8-甲基-2-吡啶-2-基喹啉-4-羧酸 | 107027-35-0

• 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
• 中文名称: 8-甲基-2-吡啶-2-基喹啉-4-羧酸
• 中文别名: 8-甲基-2-(2-吡啶基)-喹啉-4-羧酸
• 英文名称: 8-methyl-2-(2-pyridyl)quinoline-4-carboxylic acid
• 英文别名: 8-Methyl-2-(pyridin-2-yl)quinoline-4-carboxylic acid；8-Methyl-2-pyridin-2-ylquinoline-4-carboxylic acid
• CAS: 107027-35-0
• 化学式: C₁₆H₁₂N₂O₂
• mdl: MFCD03421963
• 分子量: 264.283
• InChiKey: OCXAIJJVNVWYHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  63.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  8-甲基-2-吡啶-2-基喹啉-4-羧酸 在 盐酸 、 selenium(IV) oxide 、 铜 、 N,N'-羰基二咪唑 作用下， 反应 0.58h， 生成 N-<2-(dimethylamino)ethyl>-2-(2-pyridyl)quinoline-8-carboxamide hydrochloride
  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-乙酰基吡啶 、 7-甲基靛红 以 乙醇 、 水 为溶剂， 以73 %的产率得到8-甲基-2-吡啶-2-基喹啉-4-羧酸
  参考文献：
  名称：

  空间要求高的吡啶-喹啉锚定配体作为铜 (I) 基染料敏化太阳能电池 (DSSC) 配合物的构建单元

  摘要：

  Pfitzinger缩合反应用于合成具有羧酸锚定基团的N^N空间要求配体，即2,2'-吡啶基-喹啉-4-羧酸（pqca），6'-甲基-2,2'-吡啶基-喹啉-4-羧酸 ( 6'-Mepqca )、8-甲基-2,2'-吡啶基-喹啉-4-羧酸 ( 8-Mepqca ) 和 8,6'-二甲基-2,2'-吡啶基-喹啉-4-羧酸（8,6'-Me 2 pqca）。还描述了甲酯类似物6'-Mepqcame、8-Mepqcame和8,6'-Me 2 pqcame的制备。所有配体均已完全表征，包括pqca的 X 射线结构，6'-Mepqca和8-Mepqca。我们还描述了分子式 [Cu(N^N) 2 ][PF 6 ] (N^N = pqca ( 1 ), 6'-Mepqca ( 2 ), 8的七种均配铜 ( I ) 配合物的合成和表征-Mepqcame ( 3 )、8,6'-Me 2 pqcame ( 4 )、6'-Mepqcame

  DOI：

  10.1039/d2dt02382b

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。
• 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.
• Sterically demanding pyridine-quinoline anchoring ligands as building blocks for copper(<scp>i</scp>)-based dye-sensitized solar cell (DSSC) complexes
  作者：Anastasios Peppas、Demetrios Sokalis、Dorothea Perganti、Gregor Schnakenburg、Polycarpos Falaras、Athanassios I. Philippopoulos

  DOI：10.1039/d2dt02382b

  日期：——

  ligands were fully characterised including the X-ray structures of pqca, 6′-Mepqca and 8-Mepqca. We also describe the synthesis and characterisation of seven homoleptic copper(I) complexes of the formula [Cu(N^N)2][PF6] (N^N = pqca (1), 6′-Mepqca (2), 8-Mepqca (3), 8,6′-Me2pqca (4), 6′-Mepqcame (6), 8-Mepqcame (7) and 8,6′-Me2pqcame (8)). Characterisation of the copper(I) complexes includes FT-IR, elemental

  Pfitzinger缩合反应用于合成具有羧酸锚定基团的N^N空间要求配体，即2,2'-吡啶基-喹啉-4-羧酸（pqca），6'-甲基-2,2'-吡啶基-喹啉-4-羧酸 ( 6'-Mepqca )、8-甲基-2,2'-吡啶基-喹啉-4-羧酸 ( 8-Mepqca ) 和 8,6'-二甲基-2,2'-吡啶基-喹啉-4-羧酸（8,6'-Me 2 pqca）。还描述了甲酯类似物6'-Mepqcame、8-Mepqcame和8,6'-Me 2 pqcame的制备。所有配体均已完全表征，包括pqca的 X 射线结构，6'-Mepqca和8-Mepqca。我们还描述了分子式 [Cu(N^N) 2 ][PF 6 ] (N^N = pqca ( 1 ), 6'-Mepqca ( 2 ), 8的七种均配铜 ( I ) 配合物的合成和表征-Mepqcame ( 3 )、8,6'-Me 2 pqcame ( 4 )、6'-Mepqcame