(S)-2-(2-hydroxy-benzylamino)-3-(1H-imidazol-4-ylpropanoic acid) | 58813-19-7

• 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)-2-(2-hydroxy-benzylamino)-3-(1H-imidazol-4-ylpropanoic acid)
• 英文别名: (S)-2-(2-hydroxybenzylamino)-3-(1H-imidazol-4-yl)propionic acid；N-(2-hydroxybenzyl)-L-histidine；(2S)-2-[(2-hydroxyphenyl)methylamino]-3-(1H-imidazol-5-yl)propanoic acid
• CAS: 58813-19-7
• 化学式: C₁₃H₁₅N₃O₃
• 分子量: 261.28
• InChiKey: XOHSJPOQKQXJMI-NSHDSACASA-N

物化性质

• 熔点：
  219-220 °C
• 沸点：
  568.6±50.0 °C(Predicted)
• 密度：
  1.376±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  98.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-(2-hydroxy-benzylamino)-3-(1H-imidazol-4-ylpropanoic acid) 、 nickel(II) nitrate hexahydrate 、 水 在 NaOH 作用下， 以 甲醇 为溶剂， 以70%的产率得到[Ni((S)-2-(2-hydroxybenzylamino)-3-(1H-imidazol-4-yl)propionic acid-H)2]*H2O
  参考文献：
  名称：

  Effect of metal coordination and intra-molecular H-bond on the acidity of phenolic proton in a set of structurally characterized octahedral Ni(II) complexes of l-histidine derivative

  摘要：

  Four different mononuclear octahedral Ni(II) complexes with protonated and deprotonated form of the same ligand have been synthesized by controlling reaction conditions and structurally characterized. The complexes are [Ni(HLL-his)(benzoate)(MeOH)] (1), [Ni(HLL-his)(SCN)(MeOH)] (2), [Ni(HLL-his) 2] (3) and [Ni(LL-his)(imidazole)(2)] (4) where H2LL-his is (S)-2-(2-hydroxybenzylamino)-3-(1H-imidazol-4-yl)-propionic acid. The ligand behaves as a monobasic tetradentate ligand in 1 and 2, monobasic tridentate ligand in 3 and dibasic tetradentate ligand in 4. Ni(II) coordinated phenolic proton of the ligand in the complexes 1-2 shows strong intra-molecular H-bonding with benzoate in 1 and lattice water in 2, whereas 3 shows intermolecular H-bonding between uncoordinated phenols with neighbouring carboxylate. The pH titration of the complexes revealed that metal coordination and H-bond in complexes 1 and 2 considerably lowers the acidity of ligand phenol (pK(a) 6.8 and 7.0 respectively) compared to phenol (pK(a) 10). The complex 4 does not show any proton loss due to the absence of phenolic proton. All the complexes show extensive H-bonded network in the crystals including narrow (7.8 x 5.2 angstrom) water filled one dimensional channel in 2. (C) 2010 Elsevier B. V. All rights reserved.

  DOI：

  10.1016/j.ica.2010.03.051
• 作为产物：
  描述：

  水杨醛 在 sodium hydroxide 、 sodium borohydrid 作用下， 以 L-组氨酸 为溶剂， 生成 (S)-2-(2-hydroxy-benzylamino)-3-(1H-imidazol-4-ylpropanoic acid)
  参考文献：
  名称：

  Amino acid derivatives and anti-active oxygen agents

  摘要：

  一种新型的抗活性氧化剂，其活性成分为以下通式（I）所示的氨基酸衍生物：##STR1## 其中Ar代表2-羟基苯基，2-羟基-1-萘基或吡啶基，这些基团的芳环上的一个或多个氢原子可以被卤素原子，烷基，羟基，羟基烷基，硝基，烷氧基或羧基取代; R代表氨基酸的侧链; X代表--CH.sub.2--NH--或--CH.dbd.N--; Y代表氢原子，--COOR.sup.1，--SO.sub.3H，--CON（R.sup.2）R.sup.3，--CONHCH（R.sup.5）COOR.sup.4或--CH.sub.2OH（其中每个R.sup.1到R.sup.4代表氢原子或烷基，R.sup.5代表氨基酸的侧链）; n代表0或1的整数; 或其盐。该抗氧化剂具有高安全性，可以抑制活性氧化物的产生，并且可以以相对较低的成本制备。

