6-ethyl-8-iodo-2,3-dihydro-1H-quinolin-4-one | 263896-28-2

• 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: 6-ethyl-8-iodo-2,3-dihydro-1H-quinolin-4-one
• CAS: 263896-28-2
• 化学式: C₁₁H₁₂INO
• 分子量: 301.127
• InChiKey: BWBFAUULYRQFQW-UHFFFAOYSA-N

物化性质

• 沸点：
  406.0±45.0 °C(Predicted)
• 密度：
  1.639±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-ethyl-8-iodo-2,3-dihydro-1H-quinolin-4-one 、 N1-(4-(4-methoxybenzyloxy)quinolin-2-yl)propane-1,3-diamine 在 resin-bound cyanoborohydride 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 2-[3-(6-Ethyl-8-iodo-1,2,3,4-tetrahydro-quinolin-4-ylamino)-propylamino]-1H-quinolin-4-one
  参考文献：
  名称：

  Optimisation of aryl substitution leading to potent methionyl tRNA synthetase inhibitors with excellent gram-Positive antibacterial activity

  摘要：

  Optimisation of the left-hand-side aryl moiety of a file compound screening hit against Staphylococcus aureus methionyl tRNA synthetase led to the identification of a series of potent nanomolar inhibitors. The best compounds showed excellent antibacterial activity against staphylococcal and enterococcal pathogens. including strains resistant to clinical antibiotics. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)01027-2
• 作为产物：
  描述：

  4-乙基苯胺 在 磷酸酐 、 PPA 、 一氯化碘 作用下， 以 盐酸 、 乙腈 为溶剂， 反应 6.17h， 生成 6-ethyl-8-iodo-2,3-dihydro-1H-quinolin-4-one
  参考文献：
  名称：

  Nanomolar Inhibitors of Staphylococcus aureus Methionyl tRNA Synthetase with Potent Antibacterial Activity against Gram-Positive Pathogens

  摘要：

  Potent nanomolar inhibitors of Staphylococcus aureus methionyl tRNA synthetase have been derived from a file compound high throughput screening hit. Optimized compounds show excellent antibacterial activity against staphylococcal and enterococcal pathogens, including strains resistant to clinical antibiotics. Compound II demonstrated in vivo efficacy in an S. aureus rat abscess infection model.

  DOI：

  10.1021/jm025502x

文献信息

• [EN] QUINOLONES AS T-RNA SYNTHETASE INHIBITORS AND ANTIBACTERIAL AGENTS<br/>[FR] QUINOLONES TENANT LIEU D'INHIBITEURS D'ARNT SYNTHETASE ET D'AGENTS ANTIBACTERIENS
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2000021949A1

  公开（公告）日：2000-04-20

  Compounds of formula (I), in which: R1 is aryl or heteroaryl; R2 is hydrogen, C¿(1-6)?alkyl, arylC(1-4)alkyl, arylC(2-4)alkenyl or C(1-6)alkylcarbonyl; R?3¿ is selected from halo, cyano, hydroxy, (C¿1-6)?alkyl (optionally substituted by halo, hydroxy, amino, carboxy or (C1-6)alkoxycarbonyl), (C3-7)cycloalkyl, C(1-6)alkoxy, amino, mono- or di-(C1-6)alkylamino, acylamino, carboxy, (C1-6)alkoxycarbonyl, carboxy(C1-6)alkyloxy, (C1-6)alkylthio, (C1-6)alkylsulphinyl, (C1-6)alkylsulphonyl, sulphamoyl, mono- and di-(C1-6)alkylsulphonyl, carbamoyl, mono- and di-(C1-6)alkylcarbamoyl, and heterocyclyl; m is 0 or an integer from 1 to 3; R?4¿ and a substituent on R1 are linked to form a saturated bridge comprising one or two carbon atoms and a heteroatom selected from O and NR5; R5 is hydrogen or C¿(1-6)?alkyl; Y is a linker group having from 2 to 6 methylene groups in a straight chain and in which one or more alkylene groups may have one or more C(1-6) alkyl substituents and which substituents may be linked to form a C2 or C3 alkylene bridge; Z is NH or O; and salts thereof, preferably pharmaceutically acceptable salts; are inhibitors of Saureus methionyl tRNA synthetase and thereof of use in therapy as antibacterial agents.

  化合物的公式（I），其中：R1是芳基或杂环芳基；R2是氢，C（1-6）烷基，芳基C（1-4）烷基，芳基C（2-4）烯基或C（1-6）烷基羰基；R3是选自卤素，氰基，羟基，（C1-6）烷基（可选地被卤素，羟基，氨基，羧基或（C1-6）烷氧羰基取代），（C3-7）环烷基，C（1-6）烷氧基，氨基，单或双（C1-6）烷基氨基，酰胺基，羧基，（C1-6）烷氧羰基，羧基（C1-6）烷氧基，（C1-6）烷基硫醇，（C1-6）烷基亚磺酰基，（C1-6）烷基磺酰基，磺酰胺基，单和双（C1-6）烷基磺酰基，氨基甲酰基，单和双（C1-6）烷基氨基甲酰基和杂环基；m为0或1至3的整数；R4和R1上的取代基连接形成饱和桥，包括一个或两个碳原子和一个选自O和NR5的杂原子；R5是氢或C（1-6）烷基；Y是具有2至6个亚甲基基团的连接基，在其中一个或多个亚甲基基团中可能有一个或多个C（1-6）烷基取代基，并且这些取代基可能连接形成C2或C3烷基桥；Z是NH或O；及其盐，优选为药物可接受盐；是Saureus甲硫氨酰-tRNA合成酶的抑制剂，因此在治疗中作为抗菌剂使用。
• 2-NH-heteroarylimidazoles with antibacterial activity
  申请人：Berge John

  公开号：US20060014748A1

  公开（公告）日：2006-01-19

  Compounds of formula (I): are inhibitors of bacterial methionyl tRNA synthetase and are of use in treating bacterial infections.

  公式（I）的化合物是细菌甲硫氨酸tRNA合成酶的抑制剂，可用于治疗细菌感染。
• 2-NH-HETEROARYLIMIDAZOLES WITH ANTIBACTERIAL ACTIVITY
  申请人：Berge John

  公开号：US20070213362A1

  公开（公告）日：2007-09-13

  A method of inhibiting MetRS activity comprises administering to a patient in need thereof a MetRS inhibiting effective amount of a compound of the formula (I). A method of treating a resistant or multiply-resistant E. faecalis infection, a resistant or multiply-resistant S. aureus infection, and/or a resistant or multiply-resistant S. epidermidis infection comprises administering to a patient in need thereof an antibacterially effective amount of a compound of the formula (I).

  一种抑制MetRS活性的方法包括向需要治疗的患者投予化合物(I)的抑制剂有效量。一种治疗耐药或多重耐药E. faecalis感染，耐药或多重耐药S. aureus感染和/或耐药或多重耐药S. epidermidisinfection的方法包括向需要治疗的患者投予化合物(I)的抗菌有效量。
• US6943175B2
  申请人：——

  公开号：US6943175B2

  公开（公告）日：2005-09-13
• US7220757B2
  申请人：——

  公开号：US7220757B2

  公开（公告）日：2007-05-22