N-(4-carboxybenzyl)pyridinium bromide | 6941-09-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-carboxybenzyl)pyridinium bromide
• 英文别名: 4-[(Pyridin-1-ium-1-yl)methyl]benzoate--hydrogen bromide (1/1)；4-(pyridin-1-ium-1-ylmethyl)benzoate;hydrobromide
• CAS: 6941-09-9
• 化学式: Br*C₁₃H₁₂NO₂
• 分子量: 294.148
• InChiKey: OOZKXDGSKDMTKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.28
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  41.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-carboxybenzyl)pyridinium bromide 、 cadmium(II) bromide 以 水 为溶剂， 反应 0.5h， 以63%的产率得到Bis-(μ2-(4-carboxybenzyl)-methylene-4-pyridine-O,O')-dibromo-cadmium complex
  参考文献：
  名称：

  You, Xiuli; Hu, Tao, Asian Journal of Chemistry, 2013, vol. 25, # 3, p. 1471 - 1473

  摘要：

  DOI：
• 作为产物：
  描述：

  吡啶 、 对溴甲基苯甲酸 以 丙酮 为溶剂， 反应 1.0h， 以68%的产率得到N-(4-carboxybenzyl)pyridinium bromide
  参考文献：
  名称：

  Reparametrization and/or Determination of Hammett, Inductive, Mesomeric and AISE Substituent Constants for Five Substituents: N+(CH3)3, CH2N+(CH3)3, CH2Py+, CH2SO2CH3 and PO(OCH3)2

  摘要：

  合成了十种带有取代基N+ (CH3) 3、CH2N+ (CH3) 3、CH2Py+、CH2SO2CH3和PO (OCH3) 2的苯甲酸类衍生物。在25°C下，测定了这些酸在五种溶剂（水、乙醇、甲醇、N，N-二甲基甲酰胺、二甲基亚砜）中的解离常数。从文献中选取了其他取代基为H、CH3、NHCOCH3、OCH3、F、Cl、Br、I、COCH3、CN、NO2、SO2CH3的苯甲酸衍生物的解离常数（校准集）。通过非线性和PLS（偏最小二乘法）校准，在三个相关模型中计算了取代基N+ (CH3) 3、CH2N+ (CH3) 3、CH2Py+、CH2SO2CH3和PO (OCH3) 2的取代基常数σm、σp、σI、σR和σi。非线性回归比PLS校准更适用和更普遍。非线性回归的优点是不依赖于给定溶剂中可能缺失的数据，可以评估精度（标准偏差），易于计算所需的软件和易于计算。然而，与PLS校准相比，这种方法在描述取代基特性（取代基常数σI、σR）时失败。得到的取代基常数值与文献中发表的值相符。

  DOI：

  10.1135/cccc20042239

文献信息

• Towards polynuclear metal complexes with enhanced bioactivities: Synthesis, crystal structures and DNA cleaving activities of CuII, NiII, ZnII, CoII and MnII complexes derived from 4-carboxy-1-(4-carboxybenzyl) pyridinium bromide
  作者：Ming Chen、Ming-Zhen Chen、Chun-Qiong Zhou、Wei-Er Lin、Jin-Xiang Chen、Wen-Hua Chen、Zhi-Hong Jiang

  DOI：10.1016/j.ica.2013.02.008

  日期：2013.8

  OH (M = ZnII (3), CoII (4), MnII (5)), and [Cu(Cbp)2(H2O)2](NO3)2·4H2O (6) were synthesized from the reaction of 4-carboxy-1-(4-carboxybenzyl)pyridinium bromide (H2CcbpBr) and N-(4-carboxybenzyl)pyridinium bromide (HCbpBr) with the corresponding metal salts in the presence of NaOH, respectively. All these metal complexes were characterized by IR, elemental analyses and single crystal X-ray crystallography

  六个过渡金属配合物，即[Cu（Ccbp）2 ]·4H 2 O} n（1），[Ni（H 2 O）6 ]（Ccbp）2 ·4H 2 O（2），[M（ Ccbp）2（H 2 O）4 ]·2H 2 O·2MeOH（M = Zn II（3），Co II（4），Mn II（5））和[Cu（Cbp）2（H 2 O）2 ]（NO 3）2 ·4H 2 O（6）由4-羧基-1-（4-羧基苄基）溴化吡啶鎓（H 2 CcbpBr）和N-（4-羧基苄基）溴化吡啶鎓（HCbpBr）与相应的金属盐在NaOH存在下反应合成，分别。所有这些金属配合物均通过红外，元素分析和单晶X射线晶体学表征。在复杂的1，每两个CCBP -离子桥接两个铜2+通过四端羧酸根离子离子单齿配位模式，从而形成一维聚合物结构。络合物2是由分离的[M（H 2 O）6 ] 2+组成的离子金属络合物二价阳离子和CCBP -阴离子。配合物3 - 5具有相似
• Willems; Nys, Bulletin des Societes Chimiques Belges, 1957, vol. 66, p. 502,504
  作者：Willems、Nys

