7-(4-nitrophenyl)heptanoic acid | 66147-99-7

• 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: 7-(4-nitrophenyl)heptanoic acid
• 英文别名: 7-(4'-Nitrophenyl)-heptansaeure
• CAS: 66147-99-7
• 化学式: C₁₃H₁₇NO₄
• 分子量: 251.282
• InChiKey: DKGPAKSYZIIBBX-UHFFFAOYSA-N

物化性质

• 熔点：
  73-74 °C(Solv: isopropyl ether (108-20-3))
• 沸点：
  445.4±28.0 °C(Predicted)
• 密度：
  1.189±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-(4-nitrophenyl)heptanoic acid 在 palladium on activated charcoal 硫酸 、 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl 7-(4-aminophenyl)heptanoate
  参考文献：
  名称：

  DNA-directed alkylating agents. 1. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the reactivity of the mustard

  摘要：

  A series of DNA-targeted aniline mustards have been prepared, and their chemical reactivity and in vitro and in vivo cytotoxicity have been evaluated and compared with that of the corresponding simple aniline mustards. The alkylating groups were anchored to the DNA-intercalating 9-aminoacridine chromophore by an alkyl chain of fixed length attached at the mustard 4-position through a link group X, while the corresponding simple mustards possessed an electronically identical small group at this position. The link group was varied to provide a series of compounds of similar geometry but widely differing mustard reactivity. Variation in biological activity should then largely be a consequence of this varying reactivity. Rates of mustard hydrolysis in the two series related only to the electronic properties of the link group, with attachment of the intercalating chromophore having no effect. The cytotoxicities of the simple mustards correlated well with group electronic properties (with a 200-300-fold range in IC50S). The corresponding DNA-targeted mustards were much more potent (up to 100-fold), but their IC50 values varied much less with linker group electronic properties. Most of the DNA-targeted mustards showed in vivo antitumor activity, being both more active and more dose-potent than either the corresponding untargeted mustards and chlorambucil. These results show that targeting alkylating agents to DNA by attachment to DNA-affinic units may be a useful strategy.

  DOI：

  10.1021/jm00166a015
• 作为产物：
  描述：

  6-苄酰基己酸 在 硝酸 作用下， 生成 7-(4-nitrophenyl)heptanoic acid
  参考文献：
  名称：

  潜在的抗肿瘤药。27.ω-[4-（9-ac啶基氨基）苯基]链烷酸的定量结构-抗白血病（L1210）活性关系。

  摘要：

  9-苯胺基cr啶的简单羧酸衍生物（例如1，R = -COOH）具有很高的实验抗白血病（L1210）活性。同源的1'-（CH2）nCOOH同系物也被证明具有活性，并且L1210试验中寿命的最大增长与用作衡量亲脂性-亲水性平衡剂的Rm值之间存在抛物线关系。相应的羧酰胺[1'-（CH2）nCONH2]具有相似的抛物线关系，具有最佳的Rm值，与酸的值相比有所偏离。较早检查的1'-NHSO2（CH2）nCH3变体，它们的3-NHCOCH3同系物以及羧酰胺[1'-（CH2）nCONH2]和磺酰胺[1'-（CH2）nSO2NH2]同源物可被视为一组得到的相关方程与仅羧酰胺变体的相关方程相同。该组的最佳Rm值与酸的最佳Rm值相等于辛醇-水规模的1.8 log P单位。在该药物系列中，羧酸残基充当可接受的亲水性单元，在未电离的酸和完全电离的羧酸根阴离子之间提供log P贡献中间值。在含有羧酸或链烷磺酰胺侧链

  DOI：

  10.1021/jm00203a005

文献信息

• [EN] HYDROXAMIC ACID DERIVATIVES<br/>[FR] DÉRIVÉS D'ACIDE HYDROXAMIQUE
  申请人：CRYSTAL BIOPHARMACEUTICAL LLC

  公开号：WO2010085377A3

  公开（公告）日：2011-03-31
• GOURDIE, TRUDI A.;VALU, KISIONE K.;GRAVATT, G. LANCE;BORITZKI, THEODORE J+, J. MED. CHEM., 33,(1990) N, C. 1177-1186
  作者：GOURDIE, TRUDI A.、VALU, KISIONE K.、GRAVATT, G. LANCE、BORITZKI, THEODORE J+

  DOI：——

  日期：——
• DENNY W. A.; CAIN B. F., J. MED. CHEM., 1978, 21, NO 5, 430-437
  作者：DENNY W. A.、 CAIN B. F.

