3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine | 87628-50-0

• 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-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine
• CAS: 87628-50-0
• 化学式: C₁₂H₁₃N₃
• mdl: MFCD07403541
• 分子量: 199.255
• InChiKey: TZFHJMGEXWVRKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  40.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine 在 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 N-(4-acetylphenyl)-1-benzoyl-3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide
  参考文献：
  名称：

  Development of 3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine derivatives as novel Mycobacterium tuberculosis pantothenate synthetase inhibitors

  摘要：

  Forty 3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine derivatives were synthesized from piperidin-4-one by five step synthesis and evaluated for Mycobacterium tuberculosis (MTB) pantothenate synthetase (PS) inhibition study, in vitro activities against MTB, cytotoxicity against RAW 264.7 cell line. Among the compounds, 1-benzoyl-N-(4-nitrophenyl)-3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide (6ac) was found to be the most active compound with IC50 of 21.8 +/- 0.8 mu M against MTB PS, inhibited MTB with MIC of 26.7 mu M and it was non-cytotoxic at 50 RM. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.036
• 作为产物：
  描述：

  4-氧代哌啶酮盐酸盐 在 吗啉 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 作用下， 以 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 56.0h， 生成 3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine
  参考文献：
  名称：

  Development of 3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine derivatives as novel Mycobacterium tuberculosis pantothenate synthetase inhibitors

  摘要：

  Forty 3-phenyl-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine derivatives were synthesized from piperidin-4-one by five step synthesis and evaluated for Mycobacterium tuberculosis (MTB) pantothenate synthetase (PS) inhibition study, in vitro activities against MTB, cytotoxicity against RAW 264.7 cell line. Among the compounds, 1-benzoyl-N-(4-nitrophenyl)-3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxamide (6ac) was found to be the most active compound with IC50 of 21.8 +/- 0.8 mu M against MTB PS, inhibited MTB with MIC of 26.7 mu M and it was non-cytotoxic at 50 RM. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.036

文献信息

• Development of Predictive Classification Models for Whole Cell Antimycobacterial Activity of Benzothiazinones
  作者：Sebastian Schieferdecker、Freddy A. Bernal、K. Philip Wojtas、François Keiff、Yan Li、Hans-Martin Dahse、Florian Kloss

  DOI：10.1021/acs.jmedchem.2c00098

  日期：2022.5.12

  against Mycobacterium tuberculosis. However, relationships between their structural properties and whole cell activity remain poorly predictable. Herein, we present the synthesis and antimycobacterial evaluation of a diverse set of BTZs. High potency was predominantly achieved by piperidine and piperazine substitutions, whereupon three compounds were identified as promising candidates, showing preferable

  硝基苯并噻嗪酮 (BTZ) 是一类非常有效的抗结核分枝杆菌的抗生素. 然而，它们的结构特性和全细胞活性之间的关系仍然很难预测。在此，我们介绍了多种 BTZ 的合成和抗分枝杆菌评估。高效力主要通过哌啶和哌嗪取代来实现，因此三种化合物被确定为有希望的候选物，显示出较好的代谢稳定性。效力和计算的结合能之间缺乏相关性表明靶抑制不是获得合适的抗分枝杆菌剂的唯一要求。相比之下，通过广泛验证的机器学习模型成功地完成了全细胞活动类别的预测。通过对大量报告的 BTZ 进行 >70% 的正确类别预测，进一步验证了卓越模型的性能。
• DERIVATIVES AND METHODS OF TREATING HEPATITIS B INFECTIONS
  申请人：Novira Therapeutics, Inc.

  公开号：US20160185779A1

  公开（公告）日：2016-06-30

  Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.

  本文提供了用于治疗需要治疗HBV感染患者的化合物，其制药组合物，以及抑制、抑制或预防该患者HBV感染的方法。
• Derivatives and methods of treating hepatitis B infections
  申请人：Novira Therapeutics, Inc.

  公开号：US10077264B2

  公开（公告）日：2018-09-18

  Provided herein are compounds useful for the treatment of HBV infection in a subject in need thereof, pharmaceutical compositions thereof, and methods of inhibiting, suppressing, or preventing HBV infection in the subject.

  本文提供了用于治疗有需要的受试者 HBV 感染的化合物、其药物组合物以及抑制、抑制或预防受试者 HBV 感染的方法。
• [EN] PRMT5 INHIBITORS AND USES THEREOF<br/>[FR] INHIBITEURS DE PRMT5 ET LEURS UTILISATIONS
  申请人：EPIZYME INC

  公开号：WO2015200677A8

  公开（公告）日：2017-01-19
• Synthesis, in vitro [3H]prazosin displacement, and in vivo activity of 3-aryl-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridines, a new class of antihypertensive agents
  作者：Giorgio Winters、Alberto Sala、Domenico Barone、Emiliana Baldoli

  DOI：10.1021/jm00145a015

  日期：1985.7

  A series of new 3-aryl-4,5,6,7-tetrahydropyrazolo[4,3-c]pyridines was synthesized and screened for in vitro [3H]prazosin displacement activity. The results correlated well with their antihypertensive activity in spontaneous hypertensive rats. 1-Benzyl-3-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[4,3-c]pyrid ine (50, L 16052) was selected for further pharmacological evaluations of its potency when administered orally to conscious renal hypertensive dogs.