5-异丙基-2-苯基-2H-吡唑-3-甲酸 | 299165-57-4

• 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-异丙基-2-苯基-2H-吡唑-3-甲酸
• 英文名称: 2-phenyl-5-isopropyl-2H-pyrazole-3-carboxylic acid
• 英文别名: 5-Isopropyl-2-phenyl-2H-pyrazole-3-carboxylic acid；2-phenyl-5-propan-2-ylpyrazole-3-carboxylic acid
• CAS: 299165-57-4
• 化学式: C₁₃H₁₄N₂O₂
• mdl: MFCD02731439
• 分子量: 230.266
• InChiKey: DMPWMPQUUGGLKC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  5-异丙基-2-苯基-2H-吡唑-3-甲酸 在 吡啶 、 氯化亚砜 作用下， 以 乙腈 为溶剂， 反应 16.0h， 生成 [(2E)-3,7-dimethylocta-2,6-dienyl] 2-phenyl-5-propan-2-ylpyrazole-3-carboxylate
  参考文献：
  名称：

  New Analogues of (E)-β-Farnesene with Insecticidal Activity and Binding Affinity to Aphid Odorant-Binding Proteins

  摘要：

  (E)-β-НАРСЕС is a strong and efficient ALARM PHENOMONE in most aphid species. However, its applications in agriculture are hindered by its relatively high VOLATILITY, susceptibility to OXIDATION, and complex and costly SYNTHESIS. In an effort to develop novel chemical entities for aphid CONTROL, we have designed and synthesized ANALOGUES of (E)-β-НАРСЕС, each bearing a PYRAZOLE moiety, a structural feature commonly found in several INSECTICIDES. Their structural analyses have been confirmed via (1)H NMR, ELEMENTAL ANALYSIS, HIGH-RESOLUTION MASS SPECTROSCOPY, and INFRARED SPECTROSCOPY. Binding activities to three ODDOR glVertex proteins (OBVs) of the pea aphid Acythosiphon pisum have been evaluated and correlative with the compounds' structures as a reference to (E)-β-НАРСЕС. Several derivatives were found to bind to A. pisum OBDs with a specificity comparable to that of (E)-β-НАРСЕС and exhibited ENTICING activity akin to that of thiacloprid, a widely used COMMERCIAL INSECTICIDE. The compounds synthesized in this study represent novel POTENTIAL AGENTS for POPULATION CONTROL of aphids and offer guidance for the design of ANALOGS of (E)-β-НАРСЕES endowed with both INSECTICIDAL and repellent properties for aphids.

  DOI：

  10.1021/jf104712c
• 作为产物：
  描述：

  2,4-二氧代-5-甲基-己酸乙酯 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 5.5h， 生成 5-异丙基-2-苯基-2H-吡唑-3-甲酸
  参考文献：
  名称：

  靶向EcR / USP受体的新型取代吡唑酰胺衍生物的设计，合成和生物学活性

  摘要：

  摘要为了发现高活性蜕皮激素类似物，在两种活性化合物N-（3）的核心结构的基础上，采用结构导向的优化方法，获得了一系列新的取代吡唑酰胺衍生物，并对其杀虫活性进行了筛选。 -甲氧基苯基）-3-（叔丁基）-1-苯基-1H-吡唑-5-羧酰胺（6e）和N-（4-（叔丁基）苯基）-3-（叔丁基）-1-苯基-1H-吡唑-5-羧酰胺（6i），以前由我们提供。通过光谱分析鉴定标题化合物的化学结构。初步的生物测定结果表明，合成的吡唑衍生物中的一种，化合物34，对Mythimna Separata的活性为10 mg / L，与阳性对照tebufenozide的活性相当。此外，分子对接和分子动力学研究的例子表明，34可能是EcR的潜在抑制剂，其对接构象与tebufenozide相似。另外，增加疏水作用并考虑对吡唑环的合适的整体作用有利于抑制EcR的活性和体内活性。

