N¹-(2-ammonioethyl)-2,3-dihydrobenzamide | 153801-67-3

• 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: N¹-(2-ammonioethyl)-2,3-dihydrobenzamide
• 英文别名: N-(aminoethyl)-2,3-bis(hydroxy)benzamide；N-(2-aminoethyl)-2,3-dihydroxybenzamide
• CAS: 153801-67-3
• 化学式: C₉H₁₂N₂O₃
• 分子量: 196.206
• InChiKey: KKQIDYHLFDAGKP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.6
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dioxosulfinylbenzoyl chloride 、 N¹-(2-ammonioethyl)-2,3-dihydrobenzamide 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N,N'-bis(2,3-dihydroxybenzoyl)ethylenediamine
  参考文献：
  名称：

  2,3-Dihydro-6,7-dihydroxy-1H-isoindol-1-one-Based HIV-1 Integrase Inhibitors

  摘要：

  The bis-salicylhydrazides class of HIV-1 integrase (IN) inhibitors has been postulated to function by metal chelation. However, members of this series exhibit potent inhibition only when Mn2+ is used as cofactor. The current study found that bis-aroylhydrazides could acquire inhibitory potency in Mg2+ using dihydroxybenzoyl substituents as both the right and left components of the hydrazide moiety. Employing a 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one ring system as a conformationally constrained 2,3-dihydroxybenzoyl equivalent provided good selectivity for IN-catalyzed strand transfer versus the 3'-processing reactions as well as antiviral efficacy in cells using HIV-1 based vectors.

  DOI：

  10.1021/jm070715d
• 作为产物：
  描述：

  苯甲酸,二羟基- 在 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 34.0h， 生成 N¹-(2-ammonioethyl)-2,3-dihydrobenzamide
  参考文献：
  名称：

  Selective Inhibition of Fe- versus Cu/Zn-Superoxide Dismutases by 2,3-Dihydroxybenzoic Acid Derivatives.

  摘要：

  一系列儿茶酚衍生物被合成并测试其抑制大肠杆菌中含铁超氧化物歧化酶（Fe-SOD）和牛红细胞铜/锌超氧化物歧化酶（Cu/Zn-SOD）的能力。儿茶酚与Fe-SOD或Cu/Zn-SOD的孵育导致酶活性的时间依赖性丧失，对依赖铁的酶具有高度选择性抑制作用。儿茶酚诱导的SOD失活与儿茶酚化合物自氧化为相应的邻醌衍生物相关，这一过程的发生并不依赖于酶的存在。对儿茶酚孵育的Fe-SOD进行的质谱电喷雾实验为抑制过程的不可逆性提供了证据，形成了一种修改蛋白的复杂混合物。

  DOI：

  10.1248/cpb.50.578

文献信息

• Synthesis of a tetrazine-based catecholamide derivative and its evaluation as a chelating agent for removal of Cd(II), Co(II), and Cu(II)
  作者：Shan Lei、Bo Jin、Rufang Peng、Qingchun Zhang、Shijin Chu

  DOI：10.1080/00958972.2017.1340644

  日期：2017.7.18

  Abstract The synthesis and structural characterization of a tetrazine-based catecholamide (CAM) ligand, N,N′-bis(N″-(aminoethyl)-2,3-bis(hydroxy)benzamide)-1,2,4,5-tetrazine-3,6-diamine (5), were investigated. All compounds were characterized by 1H NMR spectroscopy, 13C NMR spectroscopy, and FTIR spectroscopy. The protonation equilibria of 5 and complexation capacities (log βpqr) of Cd2+, Co2+, and

  摘要 四嗪基儿茶酚酰胺 (CAM) 配体 N,N'-双(N"-(氨基乙基)-2,3-双(羟基)苯甲酰胺)-1,2,4,5-的合成和结构表征研究了四嗪-3,6-二胺 (5)。所有化合物均通过 1H NMR 光谱、13C NMR 光谱和 FTIR 光谱表征。分别通过电位滴定和分光光度滴定评估了 5 的质子化平衡和 5 的 Cd2+、Co2+ 和 Cu2+ 络合物的络合能力（log βpqr）。物种独立的 pM 值（=-log [M] 游离）用于比较金属亲和力与最终序列 Cu2+ > Cd2+ > Co2+。结果表明5具有去除重金属的潜力。
• Synthesis and antimicrobial activity of an SO2-releasing siderophore conjugate
  作者：Conor M. Black、Adrian J. Chu、Gavin H. Thomas、Anne Routledge、Anne-Kathrin Duhme-Klair

  DOI：10.1016/j.jinorgbio.2022.111875

  日期：2022.9
• 2,3-Dihydro-6,7-dihydroxy-1H-isoindol-1-one-Based HIV-1 Integrase Inhibitors
  作者：Xue Zhi Zhao、Elena A. Semenova、B. Christie Vu、Kasthuraiah Maddali、Christophe Marchand、Stephen H. Hughes、Yves Pommier、Terrence R. Burke

  DOI：10.1021/jm070715d

  日期：2008.1.1

  The bis-salicylhydrazides class of HIV-1 integrase (IN) inhibitors has been postulated to function by metal chelation. However, members of this series exhibit potent inhibition only when Mn2+ is used as cofactor. The current study found that bis-aroylhydrazides could acquire inhibitory potency in Mg2+ using dihydroxybenzoyl substituents as both the right and left components of the hydrazide moiety. Employing a 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one ring system as a conformationally constrained 2,3-dihydroxybenzoyl equivalent provided good selectivity for IN-catalyzed strand transfer versus the 3'-processing reactions as well as antiviral efficacy in cells using HIV-1 based vectors.
• Selective Inhibition of Fe- versus Cu/Zn-Superoxide Dismutases by 2,3-Dihydroxybenzoic Acid Derivatives.
  作者：Laurent Soulère、Cécile Viodé、Jacques Périé、Pascal Hoffmann

  DOI：10.1248/cpb.50.578

  日期：——

  A series of catechol derivatives were synthesised and tested for their ability to inactivate the iron-containing superoxide dismutase (Fe-SOD) from Escherichia coli and the bovine erythrocytes Cu/Zn-SOD. Incubation of catechols with Fe- or Cu/Zn SODs resulted in a time-dependent loss of enzyme activity with highly selective inhibition for the iron-dependent enzyme. Catechol-induced inactivation of SODs was correlated with the auto-oxidation of the catechol compounds to their corresponding ortho-quinone derivatives, which was found to be non-dependent on the presence of enzymes. Mass electrospray experiments on catechol-incubated Fe-SOD provided evidence for the irreversible nature of the inhibition process, yielding to a complex mixture of modified proteins.

  一系列儿茶酚衍生物被合成并测试其抑制大肠杆菌中含铁超氧化物歧化酶（Fe-SOD）和牛红细胞铜/锌超氧化物歧化酶（Cu/Zn-SOD）的能力。儿茶酚与Fe-SOD或Cu/Zn-SOD的孵育导致酶活性的时间依赖性丧失，对依赖铁的酶具有高度选择性抑制作用。儿茶酚诱导的SOD失活与儿茶酚化合物自氧化为相应的邻醌衍生物相关，这一过程的发生并不依赖于酶的存在。对儿茶酚孵育的Fe-SOD进行的质谱电喷雾实验为抑制过程的不可逆性提供了证据，形成了一种修改蛋白的复杂混合物。