  DOI：——

  日期：——
• Potential antitumor agents. 27. Quantitative structure-antileukemic (L1210) activity relationships for the .omega.[4-(9-acridinylamino)phenyl]alkanoic acids
  作者：William A. Denny、Bruce F. Cain

  DOI：10.1021/jm00203a005

  日期：1978.5

  activity. The homologous 1'-(CH2)nCOOH congeners also prove active, and there is a parabolic interrelationship between maximum increase in life span in L1210 tests and Rm values used as a measure of agent lipophilic--hydrophilic balance. The corresponding carboxamides [1'-(CH2)nCONH2] provide a similar parabolic relationship, which has an optimum Rm value displaced from that of the acids. Earlier examined

  9-苯胺基cr啶的简单羧酸衍生物（例如1，R = -COOH）具有很高的实验抗白血病（L1210）活性。同源的1'-（CH2）nCOOH同系物也被证明具有活性，并且L1210试验中寿命的最大增长与用作衡量亲脂性-亲水性平衡剂的Rm值之间存在抛物线关系。相应的羧酰胺[1'-（CH2）nCONH2]具有相似的抛物线关系，具有最佳的Rm值，与酸的值相比有所偏离。较早检查的1'-NHSO2（CH2）nCH3变体，它们的3-NHCOCH3同系物以及羧酰胺[1'-（CH2）nCONH2]和磺酰胺[1'-（CH2）nSO2NH2]同源物可被视为一组得到的相关方程与仅羧酰胺变体的相关方程相同。该组的最佳Rm值与酸的最佳Rm值相等于辛醇-水规模的1.8 log P单位。在该药物系列中，羧酸残基充当可接受的亲水性单元，在未电离的酸和完全电离的羧酸根阴离子之间提供log P贡献中间值。在含有羧酸或链烷磺酰胺侧链
• DNA-directed alkylating agents. 1. Structure-activity relationships for acridine-linked aniline mustards: consequences of varying the reactivity of the mustard
  作者：Trudi A. Gourdie、Kisione K. Valu、G. Lance Gravatt、Theodore J. Boritzki、Bruce C. Baguley、Laurence P. G. Wakelin、William R. Wilson、Paul D. Woodgate、William A. Denny

  DOI：10.1021/jm00166a015

  日期：1990.4

  A series of DNA-targeted aniline mustards have been prepared, and their chemical reactivity and in vitro and in vivo cytotoxicity have been evaluated and compared with that of the corresponding simple aniline mustards. The alkylating groups were anchored to the DNA-intercalating 9-aminoacridine chromophore by an alkyl chain of fixed length attached at the mustard 4-position through a link group X, while the corresponding simple mustards possessed an electronically identical small group at this position. The link group was varied to provide a series of compounds of similar geometry but widely differing mustard reactivity. Variation in biological activity should then largely be a consequence of this varying reactivity. Rates of mustard hydrolysis in the two series related only to the electronic properties of the link group, with attachment of the intercalating chromophore having no effect. The cytotoxicities of the simple mustards correlated well with group electronic properties (with a 200-300-fold range in IC50S). The corresponding DNA-targeted mustards were much more potent (up to 100-fold), but their IC50 values varied much less with linker group electronic properties. Most of the DNA-targeted mustards showed in vivo antitumor activity, being both more active and more dose-potent than either the corresponding untargeted mustards and chlorambucil. These results show that targeting alkylating agents to DNA by attachment to DNA-affinic units may be a useful strategy.