3-phenylpyrazol-5-one | 95884-09-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-phenylpyrazol-5-one
• 英文别名: 3-phenyl-5-pyrazolone；3-phenyl-2-pyrazolin-5-one；5-phenyl-pyrazol-3-one；3-phenyl-1H-pyrazol-5(4H)-one；5-Phenylpyrazol-3-one
• CAS: 95884-09-6
• 化学式: C₉H₆N₂O
• 分子量: 158.159
• InChiKey: FEGXBUUVCAOZEL-UHFFFAOYSA-N

物化性质

• 沸点：
  286.3±43.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-phenylpyrazol-5-one 在 sodium nitrite 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  新的Ni（II），Pd（II）和Pt（II）配合物与偶氮吡唑酮配体配合使用，具有强大的抗肿瘤活性：合成，表征，DFT和DNA裂解研究

  摘要：

  对抗某种类型的肿瘤的绝对必要性被视为严重的健康问题，因此迫切需要发现和开发有效的抗癌剂。（E）-4-（（（2-羟基苯基）二氮烯基）-3-苯基-1 H-吡唑-5（4 H）-one，HL及其Ni（II），Pd（II）和Pt（II）合成了复合物，并评估了其抗肿瘤，抗氧化和抗菌活性以及DNA裂解的生物活性。根据元素分析，电导率，磁矩，光谱测量（IR，1HNMR，质量和UV-Vis）和热分析。使用DFT方法进行的3D分子建模证实了几何结构与建议的实验结构吻合良好。使用MTT测定法评估了针对四种不同细胞系的抗肿瘤活性。与5-氟尿嘧啶作为参考药物相比，配体HL显示出有效的细胞毒性活性。对于金属络合物，活性顺序为：Pd（II）> Ni（II）> Pt（II）。对配体HL具有显着的抗氧化活性被记录。它高于金属配合物。抗菌实验结果表明，所有化合物对选定的细菌菌株均具有中等至高度的活性，但除Pd（II）具有中等

  DOI：

  10.1002/aoc.4104
• 作为产物：
  描述：

  propyl 3-oxo-3-phenylpropanoate 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 3-phenylpyrazol-5-one
  参考文献：
  名称：

  [EN] PYRAZOLYL SUBSTITUTED CARBONIC ACID DERIVATIVES AS MODULATORS OF THE PROSTACYCLIN (PGI2) RECEPTOR USEFUL FOR THE TREATMENT OF DISORDERS RELATED THERETO
  [FR] DÉRIVÉS D'ACIDE CARBONIQUE SUBSTITUÉS PAR PYRAZOLYLE EN TANT QUE MODULATEURS DU RÉCEPTEUR DE LA PROSTACYCLINE PGI2 ADAPTÉS AU TRAITEMENT DE TROUBLES LE FAISANT INTERVENIR

  摘要：

  Formula Ia的吡唑衍生物及其药物组成物，可调节PGI2受体的活性。本发明的化合物和药物组成物用于治疗以下疾病：肺动脉高压（PAH）及相关疾病；血小板聚集；冠状动脉疾病；心肌梗死；短暂性缺血性发作；心绞痛；中风；缺血再灌注损伤；再狭窄；心房颤动；血栓形成在冠状动脉成形术或冠状动脉旁路手术个体中或在患有心房颤动的个体中；动脉粥样硬化；动脉粥样血栓形成；哮喘或其症状；糖尿病相关疾病，如糖尿病周围神经病变、糖尿病肾病或糖尿病视网膜病变；青光眼或其他眼睛异常眼压疾病；高血压；炎症；牛皮癣；银屑病性关节炎；类风湿性关节炎；克罗恩病；移植排斥；多发性硬化症；系统性红斑狼疮（SLE）；溃疡性结肠炎；缺血再灌注损伤；再狭窄；动脉粥样硬化；痤疮；1型糖尿病；2型糖尿病；败血症；慢性阻塞性肺疾病（COPD）。

  公开号：

  WO2010068242A1

文献信息

• Design, Synthesis, and Evaluation of Dihydropyranopyrazole Derivatives as Novel PDE2 Inhibitors for the Treatment of Alzheimer’s Disease
  作者：Yan Zhou、Jinjian Li、Han Yuan、Rui Su、Yue Huang、Yi-You Huang、Zhe Li、Yinuo Wu、Hai-Bin Luo、Chen Zhang、Ling Huang

  DOI：10.3390/molecules26103034

  日期：——

  2 (PDE2) has been regarded as a novel target for the treatment of Alzheimer’s disease (AD). In this study, we obtained (R)-LZ77 as a hit compound with moderate PDE2 inhibitory activity (IC50 = 261.3 nM) using a high-throughput virtual screening method based on molecular dynamics. Then, we designed and synthesized 28 dihydropyranopyrazole derivatives as PDE2 inhibitors. Among them, compound (+)-11h was

