6,7-dimethoxy-N-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-3-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 6,7-dimethoxy-N-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-3-amine
• 英文别名: (6,7-Dimethoxy-2,4-dihydroindeno[1,2-c]pyrazol-3-yl)-phenyl amine
• 化学式: C₁₈H₁₇N₃O₂
• 分子量: 307.352
• InChiKey: RWKBPANRHRUTJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  59.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5,6-二甲氧基茚酮 、 硫代异氰酸苯酯 在 lithium hexamethyldisilazane 、 一水合肼 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 36.0h， 以69%的产率得到6,7-dimethoxy-N-phenyl-1,4-dihydroindeno[1,2-c]pyrazol-3-amine
  参考文献：
  名称：

  Discovery of Indenopyrazoles as a New Class of Hypoxia Inducible Factor (HIF)-1 Inhibitors

  摘要：

  The indenopyrazole framework was investigated as a new class of HIP-la inhibitors. Indenopyrazole 21 was found to most strongly inhibit the hypoxia-induced HIF-1 alpha transcriptional activity (IC50 = 0.014 mu M) among all of the known compounds having relatively simple structures, unlike manassantins. Indenopyrazole 21 suppressed HIP-la transcriptional activity without affecting both HIF-1 alpha protein accumulation and HIF-1 alpha HIF-1 beta heterodimerization in nuclei under the hypoxic conditions, suggesting that 21 probably affected the transcriptional pathway induced by the HIF-1 alpha/HIF-1 beta heterodimer.

  DOI：

  10.1021/ml3004632

文献信息

• [EN] N-SUBSTITUTED TRICYCLIC 3-AMINOPYRAZOLES AS PDFG RECEPTOR INHIBITORS<br/>[FR] 3-AMINOPYRAZOLES TRICYCLIQUES N-SUBSTITUES COMME INHIBITEURS DES RECEPTEURS DU PDFG
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2003097609A1

  公开（公告）日：2003-11-27

  The invention is directed to N-substituted tricyclic 3-AMINOPYRAZOLE derivatives, which are useful as inhibitors of platelet-derived growth factor receptor (PDGF-R) kinase, and methods for the preparation of said derivatives. The present invention is further directed to pharmaceutical compositions comprising the compounds of the presentinvention and to methods for treating conditions such as tumors and other cell proliferative disorders.

  本发明涉及N-取代的三环3-氨基吡唑衍生物，其作为血小板源性生长因子受体（PDGF-R）激酶的抑制剂具有用途，以及制备该衍生物的方法。本发明还涉及包含本发明化合物的制药组合物，以及用于治疗肿瘤和其他细胞增殖性疾病的方法。
• N-substituted tricyclic 3-aminopyrazoles as inhibitors for the treatment of cell proliferative disorders
  申请人：——

  公开号：US20040082639A1

  公开（公告）日：2004-04-29

  The invention is directed to N-substituted tricyclic 3-AMINOPYRAZOLE derivatives, which are useful as inhibitors of platelet-derived growth factor receptor (PDGF-R) kinase, and methods for the preparation of said derivatives. The present invention is further directed to pharmaceutical compositions comprising the compounds of the present invention and to methods for treating conditions such as tumors and other cell proliferative disorders.

  该发明涉及N-取代的三环3-氨基吡唑衍生物，它们可用作血小板源性生长因子受体（PDGF-R）激酶的抑制剂，以及制备该衍生物的方法。本发明还涉及包含本发明化合物的药物组合物，以及治疗肿瘤和其他细胞增殖性疾病的方法。
• N-substituted tricyclic 1-aminopyrazoles as inhibitors for the treatment of cell proliferative disorders
  申请人：Ho Yung Chih

  公开号：US20070142305A1

  公开（公告）日：2007-06-21

  The invention is directed to N-substituted tricyclic 3-AMINOPYRAZOLE derivatives, which are useful as inhibitors of platelet-derived growth factor receptor (PDGF-R) kinase, and methods for the preparation of said derivatives. The present invention is further directed to pharmaceutical compositions comprising the compounds of the present invention and to methods for treating conditions such as tumors and other cell. proliferative disorders.

  本发明涉及N-取代的三环3-氨基吡唑衍生物，其可用作血小板源性生长因子受体（PDGF-R）激酶的抑制剂，以及制备该衍生物的方法。本发明进一步涉及包含本发明化合物的制药组合物，并用于治疗肿瘤和其他细胞增殖性疾病的方法。
• (6,7-Dimethoxy-2,4-dihydroindeno[1,2-<i>c</i>]pyrazol-3-yl)phenylamines:  Platelet-Derived Growth Factor Receptor Tyrosine Kinase Inhibitors with Broad Antiproliferative Activity against Tumor Cells
  作者：Chih Y. Ho、Donald W. Ludovici、Umar S. M. Maharoof、Jay Mei、Jan L. Sechler、Robert W. Tuman、Eric D. Strobel、Laura Andraka、Hwa-Kwo Yen、Gregory Leo、Jian Li、Harold Almond、Hong Lu、Ann DeVine、Rose M. Tominovich、Judith Baker、Stuart Emanuel、Robert H. Gruninger、Steven A. Middleton、Dana L. Johnson、Robert A. Galemmo

  DOI：10.1021/jm050680m

  日期：2005.12.1

  A series of (6,7-dimethoxy-2,4-dihydroindeno[1,2-c]pyrazol-3-yl)phenylamines has been optimized to preserve both potent kinase inhibition activity against the angiogenesis target, the receptor tyrosine kinase of Platelet-Derived Growth Factor-BB (PDGF-BB), and to improve the broad tumor cell antiproliferative activity of these compounds. This series culminates in the discovery of 17 (JNJ-10198409), a compound with anti-PDGFR-beta kinase activity (IC50 = 0.0042 mu M) and potent antiproliferative activity in six of eight human tumor cell lines (IC50 < 0.033 mu m).
• N-SUBSTITUTED TRICYCLIC 3-AMINOPYRAZOLES AS PDGF RECEPTOR INHIBITORS
  申请人：Janssen Pharmaceutica NV

  公开号：EP1506175B1

  公开（公告）日：2009-04-01