(E)-3-(6-amino-5-methylpyridin-3-yl)acrylic acid | 335030-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (E)-3-(6-amino-5-methylpyridin-3-yl)acrylic acid
• 英文别名: 3-(6-Amino-5-methylpyridin-3-yl)prop-2-enoic acid；(E)-3-(6-amino-5-methylpyridin-3-yl)prop-2-enoic acid
• CAS: 335030-98-3
• 化学式: C₉H₁₀N₂O₂
• 分子量: 178.191
• InChiKey: SGSUUMYVPQMZMR-NSCUHMNNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  特比萘芬-int F 、 (E)-3-(6-amino-5-methylpyridin-3-yl)acrylic acid 以87%的产率得到(E)-3-(6-amino-5-methylpyridin-3-yl)-N-methyl-N-(naphthalen-2-ylmethyl)acrylamide
  参考文献：
  名称：

  FAB I INHIBITORS

  摘要：

  公开号：

  EP1226138B1
• 作为产物：
  描述：

  2-氨基-3-甲基-5-溴吡啶 在 palladium diacetate 、 P(tolyl)3 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.5h， 生成 (E)-3-(6-amino-5-methylpyridin-3-yl)acrylic acid
  参考文献：
  名称：

  Indole Naphthyridinones as Inhibitors of Bacterial Enoyl-ACP Reductases FabI and FabK

  摘要：

  Bacterial enoyl-ACP reductase (FabI) is responsible for catalyzing the final step of bacterial fatty acid biosynthesis and is an attractive target for the development of novel antibacterial agents. Previously we reported the development of FabI inhibitor 4 with narrow spectrum antimicrobial activity and in vivo efficacy against Staphylococcus aureus via intraperitoneal. (ip) administration. Through iterative medicinal chemistry aided by X-ray crystal structure analysis, a new series of inhibitors has been developed with greatly increased potency against FabI-containing organisms. Several of these new inhibitors have potent antibacterial activity against multidrug resistant strains of S. aureus, and compound 30 demonstrates exceptional oral (po) in vivo efficacy in a S. aureus infection model in rats. While optimizing FabI inhibitory activity, compounds 29 and 30 were identified as having low micromolar FabK inhibitory activity, thereby increasing the antimicrobial spectrum of these compounds to include the FabK-containing pathogens Streptococcus pneumoniae and Enterococcus faecalis. The results described herein support the hypothesis that bacterial enoyl-ACP reductases are valid targets for antibacterial agents.

  DOI：

  10.1021/jm0204035

文献信息

• [EN] FAB I INHIBITORS<br/>[FR] INHIBITEURS DE FAB I
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2001027103A1

  公开（公告）日：2001-04-19

  Compounds of formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections. In said formula, (A) is (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l), (m), (n), (o) or (p); (I) wherein R1 is H or C¿1-4?alkyl; R?2¿ is H, C¿1-4?alkyl or C3-6cycloalkyl; R?3¿ is (q), (r), (s), (t), (u), (v) or (w); R4 is H or C¿1-4?alkyl; (x) indicates that one of the two designated bonds is a double bond and the other is a single bond; R?5¿ is CH¿2? when the bond to which it is attached is a double bond; or R?5¿ is H or C¿1-4?alkyl when the bond to which it is attached is a single bond; R?6¿ is H or C¿1-4?alkyl; R?7¿ is H, C¿1-6?alkyl or -C0-6alkyl-Ar; Y is H, C1-4alkyl, N(R')2, NHC(O)R', NHCH2C(O)R' or NHC(O)CH=CHR'; each X independently is H, C1-4alkyl, CH2OH, OR', SR', CN, N(R')2, CH2N(R')2, NO2, CF3, CO2R', CON(R')2, COR', NR'C(O)R', F, Cl, Br, I or -S(O)rCF3; W is S or O, Q is H or C1-4alkyl; M is CH2 or O; L is CH2 or C(O); E is O or NR'; each R' independently is H, C1-6alkyl or -C0-6alkyl-Ar; and r is 0, 1 or 2; or a pharmaceutically acceptable salt thereof.

  公开了式（I）的化合物，它们是Fab I抑制剂，可用于治疗细菌感染。在所述式中，（A）是（a），（b），（c），（d），（e），（f），（g），（h），（i），（j），（k），（l），（m），（n），（o）或（p）;（I），其中R1为H或C1-4烷基; R?2¿为H，C1-4烷基或C3-6环烷基; R?3¿为（q），（r），（s），（t），（u），（v）或（w）; R4为H或C1-4烷基;（x）表示两个指定键中的一个是双键，另一个是单键;当其所连接的键是双键时，R?5¿为CH2;当其所连接的键是单键时，R?5¿为H或C1-4烷基; R?6¿为H或C1-4烷基; R?7¿为H，C1-6烷基或-C0-6烷基-Ar; Y为H，C1-4烷基，N（R'）2，NHC（O）R'，NHCH2C（O）R'或NHC（O）CH = CHR';每个X独立地为H，C1-4烷基，CH2OH，OR'，SR'，CN，N（R'）2，CH2N（R'）2，NO2，CF3，CO2R'，CON（R'）2，COR'，NR'C（O）R'，F，Cl，Br，I或-S（O）rCF3; W为S或O，Q为H或C1-4烷基; M为CH2或O; L为CH2或C（O）; E为O或NR';每个R'独立地为H，C1-6烷基或-C0-6烷基-Ar; r为0、1或2;或其药学上可接受的盐。
• FAB I inhibitors
  申请人：Miller H. William

  公开号：US20050250810A1

  公开（公告）日：2005-11-10

  Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

  公式（I）的化合物被揭示为Fab I抑制剂，可用于治疗细菌感染。
• Fab I Inhibitors
  申请人：Miller William H.

  公开号：US20080125423A1

  公开（公告）日：2008-05-29

  Compounds of the formula (I) are disclosed which are Fab I inhibitors and are useful in the treatment of bacterial infections.

  公式（I）的化合物被揭示为Fab I抑制剂，可用于治疗细菌感染。
• EP1226138A4
  申请人：——

  公开号：EP1226138A4

  公开（公告）日：2003-03-05
• US6846819B1
  申请人：——

  公开号：US6846819B1

  公开（公告）日：2005-01-25