3-amino-5-pyrazolone | 74586-24-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-amino-5-pyrazolone
• 英文别名: 5-amino-3H-pyrazol-3-one；5-aminopyrazol-3-one
• CAS: 74586-24-6
• 化学式: C₃H₃N₃O
• 分子量: 97.0763
• InChiKey: ACOIYJJFAXRSHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3-amino-5-pyrazolone 、 8-羟基-5-喹啉磺酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 以85%的产率得到5-(5-oxo-1,2-dihydropyrazol-3-yl)sulphonamido-8-hydroxyquinoline
  参考文献：
  名称：

  Synthesis, antimicrobial, and antiviral activities of some new 5-sulphonamido-8-hydroxyquinoline derivatives

  摘要：

  一系列融合的吡嗪并吡喃类化合物，即5-(3,6-二氨基-4-芳基-5-氰基-吡喃(2,3-c)吡嗪-2-基)磺酰基-8-羟基喹啉（5a-e）、5-(6-氨基-4-芳基-5-氰基-吡喃(2,3-c)吡嗪-3-基)磺酰胺-8-羟基喹啉（6a-e）、5-(2-硫酮-4-芳基-5-氰基-6-氨基-吡喃(2,3-d)咪唑-2-基)磺酰基-8-羟基喹啉（10a-e），以及5-(2-氧代-4-芳基-5-氰基-6-氨基-吡喃(2,3-d)咪唑-2-基)磺酰基-8-羟基喹啉（11a-e），通过将一些芳基二苯乙亚胺与5-磺酰胺-8-羟基喹啉衍生物3、4、8和9进行缩合反应制备而成。所有合成的化合物均进行了抗微生物活性筛选，大多数测试化合物对大肠杆菌和铜绿假单胞菌（阴性菌）表现出强效的抑菌活性。此外，六种选择的化合物还被测试其对禽类副黏病毒1型（APMV-1）和喉气管炎病毒（LTV）的抗病毒活性，结果显示，2、3和4号化合物在浓度范围为每毫升3-4 μg时，对APMV-1（5000组织培养感染剂量五十TCID50）和LTV（500 TCID50）具有显著的病毒抑制活性，基于其细胞病变效应。鸡胚实验表明，2、3和4号化合物在体外对禽类APMV-1和LTV具有高抗病毒活性，抑制浓度五十（IC50）范围为每个鸡蛋3–4 μg，毒性浓度五十（CC50）范围为每个鸡蛋200–300 μg。

  DOI：

  10.1007/s12272-012-0602-0

文献信息

• 1,2,4,7-tetrahydro-2-oxopyrazolo[1,5-a]pyrimidine derivatives
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04746656A1

  公开（公告）日：1988-05-24

  Cardiovascular activity is exhibited by compounds having the formula ##STR1## or a pharmaceutically acceptable salt thereof, wherein R.sub.1 is aryl or heterocyclo; R.sub.2 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, aryl, --(CH.sub.2).sub.n --Y.sub.1, or halo substituted alkyl; R.sub.3 is hydrogen, alkyl, cycloalkyl, aryl, heterocyclo, --(CH.sub.2).sub.n --Y.sub.2, --(CH.sub.2).sub.p --Y.sub.3, or halo substituted alkyl; R.sub.4 is hydrogen, alkyl, alkenyl, alkynyl, --(CH.sub.2).sub.n --Y.sub.2, --(CH.sub.2).sub.p --Y.sub.3, halo substituted alkyl, or ##STR2## Y.sub.1 is cycloalkyl, aryl, heterocyclo, hydroxyl, alkoxy, aryl--(CH.sub.2).sub.m --O--, mercapto, alkylthio, aryl--(CH.sub.2).sub.m --S--, amino, substituted amino, carbamoyl, ##STR3## Y.sub.2 is cycloalkyl, aryl, heterocyclo, carbamoyl, ##STR4## Y.sub.3 is hydroxyl, alkoxy, aryl--(CH.sub.2).sub.m --O--, mercapto, alkylthio, aryl--(CH.sub.2).sub.m --S--, ##STR5## amino, or substituted amino; Y.sub.4 is alkyl, cycloalkyl, aryl, heterocyclo, --(CH.sub.2).sub.n --Y.sub.1 or halo substituted alkyl; m is 0 or an integer of 1 to 6; n is an integer of 1 to 6; and p is an integer of 2 to 6.

