5-(3-chlorophenyl)-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(3-chlorophenyl)-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
• 英文别名: 5-(3-chlorophenyl)-6-methyl-1-phenylpyrazolo[3,4-d]pyrimidin-4-one
• 化学式: C₁₈H₁₃ClN₄O
• mdl: MFCD01461052
• 分子量: 336.78
• InChiKey: UKTKKTVGDZERNW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  50.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-氨基-4-乙氧羰基-1-苯基吡唑 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-(3-chlorophenyl)-6-methyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one
  参考文献：
  名称：

  新型吡唑并嘧啶酮作为糖尿病中DPP-IV抑制剂的设计，合成和生物学评估。

  摘要：

  我们报告了一系列新型吡唑并[3,4-d]嘧啶酮作为糖尿病中的DPP-IV抑制剂的设计，合成，生物学活性和对接研究。合成分子并评估其对DPP-IV的抑制活性。发现化合物5e，5k，5o和6a是DPP-IV酶的有效抑制剂。在所有合成的化合物中，发现6-甲基-5-（4-甲基吡啶-2-基）-1-苯基-1H-吡唑并[3,4-d]嘧啶-4（5H）-一（5k）根据体外DPP-IV研究，它是最活跃的，并且在雄性Wistar大鼠中也显示出有希望的体内降血糖活性。

  DOI：

  10.1016/j.bmcl.2015.09.015

文献信息

• Rapid hit to lead evaluation of pyrazolo[3,4-d]pyrimidin-4-one as selective and orally bioavailable mGluR1 antagonists
  作者：Xueqing Wang、Teodozyi Kolasa、Odile F. El Kouhen、Linda E. Chovan、Candace L. Black-Shaefer、Frank L. Wagenaar、Jennifer A. Garton、Robert B. Moreland、Prisca Honore、Yau Yi Lau、Peter J. Dandliker、Jorge D. Brioni、Andrew O. Stewart

  DOI：10.1016/j.bmcl.2007.05.028

  日期：2007.8

  Our HTS effort yielded a preferential mGluR1 pyrimidinone antagonist I with lead-like characteristics. Rapid hit to lead (HTL) study identified compounds with improved functional activity and selectivity such as lb with little improvements in ADME properties. Addition of an ammosulfonyl group on the N-1 aromatic ring led to 2f, a compound with similar in vitro biochemical profiles as those of lb but drastically improved in vitro ADME properties. These improvements were paralleled by rat PK study characterized by low clearance and quantitative bioavailability. Compound 2f represented a true lead-like molecule that is amenable for further lead optimization (LO) evaluation. (c) 2007 Elsevier Ltd. All rights reserved.
• Pathak, U. S.; Gandhi, Sudha; Rathod, I. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 8, p. 734 - 737
  作者：Pathak, U. S.、Gandhi, Sudha、Rathod, I. S.

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of novel pyrazolo-pyrimidinones as DPP-IV inhibitors in diabetes
  作者：Sneha R. Sagar、Jessica K. Agarwal、Dhaivat H. Pandya、Ranjeet Prasad Dash、Manish Nivsarkar、Kamala K. Vasu

  DOI：10.1016/j.bmcl.2015.09.015

  日期：2015.10

  design, synthesis, biological activity and docking studies of series of novel pyrazolo[3,4-d]pyrimidinones as DPP-IV inhibitors in diabetes. Molecules were synthesized and evaluated for their DPP-IV inhibition activity. Compounds 5e, 5k, 5o and 6a were found to be potent inhibitors of DPP-IV enzyme. Amongst all the synthesized compounds, 6-methyl-5-(4-methylpyridin-2-yl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

  我们报告了一系列新型吡唑并[3,4-d]嘧啶酮作为糖尿病中的DPP-IV抑制剂的设计，合成，生物学活性和对接研究。合成分子并评估其对DPP-IV的抑制活性。发现化合物5e，5k，5o和6a是DPP-IV酶的有效抑制剂。在所有合成的化合物中，发现6-甲基-5-（4-甲基吡啶-2-基）-1-苯基-1H-吡唑并[3,4-d]嘧啶-4（5H）-一（5k）根据体外DPP-IV研究，它是最活跃的，并且在雄性Wistar大鼠中也显示出有希望的体内降血糖活性。