5-氨基-1-甲基-3-三氟甲基-1H-吡唑-4-羧酸 | 317806-51-2

• 物质功能分类: 生物化工 - 氨基酸及其衍生物 - 其他氨基酸衍生物
• 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-氨基-1-甲基-3-三氟甲基-1H-吡唑-4-羧酸
• 中文别名: 5-氨基-1-甲基-3-(三氟甲基)-1H-吡唑-4-羧酸
• 英文名称: 5-amino-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid
• 英文别名: 5-amino-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid；5-amino-1-methyl-3-(trifluoromethyl)pyrazole-4-carboxylic acid
• CAS: 317806-51-2
• 化学式: C₆H₆F₃N₃O₂
• 分子量: 209.128
• InChiKey: RELBWNKENZUWTK-UHFFFAOYSA-N

物化性质

• 沸点：
  340.6±42.0 °C(Predicted)
• 密度：
  1.73±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  7

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-氨基-1-甲基-3-三氟甲基-1H-吡唑-4-羧酸 在 氯化亚砜 作用下， 反应 3.0h， 生成 5-Amino-1-methyl-3-(trifluoromethyl)pyrazole-4-carbonyl chloride
  参考文献：
  名称：

  Novel Protoporphyrinogen Oxidase Inhibitors: 3H-Pyrazolo[3,4-d][1,2,3]triazin-4-one Derivatives

  摘要：

  A series of 3H-pyrazolo[3,4-d][1,2,3]triazin-4-one derivatives were synthesized as candidate herbicides by diazotization of different 5(3)-amino-N-phenyl-1H-pyrazole-4-carboxamide derivatives prepared by the reaction of substituted 5(3)-amino-pyrazole-4-carbonyl chloride with a substituted aniline. Their structures were identified by H-1 NMR and elemental analyses. The isomers D and E were isolated, and their structures were identified by two-dimensional NMR analyses (heteronuclear single quantum coherence and heteronuclear multiple-bond correlation) and single-crystal X-ray diffraction analysis. The bioassay results showed that some of the title compounds exhibited both excellent herbicidal activity at a dose of 93.75 g/ha and strong inhibition against protoporphyrinogen oxidase activity in vitro. The structure-activity relationship showed that D16 possessed the highest activities both in vivo and in vitro when the N-substituted group of the pyrazole ring was allyl and the N-substituted group of benzooxazinone was propargyl.

  DOI：

  10.1021/jf801774k
• 作为产物：
  描述：

  5-氨基-1-甲基-3-(三氟甲基)-1H-吡唑-4-羧酸乙酯 在 盐酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 以85%的产率得到5-氨基-1-甲基-3-三氟甲基-1H-吡唑-4-羧酸
  参考文献：
  名称：

  5-aminopyrazole-4-carboxylate derivative and process for preparing the same

  摘要：

  通过反应式（C）的反应，将式（2）所代表的化合物与式（3）或其水合物、盐（如盐酸盐、溴化物盐或硫酸盐）所代表的肼化合物反应，制备出式（1）所代表的5-氨基吡唑-4-羧酸衍生物。其中，R1为直链或支链的C1到C4烷基，可被卤素原子取代；R2为氢原子、直链或支链的C1到C4烷基或未取代或取代的苯基；R3为直链或支链的C1到C4烷基；M为碱金属。本发明制备过程得到的5-氨基吡唑-4-羧酸衍生物可用作农药和药物的中间体，特别是杀菌剂。

  公开号：

  US06235911B1

文献信息

• [EN] SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES BICYCLIQUES SUBSTITUÉS UTILISÉS EN TANT QU'INHIBITEURS DE NADPH OXYDASE
  申请人：GLENMARK PHARMACEUTICALS SA

  公开号：WO2018203298A1

  公开（公告）日：2018-11-08

  The present application relates to substituted fused heteroaryl and heterocyclic compounds, useful as nicotinamide adenine dinucleotide phosphate oxidase inhibitors (NADPH oxidase inhibitors), processes for their preparation, pharmaceutical compositions comprising the compounds, and the use of the compounds or the compositions in the treatment or prevention of various diseases, conditions and/or disorders mediated by NADPH oxidase. (Formula I)

  本申请涉及取代的融合杂环芳基和杂环化合物，用作烟酰胺腺嘌呤二核苷酸磷酸酶抑制剂（NADPH氧化酶抑制剂），其制备方法，包含这些化合物的药物组合物，以及这些化合物或组合物在治疗或预防由NADPH氧化酶介导的各种疾病、症状和/或障碍中的用途。 (分子式I)
• 5-Aminopyrazole-4-carboxylate derivative and process for preparing the same
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1067121A2

  公开（公告）日：2001-01-10

  A 5-aminopyrazole-4-carboxylate derivative represented by the formula (1) is prepared by reacting a compound represented by the formula (2) with a hydrazine compound represented by the formula (3) or hydrate, hydrochloride, hydrobromide or sulfate of the same according to the reaction formula (C): wherein R1 is a straight or branched C1 to C4 alkyl group which can be substituted with a halogen atom, R2 is a hydrogen atom, straight or branched C1 to C4 alkyl group or an unsubstituted or substituted phenyl group, and R3 is a straight or branched C1 to C4 alkyl group, and M is an alkali metal. The 5-aminopyrazole-4-carboxylate derivative obtained by the preparation process of the invention is useful for an intermediate of agricultural chemicals and medicines, fungicides in particular.

  式(1)代表的5-氨基吡唑-4-羧酸盐衍生物是由式(2)代表的化合物与式(3)代表的肼化合物或其水合物、盐酸盐、氢溴酸盐或硫酸盐按反应式(C)反应制备的： 其中 R1 是可被卤原子取代的直链或支链 C1 至 C4 烷基，R2 是氢原子、直链或支链 C1 至 C4 烷基或未取代或取代的苯基，R3 是直链或支链 C1 至 C4 烷基，M 是碱金属。 通过本发明的制备工艺得到的 5-氨基吡唑-4-羧酸酯衍生物可用作农用化学品和药物，特别是杀菌剂的中间体。
• SUBSTITUTED BICYCLIC HETEROCYCLIC COMPOUNDS AS NADPH OXIDASE INHIBITORS
  申请人：Glenmark Pharmaceuticals S.A.

  公开号：EP3619209A1

  公开（公告）日：2020-03-11
• US6235911B1
  申请人：——

  公开号：US6235911B1

  公开（公告）日：2001-05-22