N,N'-bis(2,3-dihydroxybenzoyl)-α,α-diaminopropane | 76218-83-2

• 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,N'-bis(2,3-dihydroxybenzoyl)-α,α-diaminopropane
• 英文别名: N,N'-bis(2,3-dihydroxybenzoyl)-1,3-diaminopropane；propanochelin；N,N'-1,3-propanediylbis[2,3-dihydroxybenzamide]；N-[3-[(2,3-dihydroxybenzoyl)amino]propyl]-2,3-dihydroxybenzamide
• CAS: 76218-83-2
• 化学式: C₁₇H₁₈N₂O₆
• 分子量: 346.34
• InChiKey: VIKJLUHSZSBRPD-UHFFFAOYSA-N

物化性质

• 沸点：
  634.0±55.0 °C(Predicted)
• 密度：
  1.435±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  139
• 氢给体数：
  6
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium molybdate(VI) 、 N,N'-bis(2,3-dihydroxybenzoyl)-α,α-diaminopropane 以 甲醇 、 水 为溶剂， 以75%的产率得到
  参考文献：
  名称：

  Synthesis and Structure of the Molecular Rectangle [{MoO2(C17H14N2O6)}2]4-

  摘要：

  Reaction of the dinucleating ligand N,N'-bis(2,3-dihydroxybenzoyl)-alpha,alpha-diaminopropane H-4-1 with molybdate results in the formation of the meso-helicate type molecular rectangle Delta, Lambda-[{MoO2(1)}(2)](4-) as confirmed by NMR-spectroscopy and X-ray crystallography. Thereby the cis-dioxo Mo(VI) moieties act as shape defining corner units. The potassium salt of the complex crystallised in the centrosymmetric space group P (1) over bar with unit cell parameters a = 12.370(2), b = 13.900(3), c = 14.340(3) Angstrom; alpha =116.34(3), beta = 99.12(3), gamma = 96.68(3)degrees; V = 2132.6(7) Angstrom(3) Z = 2.

  DOI：

  10.1002/(sici)1521-3749(1998110)624:11<1922::aid-zaac1922>3.0.co;2-i
• 作为产物：
  描述：

  地匹乙酯 在 吡啶 、 sodium hydroxide 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 N,N'-bis(2,3-dihydroxybenzoyl)-α,α-diaminopropane
  参考文献：
  名称：

  新化合物：N1，N8-双（2,3-二羟基苯甲酰基）亚精胺和类似物作为潜在的铁螯合药物。

  摘要：

  合成了N1，N8-双（2,3-二羟基苯甲酰基）亚精胺，并将其评价为铁螯合剂。制备同源物并与一系列N，N′-双（2，3-二羟基苯甲酰基）-α，ω-二氨基烷烃一起评估。还合成和评估了类似的2-羟基苯甲酰基化合物。

  DOI：

  10.1002/jps.2600690836

文献信息

• 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.
• Self-assembled macrocycles with pentavalent silicon linkages
  作者：Joseph B Lambert、Stephanie R Singer

  DOI：10.1016/j.jorganchem.2004.04.011

  日期：2004.7

  Organic substrates containing two catechol (ortho-dihydroxybenzene) components at opposite ends self-assemble with a silicon substrate containing three nucleofugic groups (methoxy or ethoxy) under basic conditions to produce macrocycles ranging from monomers to pentamers. Silicon in all the macrocycles is pentacoordinate, negatively charged, and possessed of one organic monodentate ligand attached via carbon and two catechol bidentate ligands attached via oxygen. The organic materials with the two catechol structures thus serve as struts between the corners provided by the pentacoordinate silicon atoms. (C) 2004 Elsevier B.V. All rights reserved.
• [EN] HYDRAZIDE, AMIDE, PHTHALIMIDE AND PHTHALHYDRAZIDE ANALOGS AS INHIBITORS OF RETROVIRAL INTEGRASE<br/>[FR] ANALOGUES D'HYDRAZIDE, D'AMIDE, DE PHTALIMIDE ET DE PHTALHYDRAZIDE EN TANT QU'INHIBITEURS DE L'INTÉGRASE RÉTROVIRALE
  申请人：US GOV HEALTH & HUMAN SERV

  公开号：WO2009026248A2

  公开（公告）日：2009-02-26

  The present invention provides catechol-containing hydrazides, amides, phthalimide and phthalhydrazide analogs. These compounds are inhibitors of retroviral integrase, an essential enzyme for the proliferation of retroviruses such as HIV-1. Also provided are pharmaceutical compositions comprising at least one of the catechol-containing hydrazides, amides, phthalimide or phthalhydrazide analogs and a method of using the hydrazide, amide, phthalimide and phthalhydrazide analogs to inhibit retroviral proliferation and as therapeutics for the treatment of AIDS.
• New compounds: N-1, N8-bis(2, 3-dihydroxybenzoyl)spermidine and analogs as potential iron-chelating drugs
  作者：K.K. Bhargava、R.W. Grady、A. Cerami

  DOI：10.1002/jps.2600690836

  日期：1980.8

  N1,N8-bis(2,3-dihydroxybenzoyl)spermidine was synthesized and evaluated as an iron-chelating drug. Homologs were prepared and evaluated together with a series of N,N'-bis(2,3-dihydroxybenzoyl)-alpha,omega-diaminoalkanes. Analogous 2-hydroxbenzoyl compounds also were synthesized and evaluated.

  合成了N1，N8-双（2,3-二羟基苯甲酰基）亚精胺，并将其评价为铁螯合剂。制备同源物并与一系列N，N′-双（2，3-二羟基苯甲酰基）-α，ω-二氨基烷烃一起评估。还合成和评估了类似的2-羟基苯甲酰基化合物。
• Synthesis and Structure of the Molecular Rectangle [{MoO2(C17H14N2O6)}2]4-
  作者：Anne-Kathrin Duhme

  DOI：10.1002/(sici)1521-3749(1998110)624:11<1922::aid-zaac1922>3.0.co;2-i

  日期：1998.11

  Reaction of the dinucleating ligand N,N'-bis(2,3-dihydroxybenzoyl)-alpha,alpha-diaminopropane H-4-1 with molybdate results in the formation of the meso-helicate type molecular rectangle Delta, Lambda-[MoO2(1)}(2)](4-) as confirmed by NMR-spectroscopy and X-ray crystallography. Thereby the cis-dioxo Mo(VI) moieties act as shape defining corner units. The potassium salt of the complex crystallised in the centrosymmetric space group P (1) over bar with unit cell parameters a = 12.370(2), b = 13.900(3), c = 14.340(3) Angstrom; alpha =116.34(3), beta = 99.12(3), gamma = 96.68(3)degrees; V = 2132.6(7) Angstrom(3) Z = 2.