6-(2,6-dibromophenyl)-2-N-[3-(diethylamino)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine | 179343-24-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(2,6-dibromophenyl)-2-N-[3-(diethylamino)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine
• CAS: 179343-24-9
• 化学式: C₂₀H₂₄Br₂N₆
• 分子量: 508.259
• InChiKey: KICNNRAJZZOWST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(2,6-dibromophenyl)-2-N-[3-(diethylamino)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine 、 叔丁基异氰酸酯 在 crude residue 、 EtOH ethyl acetate triethylamine 、 Trifluoroacetic acid monohydrate 、 trifluoroacetic acid-acetonitrile 、 乙腈 作用下， 以to give 0.214 g of the title compound, ESMS (20/80 MEOH/CH3CN+0.1% AcOH)的产率得到1-tert-Butyl-3-[6-(2,6-dibromo-phenyl)-2-(3-diethylamino-propylamino)-pyrido[2,3-d]pyrimidin-7-yl]-urea
  参考文献：
  名称：

  6-aryl naphthyridines for inhibiting protein tyrosine kinase mediated

  摘要：

  6-芳基萘啶是蛋白酪氨酸激酶的抑制剂，因此在治疗细胞增殖介导的疾病方面非常有用。这些化合物在治疗动脉粥样硬化、再狭窄、牛皮癣以及细菌感染方面尤其有用。

  公开号：

  US05952342A1
• 作为产物：
  描述：

  2,4-二氨基嘧啶-5-甲醛 在 氨基磺酸 、 sodium 2-ethoxyethoxide 作用下， 反应 9.0h， 生成 6-(2,6-dibromophenyl)-2-N-[3-(diethylamino)propyl]pyrido[2,3-d]pyrimidine-2,7-diamine
  参考文献：
  名称：

  Soluble 2-Substituted Aminopyrido[2,3-d]pyrimidin-7-yl Ureas. Structure−Activity Relationships against Selected Tyrosine Kinases and Exploration of in Vitro and in Vivo Anticancer Activity

  摘要：

  continuing our search for medicinal agents to treat proliferative diseases, we have discovered 2-substituted aminopyrido[2,3-d]pyrimidin-7-yl ureas as a novel class of soluble, potent, broadly active tyrosine kinase (TK) inhibitors. An efficient route was developed that enabled the synthesis of a wide variety of analogues with substitution on several positions of the template. From the lead structure 1, several series of analogues were made that examined the C-6 aryl substituent, a variety of water solublizing substitutents at the C-2 position, and urea or other acyl functionality at the N-7 position. Compounds of this series were competitive with ATP and displayed submicromolar to low nanomolar potency against a panel of TKs, including receptor (platelet-derived growth factor, PDGFr; fibroblast growth factor, FGFr;) and nonreceptor (c-Src) classes. Several of the most potent compounds displayed submicromolar inhibition of PDGF-mediated receptor autophosphorylation in rat aortic vascular smooth muscle cells and low micromolar inhibition of cellular growth in five human tumor cell lines. One of the more thoroughly evaluated members, 32, with IC50 values of 0.21 muM (PDGFr), 0.049 muM (bFGFr), and 0.018 muM (c-Src), was evaluated in in vivo studies against a panel of five human tumor xenografts, with known and/or inferred dependence on the EGFr, PDGFr, and c-Src TKs. Compound 32 produced a tumor growth delay of 14 days against the Cole-205 colon xenograft model.

  DOI：

  10.1021/jm0004291

文献信息

• 6-ARYL PYRIDO( 2,3-d]PYRIMIDINES AND NAPHTHYRIDINES FOR INHIBITING PROTEIN TYROSINE KINASE MEDIATED CELLULAR PROLIFERATION
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0790997A2

  公开（公告）日：1997-08-27
• 6-ARYL PYRIDO[2,3-d]PYRIMIDINES AND NAPHTHYRIDINES FOR INHIBITING PROTEIN TYROSINE KINASE MEDIATED CELLULAR PROLIFERATION
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0790997B1

  公开（公告）日：2000-03-22
• [EN] 6-ARYL PYRIDO[2,3-d]PYRIMIDINES AND NAPHTHYRIDINES FOR INHIBITING PROTEIN TYROSINE KINASE MEDIATED CELLULAR PROLIFERATION<br/>[FR] 6-ARYLE PYRIDO[2,3-d]PYRIMIDINES ET NAPHTYRIDINES DESTINEES A L'INHIBITION DE LA PROLIFERATION CELLULAIRE INDUITE PAR PROTEINE TYROSINE KINASE
  申请人：——

  公开号：WO1996015128A2

  公开（公告）日：1996-05-23

  [EN] 6-Aryl pyrido[2,3-d]pyrimidines and naphthyridines are inhibitors of protein tyrosine kinase, and are thus useful in treating cellular proliferation mediated thereby. The compounds are especially useful in treating atherosclerosis, restenosis, psoriasis, as well as bacterial infections.
  [FR] Les 6-aryle pyrido[2,3-d]pyrimidines et les naphtyridines sont des inhibiteurs de la protéine tyrosine kinase, et conviennent ainsi au traitement de la prolifération cellulaire induite par cette dernière. Ces composés conviennent particulièrement au traitement de l'athérosclérose, de la resténose, du psoriasis, ainsi que des infections bactériennes.