N,N'-bis{(S)-(+)-1-methoxycarbonyl-2-(4-imidazolyl)ethyl}-2,6-pyridinedicarboxamide | 185031-56-5

• 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: N,N'-bis{(S)-(+)-1-methoxycarbonyl-2-(4-imidazolyl)ethyl}-2,6-pyridinedicarboxamide
• 英文别名: (S)-3-(imidazol-4-yl)-2-[(6-{[(S)-2-(imidazol-4-yl)-1-methoxycarbonylethylimino]carbonyl}pyridine-2-carbonyl)imino]propionic acid methyl ester；methyl (2S)-3-(1H-imidazol-5-yl)-2-[[6-[[(2S)-3-(1H-imidazol-5-yl)-1-methoxy-1-oxopropan-2-yl]carbamoyl]pyridine-2-carbonyl]amino]propanoate
• CAS: 185031-56-5
• 化学式: C₂₁H₂₃N₇O₆
• 分子量: 469.457
• InChiKey: JLXVPCPONQNJDF-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  181
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N,N'-bis{(S)-(+)-1-methoxycarbonyl-2-(4-imidazolyl)ethyl}-2,6-pyridinedicarboxamide 、 间二溴苄 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 21.0h， 以50%的产率得到dimethyl (8S,18S)-10,16-dioxo-3,5,9,17,21,23,31-heptazapentacyclo[23.3.1.13,6.111,15.120,23]dotriaconta-1(29),4,6(32),11(31),12,14,20(30),21,25,27-decaene-8,18-dicarboxylate
  参考文献：
  名称：

  新型手性咪唑环烷受体：氨基酸衍生物的合成和对映选择性识别。

  摘要：

  通过在NaH存在下用二溴化物对桥接的组氨酸二酯2的咪唑基1N位进行高选择性N-烷基化，合成了新型手性咪唑环烷受体。这些受体在25.0摄氏度的CHCl3中对L-和D-氨基酸衍生物的对映异构体（高达KD / KL = 3.52，δdelta G0 = -3.11 kJ mol-1）表现出良好的手性识别。

  DOI：

  10.1039/b103325p
• 作为产物：
  描述：

  L-组氨酸 在 氢氧化钾 、 氯化亚砜 作用下， 以 四氢呋喃 为溶剂， 反应 27.5h， 生成 N,N'-bis{(S)-(+)-1-methoxycarbonyl-2-(4-imidazolyl)ethyl}-2,6-pyridinedicarboxamide
  参考文献：
  名称：

  含吡啶环和功能臂的新型螯合大环四氧多胺的合成

  摘要：

  摘要 合成了七种新型手性大环四氧多胺，分别由L-组氨酸、L-丙氨酸、L-亮氨酸和L-苯丙氨酸衍生而来，并通过MS、1H NMR和元素分析对其进行表征。

  DOI：

  10.1080/00397919908086251

文献信息

• Synthesis, characterization, and spectroscopic properties of three novel pentadentate copper(II) complexes related to the metal-chelating inhibitors against DNA binding with HIV-EP1
  作者：Hiromasa Kurosaki、Rakesh Kumar Sharma、Sachiko Aoki、Teruhiko Inoue、Yoshinari Okamoto、Yukio Sugiura、Mitsunobu Doi、Toshimasa Ishida、Masami Otsuka、Masafumi Goto

  DOI：10.1039/b006949n

  日期：——

  Three potentially five-coordinate peptide ligands having a pyridine and two histidine moieties, were synthesized to study their copper(II) complexation. Blue copper(II) complexes with deprotonated amide groups were isolated from methanolic solutions of the corresponding ligands with equimolar Cu(OAc)2·H2O. The structures of two of them were determined by X-ray crystallography. The Cu is coordinated to five nitrogen atoms in both complexes; the coordination geometry was a distorted square pyramid in one, and intermediate between a square pyramid and trigonal bipyramid in the other. EPR spectra in frozen methanol solutions at 77 K as well as visible absorption spectra indicate that the distortion of the geometry around the copper is reduced by the introduction of an alkylamine substituent on the pyridine of the ligand and that the substituted complexes distort toward trigonal bipyramidal geometry compared to the unsubstituted one in solution.

