5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylic acid | 171670-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylic acid
• 英文别名: 5-(Boc-aminomethyl)pyrrole-2-carboxylic acid；5-[[(2-methylpropan-2-yl)oxycarbonylamino]methyl]-1H-pyrrole-2-carboxylic acid
• CAS: 171670-08-9
• 化学式: C₁₁H₁₆N₂O₄
• 分子量: 240.259
• InChiKey: CAAXOQWUAJDOND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  91.4
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylic acid 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 以74%的产率得到5-(aminomethyl)-1H-pyrrole-2-carboxylic acid;hydrochloride
  参考文献：
  名称：

  Synthesis and evaluation of novel heteroaromatic substrates of GABA aminotransferase

  摘要：

  Two principal neurotransmitters are involved in the regulation of mammalian neuronal activity, namely, gamma-aminobutyric acid (GABA), an inhibitory neurotransmitter, and L-glutamic acid, an excitatory neurotransmitter. Low GABA levels in the brain have been implicated in epilepsy and several other neurological diseases. Because of GABA's poor ability to cross the blood-brain barrier (BBB), a successful strategy to raise brain GABA concentrations is the use of a compound that does cross the BBB and inhibits or inactivates GABA aminotransferase (GABA-AT), the enzyme responsible for GABA catabolism. Vigabatrin, a mechanism-based inactivator of GABA-AT, is currently a successful therapeutic for epilepsy, but has harmful side effects, leaving a need for improved GABA-AT inactivators. Here, we report the synthesis and evaluation of a series of heteroaromatic GABA analogues as substrates of GABA-AT, which will be used as the basis for the design of novel enzyme inactivators. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.009
• 作为产物：
  描述：

  吡咯-2-羧酸 在 lithium hydroxide 、 sodium tetrahydroborate 、 sodium azide 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.17h， 生成 5-(((tert-butoxycarbonyl)amino)methyl)-1H-pyrrole-2-carboxylic acid
  参考文献：
  名称：

  Development of 5-(aminomethyl)pyrrole-2-carboxylic acid as a constrained surrogate of Gly-ΔAla and its application in peptidomimetic studies

  摘要：

  A new peptidomimetic scaffold based on 5-(aminomethyl)pyrrole-2-carboxylic acid (1) is developed for the first time and used as a conformationally constrained surrogate of the Gly-DeltaAla dipeptide isostere (2) to prepare peptides 3 and 4. (C) 2002 Published by Elsevier Science.

  DOI：

  10.1016/s0040-4039(02)00342-8

文献信息

• Nucleation of β-hairpin structure in a pyrrole amino acid containing peptide
  作者：Tushar K. Chakraborty、B.Krishna Mohan、S.Kiran Kumar、Ajit C. Kunwar

  DOI：10.1016/s0040-4039(02)02593-5

  日期：2003.1

  Synthesis and conformational studies of two short peptides containing pyrrole amino acids (1, Paa), Boc-Paa-Paa-d-Pro-Gly-Xaa-Paa-Paa-OMe (2: Xaa=Ala; 3: Xaa=Val), were carried out in which it was established that replacement of Ala in 2 with a Val residue helps peptide 3 to adopt a well-defined β-hairpin conformation in a nonpolar solvent, like CDCl3.

  两种含有吡咯氨基酸（1，Paa）的短肽（Boc-Paa-Paa-d-Pro-Gly-Xaa-Paa-Paa-OMe）的合成和构象研究（2：Xaa = Ala; 3：Xaa = Val）证实了用Val残基取代2中的Ala有助于肽3在非极性溶剂如CDCl 3中采用明确定义的β-发夹构象。
• Synthesis and anion recognition properties of pyrrole-bearing acyclic receptors
  作者：Yanhua Zhang、Zhenming Yin、Zucheng Li、Jiaqi He、Jin-Pei Cheng

  DOI：10.1016/j.tet.2007.05.054

  日期：2007.8

  A new series of acyclic anion receptors (1–4) based on methyl 5-(aminomethyl)-1H-pyrrole-2-carboxylate were designed and synthesized. The anion recognition properties of these receptors were examined by 1H NMR spectroscopy and rationalized by density functional theoretical calculation. Receptor 1 displays the highest affinity and selectivity for anionic guests mainly due to the intramolecular hydrogen

  一系列新的无环的阴离子受体（的1 - 4）的基础上的5-（氨基甲基）-1 ħ吡咯-2-羧酸甲酯，设计并合成。这些受体的阴离子识别特性通过1 H NMR光谱检查，并通过密度泛函理论计算合理化。受体1对阴离子客体显示出最高的亲和力和选择性，这主要归因于分子内氢键和刚性分子的几何形状。
• Microcin B17 Analogs And Methods For Their Preparation And Use
  申请人：Coquin Laurence

