2-(4-Nitrophenyl)quinoline-8-carboxylic acid | 107027-77-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-Nitrophenyl)quinoline-8-carboxylic acid
• 英文别名: 2(4-Nitrophenyl)quinoline-8-carboxylic acid
• CAS: 107027-77-0
• 化学式: C₁₆H₁₀N₂O₄
• 分子量: 294.266
• InChiKey: NRCOSTBHUJDNEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  96
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4-Nitrophenyl)quinoline-8-carboxylic acid 在 盐酸 、 铁粉 、 溶剂黄146 、 N,N'-羰基二咪唑 作用下， 以 乙醇 为溶剂， 反应 1.58h， 生成 N-<2-(dimethylamino)ethyl>-2-(4-aminophenyl)quinoline-8-carboxamide dihydrochloride
  参考文献：
  名称：

  Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity

  摘要：

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.

  DOI：

  10.1021/jm00122a018
• 作为产物：
  描述：

  2-甲基喹啉 在 CrO₃ 作用下， 以 aqueous KOH 、 conc. H2 SO4 、 水 为溶剂， 以64%的产率得到2-(4-Nitrophenyl)quinoline-8-carboxylic acid
  参考文献：
  名称：

  Substituted quinoline derivatives and pharmaceutical compositions thereof

  摘要：

  被一般式(I)所代表的取代喹啉新类化合物，其中R.sub.1和R.sub.2各自代表H或最多三个低碳链烷基、卤素、CF.sub.3、CN、SO.sub.2 CH.sub.3、NO.sub.2、OH、NH.sub.2、NHSO.sub.2 R.sub.3、NHCOOR.sub.3、OR.sub.3、SR.sub.3、NHR.sub.3或NR.sub.3 R.sub.3（其中R.sub.3是低碳链烷基，可选地取代羟基、氨基或醚基功能），且R.sub.1和R.sub.2各自还可以分别代表在每个碳环中的一个或两个亚胺（--N.dbd.）基取代一个或两个亚甲烷（--CH.dbd.）基，且R.sub.1还可以代表仅在2'、3'或4'位置的苯环，该苯环可选择性地进一步取代为低碳链烷基、卤素、CF.sub.3、CN、SO.sub.2 CH.sub.3、NO.sub.2、OH、NH.sub.2、NHCOR.sub.3、NHCOOR.sub.3、OR.sub.3、SR.sub.3、NHR.sub.3或NR.sub.3 R.sub.3（其中R.sub.3是低碳链烷基，可选地取代羟基、氨基或醚基功能）；Y代表C(NH)NH.sub.2、NHC(NH)NH.sub.2或NR.sub.4 R.sub.5，其中R.sub.4和R.sub.5各自是H或低碳链烷基，可选择性地取代羟基、氨基或醚基功能，或者R.sub.4和R.sub.5与氮原子一起形成杂环；n为2至6；以及其酸盐和1-N-氧化物具有抗菌和抗肿瘤性能。

  公开号：

  US04904659A1

文献信息

• Substituted quinoline derivatives
  申请人：CANCER RESEARCH CAMPAIGN TECHNOLOGY LIMITED

  公开号：EP0206802B1

  公开（公告）日：1993-09-01
• Potential antitumor agents. 57. 2-Phenylquinoline-8-carboxamides as minimal DNA-intercalating antitumor agents with in vivo solid tumor activity
  作者：Graham J. Atwell、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00122a018

  日期：1989.2

  A series of phenyl-substituted derivatives of the "minimal" DNA-intercalating agent N-[2-(dimethylamino)-ethyl]-2-phenylquinoline-8-carboxamide (1) have been synthesized and evaluated for in vivo antitumor activity, in a continuing search for active compounds of this class with the lowest possible DNA association constants. Substitution on the 2'-position of the phenyl ring gave compounds of lower DNA binding ability that did not intercalate DNA, indicating that it is necessary for the phenyl ring to be essentially coplanar with the quinoline for intercalative binding. An extensive series of 4'-substituted derivatives was evaluated, but there was no overall relationship between biological activity and substituent lipophilic or electronic properties. However, several compounds showed good solid tumor activity, with the 4'-aza derivative 18 being clearly superior to the parent compound, effecting about 50% cures in both leukemia and solid tumor models.
• Substituted quinoline derivatives and pharmaceutical compositions thereof
  申请人：Development Finance Corporation of New Zeland