  DOI：

  10.1016/j.cclet.2016.02.009

文献信息

• Inhibitors of P2X3
  申请人：Brotherton-Pleiss E. Christine

  公开号：US20070037974A1

  公开（公告）日：2007-02-15

  Compounds of formula 1 are modulators of P2X3 useful for the treatment of pain and genito-urinary, gastrointestinal, and respiratory disorders: wherein R 1 is —C(═S)CH 3 , pyridyl, pyrimidinyl, pyrazinyl, thiazolyl, furyl, furylcarbonyl, acetyl, or carbamoyl; R 2a and R 2b are independently H, methyl, or ethyl; R 3 is H or methyl; Y is a bond, —(CR 4 R 5 ) n — or —CR 4 ═CR 5 —; wherein R 4 and R 5 are each independently H or methyl and n is 1 or 2; X is N or CH; A is phenyl, 5-membered heterocyclyl, or 6-membered heterocyclyl; R 6 , R 7 and R 8 are each independently H, halo, lower alkyl, cycloalkyl, alkylthio, alkylthio-lower alkyl, alkylsulfonyl-lower alkyl, di(lower alkyl)amino-lower alkyl, morpholinyl-lower alkyl, 4-methyl-piperazinyl-methyl, trifluoromethyl, pyridyl, tetrazolyl, thiophenyl, phenyl, biphenyl, or benzyl (where thiophenyl, phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoromethyl, lower alkoxy or lower alkylthio) or R 6 and R 7 together form a 5-membered or 6-membered carbocyclic or heterocyclic ring substituted with 0-3 substituents selected from the group consisting of lower alkyl, lower alkoxy, oxo, halo, thiophenyl-lower alkyl, phenyl, benzyl (where phenyl and benzyl are substituted with 0-3 lower alkyl, halo, sulfonamido, trifluoro-methyl, lower alkoxy, lower alkylthio, amino-lower alkyl, lower alkylamino-lower alkyl, or di(lower alkyl)amino-lower alkyl); and pharmaceutically acceptable salts thereof; wherein when R 1 is pyrimidin-2-yl, X is N, Y is a bond and A is oxazol-5-yl the carbon atom at position 4 in said oxazol-5-yl is not substituted by propyl when the carbon atom at position 2 in said oxazol-5-yl is substituted by substituted phenyl and the carbon atom at position 4 in said oxazol-5-yl is not substituted by phenyl when the carbon atom at position 2 is substituted by unsubstituted or substituted phenyl.

  式1的化合物是P2X3的调节剂，用于治疗疼痛和泌尿生殖、胃肠和呼吸系统疾病： 其中 R 1 为—C(═S)CH 3 ，吡啶基，嘧啶基，吡嗪基，噻唑基，呋喃基，呋喃甲酰基，乙酰基或氨基甲酰基；R 2a 和R 2b 独立地为H，甲基或乙基；R 3 为H或甲基；Y为键，—(CR 4 R 5 ) n —或—CR 4 ═CR 5 —；其中R 4 和R 5 各自独立地为H或甲基，n为1或2；X为N或CH；A为苯基，5-成员杂环基或6-成员杂环基；R 6 ，R 7 和R 8 各自独立地为H，卤素，低碳基，环烷基，烷基硫醚，烷基硫醚-低碳基，烷基磺酰基-低碳基，二(低碳基)氨基-低碳基，吗啉基-低碳基，4-甲基哌嗪基-甲基，三氟甲基，吡啶基，四唑基，噻吩基，苯基，联苯基或苄基（其中噻吩基，苯基和苄基被0-3个低碳基，卤素，磺酰胺基，三氟甲基，低烷氧基或低烷硫基取代）或R 6 和R 7 一起形成一个被0-3个取自由低碳基，低烷氧基，氧代基，卤素，噻吩基-低碳基，苯基，苄基（其中苯基和苄基被0-3个低碳基，卤素，磺酰胺基，三氟甲基，低烷氧基，低烷硫基，氨基-低碳基，烷基氨基-低碳基或二(低碳基)氨基-低碳基取代）的5-成员或6-成员碳环或杂环取代环；及其药学上可接受的盐；其中当R 1 为嘧啶-2-基时，X为N，Y为键，A为噁唑-5-基时，所述噁唑-5-基中位置4的碳原子在所述噁唑-5-基中位置2的碳原子被取代的苯基取代时不被丙基取代，且所述噁唑-5-基中位置4的碳原子在位置2被取代的苯基取代时不被苯基取代。
• N-arylheteroaromatic products compositions containing them and use thereof
  申请人：Le-Brun Alain

  公开号：US20050130989A1

  公开（公告）日：2005-06-16

  N-Arylheteroaromatic products, compositions containing them and use thereof. The present invention relates to novel chemical compounds, particularly to novel N-arylheteroaromatic products, to compositions containing them and to their use as medicinal products, in particular in oncology.

  N-芳基杂芳产物，含有它们的组合物及其用途。本发明涉及新型化合物，特别是新型N-芳基杂芳产物，含有它们的组合物以及它们作为药用产品的用途，特别是在肿瘤学中的用途。
• Calpain modulators and therapeutic uses thereof
  申请人：Blade Therapeutics, Inc.

  公开号：US10934261B2

  公开（公告）日：2021-03-02

  Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

  本文公开了小分子钙蛋白酶调节剂组合物、药物组合物及其用途和制备方法。
• PIPERIDINE AND PIPERAZINE DERIVATIVES AS P2X3 ANTAGONISTS
  申请人：F.HOFFMANN-LA ROCHE AG

  公开号：EP1917262A1

  公开（公告）日：2008-05-07
• US7491821B2
  申请人：——

  公开号：US7491821B2

  公开（公告）日：2009-02-17