2-(5-fluoro-2-nitrophenylamino)propanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-(5-fluoro-2-nitrophenylamino)propanoic acid
• 英文别名: 2-(5-Fluoro-2-nitroanilino)propanoic acid
• 化学式: C₉H₉FN₂O₄
• 分子量: 228.18
• InChiKey: IUTUZGJZYOAMJD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(5-fluoro-2-nitrophenylamino)propanoic acid 在 sodium dithionite 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 以74%的产率得到6-氟-3-甲基-3,4-二氢-2(1H)-喹喔啉酮
  参考文献：
  名称：

  Synthesis and biological evaluation of N4-(hetero)arylsulfonylquinoxalinones as HIV-1 reverse transcriptase inhibitors

  摘要：

  A series of novel N-4-(hetero) arylsulfonylquinoxalinone derivatives were prepared in a straight and efficient way. Of all the synthesized compounds, five compounds exhibited potent anti-HIV-1 replication activities with IC50 value at the level of 10(-7) mol/L. Preliminary structure-activity relationships were studied in details and that will shed light on the discovery of more potent non-nucleoside reverse-transcriptase inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.039
• 作为产物：
  描述：

  2,4-二氟硝基苯 、 DL-丙氨酸 在 potassium carbonate 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 12.0h， 以66%的产率得到2-(5-fluoro-2-nitrophenylamino)propanoic acid
  参考文献：
  名称：

  Synthesis and biological evaluation of N4-(hetero)arylsulfonylquinoxalinones as HIV-1 reverse transcriptase inhibitors

  摘要：

  A series of novel N-4-(hetero) arylsulfonylquinoxalinone derivatives were prepared in a straight and efficient way. Of all the synthesized compounds, five compounds exhibited potent anti-HIV-1 replication activities with IC50 value at the level of 10(-7) mol/L. Preliminary structure-activity relationships were studied in details and that will shed light on the discovery of more potent non-nucleoside reverse-transcriptase inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.039

文献信息

• Heterocyclic compounds
  申请人：ZENECA LIMITED

  公开号：EP0442654A2

  公开（公告）日：1991-08-21

  A herbicidal compound of formula (I): in which the dotted line indicates the presence of two double bonds arranged so as to form a fused hetro-aromatic ring system; Py is an optionally substituted pyrazole ring; W is O or NR¹; where R¹ is hydrogen or lower alkyl; X is (CH₂)n, CH=CH, CH(OR⁵)CH₂, COCH₂; where n is O, 1 or 2; R² and R³ are independently selected from H, optionally substituted alkyl, alkenyl or alkynyl, halogen, NR⁶R⁷, or R² and R³ together with the carbon to which they are attached form an optionally substituted alkenyl or cycloalkyl group; R⁴ is CO₂R⁸, CN, COR⁸, CH₂OR⁸, CH(OH)R⁸, CH(OR⁸)R⁹, CSNH₂, COSR⁸, CSOR⁸, CONHSO₂R⁸, CONR¹⁰R¹¹, CONHNR¹⁰R¹¹, CONHN⁺R¹⁰R¹¹R¹²R¹⁴⁻, CO₂⁻R¹⁵⁺ or COON=CR¹⁰R¹¹; R¹⁵⁺ is an agriculturally acceptable cation and R¹⁴⁻ is an agriculturally acceptable anion. R⁵, R⁸ and R⁹ are independently selected from H or an optionally substituted alkyl, aryl, alkenyl or alkynyl group; R⁶, R⁷, R¹⁰, R¹¹ and R¹² are independently selected from H or an optionally substituted alkyl, alkenyl, aryl or alkynyl group; or any two of R⁶, R⁷, R¹⁰, R¹¹ and R¹² together with the atom to which they are attached form a cycloalkyl or heterocyclic ring. Processes for the preparation of these compounds and compositions containing them are also described.

  式(I)的除草化合物： 其中 虚线表示存在两个双键，其排列方式形成一个融合的 hetro-aromatic 环系统； Py 是任选取代的吡唑环； W 是 O 或 NR¹；其中 R¹ 是氢或低级烷基； X 是 (CH₂)n、CH=CH、CH(OR⁵)CH₂、COCH₂； 其中 n 为 O、1 或 2； R² 和 R³ 独立选自 H、任选取代的烷基、烯基或炔基、卤素、NR⁶R⁷，或 R² 和 R³ 与它们所连接的碳一起形成任选取代的烯基或环烷基； R⁴是CO₂R⁸、CN、COR⁸、CH₂OR⁸、CH(OH)R⁸、CH(OR⁸)R⁹、CSNH₂、COSR⁸、CSOR⁸、CONHSO₂R⁸、CONR¹⁰R¹¹、CONHNR¹⁰R¹¹、CONHNSm_207A↩R¹⁰R¹¹⁴-、CO₂-R¹⁵⁺或COON=CR¹⁰R¹¹； R¹⁵⁺ 是农业上可接受的阳离子，R¹⁴- 是农业上可接受的阴离子。 R⁵、R⁸ 和 R𠞙 独立选自 H 或任选取代的烷基、芳基、烯基或炔基； R⁶、R⁷、R¹⁰、R¹¹和R¹²独立选自H或任选取代的烷基、烯基、芳基或炔基；或R⁶、R⁷、R¹⁰、R¹¹和R¹²中的任意两个与所连接的原子一起形成环烷基或杂环。 此外，还描述了这些化合物的制备过程以及含有这些化合物的组合物。
• US5190574A
  申请人：——

  公开号：US5190574A

  公开（公告）日：1993-03-02
• Synthesis and biological evaluation of N4-(hetero)arylsulfonylquinoxalinones as HIV-1 reverse transcriptase inhibitors
  作者：Bailing Xu、Yan Sun、Ying Guo、Yingli Cao、Tao Yu

  DOI：10.1016/j.bmc.2009.02.039

  日期：2009.4

  A series of novel N-4-(hetero) arylsulfonylquinoxalinone derivatives were prepared in a straight and efficient way. Of all the synthesized compounds, five compounds exhibited potent anti-HIV-1 replication activities with IC50 value at the level of 10(-7) mol/L. Preliminary structure-activity relationships were studied in details and that will shed light on the discovery of more potent non-nucleoside reverse-transcriptase inhibitors. (c) 2009 Elsevier Ltd. All rights reserved.