7-chloroquinoline-3,4-diamine | 110643-79-3

• 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
• 英文名称: 7-chloroquinoline-3,4-diamine
• 英文别名: 7-chloro-quinoline-3,4-diyldiamine；7-Chlor-chinolin-3,4-diyldiamin
• CAS: 110643-79-3
• 化学式: C₉H₈ClN₃
• 分子量: 193.636
• InChiKey: LFFPXWYOCOMCOO-UHFFFAOYSA-N

物化性质

• 沸点：
  416.2±40.0 °C(Predicted)
• 密度：
  1.452±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 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：
  64.9
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7-chloroquinoline-3,4-diamine 在 sodium pyrosulfate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成
  参考文献：
  名称：

  7-Phenyl-imidazoquinolin-4(5H)-one derivatives as selective and orally available mPGES-1 inhibitors

  摘要：

  To identify compounds with strong mPGES-1 inhibitory activity and clear in vitro ADME profile, we optimized the lead compound 1 by carrying our substitutions at the C(7)-and C(8)-positions. Replacement of the bromine atom of 1 with various substituents led to identification of the phenyl group as the best C(7)-substituent giving strong inhibitory activity with good in vitro ADME profile. Further SAR examination on both the C(2)-and the C(7)-phenyl groups provided compound 39 as the best candidate for further development. Compound 39 exhibited strong mPGES-1 inhibitory activity (IC50 = 4.1 nM), potent cell-based functional activity (IC50 = 33 nM) with good mPGES-1 selectivity (over 700-fold), excellent in vitro ADME profile, and good oral absorption in rat PK study. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.069
• 作为产物：
  描述：

  7-氯-4-羟基喹啉 在 乙醇 、 氨 、 水 、 硝酸 、 铁粉 、 溶剂黄146 、 三氯氧磷 、 正丁醇 作用下， 生成 7-chloroquinoline-3,4-diamine
  参考文献：
  名称：

  The Synthesis of Some 3-Nitro- and 3-Amino-4-dialkylaminoalkylaminoquinoline Derivatives

  摘要：

  DOI：

  10.1021/ja01150a002

文献信息

• Synthesis and Structure−Activity Relationships of Fused Imidazopyridines:  A New Series of Benzodiazepine Receptor Ligands
  作者：Susumu Takada、Takashi Sasatani、Nobuo Chomei、Makoto Adachi、Toshio Fujishita、Masami Eigyo、Shunji Murata、Kazuo Kawasaki、Akira Matsushita

  DOI：10.1021/jm9600609

  日期：1996.1.1

  synthesized and evaluated as benzodiazepine receptor ligands. Affinity to the receptors was greatly affected by the bulkiness of the aryl group at the 2-position, compared to the pyrazoloquinolines such as CGS-9896. Derivatives with an isoxazole moiety at the 2-position showed high binding affinity and in vivo activity. In the imidazo[4,5-c]quinoline series, substitution at the 6-position decreased or abolished

  合成了2-Arylimidazo [4,5-c]喹啉和类似的稠合咪唑并吡啶，并评价为苯并二氮杂receptor受体配体。与吡唑并喹啉如CGS-9896相比，与受体的亲和力受2-位芳基庞大性的影响。在2-位具有异恶唑部分的衍生物显示出高结合亲和力和体内活性。在咪唑并[4,5-c]喹啉系列中，在6-位的取代降低或消除了活性。除7-卤代类似物外，大多数具有未取代异恶唑基的衍生物均表现出拮抗或反向激动剂活性。另一方面，5-甲基异恶唑-3-基或3-甲基异恶唑-5-基衍生物通常表现出激动剂活性。在与非芳族环稠合的咪唑并吡啶中观察到对异恶唑部分的类似取代作用。根据详细的药理评估，S-8510，2-（3-异恶唑基）-3,6,7,9-四氢咪唑并[4,5-d]吡喃++ + [4,3-b]吡啶一磷酸具有弱的反向激动剂选择活性作为治疗老年性痴呆某些症状的治疗候选药物。
• 7-Phenyl-imidazoquinolin-4(5H)-one derivatives as selective and orally available mPGES-1 inhibitors
  作者：Tomoya Shiro、Keisuke Kakiguchi、Hirotada Takahashi、Hidetaka Nagata、Masanori Tobe

  DOI：10.1016/j.bmc.2013.03.069

  日期：2013.6

  To identify compounds with strong mPGES-1 inhibitory activity and clear in vitro ADME profile, we optimized the lead compound 1 by carrying our substitutions at the C(7)-and C(8)-positions. Replacement of the bromine atom of 1 with various substituents led to identification of the phenyl group as the best C(7)-substituent giving strong inhibitory activity with good in vitro ADME profile. Further SAR examination on both the C(2)-and the C(7)-phenyl groups provided compound 39 as the best candidate for further development. Compound 39 exhibited strong mPGES-1 inhibitory activity (IC50 = 4.1 nM), potent cell-based functional activity (IC50 = 33 nM) with good mPGES-1 selectivity (over 700-fold), excellent in vitro ADME profile, and good oral absorption in rat PK study. (C) 2013 Elsevier Ltd. All rights reserved.
• The Synthesis of Some 3-Nitro- and 3-Amino-4-dialkylaminoalkylaminoquinoline Derivatives
  作者：Alexander R. Surrey、Royal A. Cutler

  DOI：10.1021/ja01150a002

  日期：1951.6