  公开号：US20080234132A1

  公开（公告）日：2008-09-25

  The present invention pertains to synthetic analogues of microcin B17 component units, methods of making and using these analogues, including, for example, as inhibitors of DNA gyrase. More particularly, the present invention pertains to compounds of the Formula wherein: W is independently: —H or a peptide group; Z is independently: —OH or a peptide group; wherein each peptide group, if present, is: an amino acid group and comprises exactly one amino acid, or: a poly(amino acid) group and comprises two or more amino acids; R N3 is independently: —H, C 1-6 alkyl, C 2-6 alkenyl, C 3-6 cycloalkyl, or C 3-6 cycloalkenyl, C 6-14 -carboaryl, C 5-14 heteroaryl, C 6-14 carboaryl-C 1-6 alkyl, C 5-14 heteroaryl-C 1-6 alkyl, and is optionally substituted; the circle represents a mono-heterocycle or a bis-heterocycle, wherein the heterocycle, or each of the two heterocycles, is a five membered ring having at least a first ring heteroatom that is N, and optionally a second ring heteroatom that is selected from N, O, and S; and the heterocycle, or each of the two heterocycles, is optionally substituted with one or more substituents; and pharmaceutically acceptable salts, amides, esters, solvates, and hydrates thereof. The present invention also pertains to uses of such compounds, for example, to inhibit DNA Gyrase activity in a cell and in methods of therapy, for example, to treat a disease or condition that is ameliorated by the inhibition of DNA Gyrase, such as a bacterial infection, cancer, etc.; as a herbicide; as a microbicide; as a bactericide; etc.

  本发明涉及微小肽B17组分单元的合成类似物，制备和使用这些类似物的方法，包括作为DNA酶抑制剂。更具体地说，本发明涉及以下式的化合物：其中：W独立地为：—H或肽基团；Z独立地为：—OH或肽基团；其中每个肽基团，如果存在，则为：氨基酸基团，包括恰好一个氨基酸，或：多肽（氨基酸）基团，包括两个或更多氨基酸；RN3独立地为：—H、C1-6烷基、C2-6烯基、C3-6环烷基或C3-6环烯基、C6-14芳基、C5-14杂芳基、C6-14芳基-C1-6烷基、C5-14杂芳基-C1-6烷基，并且可选地被取代；圆圈表示单杂环或双杂环，其中杂环或两个杂环中的每一个都是具有至少一个第一环杂原子的五元环，该原子是N，可选地，第二环杂原子是从N、O和S中选择的；并且该杂环或两个杂环可选地被一个或多个取代基取代；以及其药学上可接受的盐、酰胺、酯、溶剂化物和水合物。本发明还涉及这些化合物的用途，例如，在细胞中抑制DNA酶活性和治疗方法中使用，例如治疗通过抑制DNA酶改善的疾病或病况，如细菌感染、癌症等；作为除草剂；作为杀菌剂；作为杀菌剂等。
• Synthesis and DNA binding properties of pyrrole amino acid-containing peptides
  作者：Tushar Kanti Chakraborty、Bajjuri Krishna Mohan、Muthaiah Gnanamani、Souvik Maiti

  DOI：10.1016/j.tetlet.2004.11.128

  日期：2005.1

  Dimers of the pyrrole amino acid (Paa), 5-(aminomethyl)pyrrole-2-carboxylic acid, and its derivatives having Lys anchored on N- and C-termini bind in the minor groove of DNA with considerable apparent binding affinities. When the Lys unit is attached to the C-terminus, the resulting ligand binds to ds-DNA with twice the affinity, of the order of 105, than the one carrying two positive charges at the same end. (C) 2004 Elsevier Ltd. All rights reserved.
• Effective receptors for fluoride and acetate ions: synthesis and binding study of pyrrole- and cystine-based cyclopeptido-mimetics
  作者：Yanhua Zhang、Zhenming Yin、Jiaqi He、Jin-Pei Cheng

  DOI：10.1016/j.tetlet.2007.06.066

  日期：2007.8

  Two conformationally constrained pseudo-cyclopeptides (1, 2) consisting of pyrrole-, pyridine-, and cystine-moieties were designed and synthesized as neutral receptors for anionic guests. The anion recognition abilities of these two receptors were examined photometrically in acetonitrile solution. The UV-vis study revealed that the [1+1] receptor (1) formed 1:1 complexes with anions, whereas the [2+2] receptor (2) led to 1:2 mode binding with anions. Both receptors displayed good affinity and selectivity for fluoride and acetate ions. (C) 2007 Elsevier Ltd. All rights reserved.