8-氟-4-氧代-1,4-二氢-3-喹啉腈 | 71083-65-3

• 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: 8-氟-4-氧代-1,4-二氢-3-喹啉腈
• 英文名称: 8-Fluoro-4-oxo-1,4-dihydro-quinoline-3-carbonitrile
• 英文别名: 8-Fluoro-4-hydroxyquinoline-3-carbonitrile；8-fluoro-4-oxo-1H-quinoline-3-carbonitrile
• CAS: 71083-65-3
• 化学式: C₁₀H₅FN₂O
• 分子量: 188.161
• InChiKey: PENXESCTQQXUMH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-氟-4-氧代-1,4-二氢-3-喹啉腈 在 三氯氧磷 作用下， 以 二乙二醇 为溶剂， 反应 1.0h， 生成 8-fluoro-4-(4'-fluorophenylamino)quinoline-3-carbonitrile
  参考文献：
  名称：

  Novel 4-arylaminoquinoline-3-carbonitriles as Inhibitors of HIV-1 Reverse Transcriptase

  摘要：

  This paper describes the synthesis of several new 4‐arylaminoquinoline‐3‐carbonitriles derivatives. These were evaluated on the activity reverse transcriptase (RT) of HIV‐1. Most of the synthesized compounds showed significant in vitro inhibition of RT enzyme, especially derivative 3h (IC50 = <8 μM). The derivatives showed low‐level cytotoxicity.

  DOI：

  10.1002/jhet.2914
• 作为产物：
  描述：

  2-氨基-3-氟苯甲酸甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 2.5h， 生成 8-氟-4-氧代-1,4-二氢-3-喹啉腈
  参考文献：
  名称：

  Discovery of VU6027459: A First-in-Class Selective and CNS Penetrant mGlu₇ Positive Allosteric Modulator Tool Compound

  摘要：

  Herein, we report the discovery of the first selective and CNS penetrant mGlu(7) PAM (VU6027459) derived from a "molecular switch" within a selective mGlu(7) NAM chemotype. VU6027459 displayed CNS penetration in both mice (K-p = 2.74) and rats (K-p = 4.78), it was orally bioavailable in rats (%F = 69.5), and undesired activity at DAT was ablated.

  DOI：

  10.1021/acsmedchemlett.0c00432

文献信息

• Discovery of VU6027459: A First-in-Class Selective and CNS Penetrant mGlu₇ Positive Allosteric Modulator Tool Compound
  作者：Carson W. Reed、Jacob J. Kalbfleisch、Madison J. Wong、Jordan P. Washecheck、Ashton Hunter、Alice L. Rodriguez、Anna L. Blobaum、P. Jeffrey Conn、Colleen M. Niswender、Craig W. Lindsley

  DOI：10.1021/acsmedchemlett.0c00432

  日期：2020.9.10

  Herein, we report the discovery of the first selective and CNS penetrant mGlu(7) PAM (VU6027459) derived from a "molecular switch" within a selective mGlu(7) NAM chemotype. VU6027459 displayed CNS penetration in both mice (K-p = 2.74) and rats (K-p = 4.78), it was orally bioavailable in rats (%F = 69.5), and undesired activity at DAT was ablated.
• Novel 4-arylaminoquinoline-3-carbonitriles as Inhibitors of HIV-1 Reverse Transcriptase
  作者：Beatriz C. L. Melo、Alice M. R. Bernardino、Gustavo Polillo、Helena S. Pereira、Izabel C. P. Paixão、Michele S. Ribeiro、Julio C. Borges

  DOI：10.1002/jhet.2914

  日期：2017.11

  This paper describes the synthesis of several new 4‐arylaminoquinoline‐3‐carbonitriles derivatives. These were evaluated on the activity reverse transcriptase (RT) of HIV‐1. Most of the synthesized compounds showed significant in vitro inhibition of RT enzyme, especially derivative 3h (IC50 = <8 μM). The derivatives showed low‐level cytotoxicity.