5,5'-dimethyl-2,2'-(1,3-phenylenediamino)bis-benzoic acid | 195823-18-8

• 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: 5,5'-dimethyl-2,2'-(1,3-phenylenediamino)bis-benzoic acid
• 英文别名: 2-[3-(2-Carboxy-4-methylanilino)anilino]-5-methylbenzoic acid
• CAS: 195823-18-8
• 化学式: C₂₂H₂₀N₂O₄
• 分子量: 376.412
• InChiKey: YAGRFKTZJKXBPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,5'-dimethyl-2,2'-(1,3-phenylenediamino)bis-benzoic acid 在 lithium aluminium tetrahydride 、 三氯化铁 、 三氯氧磷 作用下， 反应 28.5h， 生成 2,10-dimethyldibenzo[b,j][1,7]phenanthroline
  参考文献：
  名称：

  Cyclobisintercaland Macrocycles:  Synthesis and Physicochemical Properties of Macrocyclic Polyamines Containing Two Crescent-Shaped Dibenzophenanthroline Subunits

  摘要：

  A general access to isomeric dibenzo[bj]phenanthrolinedicarboxaldehydes is described. These pentacyclic planar quinacridine compounds exhibit crescent-shaped forms that fulfill the geometrical requirements of providing broad overlap of nucleobase pairs or triplets. The dialdehyde derivatives have been condensed with various polyamines to give macrocyclic dimeric structures, cyclobisintercalands, of variable size, charge, and shape. The related water-soluble monomeric quinacridines were prepared from the dialdehydes by grafting ammonium groups; The physicochemical properties of the monomeric quinacridines and of the macrocyclic bis-quinacridines have been investigated by spectroscopic methods (UV-vis, fluorescence, NMR). The results show that some of these macrocyclic compounds could exist as semiclosed conformers suitable to accommodate a pair of nucleotides.

  DOI：

  10.1021/jo970496b
• 作为产物：
  描述：

  2-氨基-5-甲基苯甲酸 、 1,3-二碘苯 在 copper(l) iodide 、 铜 作用下， 生成 5,5'-dimethyl-2,2'-(1,3-phenylenediamino)bis-benzoic acid
  参考文献：
  名称：

  Use of polycyclic aromatic compounds for making medicines capable of inhibiting telomerase

  摘要：

  本发明涉及使用具有与G四链结构结合能力的芳香化合物来制备具有抗端粒酶效应的药物。所述化合物对应于式（I），其中：R1、R2和R3相同或不同，表示氢原子或—CH2—NH—（CH2）n—X基团，其中n是2至4的整数，X选自—NH2—、—N（CH3）2基团、如哌啶基、咪唑基、吗啉基或吲哚型缩合杂环基团等杂环基团；—Z表示CH或N，每种化合物在Z位置含有两个氮原子。本发明有助于制备抗癌药物。

  公开号：

  US20040034023A1

文献信息

• Use of polycyclic aromatic compounds for making medicines capable of inhibiting telomerase
  申请人：——

  公开号：US20040034023A1

  公开（公告）日：2004-02-19

  The invention concerns the use of aromatic compounds capable of binding with G-quadruplex structures to produce medicines with anti-telomerase effect. Said compounds correspond to formula (I) wherein: R 1 , R 2 and R 3 , identical or different, represent a hydrogen atom, or a —CH 2 —NH—(CH 2 ) n —X group, wherein n is an integer from 2 to 4, and X is selected among —NH 2 —, —N(CH 3 ) 2 radicals, a heterocyclic radical such as piperidyl, imidazolyl, morpholinyl radical, or an indole-type condensed heterocyclic radical, —Z represents CH or N, each compound comprising two nitrogen atoms in the Z positions. The invention is useful for producing anticancer medicines.

  本发明涉及使用具有与G四链结构结合能力的芳香化合物来制备具有抗端粒酶效应的药物。所述化合物对应于式（I），其中：R1、R2和R3相同或不同，表示氢原子或—CH2—NH—（CH2）n—X基团，其中n是2至4的整数，X选自—NH2—、—N（CH3）2基团、如哌啶基、咪唑基、吗啉基或吲哚型缩合杂环基团等杂环基团；—Z表示CH或N，每种化合物在Z位置含有两个氮原子。本发明有助于制备抗癌药物。
• Palladium versus copper-catalyzed N-arylation towards an efficient access to polysubstituted dibenzophenanthrolines and carbazoles
  作者：Clémence Jacquelin、Nicolas Saettel、Candide Hounsou、Marie-Paule Teulade-Fichou

  DOI：10.1016/j.tetlet.2005.02.079

  日期：2005.4

  The double amination of meta-diiodo and dibromobenzenes by anthranilic acid derivatives is described using palladium and/or copper catalysis. The resulting symmetrical and unsymmetrical phenylene diamines are key precursors to polyfunctional dibenzophenanthroline carboxaldehydes. In contrast, when ortho-dibromo benzene is used as substrate, the Pd-mediated process affords exclusively the functional

  描述了使用钯和/或铜催化的邻氨基苯甲酸衍生物对间二碘代和二溴代苯的双胺化。所得的对称和不对称亚苯基二胺是多官能二苯并菲咯啉羧酸醛的关键前体。相反，当使用邻二溴苯作为底物时，Pd介导的过程仅提供功能性咔唑。
• Cyclobisintercaland Macrocycles:  Synthesis and Physicochemical Properties of Macrocyclic Polyamines Containing Two Crescent-Shaped Dibenzophenanthroline Subunits
  作者：Olivier Baudoin、Marie-Paule Teulade-Fichou、Jean-Pierre Vigneron、Jean-Marie Lehn

  DOI：10.1021/jo970496b

  日期：1997.8.1

  A general access to isomeric dibenzo[bj]phenanthrolinedicarboxaldehydes is described. These pentacyclic planar quinacridine compounds exhibit crescent-shaped forms that fulfill the geometrical requirements of providing broad overlap of nucleobase pairs or triplets. The dialdehyde derivatives have been condensed with various polyamines to give macrocyclic dimeric structures, cyclobisintercalands, of variable size, charge, and shape. The related water-soluble monomeric quinacridines were prepared from the dialdehydes by grafting ammonium groups; The physicochemical properties of the monomeric quinacridines and of the macrocyclic bis-quinacridines have been investigated by spectroscopic methods (UV-vis, fluorescence, NMR). The results show that some of these macrocyclic compounds could exist as semiclosed conformers suitable to accommodate a pair of nucleotides.