  磷酸二酯酶2（PDE2）已被视为治疗阿尔茨海默氏病（AD）的新型靶标。在这项研究中，我们获得了（- [R ）- LZ77作为中度PDE2抑制活性（IC命中化合物50使用基于分子动力学高通量虚拟筛选方法= 261.3纳米）。然后，我们设计并合成了28种二氢吡喃并吡唑衍生物作为PDE2抑制剂。其中，化合物（+）- 11h是最有效的PDE2抑制剂，IC 50值为41.5 nM。PDE2-（+）- 11h的分子对接揭示了该化合物的4-（三氟甲基）苄基）氧基侧链进入H型口袋并与L770 / L809 / F862形成强疏水相互作用，从而提高了抑制活性。以上结果可为进一步高效优化PDE2抑制剂的结构提供见识，并可为其在AD治疗中的应用奠定基础。
• [EN] BISAZO AND TRISAZO COPPER COMPLEX DYESTUFFS<br/>[FR] COLORANTS COMPLEXES BISAZO ET TRISAZO A BASE DE CUIVRE
  申请人：CLARIANT INT LTD

  公开号：WO2003099937A1

  公开（公告）日：2003-12-04

  This invention relates to coppered bis- or trisazo dyestuffs containing at least two (for bisazo) and at least three (for trisazo) alkyl-, alkoxy- or aryl- ammonium sulfonate groups or sulfonate groups with Rhodamine B type or Rosinamine D type counterions. The invention also relates to various intermediates used in the preparation of the metallized dyes, to compositions, and to processes for preparing the metallized dyestuffs. The compounds are particularly suited for the application in lacquers.

  这项发明涉及含有至少两个（对于双偶氮）和至少三个（对于三偶氮）烷基、烷氧基或芳基-氨基磺酸盐基团或具有罗丹明B型或罗斯胺D型对离子的铜化双-或三偶氮染料。该发明还涉及用于制备金属化染料的各种中间体、组合物和制备金属化染料的方法。这些化合物特别适用于涂料的应用。
• Effects of a Calcium-Channel Blocker (CV159) on Hepatic Ischemia/Reperfusion Injury in Rats: Evaluation with Selective NO/pO2 Electrodes and an Electron Paramagnetic Resonance Spin-Trapping Method
  作者：Keizo Hataji、Taiji Watanabe、Shigeru Oowada、Masaki Nagaya、Masato Kamibayashi、Eiichi Murakami、Hiroyoshi Kawakami、Atsuko Ishiuchi、Toshio Kumai、Hiroshi Nakano、Shinichi Kobayashi、Takehito Otsubo

  DOI：10.1248/bpb.33.77

  日期：——

  Nitric oxide (NO) and the partial pressure of oxygen (pO2) in the liver were simultaneously quantified in rats with partial hepatic ischemia/reperfusion injury (PHIRI). Real-time NO/pO2 monitoring and immunohistochemical analysis for superoxide dismutase and inducible nitric oxide synthase (iNOS) and endothelial NOS (eNOS) were performed to evaluate the protective effects of a dihydropyridine-type calcium-channel blocker—CV159—on PHIRI. Serum high-mobility-group box-1 (HMGB-1) was measured to assess cellular necrosis. Moreover, we used in vitro/ex vivo electron paramagnetic resonance spin trapping to assess the hydroxyl radical (·OH)-scavenging activity (OHSA) of CV159 and the liver tissue. The NO levels were significantly higher in CV159-treated rats than in control rats throughout the ischemic phase. Immediately after reperfusion, the levels temporarily increased in waves and then gradually decreased in the treated rats but remained constant in the control rats. pO2 was continually higher in the treated rats. In these rats, hepatic eNOS expression increased, whereas iNOS expression decreased. The treated rats exhibited significantly higher cytosolic and mitochondrial concentrations NOx (NO2+NO3). The serum HMGB-1 levels significantly decreased in the treated rats. Moreover, CV159 directly scavenged ·OH and both mitochondrial and cytosolic OHSA were preserved in the treated rats. Thus, CV159-mediated inhibition of intracellular Ca2+ overloading may effectively minimize organ damage and also have ·OH-scavenging activity and the cytoprotective effects of eNOS-derived NO.

