4-amino-1,3-diphenyl-1H-pyrazole | 216854-39-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-amino-1,3-diphenyl-1H-pyrazole
• 英文别名: 1,3-diphenyl-1H-pyrazol-4-ylamine；1,3-diphenyl-1H-pyrazol-4-amine；1,3-diphenylpyrazol-4-amine
• CAS: 216854-39-6
• 化学式: C₁₅H₁₃N₃
• mdl: MFCD05270838
• 分子量: 235.288
• InChiKey: PKPYIIMUBKEZHX-UHFFFAOYSA-N

物化性质

• 熔点：
  126-128 °C
• 沸点：
  407.1±25.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  12-羟基十二酸 、 4-amino-1,3-diphenyl-1H-pyrazole 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以41%的产率得到N-(1,3-diphenyl-1H-pyrazol-4-yl)-11-hydroxyundecanamide
  参考文献：
  名称：

  Design and synthesis of novel 3,4-disubstituted pyrazoles for nanomedicine applications against malignant gliomas

  摘要：

  A series of novel 3,4-disubstituted pyrazoles were synthesized. The cytotoxicity against U87MG glioma cell line have been investigated in vitro and three of these compounds showed promising inhibitory activity on cell growth with an IC(50) lower than 90 mu M. AutoDock molecular docking into type I TGF-beta receptor (TGF-beta-RI; PDB: 1py5) has been done for lead optimization of the mentioned compounds as potential TGF-beta-RI1 inhibitors. In particular, 3-aryl-4-amido pyrazole containing long omega-amino-aliphatic chain emerged as a good candidate for further optimization. Entrapment into targetable PEG-based micelles improved growth inhibition IC(50) values up to 100 nM and this could lead to a novel drug delivery strategy for treating glioblastoma. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.01.014
• 作为产物：
  描述：

  2-(1-苯基乙酮-2-基)异吲哚啉-1,3-二酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 19.5h， 生成 4-amino-1,3-diphenyl-1H-pyrazole
  参考文献：
  名称：

  Substituent Effects of N-(1,3-Diphenyl-1H-pyrazol-5-yl)benzamides on Positive Allosteric Modulation of the Metabotropic Glutamate-5 Receptor in Rat Cortical Astrocytes

  摘要：

  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.

  DOI：

  10.1021/jm051252j

文献信息

• [EN] HETEROCYCLE SUBSTITUTED AMINO-PYRIDINE COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS AMINO-PYRIDINE SUBSTITUÉS HÉTÉROCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：EPIZYME INC

  公开号：WO2016044666A1

  公开（公告）日：2016-03-24

  The present disclosure relates to heterocycle substituted amino-pyridine compounds. The present disclosure also relates to pharmaceutical compositions containing these compounds and methods of treating cancer by administering these compounds and pharmaceutical compositions to subjects in need thereof. The present disclosure also relates to the use of such compounds for research or other non-therapeutic purposes.

  本公开涉及杂环取代的氨基吡啶化合物。本公开还涉及含有这些化合物的药物组合物，以及通过将这些化合物和药物组合物用于需要的受试者来治疗癌症的方法。本公开还涉及将这些化合物用于研究或其他非治疗目的的用途。
• [EN] INHIBITORS OF CELLULAR METABOLIC PROCESSES<br/>[FR] INHIBITEURS DE PROCESSUS MÉTABOLIQUES CELLULAIRES
  申请人：AGIOS PHARMACEUTICALS INC

  公开号：WO2018039972A1

  公开（公告）日：2018-03-08

  The invention provides inhibitor compounds of MAT2A that are useful as therapeutic agents for treating malignancies wherein the compounds have the general formula (I) : wherein ring A, ring B, ring C and, R1 are as described herein.

  该发明提供了MAT2A的抑制剂化合物，可作为治疗恶性肿瘤的治疗剂。这些化合物具有一般公式(I)：其中环A、环B、环C和R1如本文所述。
• ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
  申请人：Samsung Display Co., Ltd.

  公开号：EP3882253A1

  公开（公告）日：2021-09-22

  An organic light-emitting device includes an emission layer including a first compound represented by Formula 1, a second compound, and a third compound. The first compound may be an organometallic compound that acts as a phosphorescent dopant, and the second and third compounds may form an exciplex. The device may have a low driving voltage, high luminance, high efficiency, and a long lifespan:

  一种有机发光器件包括一个发射层，其中包括由式 1 表示的第一种化合物、第二种化合物和第三种化合物。第一种化合物可以是作为磷光掺杂剂的有机金属化合物，第二种和第三种化合物可以形成复合物。该装置可具有低驱动电压、高亮度、高效率和长寿命：
• A convenient one-pot synthesis of 4-amino-3-arylpyrazoles from α-phthaloylaminoacetophenones
  作者：Chen Chen、Keith Wilcoxen、James R. McCarthy

  DOI：10.1016/s0040-4039(98)01776-6

  日期：1998.11

  Condensation of alpha-phthaloylaminoacetophenones 1a-c with N,N-dimethylformamide dimethyl acetal afforded the novel enamines 3a-c. Cyclization of 3 with hydrazine, alkylhydrazine or phenylhydrazine salts (4a-d) gave 4-phthaloylamino-3-arylpyrazoles 7-9 in high yields. Deprotection of 7-9 was accomplished with hydrazine to provide 4-amino-3-arylpyrazoles 5 in good yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• [EN] THIAZOLIDIN-4-ONES HAVING ANTI-HEPATITIS B ACTIVITY<br/>[FR] THIAZOLIDINE-4-ONES POSSEDANT UNE ACTIVITE ANTIHEPATITE B
  申请人：VALEANT RES AND DEV

  公开号：WO2006033995A3

  公开（公告）日：2006-06-01