  公开号：

  US05594012A1

文献信息

• Structural Characterization of an Enantiopure Hydroxo-Bridged Binuclear Iron(III) Complex with Empty One-Dimensional Helical Channels
  作者：Md. Akhtarul Alam、Munirathinum Nethaji、Manabendra Ray

  DOI：10.1021/ic049145n

  日期：2005.3.1

  acetate ion assembles into a hydroxo-bridged binuclear complex with the formula [FeIII2(mu-OH)(mu-OAc)(S-L)2] x 4H2O (1) where H2S-L = S-2-(2-hydroxy-benzylamino)-3-(1H-imidazol-4-yl)-propionic acid. The crystal of 1 contains right-handed one-dimensional (1D) helical channels with 7.3-9.8 A diameter. A similar reaction with a ligand having opposite chirality forms the complex with left-handed helical channels

  具有H键的手性四齿配体Fe3 +和乙酸根离子组装成具有式[FeIII2（mu-OH）（mu-OAc）（SL）2] x 4H2O（1）的羟基桥接双核络合物，其中H2S- L ＝ S-2-（2-羟基-苄氨基）-3-（1H-咪唑-4-基）-丙酸。1的晶体包含直径为7.3-9.8 A的右手一维（1D）螺旋形通道。与具有相反手性的配体的类似反应形成具有左手螺旋通道（1a）的复合物。在减压下于95摄氏度加热1的晶体，从而选择性地从通道中除去三股水，形成​​带有空通道的对映纯多孔晶体（溶剂可进入的空隙18％v / v）。咪唑NH和1-2的酚酸氧之间的分子间氢键形成C6对称螺旋，带有桥连的羟基基团指向通道内部。配体中所有具有氢键的原子与一个水分子一起在整个晶体中形成扩展的氢键网络。将2的空通道暴露于碘蒸气表明通道中部分充满了碘。1 x 4H2O的晶体数据包括：六边形，P61，a = b = 13.164（3）A，c
• Synthesis, crystal structures, and antibacterial studies of silver(I) complexes with reduced Schiff base amino acid ligands
  作者：Hai-Yan Liu、Qing-Hua Guan、Jun Tian、Peng Du、Hong Chen

  DOI：10.1007/s11243-016-0060-5

  日期：2016.9

  Three Ag(I) complexes of reduced Schiff base amino acid ligands, [Ag2(Hshis)2]·3H2O (1), Ag(Hcgly) (2), and Ag(cala) (3) (H2shis = N-(2-hydroxybenzyl)-l-histidine, H2cgly = N-(2-hydroxy-5-chlorobenzyl)-glycine, Hcala = N-(4-chlorobenzyl)-d,l-alanine), have been synthesized and characterized by X-ray crystallography. Complex 1 shows a dimeric structure, while complex 2 shows one-dimensional zigzag chains

  三种还原席夫碱氨基酸配体的 Ag(I) 复合物 [Ag2(Hshis)2]·3H2O (1)、Ag(Hcgly) (2) 和 Ag(cala) (3) (H2shis = N-(2) -羟基苄基)-l-组氨酸，H2cgly = N-(2-羟基-5-氯苄基)-甘氨酸，Hcala = N-(4-氯苄基)-d,l-丙氨酸)，已合成并通过 X 射线表征晶体学。配合物 1 显示二聚体结构，而配合物 2 显示一维锯齿形链，通过氢键延伸成二维超分子片。复合体 3 展示了一个带有悬臂的 2D 片状结构。已经研究了复合物的抗微生物活性。
• AMINO ACID DERIVATIVE AND ANTI-ACTIVE-OXYGEN AGENT
  申请人：Ajinomoto Co., Inc.