  DOI：——

  日期：——
• Synthesis, crystal structures and biological evaluation of water-soluble zinc complexes of zwitterionic carboxylates
  作者：Jin-Xiang Chen、Wei-Er Lin、Chun-Qiong Zhou、Lee Fong Yau、Jing-Rong Wang、Bo Wang、Wen-Hua Chen、Zhi-Hong Jiang

  DOI：10.1016/j.ica.2011.06.054

  日期：2011.10

  Three water-soluble zinc complexes, [Zn(Cbp)(2)Br-2] (1) (Cbp = N-(4-carboxybenzyl)pyridinium), [Zn(BCbpy)(2)(H2O)(4)](3)Br-6 center dot 2(BCbpy)center dot 2(4,4'-bipy)} (2) (BCbpy = 1-(4-carboxybenzyl)-4,4'-bipyridinium) and [Zn-4(Bpybc)(6)(H2O)(12)](OH)(8)center dot 9H(2)O}(2n) (3) (Bpybc = 1,1'-bis(4-carboxybenzyl)-4,4'-bipyridinium), were synthesized and characterized by IR, elemental analysis and single-crystal X-ray crystallography. In complex 1, the central Zn atom adopts a distorted tetrahedral coordination geometry that is formed from two unidentate Cbp ligands and two Br atoms. For complex 2, the Zn atom in [Zn(BCbpy)(2)(H2O)(4)](2+) is strongly coordinated by four water molecules and two N atoms from two BCbpy ligands, hence forming an octahedral geometry. In complex 3, each Bpybc ligand bridges two [Zn(H2O)(3)](2+) units through two terminal carboxylate groups in a monodentate coordination mode, thus forming a flowerlike two-dimensional network. Agarose gel electrophoresis (GE) and ethidium bromide (EB) displacement experiments indicated that complex 3 was capable of converting pBR322 DNA into open circular (OC) and linear forms, and exhibited high binding affinity toward calf-thymus DNA. MTT assay showed that complex 3 displayed inhibitory activities toward the proliferation of lung adenocarcinoma A549 and mouse sarcoma S-180 cells, with the IC50 values being 27.3 and 48.8 mu M, respectively. (C) 2011 Elsevier B.V. All rights reserved.
• Synthesis and DNA photocleaving activities of ancillary ligand-containing zinc complexes of quaternized carboxylates
  作者：Jin-Xiang Chen、Wei-Er Lin、Ming Chen、Fu-Chang Que、Lei Tao、Xue-Lan Cen、Yang-Ming Zhou、Wen-Hua Chen

  DOI：10.1016/j.ica.2013.09.033

  日期：2014.1

  Three zinc complexes, that is, [Zn-2(Cbp)(2)(BDC)(2)(H2O)(2)]center dot 4H(2)O center dot MeOH}(n) (1) (Cbp = N-(4-carboxybenzyl)pyridinium, BDC = 1,4-benzenedicarboxylate), [Zn(BCbpy)(2)(H2O)(4)](2)(BDC)(2)center dot 13H(2)O (2) (BCbpy = 1-(4-carboxybenzyl)-4,4'-bipyridinium) and [Zn-2(Bpybc)(3)(BDC)(2)]center dot 4H(2)O}(n) (3) (Bpybc = 1,1'-bis(4-carboxybenzyl)-4,4'-bipyridinium), were synthesized and characterized on the basis of IR, elemental analysis and single-crystal X-ray crystallography data. Complexes 1 and 3 possess polynuclear structures, whereas complex 2 has a mononuclear structure. Agarose gel electrophoresis studies indicated that, under the irradiation of UV-A at 365 nm, complex 2 showed negligible DNA-cleaving activity, whereas complexes 1 and 3 were capable of efficiently converting pBR322 DNA into OC forms, most probably via an oxidative mechanism. Kinetic assay on complexes 1 and 3 afforded the catalytic efficiency (k(max)/K-M) of 0.63 and 10.8 h (1) mM (1), respectively. The higher cleaving efficacy of complex 3 is a likely consequence of its polynuclear structure and one more quaternary ammonium center. (C) 2013 Elsevier B.V. All rights reserved.
• Structural characterization of zinc and cadmium complexes derived from N-(4-carboxybenzyl)pyridinium: Revisiting the structure of (Cbp)2ZnBr2 and influence of the metal on carboxylate coordination mode
  作者：Daniel G. Shlian、Daymieri Narvaez、Gerard Parkin

  DOI：10.1016/j.poly.2022.116126

  日期：2023.1