(3-amino-4-(2-iodophenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-yl)(phenyl)methanone | 1286771-54-7

• 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: (3-amino-4-(2-iodophenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-yl)(phenyl)methanone
• 英文别名: [3-Amino-4-(2-iodophenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-2-yl]-phenyl-methanone；[3-amino-4-(2-iodophenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinolin-2-yl]-phenylmethanone
• CAS: 1286771-54-7
• 化学式: C₂₄H₁₉IN₂OS
• 分子量: 510.398
• InChiKey: ULEBNSVDSRATPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-cyano-3-(2-iodophenyl)-2-propenethioamide 在 哌啶 、 potassium hydroxide 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.83h， 生成 (3-amino-4-(2-iodophenyl)-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-yl)(phenyl)methanone
  参考文献：
  名称：

  3,6-Diamino-4-(2-halophenyl)-2-benzoylthieno[2,3-b]pyridine-5-carbonitriles Are Selective Inhibitors of Plasmodium falciparum Glycogen Synthase Kinase-3

  摘要：

  Plasmodium falciparum is the infective agent responsible for malaria tropica. The glycogen synthase kinase-3 of the parasite (PfGSK-3) was suggested as a potential biological target for novel antimalarial drugs. Starting from hit structures identified in a high-throughput screening campaign, 3,6-diamino-4-(2-halophenyl)-2-benzoylthieno[2,3-b]pyridine-5-carbonitriles were discovered as a new class of PfGSK-3 inhibitors. Being less active on GSK-3 homologues of other species, the title compounds showed selectivity in favor of PfGSK-3. Taking into account the X-ray structure of a related molecule in complex with human GSK-3 (HsGSK-3), a model was computed for the comparison of inhibitor complexes with the plasmodial and human enzymes. It was found that subtle differences in the ATP-binding pockets are responsible for the observed PfGSK-3 vs HsGSK-3 selectivity. Representatives of the title compound class exhibited micromolar IC₅₀ values against P. falciparum erythrocyte stage parasites. These results suggest that inhibitors of PfGSK-3 could be developed as potential antimalarial drugs.

  DOI：

  10.1021/jm301575n