2-chloro-8-methyl-4-phenylquinoline | 113431-45-1

• 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-chloro-8-methyl-4-phenylquinoline
• CAS: 113431-45-1
• 化学式: C₁₆H₁₂ClN
• mdl: MFCD11539621
• 分子量: 253.731
• InChiKey: HEOSTKBJGDQYAO-UHFFFAOYSA-N

物化性质

• 熔点：
  48.0-48.5 °C(Solv: methanol (67-56-1))
• 沸点：
  394.1±30.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-chloro-8-methyl-4-phenylquinoline 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 甲醇 、 Petroleum ether 为溶剂， 反应 12.0h， 以76%的产率得到8-methyl-4-phenylquinoline
  参考文献：
  名称：

  Potential antitumor agents. 56. Minimal DNA-intercalating ligands as antitumor drugs: phenylquinoline-8-carboxamides

  摘要：

  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.

  DOI：

  10.1021/jm00400a029
• 作为产物：
  描述：

  3-oxo-3-phenyl-N-(o-tolyl)propanamide 在 四磷十氧化物 、 磷酸 、 N,N-二甲基苯胺 、 三氯氧磷 作用下， 反应 10.5h， 生成 2-chloro-8-methyl-4-phenylquinoline
  参考文献：
  名称：

  轻松合成5-苯基二苯并[b，g] [1,8]萘啶

  摘要：

  2芳基氨基-4-苯基喹啉的Vilsmeier Haack杂环化喹啉以定量收率产生了迄今未知的5苯基二苯并[ b，g ] [1,8]萘啶。芳基胺的合成是通过苯胺在2-氯-4-苯基喹啉上的作用而实现的，苯喹啉又是通过苯甲酰乙酰苯胺的梳理反应获得的。

  DOI：

  10.1002/jhet.2256

文献信息

• Pyridine and related aza heterocycle derivatives as cardiovascular agents
  申请人：AMERICAN CYANAMID COMPANY

  公开号：EP0446604A3

  公开（公告）日：1992-02-19

  Novel pharmaceutical compounds and compositions having nitrogen containing ring systems which may be represented by the following structural formula: wherein R₁ or R₃ is a moiety of the formula: wherein R₆ is selected from either hydrogen or acetyl; R₇ is selected from 2, 3 or 4-pyridyl or 1-imidazolyl and Q is -(CH₂)n, where n is an integer from 1 to 5 and R₁ and R₂, R₂ and R₃, R₃ and R₄ or R₄ and R₅ taken together may be -CH=CH-CH=CH-. The compounds and compositions are useful as inhibitors of thromboxane synthetase and in the treatment of hypertension and arrythmia in mammals.

  具有含氮环系统的新型药物化合物和组合物，可以用以下结构式表示： 其中R₁或R₃是以下式的基团： 其中R₆从氢或乙酰中选择；R₇从2、3或4-吡啶基或1-咪唑基中选择，Q为-(CH₂)n，其中n是从1到5的整数，且R₁和R₂、R₂和R₃、R₃和R₄或R₄和R₅一起可能是-CH=CH-CH=CH-。这些化合物和组合物可用作血栓素合酶的抑制剂，并用于治疗哺乳动物的高血压和心律失常。
• Synthesis and Anticonvulsant Activity of 5-Phenyl-[1,2,4]-triazolo[4,3-<i>a</i>]quinolines
  作者：Li-Ping Guan、Qing-Hao Jin、Shou-Feng Wang、Fu-Nan Li、Zhe-Shan Quan

  DOI：10.1002/ardp.200800116

  日期：2008.12

  A series of novel 5‐phenyl‐[1,2,4]‐triazolo[4,3‐a]quinoline derivatives was synthesized by the cyclization of 2‐chloro‐4‐phenyl‐1,2‐dihydronaphthalene with formohydrazide. The starting material 2‐chloro‐4‐phenyl‐1,2‐dihydronaphthalene was synthesized from ethyl‐3‐oxo‐3‐phenylpropanoate and substituted aniline. Their anticonvulsant activities were evaluated by the maximal electroshock (MES) test and

  通过2-氯-4-苯基-1,2-二氢萘与甲酰肼的环化反应合成了一系列新型5-苯基-[1,2,4]-三唑并[4,3-a]喹啉衍生物。以 3-氧代-3-苯基丙酸乙酯和取代苯胺为原料合成了 2-氯-4-苯基-1,2-二氢萘。通过最大电休克 (MES) 试验评估它们的抗惊厥活性，通过旋转棒神经毒性试验 (Tox) 评估它们的神经毒性。最大电击试验表明，7-hexyloxy-5-phenyl-[1,2,4]-triazolo[4,3-a]quinoline 4f 是最有效的化合物，ED50 值为 6.5 mg/kg，并且保护指数（PI = ED50 / TD50）值为35.1，远高于参比药物苯妥英的PI。
• ATWELL, GRAHAM J.;BOS, CLAUDIA D.;BAGULEY, BRUCE C.;DENNY, WILLIAM A., J. MED. CHEM., 31,(1988) N 5, 1048-1052
  作者：ATWELL, GRAHAM J.、BOS, CLAUDIA D.、BAGULEY, BRUCE C.、DENNY, WILLIAM A.

  DOI：——

  日期：——
• A Facile Synthesis of 5-Phenyl-Dibenzo[<i>b</i>,<i>g</i>][1,8]Napthyridines
  作者：Natarajan Sampathkumar、Arumugam Murugesh、Subramaniam Parameswaran Rajendran

  DOI：10.1002/jhet.2256

  日期：2016.5

  The Vilsmeier Haack heterocyclization of 2‐aryl amino‐4‐phenyl quinolines quinoline yielded the hitherto unknown 5‐phenyl‐dibenzo[b,g][1,8]naphthyridines in quantitative yield. The synthesis of aryl amines was achieved by the action of anilines on 2‐chloro‐4‐phenyl quinoline, which in turn was sourced through the combes reaction of benzoyl acetanilides.

  2芳基氨基-4-苯基喹啉的Vilsmeier Haack杂环化喹啉以定量收率产生了迄今未知的5苯基二苯并[ b，g ] [1,8]萘啶。芳基胺的合成是通过苯胺在2-氯-4-苯基喹啉上的作用而实现的，苯喹啉又是通过苯甲酰乙酰苯胺的梳理反应获得的。
• 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.