  合成了三种可能具有五配位特征的肽配体，每个配体包含一个吡啶和两个组氨酸部分，旨在研究它们与铜(II)的配位作用。从相应配体与等摩尔Cu(OAc)2·H2O的甲醇溶液中分离得到了含有去质子化酰胺基团的蓝色铜(II)配合物。通过X射线晶体学确定了其中两个配合物的结构。在这两个配合物中，铜均与五个氮原子配位；其中一个的配位几何形状为扭曲的四角锥，另一个则介于四角锥和三角双锥之间。在77K下测得的冷冻甲醇溶液的EPR谱以及可见吸收光谱表明，在配体的吡啶上引入烷基胺取代基可以减少铜周围几何形状的扭曲，并且与未取代的配合物相比，取代后的配合物在溶液中更倾向于形成三角双锥几何形状。
• Chiral Helicity Induced by Hydrogen Bonding and Chirality of Podand Histidyl Moieties
  作者：Toshiyuki Moriuchi、Masahito Nishiyama、Kazuhiro Yoshida、Takuji Ishikawa、Toshikazu Hirao

  DOI：10.1021/ol0100327

  日期：2001.5.1

  D-isomer (D-BHisPA) derived from the corresponding chiral histidine revealed a left- and right-handed helical conformation, respectively, through intramolecular hydrogen bonding and chirality of the podand histidyl moieties. Furthermore, each helical molecule is connected by continuous intermolecular hydrogen bonds to afford a left- or right-handed helical assembly, respectively, in the crystal packing

  [结构：见正文] N，N'-双[（S）-（+）-1-甲氧羰基-2-（4-咪唑基）乙基] -2,6-吡啶二甲酰胺的单晶X射线结构测定（L-BHisPA）和衍生自相应手性组氨酸的D-异构体（D-BHisPA）通过分子内氢键和豆荚和组氨酸基团的手性分别显示出左旋和右旋螺旋构象。此外，每个螺旋分子通过连续的分子间氢键连接以在晶体堆积中分别提供左旋或右旋螺旋组装。
• An Artificial CuII complex with intriguing oxygen radical-quenching profile. X-ray structure, cytochrome C assay, and ESR study
  作者：Masami Otsuka、Honoo Satake、Satoru Murakami、Mitsunobu Doi、Toshimasa Ishida、Masakatsu Shibasaki、Yukio Sugiura

  DOI：10.1016/0968-0896(96)00161-7

  日期：1996.10

  A novel artificial peptide named HPH-Pep, comprising a pyridine and two histidine units, was synthesized. The HPH-Pep-Cu-II complex had unique pentacoordinated structure as shown by X-ray crystallography and exhibited superoxidescavenging activity as indicated by ESR spectroscopy. The superoxide-quenching profile of HPH-Pep-Cu-II was studied in detail by cytochrome c assay and ESR spin trapping and it was found that (1) HPH-Pep-Cu-II did not scavenge hydrogen peroxide or hydroxyl radical and hence the scavenging activity was specific to superoxide, and (2) HPH-Pep-Cu-II did not generate hydrogen peroxide upon scavenging superoxide. Copyright (C) 1996 Elsevier Science Ltd
• Synthesis of New Cheral Macrocyclic Tetraoxo Polyamines Containing Pyridine Ring and Functional Arms
  作者：Jingsong You、Xiaoqi Yu、Changlu Liu、Rugang Xie

  DOI：10.1080/00397919908086251

  日期：1999.7

  Abstract Seven new chiral macrocyclic tetraoxo polyamines containing pyridine ring and functional arms derived from L-histidine, L-alanine, L-leucine and L-phenylalanine, respectively, have been synthesized and characterized by MS, 1H NMR and elemental analysis.

  摘要 合成了七种新型手性大环四氧多胺，分别由L-组氨酸、L-丙氨酸、L-亮氨酸和L-苯丙氨酸衍生而来，并通过MS、1H NMR和元素分析对其进行表征。
• Novel chiral imidazole cyclophane receptors: synthesis and enantioselective recognition for amino acid derivatives
  作者：Jing-Song You、Xiao-Qi Yu、Qing-Xiang Xiang、Jing-Bo Lan、Ru-Gang Xie、Guo-Lin Zhang

  DOI：10.1039/b103325p

  日期：——

  Novel chiral imidazole cyclophane receptors were synthesized by highly selective N-alkylation of the imadazolyl 1N-position of the bridged histidine diester 2 with the dibromide in the presence of NaH; these receptors exhibit good chiral recognition toward the enantiomers of L- and D-amino acid derivatives (up to KD/KL = 3.52, delta delta G0 = -3.11 kJ mol-1) in CHCl3 at 25.0 degrees C.

  通过在NaH存在下用二溴化物对桥接的组氨酸二酯2的咪唑基1N位进行高选择性N-烷基化，合成了新型手性咪唑环烷受体。这些受体在25.0摄氏度的CHCl3中对L-和D-氨基酸衍生物的对映异构体（高达KD / KL = 3.52，δdelta G0 = -3.11 kJ mol-1）表现出良好的手性识别。