  具有以下公式##STR1##或其药学上可接受的盐，其中R.sub.1是芳基或杂环基; R.sub.2是氢，烷基，烯基，炔基，环烷基，芳基，--(CH.sub.2).sub.n --Y.sub.1，或卤代烷基; R.sub.3是氢，烷基，环烷基，芳基，杂环基，--(CH.sub.2).sub.n --Y.sub.2，--(CH.sub.2).sub.p --Y.sub.3，或卤代烷基; R.sub.4是氢，烷基，烯基，炔基，--(CH.sub.2).sub.n --Y.sub.2，--(CH.sub.2).sub.p --Y.sub.3，卤代烷基，或##STR2##Y.sub.1是环烷基，芳基，杂环基，羟基，烷氧基，芳基--(CH.sub.2).sub.m --O--，巯基，烷硫基，芳基--(CH.sub.2).sub.m --S--，氨基，取代氨基，氨基甲酰基，##STR3##Y.sub.2是环烷基，芳基，杂环基，氨基甲酰基，##STR4##Y.sub.3是羟基，烷氧基，芳基--(CH.sub.2).sub.m --O--，巯基，烷硫基，芳基--(CH.sub.2).sub.m --S--，##STR5##氨基或取代氨基; Y.sub.4是烷基，环烷基，芳基，杂环基，--(CH.sub.2).sub.n --Y.sub.1或卤代烷基; m为0或1至6的整数; n为1至6的整数; p为2至6的整数。
• Isoquinoline derivatives as matrix metalloproteinase inhibitors
  申请人：——

  公开号：US20040044000A1

  公开（公告）日：2004-03-04

  This invention provides compounds defined by Formula I 1 or a pharmaceutically acceptable salt thereof, wherein R 1 , Q, Y, R 2 , R 3 , R 4 , R 5 , and n are as defined in the specification. The invention also provides pharmaceutical compositions comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, as defined in the specification, together with a pharmaceutically acceptable carrier, diluent, or excipient. The invention also provides methods of inhibiting an MMP-13 enzyme in an animal, comprising administering to the animal a compound of Formula I, or a pharmaceutically acceptable salt thereof. The invention also provides methods of treating a disease mediated by an MMP-13 enzyme in a patient, comprising administering to the patient a compound of Formula I, or a pharmaceutically acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides methods of treating diseases such as heart disease, multiple sclerosis, osteo- and rheumatoid arthritis, arthritis other than osteo- or rheumatoid arthritis, cardiac insufficiency, inflammatory bowel disease, heart failure, age-related macular degeneration, chronic obstructive pulmonary disease, asthma, periodontal diseases, psoriasis, atherosclerosis, and osteoporosis in a patient, comprising administering to the patient a compound of Formula I, or a pharmaceutically acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides combinations, comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, together with another pharmaceutically active component as described in the specification.

  该发明提供了由公式I1定义的化合物或其药学上可接受的盐，其中R1、Q、Y、R2、R3、R4、R5和n的定义如规范中所述。该发明还提供了药物组合物，包括公式I中定义的化合物或其药学上可接受的盐，以及药学上可接受的载体、稀释剂或赋形剂。该发明还提供了抑制动物中MMP-13酶的方法，包括向动物给予公式I中定义的化合物或其药学上可接受的盐。该发明还提供了治疗由MMP-13酶介导的疾病的方法，包括向患者单独或与药物组合物一起给予公式I中定义的化合物或其药学上可接受的盐。该发明还提供了治疗心脏病、多发性硬化症、骨关节炎、除骨关节炎或类风湿性关节炎以外的其他关节炎、心力衰竭、炎症性肠病、心力衰竭、老年性黄斑变性、慢性阻塞性肺疾病、哮喘、牙周疾病、银屑病、动脉粥样硬化和骨质疏松症的方法，包括向患者单独或与药物组合物一起给予公式I中定义的化合物或其药学上可接受的盐。该发明还提供了组合物，包括公式I中定义的化合物或其药学上可接受的盐，以及规范中描述的另一种药学活性成分。
• BERG, D.;FEST, CH.;KUCK, K. -H.;SCHEINPFLUG, H.
  作者：BERG, D.、FEST, CH.、KUCK, K. -H.、SCHEINPFLUG, H.

