5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde | 623564-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡唑类
• 英文名称: 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde
• CAS: 623564-46-5
• 化学式: C₇H₈N₂O
• 分子量: 136.153
• InChiKey: RTZLJDDSFCFBML-UHFFFAOYSA-N

物化性质

• 熔点：
  40-42 °C
• 沸点：
  298.8±28.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde 在 magnesium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 生成 (5R)-6-[acetoxy-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-yl)methyl]-6-bromo-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid p-nitrobenzyl ester
  参考文献：
  名称：

  Mechanism of Inactivation of β-Lactamases by Novel 6-Methylidene Penems Elucidated Using Electrospray Ionization Mass Spectrometry

  摘要：

  The reactions of 6-methylidene penems 4-7 with beta-lactamases (TEM-1, SHV-1, Amp-C) were characterized by electrospray ionization mass spectrometry (ESI-MS). The kinetics of the reactions were monitored, demonstrating that only one penem. molecule reacts to form an acyl-enzyme complex. For penem 5, the ESI-MS/MS spectrum of the hydrolysis product produced in the reaction was identical to the spectrum generated from a synthesized dihydro[1,4]thiazepine 10, confirming the rearrangement of the penem ring system to a seven-membered dihydro[1,4]thiazepine structure. Gas-phase ESI-MS/MS fragmentation data were rationalized due to tautomerization between imine and enamine substructures. ESI-MS/MS analysis of the T-6 trypsin-digested fragments of TEM-1 and SHV-1 demonstrated that the penems were only attached to Ser-70 of these class A beta-lactamases and that the penem ring structures were rearranged to seven-membered dihydro[1,4]thiazepines.

  DOI：

  10.1021/jm049903j
• 作为产物：
  描述：

  (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)methanol 在 manganese(IV) oxide 作用下， 以 氯仿 为溶剂， 以58 %的产率得到5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carbaldehyde
  参考文献：
  名称：

  [EN] ISOQUINOLINONE AND QUINAZOLINONE COMPOUNDS, AND COMPOSITION AND USE THEREOF
  [FR] COMPOSÉS ISOQUINOLINONE ET QUINAZOLINONE, ET COMPOSITION ET UTILISATION DE CEUX-CI
  [ZH] 异喹啉酮类及喹唑啉酮类化合物及其组合物和用途

  摘要：

  涉及式(I)或(II)所示的异喹啉酮类及喹唑啉酮类化合物，包含所述化合物的药物组合物以及使用所述化合物及其药物组合物在制备预防、处理、治疗、和/或减轻PI3-激酶介导的疾病、病症、和/或病况，或抑制PI3-激酶活性的药物中的用途。所述化合物对目标激酶显示出优异的抑制活性和激酶选择性，具有良好的药代动力学性质，生物利用度更高。

  公开号：

  WO2023051495A1

文献信息

• 3-Cyanoquinoline inhibitors of Tpl2 kinase and methods of making and using the same
  申请人：Green Jeffrey Neal

  公开号：US20060264460A1

  公开（公告）日：2006-11-23

  The present invention provides compounds of formula (I): and pharmaceutically acceptable salts thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , m and n are defined as described herein. The invention also provides methods of making the compounds of formula (I), and methods of treating inflammatory diseases, such as rheumatoid arthritis, in a mammal comprising administering a therapeutically effective amount of a compound of formula (I) to the mammal.

  本发明提供了如下式（I）的化合物及其药用可接受的盐，其中R1、R2、R3、R4、R5、R6、R7、R8、m和n的定义如本文所述。该发明还提供了制备如式（I）化合物的方法，以及治疗炎症性疾病（如类风湿性关节炎）的方法，包括向哺乳动物施用如式（I）化合物的治疗有效量。
• Process for preparing 6-alkylidene penem derivatives
  申请人：Wyeth

  公开号：US20040132708A1

  公开（公告）日：2004-07-08

  The present invention provides a process of making compounds of formula I, which are useful for the treatment of bacterial infection or disease. 1

  本发明提供了一种制备式I化合物的方法，该化合物对治疗细菌感染或疾病有用。
• Bicyclic 6-alkylidene-penems as class-D beta-lactamases inhibitors
  申请人：Mansour Suhayl Tarek

  公开号：US20060276445A1

  公开（公告）日：2006-12-07

  This invention relates to certain bicyclic 6-alkylidene penems which act as a inhibitor of class-D enzymes. β-Lactamases hydrolyze β-lactam antibiotics, and as such serve as the primary cause of bacterial resistance. The compounds of the present invention when combined with β-lactam antibiotics will provide an effective treatment against life threatening bacterial infections. In accordance with the present invention there are provided compounds of general formula I or a pharmaceutically acceptable salt or in vivo hydrolyzable ester R 5 thereof: wherein: One of A and B denotes hydrogen and the other an optionally substituted fused bicyclic heteroaryl group; and X═O or S.

  这项发明涉及某些具有双环6-烷基亚烯基青霉素结构的化合物，其作为D类酶的抑制剂。β-内酰胺酶水解β-内酰胺类抗生素，因此是细菌耐药的主要原因。本发明的化合物与β-内酰胺类抗生素结合后，将提供一种有效的治疗方法，用于治疗威胁生命的细菌感染。根据本发明，提供了一般式I的化合物，或其药学上可接受的盐或体内可水解的酯R5：其中：A和B中的一个表示氢，另一个表示可选择取代的融合双环杂环芳基团；X＝O或S。
• [EN] BICYCLIC 6-ALKYLIDENE-PENEMS AS ß-LACTAMASES INHIBITORS<br/>[FR] PENEMES 6-ALKYLIDENE BICYCLIQUES UTILISES EN TANT QU'INHIBITEURS DE ss-LACTAMASES
  申请人：WYETH CORP

  公开号：WO2003093279A1

  公开（公告）日：2003-11-13

  The present invention provides a compound of Formula (I), pharmaceutical compositions and the use thereof for the treatment of bacterial infection or disease in a patient in need thereof.

  本发明提供了一种化合物（I）的配方、药物组合物以及其用于治疗患有细菌感染或疾病的患者的用途。
• [EN] PROCESS FOR PREPARING 6-ALKYLIDENE PENEM DERIVATIVES<br/>[FR] PROCEDE DE PREPARATION DE DERIVES DE 6-ALKYLIDENE PENEM
  申请人：WYETH CORP

  公开号：WO2003093277A1

  公开（公告）日：2003-11-13

  The present invention provides a process of making compounds of Formula (I), which are useful for the treatment of bacterial infection or disease.

  本发明提供了一种制备化合物的方法，该化合物符合式（I），对于治疗细菌感染或疾病非常有用。