4-Chloro-2-pentafluoroethyl-quinazoline | 147972-28-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-Chloro-2-pentafluoroethyl-quinazoline
• 英文别名: 4-Chloro-2-(1,1,2,2,2-pentafluoroethyl)quinazoline
• CAS: 147972-28-9
• 化学式: C₁₀H₄ClF₅N₂
• mdl: MFCD11525047
• 分子量: 282.6
• InChiKey: VBTFYMSRHQHSFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 4-Chloro-2-pentafluoroethyl-quinazoline 以 四氢呋喃 为溶剂， 生成 tert-Butyl-(2-pentafluoroethyl-quinazolin-4-yl)-amine
  参考文献：
  名称：

  Quinazolines as cyclin dependent kinase inhibitors

  摘要：

  Quinazolines have been identified as inhibitors of CDK4/D1 and CDK2/E. Aspects of the SAR were investigated using solution-phase, parallel synthesis. An X-ray crystal structure was obtained of quinazoline 51 bound in CDK2 and key interactions within the ATP binding pocket are defined.

  DOI：

  10.1016/s0960-894x(01)00185-8
• 作为产物：
  描述：

  2-pentafluoroethyl-3H-quinazolin-4-one 在 N,N-二甲基苯胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 生成 4-Chloro-2-pentafluoroethyl-quinazoline
  参考文献：
  名称：

  Quinazolines as cyclin dependent kinase inhibitors

  摘要：

  Quinazolines have been identified as inhibitors of CDK4/D1 and CDK2/E. Aspects of the SAR were investigated using solution-phase, parallel synthesis. An X-ray crystal structure was obtained of quinazoline 51 bound in CDK2 and key interactions within the ATP binding pocket are defined.

  DOI：

  10.1016/s0960-894x(01)00185-8

文献信息

• SUBSTITUTED HETEROCYCLES AS ANGIOTENSIN II ANTAGONISTS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：EP0612317A1

  公开（公告）日：1994-08-31
• US5187168A
  申请人：——

  公开号：US5187168A

  公开（公告）日：1993-02-16
• US5236925A
  申请人：——

  公开号：US5236925A

  公开（公告）日：1993-08-17
• US5256781A
  申请人：——

  公开号：US5256781A

  公开（公告）日：1993-10-26
• [EN] SUBSTITUTED HETEROCYCLES AS ANGIOTENSIN II ANTAGONISTS
  申请人：AMERICAN HOME PRODUCTS CORPORATION

  公开号：WO1993008170A1

  公开（公告）日：1993-04-29

  (EN) There are disclosed compounds of general formula (I), wherein A is O, S, NR6, -CR7=CR8-; Z is O, S, NR6, -CR7=CR8-; X is H, NR9R10, OR11, CN, F, Cl, I, Br, perfluoroalkyl, alkyl, alkyl-OH, alkoxyalkyl, -(CH2)nCO2R11, -(CH2)nCONR9R10; with the proviso that when Z=-CR7=CR8- then Y is NR13, NR13CR12R14, CR12R14NR13; with the proviso that when Z=O, S, NR6 then Y is NR13CR12R14; R1 is 5-tetrazolyl, CO2R11, SO3H, NHSO2CH3, NHSO2CF3; R2,R3, R4, R7, R8 is H, alkyl, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10, OR11, F, Cl, Br, I, NR9R10; with the proviso that when A=-CR7=CR8- then R5 is alkyl, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, H, -CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10, -OH, OR11, F, Cl, Br, I, NR9R10; with the proviso that when A=O, S, NR6 then R5 is alkyl, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, H, -CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10; R6 is H, alkyl, aralkyl; R9, R10 is H, alkyl, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl; R11 is H, alkyl, aralkyl, alkoxyalkyl; R12, R14 is H, alkyl, alkoxy, alkoxyalkyl, alkyl-OH, perfluoroalkyl, aralkyl, CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10; R13 is H, OR11, alkyl, perfluoroalkyl, aralkyl, -(CH2)nCO2R11, -(CH2)nCONR9R10; n is 0, 1, 2 or 3; wherein alkyl is defined as 1-8 carbons, branched or straight chain; perfluoroalkyl is defined as 1-6 carbons; aralkyl is defined as 7-12 carbons or 7-12 carbons substituted with fluorine, bromine or chlorine and the pharmaceutically acceptable salts, solvates and hydrates thereof, which by virtue of their ability to antagonize angiotensin II are useful for the treatment of hypertension and congestive heart failure. The compounds are also useful for reducing lipid levels in the blood plasma and are thus useful for treating hyperlipidemia and hypercholesterolemia. Also disclosed are processes for the production of said compounds and pharmaceutical compositions containing said compounds.(FR) On décrit les composés de formule générale (I), où A représente O, S, NR6, -CR7=CR8-; Z représente O, S, NR6, -CR7=CR8-; X représente H, NR9R10, OR11, CN, F, Cl, I, Br, perfluoroalkyle, alkyle, alkyle-OH, alcoxyalkyl, -(CH2)nCO2R11, -(CH2)nCONR9R10; à condition que quand Z=-CR7=CR8-, Y représente NR13, NR13CR12R14, CR12R14NR13; à condition que quand Z=O, S, NR6, Y représente NR13CR12R14; R1 représente 5-tétrazolyle, CO2R11, SO3H, NHSO2CH3, NHSO2CF3; R2, R3, R4, R7, R8 représentent H, alkyle, alcoxyalkyle, alkyle-OH, perfluoroalkyle, aralkyle, CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10, OR11, F, Cl, Br, I, NR9R10; à condition que quand A=-CR7=CR8-, R5 représente alkyle, alcoxyalkyle, alkyle-OH, perfluoroalkyle, aralkyle, H, -CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10, -OH, OR11, F, Cl, Br, I, NR9R10; à condition que quand A=O, S, NR6, R5 représente alkyle, alcoxyalkyle, alkyle-OH, perfluoroalkyle, aralkyle, H, -CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10; R6 représente H, alkyle, aralkyle; R9, R10 représente H, alkyle, alcoxyalkyle, alkyle-OH, perfluoroalkyle, aralkyle; R11 représente H, alkyle, aralkyle, alcoxyalkyle; R12, R14 représentent H, alkyle, alcoxy, alcoxyalkyle, alkyle-OH, perfluoroalkyle, aralkyle, CN, NO2, SO2R13, -(CH2)nCO2R11, -(CH2)nCONR9R10; R13 représente H, OR11, alkyle, perfluoroalkyle, aralkyle, -(CH2)nCO2R11, -(CH2)nCONR9R10; n vaut 0, 1, 2 ou 3; où alkyle se définit par 1 à 8 atomes de carbone, en chaîne droite ou ramifiée; perfluoroalkyle se définit par 1 à 6 atomes de carbone; aralkyle se définit par 7 à 12 atomes de carbone éventuellement substitués par ceux de fluor, brome, ou chlore, et ses sels, solvats et hydrates pharmaceutiquement acceptables, qui en qualité d'antagonistes de l'angiotensine II, sont utiles pour le traitement de l'hypertension et des défaillances cardiaques congestives. Ces composés sont également utiles pour réduire les niveaux des lipides se trouvant dans le plasma sanguin et donc pour traiter l'hyperlipidémie et l'hypercholestérolémie. On décrit aussi des procédés de production concernant lesdits composés et les compositions pharmaceutiques les contenant.