  DOI：——

  日期：——
• Synthesis, antimicrobial, and antiviral activities of some new 5-sulphonamido-8-hydroxyquinoline derivatives
  作者：Emad M. Kassem、Eslam R. El-Sawy、Howaida I. Abd-Alla、Adel H. Mandour、Dina Abdel-Mogeed、Mounir M. El-Safty

  DOI：10.1007/s12272-012-0602-0

  日期：2012.6

  A series of fused pyranopyrazole and pyranoimidazole, namely 5-(3,6-diamino-4-aryl-5-carbonitrile-pyrano(2,3-c)pyrazol-2-yl)sulphonyl-8-hydroxyquinolines (5a–e), 5-(6-amino-4-aryl-5-carbonitrile-pyrano(2,3-c)pyrazol-3-yl)sulphonamido-8-hydroxyquinolines (6a-e), 5-(2-thioxo-4-aryl-5-carbonitrile-6-amino-pyrano(2,3-d)imidazol-2-yl)sulphonyl-8-hydroxyquinolines (10a-e), and 5-(2-oxo-4-aryl-5-carbonitrile-6-amino-pyrano(2,3-d)imidazol-2-yl) sulphonyl-8-hydroxyquinolines (11a-e), have been prepared via condensation of some arylidine malononitriles with 5-sulphonamido-8-hydroxyquinoline derivatives 3, 4, 8 and 9. All the synthesized compounds were screened for their antimicrobial activities, and most of the tested compounds showed potent inhibition growth activity towards Escherichia coli, Pseudomonas aeruginosa (Gramnegative bacteria). Furthermore, six selected compounds were tested for their antiviral activity against avian paramyxovirus type1 (APMV-1) and laryngotracheitis virus (LTV), and the results showed that a concentration range of 3-4 μg per mL of compounds 2, 3, and 4 showed marked viral inhibitory activity for APMV-1 of 5000 tissue culture infected dose fifty (TCID50) and LTV of 500 TCID50 in Vero cell cultures based on their cytopathic effect. Chicken embryo experiments show that compounds 2, 3, and 4 possess high antiviral activity in vitro with an inhibitory concentration fifty (IC50) range of 3–4 μg per egg against avian APMV-1 and LTV and their toxic concentration fifty (CC50) of 200–300 μg per egg.

  一系列融合的吡嗪并吡喃类化合物，即5-(3,6-二氨基-4-芳基-5-氰基-吡喃(2,3-c)吡嗪-2-基)磺酰基-8-羟基喹啉（5a-e）、5-(6-氨基-4-芳基-5-氰基-吡喃(2,3-c)吡嗪-3-基)磺酰胺-8-羟基喹啉（6a-e）、5-(2-硫酮-4-芳基-5-氰基-6-氨基-吡喃(2,3-d)咪唑-2-基)磺酰基-8-羟基喹啉（10a-e），以及5-(2-氧代-4-芳基-5-氰基-6-氨基-吡喃(2,3-d)咪唑-2-基)磺酰基-8-羟基喹啉（11a-e），通过将一些芳基二苯乙亚胺与5-磺酰胺-8-羟基喹啉衍生物3、4、8和9进行缩合反应制备而成。所有合成的化合物均进行了抗微生物活性筛选，大多数测试化合物对大肠杆菌和铜绿假单胞菌（阴性菌）表现出强效的抑菌活性。此外，六种选择的化合物还被测试其对禽类副黏病毒1型（APMV-1）和喉气管炎病毒（LTV）的抗病毒活性，结果显示，2、3和4号化合物在浓度范围为每毫升3-4 μg时，对APMV-1（5000组织培养感染剂量五十TCID50）和LTV（500 TCID50）具有显著的病毒抑制活性，基于其细胞病变效应。鸡胚实验表明，2、3和4号化合物在体外对禽类APMV-1和LTV具有高抗病毒活性，抑制浓度五十（IC50）范围为每个鸡蛋3–4 μg，毒性浓度五十（CC50）范围为每个鸡蛋200–300 μg。