4-(4-acetamidophenyl)-4-amino-furo[2,3-d]pyrimidine | 501693-44-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(4-acetamidophenyl)-4-amino-furo[2,3-d]pyrimidine
• 英文别名: 4-amino-5-(4-acetamidophenyl)-furo[2,3-d]pyrimidine；N-[4-(4-aminofuro[2,3-d]pyrimidin-5-yl)phenyl]acetamide
• CAS: 501693-44-3
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: PYEOIFUSFNECHQ-UHFFFAOYSA-N

物化性质

• 沸点：
  573.2±50.0 °C(Predicted)
• 密度：
  1.386±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  94
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-acetamidophenyl)-4-amino-furo[2,3-d]pyrimidine 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 以75%的产率得到5-(4-aminophenyl)furo[2,3-d]pyrimidin-4-amine
  参考文献：
  名称：

  Orally active 4-amino-5-diarylurea-furo[2,3-d]pyrimidine derivatives as anti-angiogenic agent inhibiting VEGFR2 and Tie-2

  摘要：

  During our effort to develop dual VEGFR2 and Tie-2 inhibitors as anti-angiogenic agents for cancer therapy, we discovered 4-amino-5-(4-((2-fluoro-5-(trifluoromethyl)phenyl)-aminocarbonylamino)phenyl)furo[2,3-d]pyrimidine (8a) possessing strong inhibitory activity at both the enzyme and cellular level against VEGFR2 and Tie-2. Compound 8a demonstrated high pharmaco-kinetic exposure through oral administration, and showed marked tumor growth inhibition and anti-angiogenic activity in mouse HT-29 xenograft model via once-daily oral administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.077
• 作为产物：
  描述：

  4'-acetamido-2-hydroxyacetophenone 在 氨 、 sodium ethanolate 、 乙酸酐 、 二乙胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 4-(4-acetamidophenyl)-4-amino-furo[2,3-d]pyrimidine
  参考文献：
  名称：

  Orally active 4-amino-5-diarylurea-furo[2,3-d]pyrimidine derivatives as anti-angiogenic agent inhibiting VEGFR2 and Tie-2

  摘要：

  During our effort to develop dual VEGFR2 and Tie-2 inhibitors as anti-angiogenic agents for cancer therapy, we discovered 4-amino-5-(4-((2-fluoro-5-(trifluoromethyl)phenyl)-aminocarbonylamino)phenyl)furo[2,3-d]pyrimidine (8a) possessing strong inhibitory activity at both the enzyme and cellular level against VEGFR2 and Tie-2. Compound 8a demonstrated high pharmaco-kinetic exposure through oral administration, and showed marked tumor growth inhibition and anti-angiogenic activity in mouse HT-29 xenograft model via once-daily oral administration. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.077

文献信息

• 4-AMINO-2,3-DISUBSTITUTED THIENO [2,3,D]PYRIMIDINES AND PHARMACEUTICAL COMPOSITIONS THEREOF
  申请人：Adams Jerry Leroy

  公开号：US20080287466A1

  公开（公告）日：2008-11-20

  Furo- and thienopyrimidine derivatives, which are useful as TIE-2 and/or VEGFR-2 inhibitors are described herein. The described invention also includes methods of making such furo- and thienopyrimidine derivatives as well as methods of using the same in the treatment of hyperproliferative diseases.

  本文描述了作为TIE-2和/或VEGFR-2抑制剂有用的呋喃和噻唑嘧啶衍生物。所述发明还包括制备这种呋喃和噻唑嘧啶衍生物的方法以及使用它们治疗增生性疾病的方法。
• Rational design of 4-amino-5,6-diaryl-furo[2,3-d]pyrimidines as potent glycogen synthase kinase-3 inhibitors
  作者：Yasushi Miyazaki、Yutaka Maeda、Hideyuki Sato、Masato Nakano、Geoffrey W. Mellor

  DOI：10.1016/j.bmcl.2008.01.113

  日期：2008.3

  4-Amino-5,6-diaryl-furo[2,3-d] pyrimidines have been identified as inhibitors of glycogen synthase kinase-3b (GSK-3 beta). One representative derivative, 4-amino-5-(4-(benzenesulfonylamino)-phenyl)-6-(3-pyridyl)-furo[2,3-d] pyrimidine (12) exhibited potent GSK-3b inhibitory activity in low nanomolar level of IC50. The binding mode was proposed from a docking study. (C) 2008 Elsevier Ltd. All rights reserved.
• US7427623B2
  申请人：——

  公开号：US7427623B2

  公开（公告）日：2008-09-23
• Orally active 4-amino-5-diarylurea-furo[2,3-d]pyrimidine derivatives as anti-angiogenic agent inhibiting VEGFR2 and Tie-2
  作者：Yasushi Miyazaki、Jun Tang、Yutaka Maeda、Masato Nakano、Liping Wang、Robert T. Nolte、Hideyuki Sato、Masaki Sugai、Yuji Okamoto、Anne T. Truesdale、Daniel F. Hassler、Eldridge N. Nartey、Denis R. Patrick、Maureen L. Ho、Kazunori Ozawa

  DOI：10.1016/j.bmcl.2006.12.077

  日期：2007.3

  During our effort to develop dual VEGFR2 and Tie-2 inhibitors as anti-angiogenic agents for cancer therapy, we discovered 4-amino-5-(4-((2-fluoro-5-(trifluoromethyl)phenyl)-aminocarbonylamino)phenyl)furo[2,3-d]pyrimidine (8a) possessing strong inhibitory activity at both the enzyme and cellular level against VEGFR2 and Tie-2. Compound 8a demonstrated high pharmaco-kinetic exposure through oral administration, and showed marked tumor growth inhibition and anti-angiogenic activity in mouse HT-29 xenograft model via once-daily oral administration. (c) 2006 Elsevier Ltd. All rights reserved.