2-(1-methyl-3-isopropylpyrazol-5-ylamino)benzoic acid | 884316-48-7

• 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: 2-(1-methyl-3-isopropylpyrazol-5-ylamino)benzoic acid
• 英文别名: N-(1-methyl-3-isopropylpyrazol-5-yl)-anthranilic acid；2-[(2-Methyl-5-propan-2-ylpyrazol-3-yl)amino]benzoic acid
• CAS: 884316-48-7
• 化学式: C₁₄H₁₇N₃O₂
• 分子量: 259.308
• InChiKey: PFMAJVUIQIZALY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-methyl-3-isopropylpyrazol-5-ylamino)benzoic acid 在 三氯氧磷 作用下， 生成 4-chloro-1-methyl-3-isopropyl-1H-pyrazolo[3,4-b]quinoline
  参考文献：
  名称：

  Discovery and structure–activity relationship of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a new series of potent apoptosis inducers

  摘要：

  We report the discovery and SAR study of a series of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as potent inducers of apoptosis. N-(3-Acetylphenyl)-2,3-dihydro-1H-cyclopenta[b]quinolin-9-amine (2) was discovered through our cell- and caspase-based HTS assays as an inducer of apoptosis. Compound 2 is active against cancer cells derived from several human solid tumors, with EC50 values ranging from 400 to 700 nM. SAR study of hit 2 led to the discovery of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a novel series of potent apoptosis inducers, with 1,3-dimethyl-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinotin-amine (6b) having EC50 values ranging from 30 to 70 nM in cancer cells. These compounds also demonstrated potent activity in the cell growth inhibition assay, with GI(50) values of 16-42 nM for compound 6b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.046
• 作为产物：
  描述：

  2-碘苯甲酸 、 3-异丙基-1-甲基-1H-吡唑-5-胺 在 铜 、 potassium carbonate 作用下， 以 水 为溶剂， 生成 2-(1-methyl-3-isopropylpyrazol-5-ylamino)benzoic acid
  参考文献：
  名称：

  Discovery and structure–activity relationship of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a new series of potent apoptosis inducers

  摘要：

  We report the discovery and SAR study of a series of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as potent inducers of apoptosis. N-(3-Acetylphenyl)-2,3-dihydro-1H-cyclopenta[b]quinolin-9-amine (2) was discovered through our cell- and caspase-based HTS assays as an inducer of apoptosis. Compound 2 is active against cancer cells derived from several human solid tumors, with EC50 values ranging from 400 to 700 nM. SAR study of hit 2 led to the discovery of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a novel series of potent apoptosis inducers, with 1,3-dimethyl-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinotin-amine (6b) having EC50 values ranging from 30 to 70 nM in cancer cells. These compounds also demonstrated potent activity in the cell growth inhibition assay, with GI(50) values of 16-42 nM for compound 6b. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.09.046

文献信息

• Substituted N-Aryl-1H-Pyrazolo[3,4-B]Quinolin-4-Amines and Analogs as Activators of Caspases and Inducers of Apoptosis
  申请人：Zhang Han-Zhong

  公开号：US20070253957A1

  公开（公告）日：2007-11-01

  The present invention is directed to substituted N-aryl-1H-pyrazolo[3,4-b]quinolin-4-amines and analogs thereof, represented by the general Formula (I): wherein Q, Y, Z, R 4 -R 7 , X and Ar are defined herein. The present invention also relates to the discovery that compounds having Formula (I) are activators of caspases and inducers of apoptosis. Therefore, the activators of caspases and inducers of apoptosis of this invention can be used to induce cell death in a variety of clinical conditions in which uncontrolled growth and spread of abnormal cells occurs.

  本发明涉及被取代的N-芳基-1H-吡唑并[3,4-b]喹啉-4-胺及其类似物，其通式表示为（I）：其中Q，Y，Z，R4-R7，X和Ar在此被定义。本发明还涉及发现具有式（I）的化合物是caspase激活剂和凋亡诱导剂的事实。因此，本发明的caspase激活剂和凋亡诱导剂可用于在各种临床情况下诱导细胞死亡，其中发生异常细胞的无控制生长和扩散。
• Discovery and structure–activity relationship of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a new series of potent apoptosis inducers
  作者：Han-Zhong Zhang、Gisela Claassen、Candace Crogran-Grundy、Ben Tseng、John Drewe、Sui Xiong Cai

  DOI：10.1016/j.bmc.2007.09.046

  日期：2008.1

  We report the discovery and SAR study of a series of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as potent inducers of apoptosis. N-(3-Acetylphenyl)-2,3-dihydro-1H-cyclopenta[b]quinolin-9-amine (2) was discovered through our cell- and caspase-based HTS assays as an inducer of apoptosis. Compound 2 is active against cancer cells derived from several human solid tumors, with EC50 values ranging from 400 to 700 nM. SAR study of hit 2 led to the discovery of N-phenyl-1H-pyrazolo[3,4-b]quinolin-4-amines as a novel series of potent apoptosis inducers, with 1,3-dimethyl-N-(4-propionylphenyl)-1H-pyrazolo[3,4-b]quinotin-amine (6b) having EC50 values ranging from 30 to 70 nM in cancer cells. These compounds also demonstrated potent activity in the cell growth inhibition assay, with GI(50) values of 16-42 nM for compound 6b. (C) 2007 Elsevier Ltd. All rights reserved.