1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester | 861151-22-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester
• 英文别名: ethyl 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-(1H)-pyrazole-3-carboxylate；Ethyl 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylate；ethyl 2-(4-chlorophenyl)-3-phenyl-3,4-dihydropyrazole-5-carboxylate
• CAS: 861151-22-6
• 化学式: C₁₈H₁₇ClN₂O₂
• 分子量: 328.798
• InChiKey: BSHQFYQSIAHNPQ-UHFFFAOYSA-N

物化性质

• 熔点：
  109-111 °C(Solv: methanol (67-56-1))
• 沸点：
  462.9±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester 在 sodium hydroxide 、 水 、 盐酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 2.0h， 以78%的产率得到1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid
  参考文献：
  名称：

  1,3,5-trisubstituted 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity

  摘要：

  本发明涉及1,3,5-三取代的4,5-二氢-1H-吡唑烷衍生物作为CB1受体拮抗剂，以及制备这些化合物的方法和用于合成所述吡唑烷衍生物的新型中间体。该发明还涉及利用本文披露的化合物制造具有益处效果的药物。这些化合物具有一般式(I)，其中符号具有规范中给定的含义。

  公开号：

  US20050171179A1
• 作为产物：
  描述：

  4-氯苯肼 在 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 为溶剂， 反应 0.25h， 生成 1-(4-chlorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  [3+2]偶极环加成电化学合成吡唑啉和吡唑

  摘要：

  电化学引发的 [3 2] 环加成反应容易获得且毒性较低的起始材料使吡唑啉和吡唑的合成变得容易。双相系统和碘化钠作为介质和电解质的双重作用的应用允许选择性反应对可扩展性具有出色的鲁棒性。

  DOI：

  10.1002/anie.202214820

文献信息

• 1,3,5-trisubstituted 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity
  申请人：Lange H.M. Josephus

  公开号：US20050171179A1

  公开（公告）日：2005-08-04

  The present invention relates to 1,3,5-trisubstituted 4,5-dihydro-1H-pyrazole derivatives as CB 1 antagonists, to methods for the preparation of these compounds and to novel intermediates useful for the synthesis of said pyrazole derivatives. The invention also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. The compounds have the general formula (I) wherein the symbols have the meanings given in the specification.

  本发明涉及1,3,5-三取代的4,5-二氢-1H-吡唑烷衍生物作为CB1受体拮抗剂，以及制备这些化合物的方法和用于合成所述吡唑烷衍生物的新型中间体。该发明还涉及利用本文披露的化合物制造具有益处效果的药物。这些化合物具有一般式(I)，其中符号具有规范中给定的含义。
• (5R)-1,5-DIARYL-4,5-DIHYDRO-1H-PYRAZOLE-3-CARBOXAMIDINE DERIVATIVES HAVING CB1-ANTAGONISTIC ACTIVITY
  申请人：Lange Josephus H.M.

  公开号：US20110053983A1

  公开（公告）日：2011-03-03

  Embodiments of the invention relate to (5R)-1,5-diaryl-4,5-dihydro-1H-pyrazole-3-carboxamidine derivatives as cannabinoid-CB 1 receptor antagonists, to methods for the preparation of these compounds, to novel intermediates useful for the synthesis of said dihydropyrazole derivatives, to methods for the preparation of these intermediates, pharmaceutical compositions containing one or more of these dihydropyrazole derivatives as an active ingredient, as well as to the use of these pharmaceutical compositions for the treatment of psychiatric and neurological disorders involving cannabinoid receptors. The compounds of embodiments of the invention are compounds of formula (I) wherein the symbols have the meanings given in the specification.

  本发明实施例涉及作为大麻素-CB1受体拮抗剂的(5R)-1,5-二芳基-4,5-二氢-1H-吡唑烷-3-羧酰胺衍生物，制备这些化合物的方法，用于合成所述二氢吡唑烷衍生物的新中间体，制备这些中间体的方法，含有这些二氢吡唑烷衍生物作为活性成分的药物组合物，以及利用这些药物组合物治疗涉及大麻素受体的精神和神经疾病的用途。本发明实施例的化合物是式(I)的化合物，其中符号在说明书中给定的含义。
• Electrochemically enabled oxidative aromatization of pyrazolines
  作者：Silja Hofmann、Martin Linden、Julian Neuner、Felix N. Weber、Siegfried R. Waldvogel

  DOI：10.1039/d3ob00671a

  日期：——

  Pyrazoles are a very important structural motif widely found in pharmaceuticals and agrochemicals. An electrochemically enabled approach for the sustainable synthesis of pyrazoles via oxidative aromatization of pyrazolines is presented. Inexpensive sodium chloride is employed in a dual role as a redox mediator and supporting electrolyte in a biphasic system (aqueous/organic). The method is applicable

  吡唑是一种非常重要的结构基序，广泛存在于药物和农用化学品中。提出了一种通过吡唑啉的氧化芳构化可持续合成吡唑的电化学方法。廉价的氯化钠在双相系统（水/有机）中用作氧化还原介质和支持电解质的双重作用。该方法适用范围广，可以使用碳基电极在最简单的电解装置中进行。因此，该方法允许简单的后处理策略，例如提取和结晶，从而能够在技术相关的规模上应用这种绿色合成路线。多克规模电解的演示不会降低产量，这一点得到了强调。
• Diaryl Dihydropyrazole-3-carboxamides with Significant In Vivo Antiobesity Activity Related to CB1 Receptor Antagonism:  Synthesis, Biological Evaluation, and Molecular Modeling in the Homology Model
  作者：Brijesh Kumar Srivastava,*、Amit Joharapurkar、Saurin Raval、Jayendra Z. Patel、Rina Soni、Preeti Raval、Archana Gite、Amitgiri Goswami、Nisha Sadhwani、Neha Gandhi、Harilal Patel、Bhupendra Mishra、Manish Solanki、Bipin Pandey、Mukul R. Jain、Pankaj R. Patel

  DOI：10.1021/jm061490u

  日期：2007.11.1

  A number of analogues of diaryl dihydropyrazole-3-carboxamides have been synthesized. Their activities were evaluated for appetite suppression and body weight reduction in animal models. Depending on the chemical modification of the selected dihydropyrazole scaffold, the lead compounds-the bisulfate salt,of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 26 and the bisulfate salt of (-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4,5-dihydro-1H-pyrazole3-carboxylic acid morpholin-4-ylamide 30-showed significant body weight reduction in vivo, which is attributed to their CB1 antagonistic activity and exhibited a favorable pharmacokinetic profile. The molecular modeling studies also showed interactions of two isomers of (+/-)-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)4,5-dihydro- 1H-pyrazole-3-carboxylic acid morpholin-4-ylamide 9 with CB I receptor in the homology model similar to those of N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-pyrazole-carboxarnide (rimonabant) 1 and 4S-(-)-3-(4-chlorophenyl)-N-methyl-N'-[(4-chlorophenyl)-sulfonyl]-4-pheny1-4,5-dihydro-1H-pyrazole-1-carboxamidine (SLV-319) 2.
• 1,3,5-TRISUBSTITUTED 4,5-DIHYDRO-1H-PYRAZOLE DERIVATIVES HAVING CB1-ANTAGONISTIC ACTIVITY
  申请人：Solvay Pharmaceuticals B.V.

  公开号：EP1713475A1

  公开（公告）日：2006-10-25