5,6,7,8-四氢咪唑并[1,2-a]吡嗪-2-羧酸 | 885281-33-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 5,6,7,8-四氢咪唑并[1,2-a]吡嗪-2-羧酸
• 中文别名: 5,6,7,8-四氢-咪唑并[1,2-A]吡嗪-2-羧酸
• 英文名称: 5,6,7,8-tetrahydroimidazolo[1,2-a]pyrazine-2-carboxylic acid
• 英文别名: 5,6,7,8-Tetrahydroimidazo[1,2-a]pyrazine-2-carboxylic acid
• CAS: 885281-33-4
• 化学式: C₇H₉N₃O₂
• mdl: MFCD08059258
• 分子量: 167.167
• InChiKey: MMOJRJGERMVGKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.3
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  67.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  5,6,7,8-四氢咪唑并[1,2-a]吡嗪-2-羧酸 、 9,10-difluoro-2,3-dihydro-3-(S)-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid 以 二甲基亚砜 为溶剂， 以84%的产率得到10-[2-carboxy-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl]-9-fluoro-2,3-dihydro-3-(S)-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid
  参考文献：
  名称：

  Novel ofloxacin derivatives: Synthesis, antimycobacterial and toxicological evaluation

  摘要：

  Thirty novel 9-fluoro-2,3-dihydro-8,10-(mono/di-sub)-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acids were synthesized from 2,3,4,5-tetrafluoro benzoic acid and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from mycobacteria. Among the synthesized compounds, 10-[2-carboxy-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid was found to be the most active compound in vitro with MIC99 of 0.19 mu M and 0.09 mu M against MTB and MTR-TB, respectively. In the in vivo animal model also the same compound decreased the bacterial load in lung and spleen tissues with 1.91 and 2.91 - log 10 protections, respectively, at the dose of 50 mg/ kg body weight. Compound 10-[(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo7H-[1,4]oxazino[2,3,4-]quinoline-6-carboxylic acid was found to be the most active in the inhibition of the supercoiling activity of DNA gyrase with an IC50 of 10.0 mu g/mL. The results demonstrate the potential and importance of developing new oxazino quinolone derivatives against mycobacterial infections. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.11.110

文献信息

• [EN] HETEROCYCLIC COMPOUNDS AND METHODS FOR THEIR USE<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES ET LEURS PROCÉDÉS D'UTILISATION
  申请人：SPINIFEX PHARM PTY LTD

  公开号：WO2013110134A1

  公开（公告）日：2013-08-01

  The present invention relates to heterocyclic compounds useful for antagonising angiotensin II Type 2 (AT2) receptor. More particularly the invention relates to piperazine and diazepine compounds, compositions containing them and their use in methods of treating or preventing disorders or diseases associated with AT2 receptor function including neuropathic pain, inflammatory pain, conditions associated with neuronal hypersensitivity, impaired nerve conduction velocity, cell proliferation disorders, disorders associated with an imbalance between bone resorption and bone formation and disorders associated with aberrant nerve regeneration.

  本发明涉及对抗血管紧张素II型2（AT2）受体有用的杂环化合物。更具体地，本发明涉及哌嗪和二氮杂环化合物，含有它们的组合物以及它们在治疗或预防与AT2受体功能相关的疾病或疾病的方法中的使用，包括神经病性疼痛、炎症性疼痛、与神经元过敏、神经传导速度受损、细胞增殖紊乱、骨吸收和骨形成之间失衡以及与异常神经再生相关的疾病。
• Antimycobacterial Activities of Novel 1-(Cyclopropyl/<i>tert</i>-butyl/4-fluorophenyl)-1,4-dihydro- 6-nitro-4-oxo-7-(substituted secondary amino)-1,8-naphthyridine-3-carboxylic Acid
  作者：Dharmarajan Sriram、Palaniappan Senthilkumar、Murugesan Dinakaran、Perumal Yogeeswari、Arnab China、Valakunja Nagaraja

  DOI：10.1021/jm700999n

  日期：2007.11.1

  4-dihydro-6-nitro-4-oxo-7-(substitute d secondary amino)-1,8-naphthyridine-3-carboxylic acids were synthesized and evaluated for antimycobacterial in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB), multi-drug-resistant Mycobacterium tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis

