2,7-二氯-6-氟-喹啉-3-甲醛 | 137684-12-9

• 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: 2,7-二氯-6-氟-喹啉-3-甲醛
• 英文名称: 3-Quinolinecarbaldehyde,2,7-dichloro-6-fluoro-
• 英文别名: 2,7-dichloro-6-fluoroquinoline-3-carbaldehyde
• CAS: 137684-12-9
• 化学式: C₁₀H₄Cl₂FNO
• 分子量: 244.052
• InChiKey: JIGLBNFROBHLMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,7-二氯-6-氟-喹啉-3-甲醛 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (2,7-Dichloro-6-fluoroquinolin-3-yl)methanol
  参考文献：
  名称：

  Homocamptothecins:  Synthesis and Antitumor Activity of Novel E-Ring-Modified Camptothecin Analogues

  摘要：

  Homocamptothecin (hCPT), a camptothecin (CPT) analogue with a seven membered beta-hydroxylactone which combines enhanced plasma stability and potent topoisomerase I (Topo I)-mediated activity, is an attractive template for the elaboration of new anticancer agents. Like CPT, hCPT carries an asymmetric tertiary alcohol and displays stereoselective inhibition of Topo I. The preparation and biological screening of racemic hCPT analogues are described. The 10 hCPTs tested were better Topo I inhibitors than CPT. Fluorinated hCPTs 23c,d,f,g were found to have potent cytotoxic activity on A427 and PC-3 tumor cell lines. Their cytotoxicity remained high on the K562adr and MCF7mdr cell. lines, which overexpress a functionally active P-glycoprotein. Fluorinated hCPTs were more efficacious in vivo than CPT on HT-29 xenografts. In this model, a tumor growth delay of 25 days was reached with hCPT 23g at a daily dose of 0.32 mg/kg, compared to 4 days with CPT at 0.625 mg/kg. Thus difluorinated hCPT 23g warrants further investigation as a novel Topo I inhibitor with high cytotoxicity toward tumor cells and promising in vivo efficacy.

  DOI：

  10.1021/jm980400l
• 作为产物：
  描述：

  3-氯-4-氟苯胺 在 三乙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 1.5h， 生成 2,7-二氯-6-氟-喹啉-3-甲醛
  参考文献：
  名称：

  Synthesis and antimalarial activity of Baylis-Hillman adducts from substituted 2-chloroquinoline-3-carboxaldehydes

  摘要：

  Various quinoline carboxaldehydes were prepared from corresponding anilides using classical Vilsmeier-Haack reaction conditions and transformed into their Baylis-Hillman adducts. The synthesized Baylis-Hillman adducts were screened for their in vitro antimalarial activity against Plasmodium falciparum. Most of the compounds out of 21 compounds synthesized and screened exhibited substantial antimalarial activity.

  DOI：

  10.1515/hc.2011.024

文献信息

• Synthesis of New Seleno-Substituted Quinolines
  作者：Balaji M. Kiran、Belalakatte P. Nandeshwarappa、Gowdara K. Prakash、Vijayavittala P. Vaidya、Kittappa M. Mahadevan

  DOI：10.1080/10426500601088978

  日期：2007.3.15

  The design and synthesis of organoselenium compounds with biological activity currently constitute engaging fundamental problems in applied chemistry in both pharmaceutical and academic laboratories. In this communication we would like to report the synthesis of new organo selenium compounds under mild reaction conditions. The newly synthesized compounds were characterized by elemental analysis, IR, H-1 NMR, and mass spectral studies.
• Chemistry of Substituted Quinolines: Thieno[2,3-<b> <i>b</i> </b>] and Thiopyrano[2,3-<b> <i>b</i> </b>]quinolines
  作者：Balaji M. Kiran、Belalakatte P. Nandeshwarappa、Vijayavittala P. Vaidya、Kittappa M. Mahadevan

  DOI：10.1080/10426500601088846

  日期：2007.3.15

  The reaction of 3-formyl-2-chloroquinolines with thioglycolic acid afforded a mixture of uncyclized [(3-formylquinolin-2-yl)thio]acetic acid in a 60-70% yield and cyclized thieno[2,3-b]quinoline-2-carboxylic acids in a 30-40% yield, respectively. The uncyclized compounds on refluxing with POCl3 in various alcoholic media gave [(3-formylquinolin-2-yl)thio]acetates. Further cyclization was achieved by refluxing them with dimethylformamide (DMF) to produce thieno[2,3-b]quinoline derivatives. On the other hand, the reaction of 3-formyl-2-mercaptoquinolines with chloroacetyl chloride in DMF gave 3-chloro-2H-thiopyrano[2,3-b]quinolin-2-ones. The structures of all the newly synthesized compounds were characterized on the basis of elemental analysis, IR, H-1 NMR, and mass spectral data.
• Homocamptothecins:  Synthesis and Antitumor Activity of Novel E-Ring-Modified Camptothecin Analogues
  作者：Olivier Lavergne、Laurence Lesueur-Ginot、Francesc Pla Rodas、Philip G. Kasprzyk、Jacques Pommier、Danièle Demarquay、Grégoire Prévost、Gérard Ulibarri、Alain Rolland、Anne-Marie Schiano-Liberatore、Jeremiah Harnett、Dominique Pons、José Camara、Dennis C. H. Bigg

  DOI：10.1021/jm980400l

  日期：1998.12.1

  Homocamptothecin (hCPT), a camptothecin (CPT) analogue with a seven membered beta-hydroxylactone which combines enhanced plasma stability and potent topoisomerase I (Topo I)-mediated activity, is an attractive template for the elaboration of new anticancer agents. Like CPT, hCPT carries an asymmetric tertiary alcohol and displays stereoselective inhibition of Topo I. The preparation and biological screening of racemic hCPT analogues are described. The 10 hCPTs tested were better Topo I inhibitors than CPT. Fluorinated hCPTs 23c,d,f,g were found to have potent cytotoxic activity on A427 and PC-3 tumor cell lines. Their cytotoxicity remained high on the K562adr and MCF7mdr cell. lines, which overexpress a functionally active P-glycoprotein. Fluorinated hCPTs were more efficacious in vivo than CPT on HT-29 xenografts. In this model, a tumor growth delay of 25 days was reached with hCPT 23g at a daily dose of 0.32 mg/kg, compared to 4 days with CPT at 0.625 mg/kg. Thus difluorinated hCPT 23g warrants further investigation as a novel Topo I inhibitor with high cytotoxicity toward tumor cells and promising in vivo efficacy.
• Synthesis and antimalarial activity of Baylis-Hillman adducts from substituted 2-chloroquinoline-3-carboxaldehydes
  作者：Ejjirothu Srihari、Gangala Siva Kumar、Chebolu Naga Sesha Sai Pavan Kumar、Ratnesh Kumar Seth、Sukla Biswas、Balasubramanian Sridhar、Vaidya Jayathirtha Rao

  DOI：10.1515/hc.2011.024

  日期：2011.1.1

  Various quinoline carboxaldehydes were prepared from corresponding anilides using classical Vilsmeier-Haack reaction conditions and transformed into their Baylis-Hillman adducts. The synthesized Baylis-Hillman adducts were screened for their in vitro antimalarial activity against Plasmodium falciparum. Most of the compounds out of 21 compounds synthesized and screened exhibited substantial antimalarial activity.