1,2,3-Benzotriazol-1-yl 4[[(tert-Butyloxy)carbonyl]-amino]-1-methylimidazole-2-carboxylate | 195387-21-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 1,2,3-Benzotriazol-1-yl 4[[(tert-Butyloxy)carbonyl]-amino]-1-methylimidazole-2-carboxylate
• 英文别名: benzotriazol-1-yl 1-methyl-4-[(2-methylpropan-2-yl)oxycarbonylamino]imidazole-2-carboxylate
• CAS: 195387-21-4
• 化学式: C₁₆H₁₈N₆O₄
• 分子量: 358.357
• InChiKey: UMSGGDSZQVCEDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N,N-二甲基-1,3-二氨基丙烷 、 1,2,3-Benzotriazol-1-yl 4[[(tert-Butyloxy)carbonyl]-amino]-1-methylimidazole-2-carboxylate 、 alkaline earth salt of/the/ methylsulfuric acid 以55%的产率得到[2-(2-{2-[2-(3-dimethylamino-propylcarbamoyl)-ethylcarbamoyl]-1-methyl-1H-imidazol-4-ylcarbamoyl}-1-methyl-1H-imidazol-4-ylcarbamoyl)-1-methyl-1H-imidazol-4-yl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  A General Solution- and Solid-Phase Synthetic Procedure for Incorporating Three Contiguous Imidazole Moieties into DNA Sequence Reading Polyamides

  摘要：

  DOI：

  10.1021/jo001034s
• 作为产物：
  描述：

  4-叔丁氧羰基氨基-1-甲基-1H-咪唑-2-甲酸 、 1-羟基苯并三唑 在 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 1,2,3-Benzotriazol-1-yl 4[[(tert-Butyloxy)carbonyl]-amino]-1-methylimidazole-2-carboxylate
  参考文献：
  名称：

  A General Solution- and Solid-Phase Synthetic Procedure for Incorporating Three Contiguous Imidazole Moieties into DNA Sequence Reading Polyamides

  摘要：

  DOI：

  10.1021/jo001034s

文献信息

• Imidazopyridine/Pyrrole and Hydroxybenzimidazole/Pyrrole Pairs for DNA Minor Groove Recognition
  作者：Dorte Renneberg、Peter B. Dervan

  DOI：10.1021/ja0300158

  日期：2003.5.1

  The DNA binding properties of fused heterocycles imidazo[4,5-b]pyridine (Ip) and hydroxybenzimidazole (Hz) paired with pyrrole (Py) in eight-ring hairpin polyamides are reported. The recognition profile of Ip/Py and Hz/Py pairs were compared to the five-membered ring pairs Im/Py and Hp/Py on a DNA restriction fragment at four 6-base pair recognition sites which vary at a single position 5'-TGTNTA-3'

  报道了融合杂环咪唑并 [4,5-b] 吡啶 (Ip) 和羟基苯并咪唑 (Hz) 与吡咯 (Py) 在八环发夹聚酰胺中的 DNA 结合特性。将 Ip/Py 和 Hz/Py 对的识别特征与 DNA 限制片段上的五元环对 Im/Py 和 Hp/Py 在四个 6 碱基对识别位点进行比较，这些位点在单个位置 5'- TGTNTA-3'，其中 N = G、C、T、A。 Ip/Py 对将 GC 与 CG、TA 和 AT 区分开来，Hz/Py 对将 TA 与 AT、GC 和 CG 区分开来，提供了一个新的一组杂环对以靶向 DNA 小沟中的四个 Watson-Crick 碱基对。
• Method for the synthesis of pyrrole and imidazole carboxamides on a
  申请人：California Institute of Technology

  公开号：US06090947A1

  公开（公告）日：2000-07-18

  The present invention describes a novel method for the solid phase synthesis of polyamides containing imidazole and pyrrole carboxamides. The polyamides are prepared on a solid support from aromatic carboxylic acids and aromatic amines with high stepwise coupling yields (>99%), providing milligram quantities of highly pure polyamides. The present invention also describes the synthesis of analogs of the natural products Netropsin and Distamycin A, two antiviral antibiotics. The present invention also describes a novel method for the solid phase synthesis of imidazole and pyrrole carboxamide polyamide-oligonucleotide conjugates. This methodology will greatly increase both the complexity and quantity of minor-groove binding polyamides and minor-groove binding polyamide-oligonucleotide conjugates which can be synthesized and tested.

