3-amino-5-hydroxy-4-phenyl-2,5-dihydro-1H-pyrazole | 62538-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-amino-5-hydroxy-4-phenyl-2,5-dihydro-1H-pyrazole
• 英文别名: 5-amino-4-phenyl-1H-pyrazol-3(2H)-one；5-amino-4-phenyl-1,2-dihydro-pyrazol-3-one；5-Amino-4-phenyl-1,2-dihydro-pyrazol-3-on；5-amino-4-phenyl-1,2-dihydropyrazol-3-one
• CAS: 62538-17-4
• 化学式: C₉H₉N₃O
• mdl: MFCD13704126
• 分子量: 175.19
• InChiKey: APZQJFXKSSBKAS-UHFFFAOYSA-N

物化性质

• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-amino-5-hydroxy-4-phenyl-2,5-dihydro-1H-pyrazole 、 methyl L-N-benzoyl(1,4-cyclohexadienyl)alaninate 生成 methyl N-benzoyl-2-hydroxy-3-phenylpyrazolo<1,5-a>-pyrimidin-7-yl-L-alaninate
  参考文献：
  名称：

  Ozonolysis of (cyclohexa-1,4-dienyl)-L-alanine. An approach to the synthesis of new unnatural amino acids. X-Ray molecular structure of 2-hydroxy-7-methyl-3-phenylpyrazolo[1,5-a]pyrimidine

  摘要：

  The aromatic ring in L-phenylalanine was transformed into isoxazolyl, N-phenylpyrazolyl, and the bicyclic pyrazolo[1,5-a]pyrimidinyl groups, by a combination of Birch reduction and ozonolysis, followed by condensation with the relevant binucleophiles. The ozonolysis was carried out on the N-acylated esters of cyclohexa-1,4-dienylalanine. The resulting N-acylated esters of heterocyclic alanine derivatives were obtained without isolation of the ozonolysis products. 4-Phenylpyrazolidine-3,5-dione was used as a 'hydrazine donor' in the construction of a pyrazolyl group, as direct condensation with hydrazine was successful.

  DOI：

  10.1039/p19950002509
• 作为产物：
  描述：

  methyl 2-cyano-2-phenylacetate 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 3-amino-5-hydroxy-4-phenyl-2,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Pyrazolo[1,5-a]pyrimidin-7(4H)-ones 作为抗结核药物的构效关系

  摘要：

  Pyrazolo[1,5 - a ]pyrimidin-7(4 H )-one 通过高通量全细胞筛选被鉴定为潜在的抗结核药物。该支架的核心之前已被多次鉴定，并且与抗结核分枝杆菌( Mtb ) 的各种作用模式有关。我们通过合成一个集中的类似物库探索了这种支架，并确定了药效团的关键特征，同时实现了抗结核活性的显着改善。我们的最佳产品具有低细胞毒性，并显示出对Mtb的有希望的活性巨噬细胞内。这些化合物的作用机制与细胞壁生物合成、异戊二烯生物合成或铁吸收无关，正如其他具有这种核心结构的化合物所发现的那样。黄素腺嘌呤二核苷酸 (FAD) 依赖性羟化酶 (Rv1751) 的突变赋予了对这些化合物的抗性，该羟化酶通过分子氧的羟基化促进化合物分解代谢。我们的结果强调了化学聚集的风险，但没有建立化学相关生长抑制剂的机制相似性。

  DOI：

  10.1021/acsinfecdis.0c00851

文献信息

• HETEROCYCLIC COMPOUNDS FOR THE INHIBITION OF PASK
  申请人：McCall John M.

  公开号：US20120277224A1

  公开（公告）日：2012-11-01

  Disclosed herein are new heterocyclic compounds and compositions and their application as pharmaceuticals for the treatment of disease. Methods of inhibiting PAS Kinase (PASK) activity in a human or animal subject are also provided for the treatment of diseases such as diabetes mellitus.

  本文披露了新的杂环化合物和组合物，以及它们作为药物治疗疾病的应用。还提供了抑制PAS激酶（PASK）在人类或动物主体中活性的方法，用于治疗疾病，如糖尿病。
• [EN] GLYCINE B ANTAGONISTS<br/>[FR] ANTAGONISTES DE LA GLYCINE B
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2010139483A1

  公开（公告）日：2010-12-09

  The invention relates to pyrazolopyrimidine derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders.

  该发明涉及吡唑吡咪啉衍生物及其药用可接受的盐。该发明进一步涉及一种制备这种化合物的方法。该发明的化合物是甘氨酸B拮抗剂，因此可用于控制和预防各种疾病，包括神经系统疾病。
• Birch Reduction of (−)-Ephedrine. Formation of a New, Versatile Intermediate for Organic Synthesis
  作者：Gury Zvilichovsky、Isra Gbara-Haj-Yahia

  DOI：10.1021/jo049726u

  日期：2004.8.1

  The reduction of (−)-ephedrine by lithium in liquid ammonia resulted in the formation of S-1-(1,4-cyclohexadien-1-yl)-N-methyl-2-propanamine. In addition to the reduction of the aromatic ring, the hydroxy group was reduced as well. The resulting 1,4-cyclohexadienyl group is a potentially versatile intermediate for further synthetic transformations. The ozonolysis of this group was investigated, producing

  锂在液态氨中还原（-）-麻黄碱导致形成S -1-（1,4-环己二-1-基）-N-甲基-2-丙胺。除了芳环的还原之外，羟基也被还原。所得的1，4-环己二烯基是用于进一步合成转化的潜在通用中间体。对这组的臭氧分解进行了研究，产生了β-酮-δ-甲基氨基酯和β-酮醛的衍生物，这些衍生物随后可以转化为杂环。描述了对N-苯甲酰基-1-（1,4-环己二-1-基）-N-甲基-2-丙胺中CN键旋转的限制。
• [EN] PYRAZOLOPYRIMIDINONE COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS DE PYRAZOLOPYRIMIDINONE ET LEURS UTILISATIONS
  申请人：ADURO BIOTECH INC

  公开号：WO2019055750A1

  公开（公告）日：2019-03-21

  The present invention relates to pyrazolopyrimidinone compounds. The present invention also relates to pharmaceutical compositions containing these compounds and methods of treating autoimmune, inflammatory, and neurodegenerative diseases by administering these compounds and pharmaceutical compositions to subjects in need thereof. The present invention also relates to the use of such compounds for research or other non-therapeutic purposes.

  本发明涉及吡唑吡咪啉酮化合物。本发明还涉及含有这些化合物的药物组合物，以及通过向需要的受试者施用这些化合物和药物组合物来治疗自身免疫、炎症和神经退行性疾病的方法。本发明还涉及利用这些化合物进行研究或其他非治疗目的的用途。
• Glycine B antagonists
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP2264035A1

  公开（公告）日：2010-12-22

  The invention relates to pyrazolopyrimidine derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are glycine B antagonists and are therefore useful for the control and prevention of various disorders, including neurological disorders,

  本发明涉及吡唑嘧啶衍生物及其药学上可接受的盐类。本发明还涉及一种制备此类化合物的工艺。本发明的化合物是甘氨酸 B 拮抗剂，因此可用于控制和预防各种疾病，包括神经系统疾病、