on them were made bearing side chains corresponding to many of the protein-derived amino acids. Modeling experiments were performed to give an indication of kinetic and thermodynamic accessibilities of conformations that can mimic secondary structures. Together, peptidomimetics based on these four scaffolds can adopt conformations that resemble almost any combination of local amino acid side chains in any secondary structure. Universal peptidomimetics of this kind are likely to be most useful in the design of libraries for high-throughput screening against diverse targets. Consequently, data arising from submission of these molecules to the NIH Molecular Libraries Small Molecule Repository (MLSMR) are outlined.