  在肝局部缺血/再灌注损伤（PHIRI）大鼠中，同时测量了一氧化氮（NO）和肝脏中的氧分压（pO2）。通过实时NO/pO2监测以及超氧化物歧化酶、诱导型一氧化氮合成酶（iNOS）和内皮型一氧化氮合成酶（eNOS）的免疫组织化学分析，评估二氢吡啶类钙通道阻滞剂CV159对PHIRI的保护作用。通过测量血清高迁移率族蛋白1（HMGB-1）来评估细胞坏死。此外，我们使用体外/离体电子顺磁共振自旋捕获技术来评估CV159和肝脏组织对羟自由基（·OH）的清除活性（OHSA）。在整个缺血阶段，CV159治疗组大鼠的NO水平明显高于对照组大鼠。再灌注后，治疗组大鼠的NO水平立即呈波浪状短暂升高，然后逐渐降低，而对照组大鼠的NO水平保持恒定。治疗组大鼠的pO2持续升高。这些大鼠的肝脏eNOS表达增加，而iNOS表达减少。治疗组大鼠的细胞质和线粒体NOx（NO2+NO3）浓度明显升高。治疗组大鼠的血清HMGB-1水平明显降低。此外，CV159直接清除·OH
• 1,4-Dihydropyridine derivatives
  申请人：Tokyo Tanabe Company, Limited

  公开号：US04418197A1

  公开（公告）日：1983-11-29

  Novel 1,4-dihydropyridine derivatives of the formula [I] are provided: ##STR1## wherein R.sup.1 represents a C.sub.1-4 alkyl group or a C.sub.3-6 alkoxyalkyl group, R.sup.2 represents hydrogen or halogen, R.sup.3 is either nitro when R.sup.2 is hydrogen, or halogen when R.sup.2 is halogen, R.sup.4 represents a pyridyl group, a phenethyl group, an unsubstituted benzyl group, a substituted benzyl group having one or more suitable substituents, an unsubstituted phenyl group, or a substituted phenyl group having one or more suitable substituents, and A represents an unsubstituted hexamethylene group or a substituted hexamethylene group having one or two C.sub.1-3 alkyl groups. The 1,4-dihydropyridine derivatives have vasodilating and hypotensive activity which is kept for a long period, and are useful in the treatment of cardiovascular disease and hypertension.

  提供了式[I]的新型1,4-二氢吡啶衍生物：##STR1## 其中，R.sup.1代表C.sub.1-4烷基或C.sub.3-6烷氧基烷基，R.sup.2代表氢或卤素，当R.sup.2为氢时，R.sup.3为硝基，当R.sup.2为卤素时，R.sup.3为卤素，R.sup.4代表吡啶基，苯乙基，未取代苄基，具有一个或多个适当取代基的取代苄基，未取代苯基或具有一个或多个适当取代基的取代苯基，A代表未取代的六亚甲基或具有一个或两个C.sub.1-3烷基的取代六亚甲基。1,4-二氢吡啶衍生物具有扩血管和降压活性，该活性长时间保持，并且在心血管疾病和高血压的治疗中有用。
• Pyrazolone Derivative
  申请人：Gomi Noriaki

  公开号：US20100324091A1

  公开（公告）日：2010-12-23

  A pyrazolone derivative represented by formula (I) below: wherein R 1 to R 3 are the same as defined in claims; or an optical isomer, a pharmaceutically acceptable salt thereof, or a hydrate or solvate thereof is provided. The novel pyrazolone derivative according to the present invention has a PAI-1 production inhibitory activity, a tissue fibrosis inhibitory activity, and a fibrolytic activity, and is effective for preventing and/or treating tissue fibrotic diseases (lung fibrosis, kidney fibrosis, etc.) and diseases of which a pathological thrombus becomes the cause, such as ischemic cardiac diseases (cardiac infarction and angina pectoris), atrial thrombus, lung embolism, deep thrombophlebitis, disseminated intravascular clotting, ischemic brain diseases (brain infarction, brain hemorrhage), and arterial sclerosis. In addition, a pharmaceutical agent for preventing and/or treating the disease conditions or the symptoms mediated by plasminogen activator inhibitor-1, comprising the novel pyrazolone derivative according to the present invention is also provided.

  本发明提供了一种由以下式（I）表示的吡唑酮衍生物：其中，R1至R3与权利要求中定义的相同；或其光学异构体、药学上可接受的盐或其水合物或溶剂化物。根据本发明，这种新型的吡唑酮衍生物具有PAI-1生产抑制活性、组织纤维化抑制活性和纤溶活性，对于预防和/或治疗组织纤维化疾病（肺纤维化、肾脏纤维化等）以及由病理性血栓引起的疾病（缺血性心脏病（心肌梗死和心绞痛）、心房血栓、肺栓塞、深静脉血栓性炎症、弥漫性血管内凝血、缺血性脑疾病（脑梗死、脑出血）和动脉硬化）非常有效。此外，本发明还提供了一种用于预防和/或治疗由纤溶酶原激活剂抑制物-1介导的疾病状况或症状的药物制剂，其包括根据本发明的新型吡唑酮衍生物。