5-(1,1-dimethylethyl)-1-methyl-1H-pyrazol-3-ol | 143706-73-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 5-(1,1-dimethylethyl)-1-methyl-1H-pyrazol-3-ol
• 英文别名: 3-tert-butyl-2-methyl-1H-pyrazol-5-one
• CAS: 143706-73-4
• 化学式: C₈H₁₄N₂O
• 分子量: 154.212
• InChiKey: NZMSOQFNCYMXDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  32.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  α-(pivaloyl)-α-(ethoxycarbonyl)methylenetriphenylphosphorane 以 甲醇 、 水 为溶剂， 150.0~220.0 ℃ 、1.33 kPa 条件下， 反应 72.0h， 生成 5-(1,1-dimethylethyl)-1-methyl-1H-pyrazol-3-ol
  参考文献：
  名称：

  Cyclocondensation of alkylhydrazines and .beta.-substituted acetylenic esters: synthesis of 3-hydroxypyrazoles

  摘要：

  Addition of monosubstituted alkylhydrazines to acetylenic esters with either electron-withdrawing or sterically bulky beta-substituents afforded 1-alkyl-3-hydroxy-5-substituted-pyrazoles 1 as the major regioisomeric product. By comparison, the classical cyclocondensation of alkylhydrazines with beta-keto esters gives the regioisomeric pyrazol-5-ones 2. The reaction solvent employed in these cyclocondensations can have a profound effect on regioisomeric product ratios. Addition of methylhydrazine to 5g in methylene chloride gave regiospecific formation of pyrazolinone 2o, whereas addition in water-methanol mixtures afforded hydroxypyrazole 1o as the major product. Structural assignment of regioisomers 1 and 2 are based on C-13 NMR chemical shifts, long-range heteronuclear coupling constants, and comparisons with regiochemically known hydroxypyrazoles and/or pyrazolinones. Additions of acetylene 5b to 1,1-dimethylhydrazine afforded either acyclic enehydrazone 12 or pyrazolium betaine 13 depending on the reaction conditions.

  DOI：

  10.1021/jo00047a021

文献信息

• HETEROCYCLIC COMPOUNDS AND USES THEREOF
  申请人：Ren Pingda

  公开号：US20120122838A1

  公开（公告）日：2012-05-17

  Compounds and pharmaceutical compositions that modulate kinase activity, including PI3 kinase activity, and compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

  调节激酶活性的化合物和药物组合物，包括PI3激酶活性，以及与激酶活性相关的疾病和病况的化合物、药物组合物和治疗方法在此进行描述。
• Arginase Inhibitors and Their Therapeutic Applications
  申请人：OncoArendi Therapeutics S.A.

  公开号：US20170319536A1

  公开（公告）日：2017-11-09

  Disclosed are small molecule therapeutic compounds that are potent inhibitors of arginase 1 and arginase 2 activity. Also disclosed are pharmaceutical compositions comprising the compounds, and methods for using the compounds for treating or preventing a disease or condition associated with arginase activity.

  揭示了一种小分子治疗化合物，它们是较强的精氨酸酶1和精氨酸酶2活性抑制剂。还揭示了包含这些化合物的药物组合物，以及使用这些化合物治疗或预防与精氨酸酶活性相关的疾病或状况的方法。
• NOVEL CYP-EICOSANOID DERIVATIVES
  申请人：MAX-DELBRÜCK-CENTRUM FÜR MOLEKULARE MEDIZIN

  公开号：US20170008918A1

  公开（公告）日：2017-01-12

  The present invention relates to compounds according to general formula (I) which are analogues of epoxymetabolites produced by cytochrome P450 (CYP) enzymes from omega-3 (n-3) polyunsaturated fatty acids (PUFAs). The present invention further relates to compositions containing one or more of these compounds and to the use of these compounds or compositions for C the treatment or prevention of conditions and diseases associated with inflammation, proliferation, hypertension, coagulation, immune function, pathologic angiogenesis, heart failure and cardiac arrhythmias.

  本发明涉及一般式（I）的化合物，这些化合物是由细胞色素P450（CYP）酶从ω-3（n-3）多不饱和脂肪酸（PUFAs）产生的环氧代谢产物的类似物。本发明还涉及含有这些化合物中的一个或多个的组合物，以及利用这些化合物或组合物用于治疗或预防与炎症、增殖、高血压、凝血、免疫功能、病理性血管生成、心力衰竭和心律失常相关的疾病和症状。
• SMALL MOLECULE INHIBITORS OF DYRK/CLK AND USES THEREOF
  申请人：Arizona Board of Regents on Behalf of the University of Arizona

  公开号：US20200039989A1

  公开（公告）日：2020-02-06

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having a 6,5-heterocyclic structure (e.g., compounds having a imidazopyridine, imidazopyrimidine, imidazopyrazine, imidazopyridazine, imidazotriazine, benzoimidazole, benzotriazole, benzoisoxazole, purine, indazole, triazolotriazine, triazolopyridazine, triazolopyrimidine, triazolopyrazine, triazolotetrazine, triazolopyridine, pyrazolopyrazine, pyrazolopyrimidine, pyrazolopyridazine, pyrazolotriazine, pyrazolopyridine, isoxazolopyrazine, isoxazolopyrimidine, isoxazolopyrdiazine, isoxazolotriazine, or isoxalopyridine structure) which function as inhibitors of DYRK1A, DYRK1B, and Clk-1, and their use as therapeutics for the treatment of Alzheimer's disease, Down syndrome, diabetes, glioblastoma, autoimmune diseases, cancer (e.g., glioblastoma, prostate cancer), inflammatory disorders (e.g., airway inflammation), and other diseases.

  这项发明属于药物化学领域。具体来说，该发明涉及一类新型小分子，具有6,5-杂环结构（例如，具有咪唑吡啶、咪唑吡嘧啶、咪唑吡嗪、咪唑吡啶嗪、咪唑三嗪、苯并咪唑、苯并三唑、苯并异嗪、嘌呤、吲唑、三唑三嗪、三唑吡啶嗪、三唑吡嘧啶、三唑吡嗪、三唑四嗪、三唑吡啶、吡唑吡嗪、吡唑吡嘧啶、吡唑吡啶嗪、吡唑三嗪、吡唑吡啶、异嗪吡嗪、异嗪吡嘧啶、异嗪吡啶嗪、异嗪三嗪、或异嗪吡啶结构），其作为DYRK1A、DYRK1B和Clk-1的抑制剂，以及它们作为治疗阿尔茨海默病、唐氏综合征、糖尿病、胶质母细胞瘤、自身免疫疾病、癌症（例如，胶质母细胞瘤、前列腺癌）、炎症性疾病（例如，气道炎症）和其他疾病的治疗药物的用途。
• SMALL MOLECULE INHIBITORS OF MCL-1 AND USES THEREOF
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：US20150284387A1

  公开（公告）日：2015-10-08

  This invention is in the field of medicinal chemistry. In particular, the invention relates to a new class of small-molecules having pyrazolopyridine structure which function as inhibitors of Mcl-1 protein, and their use as therapeutics for the treatment of cancer and other diseases.

  这项发明属于药物化学领域。具体来说，该发明涉及一类具有吡唑吡啶结构的新型小分子，其作为Mcl-1蛋白抑制剂的功能，以及它们作为治疗癌症和其他疾病的药物的用途。