  本发明描述了一种新颖的固相合成含有咪唑和吡咯羧酰胺的聚酰胺的方法。该聚酰胺是从芳香族羧酸和芳香族胺在固体支撑上制备的，其高步骤耦合收率（>99%）提供毫克级高纯度聚酰胺。本发明还描述了天然产物Netropsin和Distamycin A的类似物的合成，这是两种抗病毒抗生素。本发明还描述了一种新颖的固相合成咪唑和吡咯羧酰胺聚酰胺-寡核苷酸共轭物的方法。这种方法将大大增加可以合成和测试的小沟结合聚酰胺和小沟结合聚酰胺-寡核苷酸共轭物的复杂性和数量。
• Method for the synthesis of pyrrole and imidazole carboxamides on a solid support
  申请人：California Institute of Technology

  公开号：US06683189B1

  公开（公告）日：2004-01-27

  The present invention describes a novel method for the solid phase synthesis of polyamides containing imidazole and pyrrole carboxamides. The polyamides are prepared on a solid support from aromatic carboxylic acids and aromatic amines with high stepwise coupling yields (>99%), providing milligram quantities of highly pure polyamides. The present invention also describes the synthesis of analogs of the natural products Netropsin and Distamycin A, two antiviral antibiotics. The present invention also describes a novel method for the solid phase synthesis of imidazole and pyrrole carboxamide polyamide-oligonucleotide conjugates. This methodology will greatly increase both the complexity and quantity of minor-groove binding polyamides and minor-groove binding polyamide-oligonucleotide conjugates which can be synthesized and tested.

  本发明描述了一种新颖的固相合成含有咪唑和吡咯羧酰胺的聚酰胺的方法。该聚酰胺是从芳香羧酸和芳香胺在固体支持上制备而成，具有高的逐步耦合收率（> 99％），可提供毫克级别的高纯度聚酰胺。本发明还描述了天然产物Netropsin和Distamycin A的类似物的合成，这是两种抗病毒抗生素。本发明还描述了一种新颖的固相合成咪唑和吡咯羧酰胺聚酰胺-寡核苷酸共轭物的方法。这种方法将大大增加可以合成和测试的小沟结合聚酰胺和小沟结合聚酰胺-寡核苷酸共轭物的复杂度和数量。
• A Pyrrole-Imidazole Polyamide Motif for Recognition of Eleven Base Pair Sequences in the Minor Groove of DNA
  作者：Susanne E. Swalley、Eldon E. Baird、Peter B. Dervan

  DOI：10.1002/chem.19970031009

  日期：1997.10

  AbstractA new upper limit of binding site size is defined for the 2:1 overlapped polyamide: DNA motif. Eight‐ring polyamides composed of four‐ring subunits containing pyrrole (Py) and imidazole (Im) amino acids linked by a central β‐alanine (β) spacer („4‐β‐4 ligands”︁) were designed for recognition of eleven base pair sequences as antiparallel dimer (4‐β‐4)2.DNA complexes in the minor groove. The DNA binding properties of three polyamides, ImPyPyPy‐β‐PyPyPyPy‐β‐Dp, ImImPyPy‐β‐PyPyPyPy‐β‐Dp, and ImImImPy‐β‐PyPyPyPy‐β‐Dp, were analyzed by footprinting experiments on DNA fragments containing the respective match sites 5'‐AGTAATTTACT‐3', 5'‐AGGTATTACCT‐3', and 5'‐AGGGATTCCCT‐3' (Dp = dimethylaminopropylamide). Quantitative footprint titrations reveal that each polyamide binds its respective target site with subnanomolar affinity and 7‐fold to over 30‐fold specificity over double‐base‐pair mismatch sites. A 20‐fold decrease in binding affinity is observed for placement of a side‐by‐side β‐β pairing opposite G.C/C.G relative to placement opposite a A.T/T.A base pair. The use of side‐by‐side antiparallel β‐alanine residues as an A.T/T.A‐specific DNA binding element provides a new pairing rule for polyamide design. Expanding the DNA binding site size targeted by pyrrole‐imidazole polyamides represents an important step in the development of cell‐permeable synthetic ligands for the control of gene‐specific regulation.
• METHOD FOR THE SYNTHESIS OF POLY-PYRROLE AND POLY-IMIDAZOLE CARBOXAMIDES ON A SOLID SUPPORT
  申请人：CALIFORNIA INSTITUTE OF TECHNOLOGY

  公开号：EP0885189B1

  公开（公告）日：2002-08-28