N-(2,5-diphenyl-2H-pyrazol-3-yl)-2-nitro-benzamide | 69730-02-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2,5-diphenyl-2H-pyrazol-3-yl)-2-nitro-benzamide
• 英文别名: N-(1,3-Diphenyl-pyrazol-5-yl)-o-nitrobenzamid；2-nitro-N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamide；N-(2,5-diphenylpyrazol-3-yl)-2-nitrobenzamide
• CAS: 69730-02-5
• 化学式: C₂₂H₁₆N₄O₃
• 分子量: 384.394
• InChiKey: IVZWCRHGQVADCY-UHFFFAOYSA-N

物化性质

• 熔点：
  226-229 °C(Solv: ethanol (64-17-5))
• 沸点：
  539.4±45.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,5-diphenyl-2H-pyrazol-3-yl)-2-nitro-benzamide 以65%的产率得到
  参考文献：
  名称：

  PLESCIA S.; DAIDONE G.; SPRIO V.; AIELLO E.; DATTOLO G.; CIRRINCIONE G., J. HETEROCYCL. CHEM., 1978, 15, NO 8, 1287-1290

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氨基-1,3-二苯基哌唑 、 2-硝基苯甲酰氯 以 二氯甲烷 为溶剂， 以76%的产率得到N-(2,5-diphenyl-2H-pyrazol-3-yl)-2-nitro-benzamide
  参考文献：
  名称：

  An efficient one-pot synthesis of N-(1,3-diphenyl-1H-pyrazol- 5-yl)amides

  摘要：

  Abstractmagnified image A “one‐pot” method for the synthesis of N‐(1,3‐diphenyl‐1H‐pyrazol‐5‐yl)amides was developed by cyclization of benzoylacetonitrile (1) and phenylhydrazine in neat condition followed by acylation. The corresponding N‐(1,3‐diphenyl‐1H‐pyrazol‐5‐yl)amides were provided in good to excellent yields (70–90%). The significant advantages of the new synthetic method are excellent yields and simple work‐up procedure without isolation and purification of intermediary 5‐amino‐1,3‐diphenyl pyrazol (2). J. Heterocyclic Chem., (2010).

  DOI：

  10.1002/jhet.343

文献信息

• Substituent Effects of <i>N</i>-(1,3-Diphenyl-1<i>H</i>-pyrazol-5-yl)benzamides on Positive Allosteric Modulation of the Metabotropic Glutamate-5 Receptor in Rat Cortical Astrocytes
  作者：Tomas de Paulis、Kamondanai Hemstapat、Yelin Chen、Yongqin Zhang、Samir Saleh、David Alagille、Ronald M. Baldwin、Gilles D. Tamagnan、P. Jeffrey Conn

  DOI：10.1021/jm051252j

  日期：2006.6.1

  CDPPB [3-cyano-N-(1,3-diphenyl-1H-pyrazol-5-yl) benzamide] was recently described as the first centrally active, positive allosteric modulator of rat and human metabotropic glutamate receptor (mGluR) mGluR(5) subtype. We explored the structural requirements for potentiation of glutamate-induced calcium release in naturally expressed mGluR5 in cultured rat astrocytes and increasing affinity for the allosteric antagonist binding site by evaluating 50 analogues of CDPPB. In the fluorometric calcium assay, CDPPB exhibited an EC50 value of 77 +/- 15 nM in potentiating mGluR(5)-mediated responses in cortical astrocytes and a K-i value of 3760 ( 430 nM in displacing [H-3] methoxyPEPy binding in membranes of cultured HEK-293 cells expressing rat mGluR5. The structure-activity relationships showed that electronegative aromatic substituents in the para-position of the benzamide moiety of CDPPB increase potency. Both binding and functional activities were further increased with a halogen atom in the ortho-position of the 1-phenyl ring. These effects of substitution do not match those of either aromatic ring of MPEP [2-methyl-6-(phenylethynyl)-pyridine] for the antagonist allosteric binding site. Combination of the optimal substituents and aromatic positions resulted in 4-nitro-N-(1-(2-fluorophenyl)-3-phenyl-1H-pyrazol-5-yl) benzamide (VU-1545) showing K-i) 156 (29 nM and EC50) 9.6 (1.9 nM in the binding and functional assays, respectively.
• An efficient one-pot synthesis of N-(1,3-diphenyl-1H-pyrazol- 5-yl)amides
  作者：Wei-Nien Su、Tsung-Ping Lin、Kaung-Min Cheng、Kuan-Chin Sung、Shao-Kai Lin、Fung Fuh Wong

  DOI：10.1002/jhet.343

  日期：——

  Abstractmagnified image A “one‐pot” method for the synthesis of N‐(1,3‐diphenyl‐1H‐pyrazol‐5‐yl)amides was developed by cyclization of benzoylacetonitrile (1) and phenylhydrazine in neat condition followed by acylation. The corresponding N‐(1,3‐diphenyl‐1H‐pyrazol‐5‐yl)amides were provided in good to excellent yields (70–90%). The significant advantages of the new synthetic method are excellent yields and simple work‐up procedure without isolation and purification of intermediary 5‐amino‐1,3‐diphenyl pyrazol (2). J. Heterocyclic Chem., (2010).
• PLESCIA S.; DAIDONE G.; SPRIO V.; AIELLO E.; DATTOLO G.; CIRRINCIONE G., J. HETEROCYCL. CHEM., 1978, 15, NO 8, 1287-1290
  作者：PLESCIA S.、 DAIDONE G.、 SPRIO V.、 AIELLO E.、 DATTOLO G.、 CIRRINCIONE G.

  DOI：——

  日期：——