2-phenylquinoline-8-carboxylic acid | 5093-81-2

• 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-phenylquinoline-8-carboxylic acid
• 英文别名: 2-Phenyl-chinolin-8-carbonsaeure
• CAS: 5093-81-2
• 化学式: C₁₆H₁₁NO₂
• 分子量: 249.269
• InChiKey: KJLNRZNBAGSKBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 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：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-phenylquinoline-8-carboxylic acid 在 potassium hydroxide 作用下， 以 丙酮 为溶剂， 反应 33.0h， 生成 2-phenyl-8-(1-ethylbenzimidazol-2-yl)quinoline
  参考文献：
  名称：

  带有取代的8-（苯并咪唑-2-基）喹啉的二齿二氯化铁（II）配合物：合成，表征和乙烯聚合行为。

  摘要：

  该系列的Ñ -benzimidazolyl取代的2-烷基-8-（苯并咪唑-2-基）喹啉（L1 - L10）和2-苯基-8-（苯并咪唑-2-基）喹啉（L11 - L14）和它们各自的合成了二齿二齿二氯化铁（II）复合物（C1 – C14）并对其进行了充分表征。通过X射线晶体结构分析确定了代表性配体（L5）和铁配合物（C2，C7）的分子结构，并在配合物C2和C7的铁中心观察到扭曲的四面体配位几何。。用甲基铝氧烷活化铁络合物后，铁催化剂在高温（100°C）的乙烯聚合反应中显示出高达10 6 g·mol –1 ·h –1的活性，从而生成线性聚乙烯。优化了聚合反应的反应参数，讨论了不同配体的取代基对催化活性和所得聚乙烯的影响。

  DOI：

  10.1021/om200338b
• 作为产物：
  描述：

  8-甲基-2-苯基-4-喹啉羧酸 在 selenium(IV) oxide 、 铜 作用下， 反应 0.03h， 生成 2-phenylquinoline-8-carboxylic acid
  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

文献信息

• 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。
• Synthesis and evaluation of unsymmetrical bis(arylcarboxamides) designed as topoisomerase-Targeted anticancer drugs
  作者：Julie A Spicer、Swarna A Gamage、Graeme J Finlay、William A Denny

  DOI：10.1016/s0968-0896(01)00249-8

  日期：2002.1

  Symmetrical dimers of lipophilic intercalating chromophores linked by cation-containing chains have recently been shown to have broad-spectrum in vivo anticancer activity. We report the preparation and evaluation of a series of both symmetric and unsymmetric dimers of a variety of intercalating chromophores of varied DNA binding strength, including naphthalimides, acridines, phenazines, oxanthrenes and 2-phenylquinolines. The unsymmetrical dimers were prepared by sequential coupling of the chromophores to linkers with selectively protected primary terminal amines to ensure high yields and unequivocal product. Protection of the internal (secondary) amines as BOC derivatives was used to ensure complete structural specificity, and was also an aid to the purification of these very polar compounds. The growth inhibitory abilities (as IC50 values) of the compounds in a range of cell lines showed that the nature of the linker chain was important, and independent of the nature of the chromophore, with compounds containing the dicationic linker [-(CH2)(2)NH(CH2)(2)NH(CH2)(2)-] being on average 30-fold more potent than the corresponding compounds containing the monocationic linker [-(CH2)(3)NMe(CH2)(3)-]. However, the chromophores also play a role in determining biological activity, with the cytotoxicities of symmetric and unsymmetric dicationic dimers correlating with the overall DNA binding abilities of the chromophores. (C) 2001 Elsevier Science Ltd. All rights reserved.
• QUINOLINES AND RELATED ANALOGS AS SIRTUIN MODULATORS
  申请人：GlaxoSmithKline LLC

  公开号：EP2273992B1

  公开（公告）日：2016-05-25
• Potential antitumor agents. 56. Minimal DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides
  作者：Graham J. Atwell、Claudia D. Bos、Bruce C. Baguley、William A. Denny

  DOI：10.1021/jm00400a029

  日期：1988.5

  A series of isomeric phenylquinoline-8-carboxamides have been synthesized and evaluated as antitumor agents. This configuration is close to the minimum chromophore required for intercalative binding, since the binding mode of the compounds is dependent on the presence and position of the phenyl ring. If the ring is appended at the 4- or 5-position, it cannot lie within the DNA-intercalation site, and the compounds do not intercalate as shown by both unwinding and helix extension assays. In contrast, the 2-, 3-, and 6-phenyl isomers (where the phenyl ring lies coplanar with the quinoline and in the intercalation site) bind by intercalation. Only those isomers that intercalate show in vivo antitumor activity, with the 2-phenyl derivative in particular possessing broad-spectrum activity in both leukemia and solid-tumor assays.
• Synthesis of Simple 2-Phenyl-8-aminoquinoline Derivatives¹
  作者：Robert C. Elderfield、Walter J. Gensler、Thomas H. Bembry、Thurmond A. Williamson、Henry Weisl

  DOI：10.1021/ja01212a064

  日期：1946.8