  公开号：US04904659A1

  公开（公告）日：1990-02-27

  The novel class of substituted quinolines represented by the general formula (I): ##STR1## where each of R.sub.1 and R.sub.2 separately represents H or up to three of the groups lower alkyl, halogen, CF.sub.3, CN, SO.sub.2 CH.sub.3, NO.sub.2, OH, NH.sub.2, NHSO.sub.2 R.sub.3, NHCOOR.sub.3, OR.sub.3, SR.sub.3, NHR.sub.3 or NR.sub.3 R.sub.3 (where R.sub.3 is lower alkyl optionally substituted with hydroxy, amino or ether functions), and each of R.sub.1 and R.sub.2 may additionally separately represent the substitution of an aza (--N.dbd.) group for one or two of the methine (--CH.dbd.) groups in each of the carbocyclic rings, and R.sub.1 may also represent, at positions 2', 3' or 4' only, a phenyl ring optionally further substituted with lower alkyl, halogen, CF.sub.3, CN, SO.sub.2 CH.sub.3, NO.sub.2, OH, NH.sub.2, NHCOR.sub.3, NHCOOR.sub.3, OR.sub.3, SR.sub.3, NHR.sub.3 or NR.sub.3 R.sub.3 (where R.sub.3 is lower alkyl optionally substituted with hydroxy, amino or ether functions); Y represents C(NH)NH.sub.2, NHC(NH)NH.sub.2 or NR.sub.4 R.sub.5, where each of R.sub.4 and R.sub.5 is H or lower alkyl optionally substituted with hydroxy, amino or ether functions, or R.sub.4 and R.sub.5 together with the nitrogen atom form a heterocyclic ring; and n is from 2 to 6; and the acid addition salts and 1-N-oxides thereof, possess antibacterial and antitumor properties.

  被一般式(I)所代表的取代喹啉新类化合物，其中R.sub.1和R.sub.2各自代表H或最多三个低碳链烷基、卤素、CF.sub.3、CN、SO.sub.2 CH.sub.3、NO.sub.2、OH、NH.sub.2、NHSO.sub.2 R.sub.3、NHCOOR.sub.3、OR.sub.3、SR.sub.3、NHR.sub.3或NR.sub.3 R.sub.3（其中R.sub.3是低碳链烷基，可选地取代羟基、氨基或醚基功能），且R.sub.1和R.sub.2各自还可以分别代表在每个碳环中的一个或两个亚胺（--N.dbd.）基取代一个或两个亚甲烷（--CH.dbd.）基，且R.sub.1还可以代表仅在2'、3'或4'位置的苯环，该苯环可选择性地进一步取代为低碳链烷基、卤素、CF.sub.3、CN、SO.sub.2 CH.sub.3、NO.sub.2、OH、NH.sub.2、NHCOR.sub.3、NHCOOR.sub.3、OR.sub.3、SR.sub.3、NHR.sub.3或NR.sub.3 R.sub.3（其中R.sub.3是低碳链烷基，可选地取代羟基、氨基或醚基功能）；Y代表C(NH)NH.sub.2、NHC(NH)NH.sub.2或NR.sub.4 R.sub.5，其中R.sub.4和R.sub.5各自是H或低碳链烷基，可选择性地取代羟基、氨基或醚基功能，或者R.sub.4和R.sub.5与氮原子一起形成杂环；n为2至6；以及其酸盐和1-N-氧化物具有抗菌和抗肿瘤性能。