  51个1-（环丙基/叔丁基/ 4-氟苯基）-1,4-二氢-6-硝基-4-氧代-7-（取代仲氨基）-1,8-萘啶-3-羧酸合成并评估了对结核分枝杆菌H37Rv（MTB），耐多药结核分枝杆菌（MDR-TB）和耻垢分枝杆菌（MC2）的体外和体内抗分枝杆菌的作用，还测试了其抑制DNA超螺旋活性的能力耻垢分枝杆菌的促旋酶。在合成的化合物中，1-叔丁基-1,4-二氢-7-（4,4-二甲基恶唑烷-3-基）-6-硝基-4-氧代-1,8-萘吡啶-3-羧酸（10q）被发现是体外活性最高的化合物，对MTB和MDR-TB的MIC为0.1 microM，分别比异烟肼对MTB和MDR-TB的效力分别高3倍和455倍。
• Synthesis and<i>in-vitro</i>Antimycobacterial Evaluation of 1-(Cyclopropyl/2,4-difluorophenyl/<i>tert-</i>butyl)-1,4-dihydro- 8-methyl-6-nitro-4-oxo-7-(substituted secondary amino)quinoline-3-carboxylic acids
  作者：Palaniappan Senthilkumar、Murugesan Dinakaran、Yogesh Chandraseakaran、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1002/ardp.200800015

  日期：2009.2

  Fifty one newer 1‐(cyclopropyl/2,4‐difluorophenyl/tert‐butyl)‐1,4‐dihydro‐8‐methyl‐6‐nitro‐4‐oxo‐7‐(substituted secondary amino)quinoline‐3‐carboxylic acids were synthesized from 1,3‐dichloro‐2‐methylbenzene and evaluated for in‐vitro antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi‐drug resistant Mycobacterium tuberculosis (MDR‐TB), and Mycobacterium smegmatis (MC2)

  五十一种新型 1-(环丙基/2,4-二氟苯基/叔丁基)-1,4-二氢-8-甲基-6-硝基-4-氧代-7-(取代仲氨基)喹啉-3-羧酸由 1,3-二氯-2-甲苯合成，并评估了体外抗结核分枝杆菌 H37Rv (MTB)、耐多药结核分枝杆菌 (MDR-TB) 和耻垢分枝杆菌 (MC2) 的活性。在合成的化合物中，1-环丙基-1,4-二氢-7-(3,4-二氢-6,7-二甲氧基异喹啉-2(1H)-基)-8-甲基-6-硝基-4-氧喹啉-发现 3-羧酸 9p 是体外活性最强的化合物，对 MTB 的 MIC 值为 0.39 μM。抗耐多药结核病，化合物 7-(2-carboxy-5,6-dihydroimidazo[1,2-a]pyrazine-7(8H)-yl)-1-cyclopropyl-1，
• Pyrazolopyrimidines, a process for their preparation and their use as medicine
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP2085398A1

  公开（公告）日：2009-08-05

  The invention relates to pyrazolopyrimidine derivatives of Formula I wherein R1 represents chloro or bromo; A represents 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 mGluR5 modulators and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.

  本发明涉及以下式子的吡唑嘧啶衍生物（I）： 其中R1代表氯或溴； A代表 以及其药学上可接受的盐。本发明还涉及制备这种化合物的方法。本发明的化合物是mGluR5调节剂，因此对于控制和预防急性和/或慢性神经系统疾病有用。
• 3-Amino-4-phenylbutanoic acid derivatives as dipeptidyl peptidase inhibitors for the treatment or prevention of diabetes
  申请人：Duffy L Joseph

  公开号：US20060052382A1

  公开（公告）日：2006-03-09

  The present invention is directed to 3-amino-4-phenylbutanoic acid derivatives which are inhibitors of the dipeptidyl peptidase-IV enzyme (“DP-IV inhibitors”) and which are useful in the treatment or prevention of diseases in which the dipeptidyl peptidase-IV enzyme is involved, such as diabetes and particularly type 2 diabetes. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of such diseases in which the dipeptidyl peptidase-IV enzyme is involved.

  本发明涉及3-氨基-4-苯基丁酸衍生物，它们是二肽酶IV酶（“DP-IV抑制剂”）的抑制剂，对于涉及二肽酶IV酶的疾病，如糖尿病，特别是2型糖尿病的治疗或预防有用。本发明还涉及包含这些化合物的制药组合物以及这些化合物和组合物在涉及二肽酶IV酶的这类疾病的预防或治疗中的使用。