6-bromoquinoline-3,4-diamine | 1153095-14-7

• 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: 6-bromoquinoline-3,4-diamine
• CAS: 1153095-14-7
• 化学式: C₉H₈BrN₃
• 分子量: 238.087
• InChiKey: VSUQNFQMMYNTSK-UHFFFAOYSA-N

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：

  6-bromoquinoline-3,4-diamine 在 盐酸 、 sodium pyrosulfate 、 水 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 8-bromo-2-(2-chlorophenyl)imidazo[4,5-c]quinolin-4(5H)-one
  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：

  6-溴-4-氯-3-硝基喹啉 在 氨 、 铁粉 、 氯化铵 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 3.0h， 生成 6-bromoquinoline-3,4-diamine
  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

文献信息

• [EN] KETONE DERIVATIVES OF IMIDAZOLES, PHARMACEUTICAL COMBINATIONS AND USES THEREOF<br/>[FR] DÉRIVÉS CÉTONE D'IMIDAZOLES, COMBINAISONS PHARMACEUTIQUES DESDITS DÉRIVÉS ET LEUR UTILISATION<br/>[ZH] 咪唑酮类衍生物、其药物组合物和用途
  申请人：BEIJING FORELANDPHARMA CO LTD

  公开号：WO2015074516A1

  公开（公告）日：2015-05-28

  本申请涉及咪唑酮类化合物、其药学可接受的盐、溶剂化物、多晶形物或前药，还涉及包含上述物质的药物组合物和用于预防和治疗蛋白激酶相关性疾病如癌症、代谢疾病、心血管疾病等的用途。
• NOVEL IMIDAZO [4,5-C]QUINOLINE AND IMIDAZO [4,5-C][1,5]NAPHTHYRIDINE DERIVATIVES AS LRRK2 INHIBITORS
  申请人：Pfizer Inc.

  公开号：EP3350178B1

  公开（公告）日：2021-10-20
• [EN] CANCER COMBINATION THERAPY USING IMIDAZO[4,5-C]QUINOLINE DERIVATIVES<br/>[FR] MULTI-THÉRAPIE ANTI-CANCÉREUSE UTILISANT DES DÉRIVÉS DE IMIDAZO[4,5-C]QUINOLINE
  申请人：PIRAMAL ENTPR LTD

  公开号：WO2014177915A1

  公开（公告）日：2014-11-06

  The present invention relates to a pharmaceutical combination comprising a PI3K/m TOR inhibitor selected from the compounds of Formula (I) (as described herein) or pharmaceutically acceptable salts or solvates thereof; and one or more anti-proliferative agents; pharmaceutical compositions containing said the compounds of Formula (I) and one or more anti-proliferative agents; and use of the said combination in the treatment of proliferative diseases or disorders.
• [EN] NOVEL IMIDAZO [4,5-C] QUINOLINE AND IMIDAZO [4,5-C][1,5] NAPHTHYRIDINE DERIVATIVES AS LRRK2 INHIBITORS<br/>[FR] NOUVEAUX DÉRIVÉS IMIDAZO [4,5-C] QUINOLINE ET IMIDAZO [4,5-C] [1,5] NAPHTHYRIDINE UTILISÉS COMME INHIBITEURS DE LRRK2
  申请人：PFIZER

  公开号：WO2017046675A1

  公开（公告）日：2017-03-23

  The present invention provides novel imidazo[4,5-c]quinoline and imidazo[4,5-c][1,5]naphthyridine derivatives of Formula (I), and the pharmaceutically acceptable salts thereof wherein R1, R1a, R1b, R2, R4, R5, R6, X and Z are as defined in the specification. The invention is also directed to pharmaceutical compositions comprising the compounds of Formula (I) and to use of the compounds in the treatment of diseases associated with LRRK2, such as neurodegenerative diseases including Parkinson's disease or Alzheimer's disease, cancer, Crohn's disease or leprosy.
• 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.