2-[(4-甲基-1-哌嗪基)羰基]-苯甲酸 | 20320-46-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(4-甲基-1-哌嗪基)羰基]-苯甲酸
• 中文别名: 2-(4-甲基哌嗪-1基)羧基-苯甲酸
• 英文名称: 2-[(4-methylpiperazin-1-yl)carbonyl]benzoic acid
• 英文别名: Phthalsaeure-mono-(4-methyl-piperazid)；1-Methyl-4-(2-carboxy-benzoyl)-piperazin；2-(4-methyl-piperazine-1-carbonyl)-benzoic acid；2-(4-Methylpiperazin-4-ium-1-carbonyl)benzoate
• CAS: 20320-46-1
• 化学式: C₁₃H₁₆N₂O₃
• mdl: MFCD00033753
• 分子量: 248.282
• InChiKey: ZAFOSGZICIJIGO-UHFFFAOYSA-N

物化性质

• 熔点：
  270 °C
• 沸点：
  443.3±40.0 °C(Predicted)
• 密度：
  1.253±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.384
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090
• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]octan-3-amine dihydrochloride 、 2-[(4-甲基-1-哌嗪基)羰基]-苯甲酸 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以36%的产率得到N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-2-[(4-methylpiperazin-1-yl)carbonyl]benzamide
  参考文献：
  名称：

  Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition

  摘要：

  In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modi. cations on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using Clog D(7.4) values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50) = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.006
• 作为产物：
  描述：

  N-甲基哌嗪 、 苯酐 以 四氢呋喃 为溶剂， 以96%的产率得到2-[(4-甲基-1-哌嗪基)羰基]-苯甲酸
  参考文献：
  名称：

  Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition

  摘要：

  In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modi. cations on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using Clog D(7.4) values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50) = 23 nM) with much reduced CYP2D6 inhibitory activity (IC50 = 29,000 nM) compared with 1. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.08.006

文献信息

• [EN] SUBSTITUTED PYRAZOLOAZEPIN-4-ONES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS<br/>[FR] PYRAZOLOAZÉPIN-4-ONES SUBSTITUÉES ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE PHOSPHODIESTÉRASE
  申请人：LEO PHARMA AS

  公开号：WO2018108230A1

  公开（公告）日：2018-06-21

  The present invention relates to novel substituted pyrazoloazepin-4-ones with phosphodiesterase inhibitory activity, as well as to their use as therapeutic agents in the treatment of inflammatory diseases and conditions.

  本发明涉及具有磷酸二酯酶抑制活性的新型取代吡唑啉-4-酮化合物，以及它们作为治疗炎症性疾病和症状的治疗剂的用途。
• TARGETING NAD BIOSYNTHESIS IN BACTERIAL PATHOGENS
  申请人：Mackerell, JR. Alexander

  公开号：US20120190708A1

  公开（公告）日：2012-07-26

  The emergence of multidrug-resistant pathogens necessitates the search for new antibiotics acting on previously unexplored targets. Nicotinate mononucleotide adenylyltransferase of the NadD family, an essential enzyme of NAD biosynthesis in most bacteria, was selected as a target for structure-based inhibitor development. To this end, the inventors have identified small molecule compounds that inhibit bacterial target enzymes by interacting with a novel inhibitory binding site on the enzyme while having no effect on functionally equivalent human enzymes.

  多重耐药病原体的出现需要寻找作用于先前未被开发的靶标的新抗生素。Nicotinate单核苷酸腺苷转移酶（NadD家族），是大多数细菌NAD生物合成的必需酶，被选为基于结构的抑制剂开发的目标。为此，发明人已经鉴定出小分子化合物，通过与酶上的新型抑制性结合位点相互作用来抑制细菌靶标酶，而对功能相当的人类酶没有影响。
• HUSAIN M. I.; MISKA S. N.; SHUKLA M. K., J. INDIAN CHEM. SOC., 1979, 56, NO 2, 171-172
  作者：HUSAIN M. I.、 MISKA S. N.、 SHUKLA M. K.

  DOI：——

  日期：——
• SUBSTITUTED PYRAZOLOAZEPIN-4-ONES AND THEIR USE AS PHOSPHODIESTERASE INHIBITORS
  申请人：Leo Pharma A/S

  公开号：EP3551633A1

  公开（公告）日：2019-10-16
• US8785499B2
  申请人：——

  公开号：US8785499B2

  公开（公告）日：2014-07-22