  公开号：EP0629606A1

  公开（公告）日：1994-12-21

  A novel anti-active-oxygen agent which inhibits the generation of active oxygen species, is highly safe, can be preparated at a rather low cost, and contains an amino acid derivative represented by general formula (I) or a salt thereof as the active ingredient, wherein Ar represents 2-hydroxyphenyl, 2-hdyroxyl-1-naphthyl or pyridyl provided that the aromatic rings of these groups may be substituted by halogen, alkyl, hydroxy, hydroxyalkyl, nitro, alkoxy or carboxy; R represents the side chain of an amino acid; X represents -CH₂-NH- or -CH=N-; Y represents hydrogen, -COOR¹, -SO₃H, -CON(R²)R³, -CONHCH(R⁵)COOR⁴ or -CH₂OH, wherein R¹ to R⁴ represent each hydrogen or alkyl, and R⁵ represents the side chain of an amino acid; and n represents an integer of 0 or 1.

  一种新型抗活性氧制剂，可抑制活性氧的生成，安全性高，制备成本低，含有通式(I)代表的氨基酸衍生物或其盐作为活性成分，其中Ar代表2-羟基苯基、2-羟基-1-萘基或吡啶基，但这些基团的芳环可被卤素、烷基、羟基、羟烷基、硝基、烷氧基或羧基取代；R 代表氨基酸的侧链； X 代表-CH₂-NH-或-CH=N-；Y 代表氢、-COOR¹、-SO₃H、-CON(R²)R³、-CONHCH(R⁵)COOR⁴ 或 -CH₂OH，其中 R¹ 至 R⁴ 分别代表氢或烷基，R⁵ 代表氨基酸的侧链；以及 n 代表 0 或 1 的整数。
• Synthesis, structure and magnetic properties of one chiral heptanuclear Fe cluster: {Fe[(FeL)2(μ2-OH)]3(μ2-OH)6}·13H2O
  作者：Xiao-Fang Ma、Jin-Lei Tian、Wen Gu、Song Gao、Shi-Ping Yan、Dai-Zheng Liao

  DOI：10.1016/j.inoche.2007.11.019

  日期：2008.3

  One chiral heptanuclear Fe-III cluster, Fe[(FeL)(2)(mu(2)-OH)](3)(mu(2)-OH)(6)} center dot 13H(2)O (1) (H2L=N-(2-hydroxybenzyl)-L-histidine), has been synthesized and characterized structurally and magnetically. Complex 1 crystallizes in the chiral space group C2. The heptanuclear Fe-III cluster of 1 has a propeller-like [Fe-7(mu(2)-OH)(9)](12+) core, with the peripheral ligation provided by six tetradentate L2- ligands. The configurations of the C- and the N-centers of L2- is (S, R) and the central atom Fe4 is chiral Lambda configuration. All Fe-III centers are hexacoordinated, displaying a distorted octahedral coordination sphere. Variable temperature magnetic studies showed complex I is antiferromagnetic with C = 14.27 cm(3) K mol(-1) and theta = -27.56 K. Magnetisation and susceptibility measurements show that cluster 1 exhibits a ground spin state of S = 3. (C) 2007 Elsevier B.V. All rights reserved.
• Tuning one dimensional chiral channel interior in mixed ligand Cu(II) complexes of l-histidine derivative and substituted pyridine
  作者：Rik Rani Koner、Md. Serajul Haque Faizi、Manabendra Ray

  DOI：10.1016/j.ica.2011.03.044

  日期：2011.6

  Four pentacoordinated square- pyramidal Cu(II) complexes with the general formula [Cu(L)(X)], where L is a L-histidine derived tetradentate ligand and X is either 3-hydroxypyridine or 2-methylpyridine, has been synthesized. Structural analysis showed that the presence of water filled one dimensional chiral channel in the lattices. The interiors of the channels were varied using aromatic ring substitution on the ligand as well as on the monodentate ligand. The dimensions of the channels range from similar to 7 to 9 angstrom. (C) 2011 Elsevier B.V. All rights reserved.