2,3-di(tert-butoxycarbonylamino)propanal | 183499-69-6

• 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: 2,3-di(tert-butoxycarbonylamino)propanal
• 英文别名: bis-Boc 2,3-diaminopropanal；Carbamic acid, (1-formyl-1,2-ethanediyl)bis-, bis(1,1-dimethylethyl) ester；tert-butyl N-[1-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropan-2-yl]carbamate
• CAS: 183499-69-6
• 化学式: C₁₃H₂₄N₂O₅
• 分子量: 288.344
• InChiKey: WRRWVDHNVVLFHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3-di(tert-butoxycarbonylamino)propanal 、 NSC 314622 在 tetrachlorobis(tetrahydrofuran)titanium(IV) 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以45%的产率得到12-[2,3-Diamino-prop-(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：

  N,N'-双(叔丁氧基羰基)-2,3-二氨基丙酸 在 lithium aluminium tetrahydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2,3-di(tert-butoxycarbonylamino)propanal
  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

• Structural Insights Lead to a Negamycin Analogue with Improved Antimicrobial Activity against Gram-Negative Pathogens
  作者：David C. McKinney、Gregory S. Basarab、Alexis I. Cocozaki、Melinda A. Foulk、Matthew D. Miller、Anatoly M. Ruvinsky、Clay W Scott、Kumar Thakur、Liang Zhao、Ed T. Buurman、Sridhar Narayan

  DOI：10.1021/acsmedchemlett.5b00205

  日期：2015.8.13

  Negamycin is a natural product with antibacterial activity against a broad range of Gram-negative pathogens. Recent revelation of its ribosomal binding site and mode of inhibition has reinvigorated efforts to identify improved analogues with clinical potential. Translation-inhibitory potency and antimicrobial activity upon modification of different moieties of negamycin were in line with its observed ribosomal binding conformation, reaffirming stringent structural requirements for activity. However, substitutions on the N6 amine were tolerated and led to N6-(3-aminopropyl)-negamycin (31f) an analogue showing 4-fold improvement in antibacterial activity against key bacterial pathogens. This represents the most potent negamycin derivative to date and may be a stepping stone toward clinical development of this novel antibacterial class.
• Design, synthesis, and biological evaluation of cytotoxic 11-aminoalkenylindenoisoquinoline and 11-diaminoalkenylindenoisoquinoline topoisomerase I inhibitors
  作者：Xiangshu Xiao、Smitha Antony、Glenda Kohlhagen、Yves Pommier、Mark Cushman

  DOI：10.1016/j.bmc.2004.07.027

  日期：2004.10

  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.